CN112005393A - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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CN112005393A
CN112005393A CN201980027423.3A CN201980027423A CN112005393A CN 112005393 A CN112005393 A CN 112005393A CN 201980027423 A CN201980027423 A CN 201980027423A CN 112005393 A CN112005393 A CN 112005393A
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许东旭
洪性佶
许瀞午
韩美连
李在卓
梁正勋
尹喜敬
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LG Chem Ltd
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    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
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    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H10K50/13OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit

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Abstract

本说明书涉及一种有机发光器件,其中,包括:第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与上述第二电极之间的第一有机物层和第二有机物层,上述第一有机物层包含由化学式1表示的化合物,上述第二有机物层包含由化学式3表示的化合物。

Figure 201980027423

This specification relates to an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and a first organic layer and a second organic layer disposed between the first electrode and the second electrode, wherein the first organic layer comprises a compound represented by chemical formula 1, and the second organic layer comprises a compound represented by chemical formula 3.

Figure 201980027423

Description

有机发光器件Organic Light Emitting Devices

技术领域technical field

本申请主张于2018年9月3日向韩国专利局提交的韩国专利申请第10-2018-0104682号的优先权,其全部内容包含在本说明书中。This application claims priority to Korean Patent Application No. 10-2018-0104682 filed with the Korean Patent Office on September 3, 2018, the entire contents of which are incorporated herein.

本说明书涉及有机发光器件。This specification relates to organic light-emitting devices.

背景技术Background technique

通常情况下,有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机发光器件通常具有包括阳极和阴极以及位于它们之间的有机物层的结构。在这里,为了提高有机发光器件的效率和稳定性,有机物层大多情况下由分别利用不同的物质构成的多层结构形成,例如,可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。对于这样的有机发光器件的结构而言,如果在两电极之间施加电压,则空穴从阳极注入至有机物层,电子从阴极注入至有机物层,当所注入的空穴和电子相遇时会形成激子(exciton),并且当该激子重新跃迁至基态时就会发出光。In general, the organic light-emitting phenomenon refers to the phenomenon of using organic substances to convert electrical energy into light energy. An organic light-emitting device utilizing an organic light-emitting phenomenon generally has a structure including an anode and a cathode and an organic layer interposed therebetween. Here, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is usually formed of a multilayer structure composed of different substances. A transport layer, an electron injection layer, and the like are formed. For the structure of such an organic light-emitting device, if a voltage is applied between two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer. excitons, and emit light when the excitons re-transition to the ground state.

以往,作为用于有机EL器件的空穴传输材料,已知芳香族二胺衍生物或芳香族稠环二胺衍生物。但是,在这种情况下施加的电压大部分较高,因此产生器件寿命降低或耗电变大等问题。作为上述问题的解决方法,提出了在有机EL器件的空穴注入层中掺杂路易斯酸等电子接受性化合物或单独利用的方法。但是,上述的方法在空穴的注入和传输方面显示出存在局限性,因此,想要用空穴传输层或空穴调节层之间的物质组合或者空穴传输层和复数层的空穴调节层的物质引出低电压和高效率、长寿命的效果。通常的空穴传输层为取代有芳香族的叔胺,在这些物质的组合中可以发现的器件特性显示出各种结果。因此,持续要求开发用于提高空穴的传输和载流子调节带来的器件的特性的新材料。Conventionally, aromatic diamine derivatives or aromatic condensed ring diamine derivatives have been known as hole transport materials used in organic EL devices. However, in this case, since the voltage applied is mostly high, problems such as shortening the life of the device and increasing power consumption arise. As a solution to the above-mentioned problems, a method of doping an electron-accepting compound such as a Lewis acid in a hole injection layer of an organic EL device or using it alone has been proposed. However, the above-mentioned methods show limitations in the injection and transport of holes, therefore, it is desired to use a combination of substances between the hole transport layer or the hole regulation layer or the hole regulation of the hole transport layer and the plurality of layers The material of the layer elicits the effect of low voltage and high efficiency, long life. A typical hole transport layer is an aromatic-substituted tertiary amine, and the device properties found in combinations of these materials show various results. Therefore, there is a continuing need to develop new materials for improving the characteristics of devices due to hole transport and carrier modulation.

发明内容SUMMARY OF THE INVENTION

技术课题technical issues

本说明书提供有机发光器件。This specification provides organic light-emitting devices.

课题的解决方法Solution to the problem

本说明书提供一种有机发光器件,其中,包括:第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与上述第二电极之间的第一有机物层和第二有机物层,The present specification provides an organic light-emitting device comprising: a first electrode, a second electrode provided opposite to the first electrode, and a first organic layer provided between the first electrode and the second electrode and the second organic layer,

上述第一有机物层包含由下述化学式1表示的化合物,The above-mentioned first organic substance layer contains a compound represented by the following Chemical Formula 1,

上述第二有机物层包含由下述化学式3表示的化合物。The above-mentioned second organic substance layer contains a compound represented by the following Chemical Formula 3.

[化学式1][Chemical formula 1]

Figure BDA0002736434820000021
Figure BDA0002736434820000021

在化学式1中,In Chemical Formula 1,

X为O或S,X is O or S,

R1至R4彼此相同或不同,各自独立地为氢、氘、卤素基团、氰基、硝基、取代或未取代的烷基、取代或未取代的卤代烷基、取代或未取代的卤代烷氧基、取代或未取代的环烷基、取代或未取代的烯基、取代或未取代的芳基、或者取代或未取代的杂环基,或者相邻的基团彼此结合而形成取代或未取代的环,R1 to R4 are the same or different from each other and are each independently hydrogen, deuterium, halogen group, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted haloalkyl, substituted or unsubstituted haloalkoxy , substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, or adjacent groups combined with each other to form substituted or unsubstituted the ring,

R1至R4中的至少一个由下述化学式2A或2B表示,At least one of R1 to R4 is represented by the following chemical formula 2A or 2B,

n1至n4各自独立地为1至4的整数,n1 to n4 are each independently an integer of 1 to 4,

[化学式2A][Chemical formula 2A]

Figure BDA0002736434820000031
Figure BDA0002736434820000031

[化学式2B][Chemical formula 2B]

Figure BDA0002736434820000032
Figure BDA0002736434820000032

在化学式2A和2B中,In Chemical Formulas 2A and 2B,

A1至A3中的至少一个为N,其余为CH,或者与L1、L2、L3、Ar4和Ar5中的相邻的基团结合而形成取代或未取代的环,At least one of A1 to A3 is N, the rest are CH, or combined with adjacent groups in L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring,

L1至L3彼此相同或不同,各自独立地为直接键合、取代或未取代的亚芳基、或者取代或未取代的2价的杂环基,或者与A1至A3中的相邻的基团结合而形成取代或未取代的环,L1 to L3 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, or a group adjacent to A1 to A3 combine to form substituted or unsubstituted rings,

Ar4和Ar5彼此相同或不同,各自独立地为氢、氘、取代或未取代的芳基、或者取代或未取代的杂环基,或者与A1至A3中的相邻的基团结合而形成取代或未取代的环,Ar4 and Ar5 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group, or combined with adjacent groups in A1 to A3 to form a substitution or unsubstituted rings,

Ar6为氢、氘、取代或未取代的芳基、或者取代或未取代的杂环基,a为0至5的整数,Ar6 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, a is an integer from 0 to 5,

[化学式3][Chemical formula 3]

Figure BDA0002736434820000033
Figure BDA0002736434820000033

在化学式3中,In Chemical Formula 3,

Ar1和Ar2各自为取代或未取代的芳基、或者取代或未取代的杂环基,Ar1 and Ar2 are each a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

Ar3为取代或未取代的2至4价的烷基、取代或未取代的2至4价的芳基、或者取代或未取代的2至4价的环烷基,Ar3 is a substituted or unsubstituted 2- to 4-valent alkyl group, a substituted or unsubstituted 2- to 4-valent aryl group, or a substituted or unsubstituted 2- to 4-valent cycloalkyl group,

X1至X3中的至少一个为N,其余为CH,At least one of X1 to X3 is N, the rest are CH,

L为直接键合、或者取代或未取代的亚芳基,L is a direct bond, or a substituted or unsubstituted arylene group,

n5为2至4的整数,n5 is an integer from 2 to 4,

在上述化学式1至3中,上述a和n1至n5各自独立地为2以上时,括号内的取代基彼此相同或不同。In the above Chemical Formulas 1 to 3, when the above a and n1 to n5 are each independently 2 or more, the substituents in the parentheses are the same or different from each other.

发明效果Invention effect

将根据本说明书的一实施方式的化合物分别用于空穴阻挡层、电子调节层、电子传输层、或者电子注入和传输层中的有机发光器件能够实现低驱动电压、高发光效率或长寿命。An organic light emitting device using the compound according to an embodiment of the present specification in a hole blocking layer, an electron regulation layer, an electron transport layer, or an electron injection and transport layer, respectively, can achieve low driving voltage, high luminous efficiency or long lifetime.

附图说明Description of drawings

图1、3和4图示了依次层叠有基板1、阳极2、发光层3、阴极4的有机发光器件的例子。1, 3 and 4 illustrate an example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are stacked in this order.

图2图示了依次层叠有基板1、阳极2、空穴传输层5、发光层3、空穴阻挡层或电子调节层6电子注入和传输层7、以及阴极4的有机发光器件的例子。2 illustrates an example of an organic light emitting device in which a substrate 1 , an anode 2 , a hole transport layer 5 , a light emitting layer 3 , a hole blocking layer or electron regulation layer 6 , an electron injection and transport layer 7 , and a cathode 4 are stacked in this order.

[符号说明][Symbol Description]

1:基板1: Substrate

2:阳极2: Anode

3:发光层3: Light-emitting layer

4:阴极4: Cathode

5:空穴传输层5: Hole transport layer

6:空穴阻挡层或电子调节层6: hole blocking layer or electron regulating layer

7:电子注入和传输层7: Electron injection and transport layers

具体实施方式Detailed ways

下面,对本说明书更详细地进行说明。Hereinafter, the present specification will be described in more detail.

在本说明书中,当指出某一构件位于另一个构件“上”时,其不仅包括某一构件与另一构件接触的情况,还包括两构件之间存在其它构件的情况。In this specification, when a certain member is referred to as being "on" another member, it includes not only the case where the certain member is in contact with the other member, but also the case where other members exist between the two members.

在本说明书中,当指出某一部分“包括/包含”某一构成要素时,只要没有特别相反的记载,则意味着可以进一步包括其它构成要素,而不是将其它构成要素排除。In the present specification, when it is indicated that a certain part "includes/includes" a certain constituent element, unless there is no special description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

本说明书提供一种有机发光器件,其中,包括:第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与上述第二电极之间的第一有机物层和第二有机物层,上述第一有机物层包含由上述化学式1表示的化合物,上述第二有机物层包含由上述化学式3表示的化合物。The present specification provides an organic light-emitting device comprising: a first electrode, a second electrode provided opposite to the first electrode, and a first organic layer provided between the first electrode and the second electrode and a second organic layer, wherein the first organic layer contains the compound represented by the above Chemical Formula 1, and the second organic layer contains the compound represented by the above Chemical Formula 3.

根据本说明书的一实施方式,由上述化学式1表示的化合物通过具有如上所述的核结构,从而具有可以调节三重态能量的优点,且可以表现出长寿命和高效率的特性。According to an embodiment of the present specification, the compound represented by the above-mentioned Chemical Formula 1 has the above-mentioned core structure, thereby having the advantage of being able to adjust the triplet energy and exhibiting the characteristics of long life and high efficiency.

另外,在有机发光器件的第一有机物层中包含由上述化学式1表示的化合物且包含由上述化学式3表示的化合物作为有机发光器件的第二有机物层的有机发光器件具有下述式1的能量关系。In addition, an organic light-emitting device including the compound represented by the above-mentioned Chemical Formula 1 in the first organic substance layer of the organic light-emitting device and including the compound represented by the above-mentioned Chemical Formula 3 as the second organic substance layer of the organic light-emitting device has an energy relationship of the following formula 1 .

[式1][Formula 1]

EEt>EEc E Et >E Ec

在上述式1中,EEt为包含在上述第二有机物层中的由上述化学式3表示的化合物的电子亲和势(Electron Affinity(eV)),EEc为包含在上述第一有机物层中的由上述化学式1表示的化合物的电子亲和势(eV)。In the above formula 1, E Et is the electron affinity (Electron Affinity (eV)) of the compound represented by the above chemical formula 3 contained in the above-mentioned second organic layer, and E Ec is contained in the above-mentioned first organic layer. Electron affinity (eV) of the compound represented by the above Chemical Formula 1.

由上述化学式1表示的化合物和由上述化学式3表示的化合物表现出如上所述的能量关系,因此包含由上述化学式1表示的化合物的第一有机物层适当地控制从包含由上述化学式3表示的化合物的第二有机物层传递的电子量,从而可以提高有机发光器件的效率和寿命。The compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 3 exhibit the energy relationship as described above, and therefore the first organic layer containing the compound represented by the above Chemical Formula 1 is appropriately controlled from containing the compound represented by the above Chemical Formula 3. The amount of electrons transferred from the second organic layer can improve the efficiency and lifespan of the organic light-emitting device.

在本说明书中,取代基的例示在下文中进行说明,但并不限定于此。In the present specification, examples of substituents are described below, but are not limited thereto.

上述“取代”这一用语的意思是指结合于化合物的碳原子上的氢原子被替换成其它取代基,被取代的位置只要是氢原子可以被取代的位置、即取代基可以取代的位置就没有限定,当取代2个以上时,2个以上的取代基可以彼此相同或不同。The above term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. Without limitation, when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

在本说明书中,“取代或未取代的”这一用语是指被选自氢、卤素基团、腈基、硝基、羟基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的烯基、取代或未取代的胺基、取代或未取代的芳基、以及取代或未取代的杂环基中的1个或2个以上的取代基取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代,或者不具有任何取代基。例如,“2个以上的取代基连接而成的取代基”可以为联苯基。即,联苯基可以为芳基,也可以被解释为2个苯基连接而成的取代基。In this specification, the term "substituted or unsubstituted" refers to a group selected from the group consisting of hydrogen, halogen group, nitrile group, nitro group, hydroxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group , substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted amine, substituted or unsubstituted aryl, and 1 or 2 of substituted or unsubstituted heterocyclic groups The above-mentioned substituents are substituted, or are substituted with a substituent in which two or more of the above-exemplified substituents are connected, or have no substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

在本说明书中,作为卤素基团的例子,有氟、氯、溴或碘。In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

在本说明书中,上述烷基可以为直链或支链,碳原子数没有特别限定,但优选为1至60。作为具体例,有甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基等,但并不限定于此。In this specification, the above-mentioned alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably 1 to 60. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1 -Ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl- 2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-hexyl Octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1 , 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited thereto.

在本说明书中,环烷基没有特别限定,但优选为碳原子数3至60的环烷基,具体而言,有环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等,但并不限定于此。In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, and 3-methylcyclopentyl , 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl , 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but not limited thereto.

在本说明书中,上述烷氧基可以为直链、支链或环状。烷氧基的碳原子数没有特别限定,但优选碳原子数为1至20。具体而言,可以为甲氧基、乙氧基、正丙氧基、异丙氧基、异丙基氧基、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基,正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基、对甲基苄氧基等,但并不限定于此。In the present specification, the above-mentioned alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably 1 to 20 carbon atoms. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyl oxy, benzyloxy, p-methylbenzyloxy, etc., but not limited to these.

在本说明书中,上述烯基可以为直链或支链,碳原子数没有特别限定,但优选为2至40。作为具体例,有乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯-1-基、2-苯基乙烯-1-基、2,2-二苯基乙烯-1-基、2-苯基-2-(萘-1-基)乙烯-1-基、2,2-双(二苯-1-基)乙烯-1-基、茋基、苯乙烯基等,但并不限定于此。In the present specification, the above-mentioned alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl Alkenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2 -Diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene group, styryl group, etc., but not limited to this.

在本说明书中,胺基可选自-NH2、烷基胺基、N-烷基芳基胺基、芳基胺基、N-芳基杂芳基胺基、N-烷基杂芳基胺基以及杂芳基胺基,碳原子数没有特别限定,但优选为1至30。作为胺基的具体例,有甲基胺基、二甲基胺基、乙基胺基、二乙基胺基、苯基胺基、萘基胺基、联苯基胺基、蒽基胺基、9-甲基-蒽基胺基、二苯基胺基、二甲苯基胺基、N-苯基甲苯基胺基、三苯基胺基、N-苯基联苯基胺基、N-苯基萘基胺基、N-联苯基萘基胺基、N-萘基芴基胺基、N-苯基菲基胺基、N-联苯基菲基胺基、N-苯基芴基胺基、N-苯基三联苯基胺基、N-菲基芴基胺基、N-联苯基芴基胺基等,但并不限定于此。In this specification, the amine group can be selected from -NH2 , alkylamine, N-alkylarylamine, arylamine, N-arylheteroarylamine, N-alkylheteroaryl The number of carbon atoms in the amino group and the heteroarylamine group is not particularly limited, but preferably 1 to 30. Specific examples of the amino group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, and an anthracenylamino group. , 9-methyl-anthracenylamino, diphenylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N- Phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorene amino group, N-phenylterphenylamino group, N-phenanthrenylfluorenylamino group, N-biphenylfluorenylamino group, etc., but not limited thereto.

在本说明书中,上述芳基为单环芳基时,碳原子数没有特别限定,但优选碳原子数为6至25。具体而言,作为单环芳基,可以为苯基、联苯基、三联苯基等,但并不限定于此In the present specification, when the above-mentioned aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, as the monocyclic aryl group, a phenyl group, a biphenyl group, a terphenyl group, etc. may be used, but it is not limited thereto

上述芳基为多环芳基时,碳原子数没有特别限定,但优选碳原子数为10至60。具体而言,作为多环芳基,可以为萘基、蒽基、菲基、芘基、苝基、

Figure BDA0002736434820000072
基、芴基等,但并不限定于此。When the above-mentioned aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 10 to 60 carbon atoms. Specifically, as the polycyclic aryl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylene group, a
Figure BDA0002736434820000072
group, fluorene group, etc., but not limited to this.

在本说明书中,上述芴基可以被取代,相邻的取代基可以彼此结合而形成环。In the present specification, the above-mentioned fluorenyl group may be substituted, and adjacent substituent groups may be bonded to each other to form a ring.

在上述芴基被取代的情况下,可以成为

Figure BDA0002736434820000071
等,但并不限定于此。When the above-mentioned fluorenyl group is substituted, it can be
Figure BDA0002736434820000071
etc., but not limited to this.

在本说明书中,杂环基包含1个以上非碳原子即杂原子,具体而言,上述杂原子可以包含1个以上的选自O、N、Se和S等中的原子。杂环基的碳原子数没有特别限定,但优选碳原子数为2至60。作为杂环基的例子,有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、

Figure BDA0002736434820000073
唑基、
Figure BDA0002736434820000074
二唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并
Figure BDA0002736434820000081
唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲啶基(phenanthridine)、菲咯啉基(phenanthroline)、异
Figure BDA0002736434820000082
唑基、噻二唑基、二苯并呋喃基、二苯并噻咯基、吩噻
Figure BDA0002736434820000083
基(phenoxathiine)、吩
Figure BDA0002736434820000084
嗪基(phenoxazine)、吩噻嗪基(phenothiazine)、二氢茚并咔唑基、螺芴呫吨基和螺芴噻吨基等,但并不限定于此。在本说明书中,在相邻的基团彼此结合而形成的取代或未取代的环中,“环”是指取代或未取代的烃环、或者取代或未取代的杂环。In the present specification, the heterocyclic group contains one or more non-carbon atoms, that is, a heteroatom, and specifically, the heteroatom may contain one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but preferably 2 to 60 carbon atoms. As examples of heterocyclic groups, there are thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
Figure BDA0002736434820000073
azolyl,
Figure BDA0002736434820000074
oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridine, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazine base, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoyl
Figure BDA0002736434820000081
azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthridine, phenanthroline, different
Figure BDA0002736434820000082
azolyl, thiadiazolyl, dibenzofuranyl, dibenzothirolyl, phenothia
Figure BDA0002736434820000083
base (phenoxathiine), pheno
Figure BDA0002736434820000084
phenoxazine, phenothiazine, dihydroindenocarbazolyl, spirofluorenyl xanthyl, spirofluorenyl thioxanthyl and the like, but are not limited thereto. In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

在本说明书中,烃环可以为芳香族烃、脂肪族烃、或者芳香族烃与脂肪族烃的稠环,除了不是上述1价以外,可以选自上述环烷基或芳基的例示。In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon, an aliphatic hydrocarbon, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from the examples of the above-mentioned cycloalkyl group or aryl group except that it is not the above-mentioned monovalent group.

在本说明书中,芳香族烃环可以是单环或多环,除了不是1价以外,可以选自上述芳基的例示。In the present specification, the aromatic hydrocarbon ring may be a monocyclic ring or a polycyclic ring, and may be selected from the examples of the above-mentioned aryl group except that it is not monovalent.

在本说明书中,杂环包含1个以上非碳原子即杂原子,具体而言,上述杂原子可以包含1个以上的选自O、N、Se和S等中的原子。上述杂环可以为单环或多环,可以为芳香族、脂肪族、或者芳香族与脂肪族的稠环,除了不是1价以外,可以选自上述杂环基的例示。In the present specification, the heterocycle contains one or more non-carbon atoms, that is, a heteroatom, and specifically, the above-mentioned heteroatom may contain one or more atoms selected from O, N, Se, S, and the like. The above-mentioned heterocyclic ring may be monocyclic or polycyclic, aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the examples of the above-mentioned heterocyclic group except that it is not monovalent.

在本说明书中,亚芳基是指芳基中有两个结合位置的基团,即2价基团。它们除了各自为2价基团以外,可以适用上述芳基的说明。In the present specification, an arylene group refers to a group having two bonding positions in an aryl group, that is, a divalent group. Except that they are each a divalent group, the above-mentioned description of the aryl group can be applied.

在本说明书中,2价的杂环基是指杂环基中有两个结合位置的基团,即2价基团。它们除了各自为2价基团以外,可以适用上述杂环基的说明。In the present specification, a divalent heterocyclic group refers to a group having two bonding positions in the heterocyclic group, that is, a divalent group. Except that they are each a divalent group, the description of the above-mentioned heterocyclic group can be applied.

在本说明书中,2至4价的烷基是指烷基中有两个至四个结合位置的基团,即2价至4价基团。它们除了各自为2至4价基团以外,可以适用上述烷基的说明。In the present specification, a 2- to 4-valent alkyl group refers to a group having two to four bonding positions in the alkyl group, that is, a 2- to 4-valent group. Except that they are each a 2- to 4-valent group, the above description of the alkyl group can be applied.

在本说明书中,2至4价的芳基是指芳基中有两个至四个结合位置的基团,即2价至4价基团。它们除了各自为2至4价基团以外,可以适用上述芳基的说明。In the present specification, a 2- to 4-valent aryl group refers to a group having two to four bonding positions in the aryl group, that is, a 2- to 4-valent group. Except that they are each a 2- to 4-valent group, the above description of the aryl group can be applied.

在本说明书中,2至4价的环烷基是指环烷基中有两个至四个结合位置的基团,即2价至4价基团。它们除了各自为2至4价基团以外,可以适用上述环烷基的说明。In the present specification, a 2- to 4-valent cycloalkyl group refers to a group having two to four bonding positions in the cycloalkyl group, that is, a 2- to 4-valent group. Except that they are each a 2- to 4-valent group, the above description of the cycloalkyl group can be applied.

根据本说明书的一实施方式,上述R1至R4彼此相同或不同,各自独立地为氢、氘、卤素基团、氰基、硝基、取代或未取代的烷基、取代或未取代的卤代烷基、取代或未取代的卤代烷氧基、取代或未取代的环烷基、取代或未取代的烯基、取代或未取代的芳基、或者取代或未取代的杂环基,或者相邻的基团彼此结合而形成取代或未取代的环。According to one embodiment of the present specification, the above-mentioned R1 to R4 are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted haloalkyl , substituted or unsubstituted haloalkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, or adjacent groups The groups combine with each other to form substituted or unsubstituted rings.

根据本说明书的一实施方式,上述R1至R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、或者取代或未取代的杂环基。According to an embodiment of the present specification, the above R1 to R4 are the same or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl.

根据本说明书的一实施方式,上述R1至R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的芳基、或者取代或未取代的杂环基。According to one embodiment of the present specification, the above-mentioned R1 to R4 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group.

根据本说明书的一实施方式,上述R1至R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数6至60的芳基、或者取代或未取代的碳原子数2至60的杂环基。According to one embodiment of the present specification, the above-mentioned R1 to R4 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group with 6 to 60 carbon atoms, or a substituted or unsubstituted carbon number with 2 to 60 heterocyclyl.

根据本说明书的一实施方式,上述R1至R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数6至30的芳基、或者取代或未取代的碳原子数2至30的杂环基。According to an embodiment of the present specification, the above R1 to R4 are the same or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number with 2 to 30 heterocyclyl.

根据本说明书的一实施方式,上述R1至R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数6至15的芳基、或者取代或未取代的碳原子数2至15的杂环基。According to one embodiment of the present specification, the above-mentioned R1 to R4 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group with 6 to 15 carbon atoms, or a substituted or unsubstituted carbon number with 2 to 15 heterocyclyl.

根据本说明书的一实施方式,上述R1至R4中的不是下述化学式2A或2B的基团为氢或氘。According to an embodiment of the present specification, a group other than the following chemical formula 2A or 2B among the above R1 to R4 is hydrogen or deuterium.

根据本说明书的一实施方式,上述R1至R4中的不是下述化学式2A或2B的基团中的至少一个为烷基、芳基、或被烷基取代的芳基,其余为氢或氘。According to an embodiment of the present specification, at least one of the above R1 to R4 groups other than the following chemical formula 2A or 2B is an alkyl group, an aryl group, or an aryl group substituted by an alkyl group, and the rest are hydrogen or deuterium.

根据本说明书的一实施方式,上述R1至R4中的不是下述化学式A或2B的基团中的至少一个为甲基;正丁基;叔丁基;被甲基、或叔丁基取代或未取代的苯基;萘基;或者被甲基取代的芴基,其余为氢或氘。According to an embodiment of the present specification, at least one of the groups in the above R1 to R4 that is not the following chemical formula A or 2B is methyl; n-butyl; tert-butyl; substituted by methyl, or tert-butyl or Unsubstituted phenyl; naphthyl; or fluorenyl substituted with methyl, the remainder being hydrogen or deuterium.

根据本说明书的一实施方式,上述n1为2,上述相邻的R1彼此结合而形成取代或未取代的环。According to one embodiment of the present specification, the n1 is 2, and the adjacent R1s are bonded to each other to form a substituted or unsubstituted ring.

根据本说明书的一实施方式,上述n1为2,上述相邻的R1彼此结合而形成取代或未取代的烃环。According to one embodiment of the present specification, the n1 is 2, and the adjacent R1s are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

根据本说明书的一实施方式,上述n1为2,上述相邻的R1彼此结合而形成取代或未取代的芳香族烃环。According to one embodiment of the present specification, the n1 is 2, and the adjacent R1s are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

根据本说明书的一实施方式,上述n1为2,上述相邻的R1彼此结合而形成取代或未取代的苯环。According to one embodiment of the present specification, the n1 is 2, and the adjacent R1s are bonded to each other to form a substituted or unsubstituted benzene ring.

根据本说明书的一实施方式,上述n1为2,上述相邻的R1彼此结合而形成苯环。According to one embodiment of the present specification, the n1 is 2, and the adjacent R1s are bonded to each other to form a benzene ring.

根据本说明书的一实施方式,上述n2为2,上述相邻的R2彼此结合而形成取代或未取代的环。According to one embodiment of the present specification, the n2 is 2, and the adjacent R2s are bonded to each other to form a substituted or unsubstituted ring.

根据本说明书的一实施方式,上述n2为2,上述相邻的R2彼此结合而形成取代或未取代的烃环。According to one embodiment of the present specification, the n2 is 2, and the adjacent R2s are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

根据本说明书的一实施方式,上述n2为2,上述相邻的R2彼此结合而形成取代或未取代的芳香族烃环。According to one embodiment of the present specification, the n2 is 2, and the adjacent R2s are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

根据本说明书的一实施方式,上述n2为2,上述相邻的R2彼此结合而形成取代或未取代的苯环。According to one embodiment of the present specification, the n2 is 2, and the adjacent R2s are bonded to each other to form a substituted or unsubstituted benzene ring.

根据本说明书的一实施方式,上述n2为2,上述相邻的R2彼此结合而形成苯环。According to one embodiment of the present specification, the n2 is 2, and the adjacent R2s are bonded to each other to form a benzene ring.

根据本说明书的一实施方式,上述n1为2,上述相邻的R1彼此结合而形成取代或未取代的环,上述n2为2,上述相邻的R2彼此结合而形成苯环。According to an embodiment of the present specification, the n1 is 2, the adjacent R1s are bonded to each other to form a substituted or unsubstituted ring, the n2 is 2, and the adjacent R2s are bonded to each other to form a benzene ring.

根据本说明书的一实施方式,上述R1至R4中的至少一个由下述化学式2A或2B表示。According to an embodiment of the present specification, at least one of the above-mentioned R1 to R4 is represented by the following chemical formula 2A or 2B.

[化学式2A][Chemical formula 2A]

Figure BDA0002736434820000101
Figure BDA0002736434820000101

[化学式2B][Chemical formula 2B]

Figure BDA0002736434820000111
Figure BDA0002736434820000111

在化学式2A和2B中,L1至L3、Ar4至Ar6、A1至A3和a的定义与上述的定义相同。In Chemical Formulas 2A and 2B, the definitions of L1 to L3, Ar4 to Ar6, A1 to A3 and a are the same as those described above.

根据本说明书的一实施方式,上述R1至R4中的一个由上述化学式2A或2B表示。According to an embodiment of the present specification, one of the above-mentioned R1 to R4 is represented by the above-mentioned Chemical Formula 2A or 2B.

根据本说明书的一实施方式,上述R1至R4中的2个由上述化学式2A或2B表示。According to an embodiment of the present specification, two of the above-mentioned R1 to R4 are represented by the above-mentioned chemical formula 2A or 2B.

根据本说明书的一实施方式,上述R2中的一个和上述R3中的一个由上述化学式2A或2B表示。According to an embodiment of the present specification, one of the above-mentioned R2 and one of the above-mentioned R3 is represented by the above-mentioned Chemical Formula 2A or 2B.

根据本说明书的一实施方式,上述A1至A3中的至少一个为N,其余为CH,或者与上述L1、L2、L3、Ar4和Ar5中的相邻的基团结合而形成取代或未取代的环。According to an embodiment of the present specification, at least one of the above A1 to A3 is N, and the rest are CH, or combined with adjacent groups in the above L1, L2, L3, Ar4 and Ar5 to form substituted or unsubstituted ring.

根据本说明书的一实施方式,上述L1至L3彼此相同或不同,各自独立地为直接键合、取代或未取代的亚芳基、或者取代或未取代的杂环基,或者与上述A1至A3中的相邻的基团结合而形成取代或未取代的环。According to one embodiment of the present specification, the above-mentioned L1 to L3 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group, or the same as the above-mentioned A1 to A3 Adjacent groups in it combine to form a substituted or unsubstituted ring.

根据本说明书的一实施方式,上述L1至L3彼此相同或不同,各自独立地为直接键合、取代或未取代的碳原子数6至60的亚芳基、或者取代或未取代的碳原子数2至60的杂环基。According to one embodiment of the present specification, the above L1 to L3 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted carbon atomic group. 2 to 60 heterocyclyl.

根据本说明书的一实施方式,上述L1至L3彼此相同或不同,各自独立地为直接键合、取代或未取代的碳原子数6至30的亚芳基、或者取代或未取代的碳原子数2至30的杂环基。According to an embodiment of the present specification, the above L1 to L3 are the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon atomic group 2 to 30 heterocyclyl.

根据本说明书的一实施方式,上述L1至L3彼此相同或不同,各自独立地为直接键合、取代或未取代的碳原子数6至15的亚芳基、或者取代或未取代的碳原子数2至15的杂环基。According to an embodiment of the present specification, the above L1 to L3 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted carbon atomic group. 2 to 15 heterocyclyl.

根据本说明书的一实施方式,上述L1至L3彼此相同或不同,各自独立地为直接键合、亚苯基、或亚联苯基。According to one embodiment of the present specification, the above-mentioned L1 to L3 are the same as or different from each other, and each independently is a direct bond, a phenylene group, or a biphenylene group.

根据本说明书的一实施方式,上述L3为直接键合、亚苯基、亚联苯基、亚萘基、2价的噻吩基、2价的呋喃基、2价的二苯并噻吩基、2价的二苯并呋喃基、被芳基或烷基芳基取代或未取代的2价的咔唑基、被芳基或烷基芳基取代或未取代的2价的苯并咔唑基、被烷基取代或未取代的2价的二苯并噻咯基、2价的吩噻

Figure BDA0002736434820000121
基、2价的吩
Figure BDA0002736434820000122
嗪基、2价的吩噻嗪基、2价的吡啶基、被烷基取代或未取代的2价的二氢茚并咔唑基、二苯并噻吩与苯基连接而成的2价的基团、或者咔唑与苯基连接而成的2价的基团。According to one embodiment of the present specification, the above-mentioned L3 is a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a divalent thienyl group, a divalent furyl group, a divalent dibenzothienyl group, a 2 valent dibenzofuranyl, aryl or alkylaryl substituted or unsubstituted divalent carbazolyl, aryl or alkylaryl substituted or unsubstituted divalent benzocarbazolyl, Alkyl-substituted or unsubstituted bivalent dibenzothirolyl, bivalent phenothia
Figure BDA0002736434820000121
base, divalent phene
Figure BDA0002736434820000122
Azinyl, divalent phenothiazinyl, divalent pyridyl, divalent dihydroindenocarbazolyl substituted or unsubstituted by alkyl, dibenzothiophene and phenyl linked group, or a divalent group in which carbazole and a phenyl group are linked.

根据本说明书的一实施方式,上述L3为直接键合、亚苯基、亚联苯基、亚萘基、2价的噻吩基、2价的呋喃基、2价的二苯并噻吩基、2价的二苯并呋喃基、被苯基或甲基苯基取代或未取代的2价的咔唑基、被苯基或甲基苯基取代或未取代的2价的苯并咔唑基、被甲基取代或未取代的2价的二苯并噻咯基、2价的吩噻

Figure BDA0002736434820000123
基、2价的吩
Figure BDA0002736434820000124
嗪基、2价的吩噻嗪基、2价的吡啶基、被甲基取代或未取代的2价的二氢茚并咔唑基、二苯并噻吩与苯基连接而成的2价的基团、或者咔唑与苯基连接而成的2价的基团。According to one embodiment of the present specification, the above-mentioned L3 is a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a divalent thienyl group, a divalent furyl group, a divalent dibenzothienyl group, a 2 valent dibenzofuranyl, phenyl or methylphenyl substituted or unsubstituted bivalent carbazolyl, phenyl or methylphenyl substituted or unsubstituted bivalent benzocarbazolyl, Methyl-substituted or unsubstituted bivalent dibenzothirolyl, bivalent phenothia
Figure BDA0002736434820000123
base, divalent phene
Figure BDA0002736434820000124
Azinyl, divalent phenothiazinyl, divalent pyridyl, divalent dihydroindenocarbazolyl substituted or unsubstituted by methyl, dibenzothiophene and phenyl linked group, or a divalent group in which carbazole and a phenyl group are linked.

根据本说明书的一实施方式,上述Ar4和Ar5彼此相同或不同,各自独立地为氢、氘、取代或未取代的芳基、或者取代或未取代的杂环基,或者与A1至A3中的相邻的基团结合而形成取代或未取代的环。According to an embodiment of the present specification, the above-mentioned Ar4 and Ar5 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, or the same as that of A1 to A3. Adjacent groups combine to form substituted or unsubstituted rings.

根据本说明书的一实施方式,上述Ar4和Ar5彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数6至60的芳基、或者取代或未取代的碳原子数2至60的杂环基,或者与上述A1至A3中的相邻的基团结合而形成取代或未取代的碳原子数6至60的芳香族烃环。According to an embodiment of the present specification, the above-mentioned Ar4 and Ar5 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group with 6 to 60 carbon atoms, or a substituted or unsubstituted aryl group with 2 carbon atoms A heterocyclic group of 60 to 60, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms is formed by combining with the adjacent groups in the above-mentioned A1 to A3.

根据本说明书的一实施方式,上述Ar4和Ar5彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数6至30的芳基、或者取代或未取代的碳原子数2至30的杂环基,或者与上述A1至A3中的相邻的基团结合而形成取代或未取代的苯环。According to one embodiment of the present specification, the above-mentioned Ar4 and Ar5 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number with 2 A heterocyclic group of to 30, or a substituted or unsubstituted benzene ring is formed by combining with the adjacent group in the above-mentioned A1 to A3.

根据本说明书的一实施方式,上述Ar4和Ar5彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数6至20的芳基、或者取代或未取代的碳原子数2至15的杂环基,或者与上述A1至A3中的相邻的基团结合而形成取代或未取代的苯环。According to one embodiment of the present specification, the above-mentioned Ar4 and Ar5 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group with 6 to 20 carbon atoms, or a substituted or unsubstituted aryl group with 2 carbon atoms A heterocyclic group to 15, or a substituted or unsubstituted benzene ring is formed by combining with the adjacent group in the above-mentioned A1 to A3.

根据本说明书的一实施方式,上述Ar4和Ar5彼此相同或不同,各自独立地为取代或未取代的碳原子数6至20的芳基、或者取代或未取代的碳原子数2至15的杂环基,或者与上述A1至A3中的相邻的基团结合而形成取代或未取代的苯环。According to one embodiment of the present specification, the above-mentioned Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms. A cyclic group, or a substituted or unsubstituted benzene ring is formed by combining with the adjacent groups in the above-mentioned A1 to A3.

根据本说明书的一实施方式,上述Ar4和Ar5彼此相同或不同,各自独立地为被CN、烷基、烷氧基、卤代烷基、卤代烷氧基、烷基甲硅烷基、芳基、烷基芳基或杂环基取代或未取代的碳原子数6至20的芳基;或者被CN、烷基、烷氧基、卤代烷基、卤代烷氧基、烷基甲硅烷基、芳基或杂环基取代或未取代的碳原子数2至15的杂环基,或者与上述A1至A3中的相邻的基团结合而形成苯环。According to one embodiment of the present specification, the above Ar4 and Ar5 are the same as or different from each other, and each independently is represented by CN, alkyl, alkoxy, haloalkyl, haloalkoxy, alkylsilyl, aryl, alkylaryl aryl group with 6 to 20 carbon atoms substituted or unsubstituted by a radical or a heterocyclyl group; or by CN, alkyl, alkoxy, haloalkyl, haloalkoxy, alkylsilyl, aryl or heterocyclyl A substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or a benzene ring is formed by combining with the adjacent groups in the above-mentioned A1 to A3.

根据本说明书的一实施方式,上述Ar4和Ar5彼此相同或不同,各自独立地为选自苯基、联苯基、三联苯基、萘基、芴基、三亚苯基、菲基、荧蒽基、萉基、咔唑基、苯并咔唑基、二苯并呋喃基、二苯并噻吩基、二苯并噻咯基、吩噻

Figure BDA0002736434820000132
基、吩
Figure BDA0002736434820000133
嗪基、吩噻嗪基、吡啶基、二氢茚并咔唑基、芳基甲硅烷基、烷基甲硅烷基、螺芴呫吨基和螺芴噻吨基中的一个或2个以上的基团连接而成的基团,它们可以被CN、烷基、烷氧基、卤代烷基、卤代烷氧基、烷基甲硅烷基、芳基、烷基芳基或杂环基取代。在这里,作为取代基,杂环基可以为咔唑基、苯并咔唑基、二苯并呋喃基、二苯并噻吩基、二苯并噻咯基、吩噻
Figure BDA0002736434820000134
基、吩
Figure BDA0002736434820000135
嗪基、吩噻嗪基、吡啶基、或二氢茚并咔唑基,作为取代基,芳基可以为苯基、联苯基、萘基、或三亚苯基。此外,上述烷基可以为甲基或叔丁基,上述烷氧基可以为甲氧基,上述卤代烷基可以为三氟甲基,上述卤代烷氧基可以为三氟甲氧基,上述烷基甲硅烷基可以为甲基甲硅烷基。According to an embodiment of the present specification, the above-mentioned Ar4 and Ar5 are the same or different from each other, and each independently is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, triphenylene, phenanthryl, and fluoranthenyl , Acetyl, Carbazolyl, Benzocarbazolyl, Dibenzofuranyl, Dibenzothienyl, Dibenzothirolyl, Phenothiene
Figure BDA0002736434820000132
base, phen
Figure BDA0002736434820000133
One or two or more of oxazinyl, phenothiazinyl, pyridyl, dihydroindenocarbazolyl, arylsilyl, alkylsilyl, spirofluorenyl xanthyl and spirofluorenyl thioxanthyl A group formed by connecting groups, which may be substituted by CN, alkyl, alkoxy, haloalkyl, haloalkoxy, alkylsilyl, aryl, alkylaryl or heterocyclyl. Here, as a substituent, the heterocyclic group may be carbazolyl, benzocarbazolyl, dibenzofuranyl, dibenzothienyl, dibenzothirolyl, phenothia
Figure BDA0002736434820000134
base, phen
Figure BDA0002736434820000135
oxazinyl, phenothiazinyl, pyridyl, or dihydroindenocarbazolyl, and as a substituent, the aryl group may be phenyl, biphenyl, naphthyl, or triphenylene. In addition, the above-mentioned alkyl group may be methyl group or tert-butyl group, the above-mentioned alkoxy group may be methoxy group, the above-mentioned haloalkyl group may be trifluoromethyl group, the above-mentioned haloalkoxy group may be trifluoromethoxy group, the above-mentioned alkylmethyl group may be The silyl group may be a methylsilyl group.

在本说明书的一实施方式中,上述化学式1由下述化学式1-1至化学式1-5中的任一个表示。In one embodiment of the present specification, the above-mentioned Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-5.

[化学式1-1][Chemical formula 1-1]

Figure BDA0002736434820000131
Figure BDA0002736434820000131

[化学式1-2][Chemical formula 1-2]

Figure BDA0002736434820000141
Figure BDA0002736434820000141

[化学式1-3][Chemical formula 1-3]

Figure BDA0002736434820000142
Figure BDA0002736434820000142

[化学式1-4][Chemical formula 1-4]

Figure BDA0002736434820000143
Figure BDA0002736434820000143

[化学式1-5][Chemical formula 1-5]

Figure BDA0002736434820000151
Figure BDA0002736434820000151

在上述化学式1-1至化学式1-5中,In the above Chemical Formula 1-1 to Chemical Formula 1-5,

X、R1至R4、L1至L3、A1至A3、Ar4、Ar5和n1至n4的定义与上述化学式1和2A中的定义相同,L1'、L2'、L3'、A1'、A2'、A3'、Ar4'和Ar5'各自与上述L1、L2、L3、A1、A2、A3、Ar4和Ar5的定义相同。The definitions of X, R1 to R4, L1 to L3, A1 to A3, Ar4, Ar5 and n1 to n4 are the same as those in the above Chemical Formulas 1 and 2A, L1', L2', L3', A1', A2', A3 ', Ar4' and Ar5' are each the same as defined above for L1, L2, L3, A1, A2, A3, Ar4 and Ar5.

在本说明书的一实施方式中,上述化学式2A的A1至A3中的2个为N。In one embodiment of the present specification, two of A1 to A3 in the above-mentioned Chemical Formula 2A are N.

在本说明书的一实施方式中,上述化学式2A的A1至A3为N。In one embodiment of the present specification, A1 to A3 of the above Chemical Formula 2A are N.

在本说明书的一实施方式中,上述化学式2A可以选自下述结构式。In one embodiment of the present specification, the above-mentioned chemical formula 2A may be selected from the following structural formulae.

Figure BDA0002736434820000161
Figure BDA0002736434820000161

在上述结构式中,L1至L3、Ar4和Ar5的定义与上述的定义相同。In the above structural formula, L1 to L3, Ar4 and Ar5 have the same definitions as above.

在本说明书的一实施方式中,上述化学式2B的Ar6为氢。In one embodiment of the present specification, Ar6 in the above Chemical Formula 2B is hydrogen.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为取代或未取代的芳基、或者取代或未取代的杂环基。In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为取代或未取代的碳原子数6至60的芳基、或者取代或未取代的碳原子数2至60的杂环基。In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 60 carbon atoms. Heterocyclyl.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为取代或未取代的碳原子数6至30的芳基、或者取代或未取代的碳原子数2至30的杂环基。In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms. Heterocyclyl.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为取代或未取代的碳原子数6至15的芳基、或者取代或未取代的碳原子数2至15的杂环基。In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 15 carbon atoms. Heterocyclyl.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为取代或未取代的碳原子数6至15的芳基、或者取代或未取代的碳原子数2至15的杂环基。In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 15 carbon atoms. Heterocyclyl.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为被氘、CN、卤素基团、烷基、卤代烷基、烷氧基、或芳基取代或未取代的芳基;或者杂环基。In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same or different from each other, and each independently is an aryl substituted or unsubstituted by deuterium, CN, a halogen group, an alkyl group, a haloalkyl group, an alkoxy group, or an aryl group. group; or a heterocyclic group.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为被氘、CN、卤素基团、烷基、卤代烷基、烷氧基、或芳基取代或未取代的苯基;联苯基;萘基;吡啶基;或者噻吩基。In one embodiment of the present specification, the above-mentioned Ar1 and Ar2 are the same or different from each other, and each independently is a benzene substituted or unsubstituted by deuterium, CN, halogen group, alkyl group, haloalkyl group, alkoxy group, or aryl group biphenyl; naphthyl; pyridyl; or thienyl.

在本说明书的一实施方式中,上述Ar1和Ar2彼此相同或不同,各自独立地为被氘、CN、F、三氟甲基、甲基、叔丁基、甲氧基、或苯基取代或未取代的苯基;联苯基;萘基;吡啶基;或者噻吩基。In one embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, each independently substituted by deuterium, CN, F, trifluoromethyl, methyl, tert-butyl, methoxy, or phenyl, or Unsubstituted phenyl; biphenyl; naphthyl; pyridyl; or thienyl.

在本说明书的一实施方式中,上述n5为2。In one Embodiment of this specification, the said n5 is 2.

在本说明书的一实施方式中,上述n5为2,上述括号内的取代基彼此相同或不同。In one Embodiment of this specification, the said n5 is 2, and the substituents in the said parentheses are the same as or different from each other.

在本说明书的一实施方式中,上述Ar3为取代或未取代的2价的芳基、或者取代或未取代的2价的环烷基。In one embodiment of the present specification, the above-mentioned Ar3 is a substituted or unsubstituted divalent aryl group, or a substituted or unsubstituted divalent cycloalkyl group.

在本说明书的一实施方式中,上述Ar3为取代或未取代的碳原子数6至60的2价的芳基、或者取代或未取代的碳原子数3至60的2价的环烷基。In one embodiment of the present specification, Ar3 is a substituted or unsubstituted divalent aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent cycloalkyl group having 3 to 60 carbon atoms.

在本说明书的一实施方式中,上述Ar3为取代或未取代的碳原子数6至30的2价的芳基、或者取代或未取代的碳原子数3至30的2价的环烷基。In one embodiment of the present specification, Ar3 is a substituted or unsubstituted divalent aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent cycloalkyl group having 3 to 30 carbon atoms.

在本说明书的一实施方式中,上述Ar3为取代或未取代的碳原子数6至15的2价的芳基、或者取代或未取代的碳原子数3至15的2价的环烷基。In one embodiment of the present specification, Ar3 is a substituted or unsubstituted divalent aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted divalent cycloalkyl group having 3 to 15 carbon atoms.

在本说明书的一实施方式中,上述Ar3为取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的2价的菲基、或者取代或未取代的2价的环烷基。In one embodiment of the present specification, the above-mentioned Ar3 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent phenanthrenyl group, or a substituted or unsubstituted divalent Cycloalkyl.

在本说明书的一实施方式中,上述Ar3为取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的2价的菲基、或者取代或未取代的亚环己基。In one embodiment of the present specification, the above-mentioned Ar3 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent phenanthrene group, or a substituted or unsubstituted cyclohexylene group .

在本说明书的一实施方式中,上述Ar3为亚苯基、亚萘基、2价的菲基、或亚环己基。In one Embodiment of this specification, said Ar3 is a phenylene group, a naphthylene group, a divalent phenanthrene group, or a cyclohexylene group.

在本说明书的一实施方式中,上述Ar3为亚萘基、2价的菲基、或亚环己基。In one embodiment of the present specification, the above-mentioned Ar3 is a naphthylene group, a divalent phenanthrene group, or a cyclohexylene group.

在本说明书的一实施方式中,上述Ar3为取代或未取代的2价的三环以上的芳基、或者取代或未取代的2价的环烷基。In one embodiment of the present specification, Ar3 is a substituted or unsubstituted divalent tricyclic or more aryl group, or a substituted or unsubstituted divalent cycloalkyl group.

在本说明书的一实施方式中,上述Ar3为2价的三环以上的芳基、或者2价的环烷基。In one Embodiment of this specification, the said Ar3 is a divalent tricyclic aryl group or more, or a divalent cycloalkyl group.

在本说明书的一实施方式中,上述Ar3为2价的菲基、或亚环己基。In one embodiment of the present specification, the above-mentioned Ar3 is a divalent phenanthrene group or a cyclohexylene group.

在本说明书的一实施方式中,上述Ar3为取代或未取代的2价的烷基。In one Embodiment of this specification, the said Ar3 is a substituted or unsubstituted divalent alkyl group.

在本说明书的一实施方式中,上述Ar3为取代或未取代的碳原子数1至60的2价的烷基。In one embodiment of the present specification, the above-mentioned Ar3 is a substituted or unsubstituted divalent alkyl group having 1 to 60 carbon atoms.

在本说明书的一实施方式中,上述Ar3为取代或未取代的碳原子数1至30的2价的烷基。In one embodiment of the present specification, the above-mentioned Ar3 is a substituted or unsubstituted divalent alkyl group having 1 to 30 carbon atoms.

在本说明书的一实施方式中,上述Ar3为取代或未取代的碳原子数1至15的2价的烷基。In one embodiment of the present specification, the above-mentioned Ar3 is a substituted or unsubstituted divalent alkyl group having 1 to 15 carbon atoms.

在本说明书的一实施方式中,上述Ar3为被芳基取代或未取代的2价的烷基。In one embodiment of the present specification, the above-mentioned Ar3 is a divalent alkyl group substituted or unsubstituted with an aryl group.

在本说明书的一实施方式中,上述Ar3为被苯基取代或未取代的2价的烷基。In one embodiment of the present specification, the above-mentioned Ar3 is a divalent alkyl group substituted or unsubstituted with a phenyl group.

在本说明书的一实施方式中,上述Ar3为被苯基取代或未取代的亚甲基。In one embodiment of the present specification, the above-mentioned Ar3 is a methylene group substituted or unsubstituted with a phenyl group.

在本说明书的一实施方式中,上述X1至X3中的至少一个为N,其余为CH。In one embodiment of the present specification, at least one of the above-mentioned X1 to X3 is N, and the rest are CH.

在本说明书的一实施方式中,上述X1为N,其余为CH。In one embodiment of the present specification, the above-mentioned X1 is N, and the rest are CH.

在本说明书的一实施方式中,上述X2为N,其余为CH。In one embodiment of the present specification, the above-mentioned X2 is N, and the rest are CH.

在本说明书的一实施方式中,上述X3为N,其余为CH。In one embodiment of the present specification, the above-mentioned X3 is N, and the rest are CH.

在本说明书的一实施方式中,上述X1和X2为N,其余为CH。In one embodiment of the present specification, the above-mentioned X1 and X2 are N, and the rest are CH.

在本说明书的一实施方式中,上述X1和X3为N,其余为CH。In one embodiment of the present specification, the above-mentioned X1 and X3 are N, and the rest are CH.

在本说明书的一实施方式中,上述X2和X3为N,其余为CH。In one embodiment of the present specification, the above-mentioned X2 and X3 are N, and the rest are CH.

在本说明书的一实施方式中,上述X1至X3为N。In one embodiment of this specification, the above-mentioned X1 to X3 are N.

在本说明书的一实施方式中,上述L为直接键合。In one Embodiment of this specification, the said L is a direct bond.

在本说明书的一实施方式中,上述L为取代或未取代的亚芳基。In one Embodiment of this specification, the said L is a substituted or unsubstituted arylene group.

在本说明书的一实施方式中,上述L为取代或未取代的碳原子数6至60的亚芳基。In one embodiment of the present specification, the above-mentioned L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

在本说明书的一实施方式中,上述L为取代或未取代的碳原子数6至30的亚芳基。In one embodiment of the present specification, the above-mentioned L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

在本说明书的一实施方式中,上述L为取代或未取代的碳原子数6至15的亚芳基。In one embodiment of the present specification, the above-mentioned L is a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

在本说明书的一实施方式中,上述L为取代或未取代的亚苯基。In one Embodiment of this specification, the said L is a substituted or unsubstituted phenylene group.

在本说明书的一实施方式中,上述L为亚苯基。In one Embodiment of this specification, the said L is a phenylene group.

另外,在本说明书的一实施方式中,上述化学式1选自下述结构式。Moreover, in one Embodiment of this specification, the said chemical formula 1 is selected from the following structural formula.

Figure BDA0002736434820000191
Figure BDA0002736434820000191

Figure BDA0002736434820000201
Figure BDA0002736434820000201

Figure BDA0002736434820000211
Figure BDA0002736434820000211

Figure BDA0002736434820000221
Figure BDA0002736434820000221

Figure BDA0002736434820000231
Figure BDA0002736434820000231

Figure BDA0002736434820000241
Figure BDA0002736434820000241

Figure BDA0002736434820000251
Figure BDA0002736434820000251

Figure BDA0002736434820000261
Figure BDA0002736434820000261

Figure BDA0002736434820000271
Figure BDA0002736434820000271

Figure BDA0002736434820000281
Figure BDA0002736434820000281

Figure BDA0002736434820000291
Figure BDA0002736434820000291

Figure BDA0002736434820000301
Figure BDA0002736434820000301

Figure BDA0002736434820000311
Figure BDA0002736434820000311

Figure BDA0002736434820000321
Figure BDA0002736434820000321

Figure BDA0002736434820000331
Figure BDA0002736434820000331

Figure BDA0002736434820000341
Figure BDA0002736434820000341

Figure BDA0002736434820000351
Figure BDA0002736434820000351

Figure BDA0002736434820000361
Figure BDA0002736434820000361

Figure BDA0002736434820000371
Figure BDA0002736434820000371

Figure BDA0002736434820000381
Figure BDA0002736434820000381

Figure BDA0002736434820000391
Figure BDA0002736434820000391

Figure BDA0002736434820000401
Figure BDA0002736434820000401

Figure BDA0002736434820000411
Figure BDA0002736434820000411

Figure BDA0002736434820000421
Figure BDA0002736434820000421

Figure BDA0002736434820000431
Figure BDA0002736434820000431

Figure BDA0002736434820000441
Figure BDA0002736434820000441

Figure BDA0002736434820000451
Figure BDA0002736434820000451

Figure BDA0002736434820000461
Figure BDA0002736434820000461

Figure BDA0002736434820000471
Figure BDA0002736434820000471

Figure BDA0002736434820000481
Figure BDA0002736434820000481

Figure BDA0002736434820000491
Figure BDA0002736434820000491

Figure BDA0002736434820000501
Figure BDA0002736434820000501

Figure BDA0002736434820000511
Figure BDA0002736434820000511

Figure BDA0002736434820000521
Figure BDA0002736434820000521

Figure BDA0002736434820000531
Figure BDA0002736434820000531

Figure BDA0002736434820000541
Figure BDA0002736434820000541

Figure BDA0002736434820000551
Figure BDA0002736434820000551

Figure BDA0002736434820000561
Figure BDA0002736434820000561

Figure BDA0002736434820000571
Figure BDA0002736434820000571

Figure BDA0002736434820000581
Figure BDA0002736434820000581

Figure BDA0002736434820000591
Figure BDA0002736434820000591

Figure BDA0002736434820000601
Figure BDA0002736434820000601

Figure BDA0002736434820000611
Figure BDA0002736434820000611

Figure BDA0002736434820000621
Figure BDA0002736434820000621

Figure BDA0002736434820000631
Figure BDA0002736434820000631

Figure BDA0002736434820000641
Figure BDA0002736434820000641

Figure BDA0002736434820000651
Figure BDA0002736434820000651

Figure BDA0002736434820000661
Figure BDA0002736434820000661

Figure BDA0002736434820000671
Figure BDA0002736434820000671

Figure BDA0002736434820000681
Figure BDA0002736434820000681

Figure BDA0002736434820000691
Figure BDA0002736434820000691

Figure BDA0002736434820000701
Figure BDA0002736434820000701

Figure BDA0002736434820000711
Figure BDA0002736434820000711

Figure BDA0002736434820000721
Figure BDA0002736434820000721

Figure BDA0002736434820000731
Figure BDA0002736434820000731

Figure BDA0002736434820000741
Figure BDA0002736434820000741

Figure BDA0002736434820000751
Figure BDA0002736434820000751

Figure BDA0002736434820000761
Figure BDA0002736434820000761

Figure BDA0002736434820000771
Figure BDA0002736434820000771

Figure BDA0002736434820000781
Figure BDA0002736434820000781

Figure BDA0002736434820000791
Figure BDA0002736434820000791

另外,在本说明书的一实施方式中,上述化学式3选自下述结构式。Moreover, in one Embodiment of this specification, the said chemical formula 3 is selected from the following structural formula.

Figure BDA0002736434820000801
Figure BDA0002736434820000801

Figure BDA0002736434820000811
Figure BDA0002736434820000811

Figure BDA0002736434820000821
Figure BDA0002736434820000821

Figure BDA0002736434820000831
Figure BDA0002736434820000831

Figure BDA0002736434820000841
Figure BDA0002736434820000841

Figure BDA0002736434820000851
Figure BDA0002736434820000851

Figure BDA0002736434820000861
Figure BDA0002736434820000861

Figure BDA0002736434820000862
Figure BDA0002736434820000862

Figure BDA0002736434820000871
Figure BDA0002736434820000871

Figure BDA0002736434820000872
Figure BDA0002736434820000872

Figure BDA0002736434820000881
Figure BDA0002736434820000881

Figure BDA0002736434820000891
Figure BDA0002736434820000891

Figure BDA0002736434820000901
Figure BDA0002736434820000901

Figure BDA0002736434820000911
Figure BDA0002736434820000911

Figure BDA0002736434820000921
Figure BDA0002736434820000921

Figure BDA0002736434820000931
Figure BDA0002736434820000931

Figure BDA0002736434820000941
Figure BDA0002736434820000941

Figure BDA0002736434820000951
Figure BDA0002736434820000951

Figure BDA0002736434820000961
Figure BDA0002736434820000961

Figure BDA0002736434820000971
Figure BDA0002736434820000971

Figure BDA0002736434820000981
Figure BDA0002736434820000981

本说明书的有机发光器件的第一和第二有机物层可以由单层结构形成,还可以由层叠有两层以上的有机物层的多层结构形成。例如,本说明书的第一有机物层可以由1至3层构成。此外,本说明书的有机发光器件可以具有包括空穴注入层、空穴传输层、发光层、电子传输层等作为有机物层的结构;或者包括空穴注入层、空穴传输层、发光层、电子注入和传输层等作为有机物层的结构。但是,有机发光器件的结构并不限定于此,可以包括更多或更少数量的有机层。The first and second organic material layers of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the first organic layer of the present specification may be composed of 1 to 3 layers. Further, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, etc. as an organic layer; or a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and the like. Implantation and transport layers, etc. as the structure of the organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a larger or smaller number of organic layers.

在本说明书的一实施方式中,上述有机发光器件还包括选自空穴注入层、空穴传输层、电子注入层、电子阻挡层和空穴阻挡层中的1层或2层以上。In one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

在本说明书的一实施方式中,上述有机发光器件还包括选自空穴注入层、空穴传输层、电子注入和传输层、电子阻挡层、以及空穴阻挡层中的1层或2层以上。In one embodiment of the present specification, the above-mentioned organic light-emitting device further includes one or more layers selected from a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, and a hole blocking layer .

在本说明书的一实施方式中,上述有机发光器件还包括选自空穴注入层、空穴传输层、电子注入和传输层、空穴调节层、以及电子调节层中的1层或2层以上。In one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection and transport layer, a hole regulation layer, and an electron regulation layer .

另外,上述有机发光器件还可以进一步包括电子电荷生成层。In addition, the above organic light emitting device may further include an electron charge generation layer.

在本说明书的一实施方式中,上述有机发光器件包括:第一电极;与上述第一电极对置而具备的第二电极;以及具备在上述第一电极与上述第二电极之间的2层以上的发光层;具备在上述2层以上的发光层与上述第一电极之间、或者上述2层以上的发光层与上述第二电极之间的2层以上的第一和第二有机物层,上述2层以上的第一和第二有机物层分别包含由上述化学式1表示的化合物或者由上述化学式3表示的化合物。In one embodiment of the present specification, the organic light-emitting device includes: a first electrode; a second electrode provided to face the first electrode; and two layers provided between the first electrode and the second electrode the above light-emitting layer; comprising two or more first and second organic material layers between the two or more light-emitting layers and the first electrode, or between the two or more light-emitting layers and the second electrode, The above-mentioned two or more first and second organic substance layers respectively contain the compound represented by the above-mentioned Chemical Formula 1 or the compound represented by the above-mentioned Chemical Formula 3.

根据本说明书的一实施方式,上述第一有机物层包括空穴阻挡层或电子调节层,上述第二有机物层包括电子传输层,上述空穴阻挡层或电子调节层包含由上述化学式1表示的化合物,上述电子传输层可以包含由上述化学式3表示的化合物。According to an embodiment of the present specification, the first organic layer includes a hole blocking layer or an electron regulating layer, the second organic layer includes an electron transport layer, and the hole blocking layer or electron regulating layer includes the compound represented by the above Chemical Formula 1 , the above-mentioned electron transport layer may contain the compound represented by the above-mentioned Chemical Formula 3.

根据本说明书的一实施方式,上述第一有机物层包括空穴阻挡层或电子调节层,上述第二有机物层包括电子注入和传输层,上述空穴阻挡层或电子调节层包含由上述化学式1表示的化合物,上述电子注入和传输层可以包含由上述化学式3表示的化合物。According to an embodiment of the present specification, the first organic layer includes a hole blocking layer or an electron regulating layer, the second organic layer includes an electron injection and transport layer, and the hole blocking layer or the electron regulating layer includes the above-mentioned chemical formula 1. The above-mentioned electron injection and transport layer may contain the compound represented by the above-mentioned Chemical Formula 3.

在本说明书的一实施方式中,上述第一和第二有机物层除了包含上述化合物的有机物层以外,还包括空穴注入层或空穴传输层,该空穴注入层或空穴传输层包含含有芳基氨基、咔唑基或苯并咔唑基的化合物。In one embodiment of the present specification, the first and second organic material layers include, in addition to the organic material layer containing the above-mentioned compound, a hole injection layer or a hole transport layer comprising a hole injection layer or a hole transport layer containing Arylamino, carbazolyl or benzocarbazolyl compounds.

在另一实施方式中,有机发光器件可以为在基板上依次层叠有阳极、1层以上的有机物层和阴极的结构(标准型(normal type))的有机发光器件。In another embodiment, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

在另一实施方式中,有机发光器件可以为在基板上依次层叠有阴极、1层以上的有机物层和阳极的逆向结构(倒置型(inverted type))的有机发光器件。In another embodiment, the organic light-emitting device may be an organic light-emitting device of an inverted structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

例如,根据本说明书的一实施方式的有机发光器件的结构例示于图1至4。For example, the structure of an organic light emitting device according to an embodiment of the present specification is illustrated in FIGS. 1 to 4 .

图4例示了依次层叠有基板1、阳极2、发光层3、阴极4的通常的有机发光器件的结构。此外,如果参考图1和3,则根据本说明书的一实施方式的有机发光器件可以包括2层以上的发光层。此外,各个发光层可以独立地包含荧光性掺杂剂或磷光性掺杂剂。发光层为2层时,一层发光层可以包含荧光性掺杂剂,另一层可以包含磷光性掺杂剂。FIG. 4 illustrates the structure of a general organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are stacked in this order. In addition, if referring to FIGS. 1 and 3 , the organic light emitting device according to an embodiment of the present specification may include 2 or more light emitting layers. In addition, each light-emitting layer may independently contain a fluorescent dopant or a phosphorescent dopant. When there are two light-emitting layers, one light-emitting layer may contain a fluorescent dopant, and the other layer may contain a phosphorescent dopant.

根据一个例子,上述有机发光器件可以在上述第一电极与第二电极之间包括发射彼此不同的波长范围的光的2层以上的发光层。According to an example, the organic light-emitting device may include two or more light-emitting layers between the first electrode and the second electrode that emit light in wavelength ranges different from each other.

另外,根据本说明书的一实施方式,上述2层以上的发光层可以沿第一电极到第二电极方向的垂直方向进行设置,也可以沿水平方向进行设置。In addition, according to an embodiment of the present specification, the above-mentioned two or more light-emitting layers may be provided in the vertical direction from the first electrode to the second electrode, or may be provided in the horizontal direction.

图2例示了依次层叠有基板1、阳极2、空穴传输层5、发光层3、空穴阻挡层或电子调节层6、电子注入和传输层7、以及阴极4的有机发光器件的结构。如果参考图2,则根据本说明书的一实施方式的有机发光器件可以包括3层以上的发光层。此外,在各发光层与发光层之间,可以进一步设置其它层。在上述发光层设置为3层以上的情况下,各个发光层可以包括蓝色荧光发光层。此外,在如图3所示的结构中,由上述化学式1表示的化合物可以包含在上述空穴阻挡层或电子调节层6中,由上述化学式3表示的化合物可以包含在电子注入和传输层7中。2 illustrates the structure of an organic light emitting device in which a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, a hole blocking layer or electron regulation layer 6, an electron injection and transport layer 7, and a cathode 4 are stacked in this order. Referring to FIG. 2 , the organic light emitting device according to an embodiment of the present specification may include three or more light emitting layers. In addition, other layers may be further provided between each light-emitting layer and the light-emitting layer. In the case where the above-mentioned light-emitting layers are provided as three or more layers, each light-emitting layer may include a blue fluorescent light-emitting layer. In addition, in the structure shown in FIG. 3 , the compound represented by the above-mentioned Chemical Formula 1 may be contained in the above-mentioned hole blocking layer or the electron regulating layer 6 , and the compound represented by the above-mentioned Chemical Formula 3 may be contained in the electron injection and transport layer 7 middle.

另外,根据本说明书的一实施方式,上述3层以上的发光层可以沿第一电极到第二电极方向的垂直方向进行设置,也可以沿水平方向进行设置。更具体而言,可以沿第一电极到第二电极方向的水平方向进行设置。In addition, according to an embodiment of the present specification, the above-mentioned three or more light-emitting layers may be provided in the vertical direction from the first electrode to the second electrode, or may be provided in the horizontal direction. More specifically, it may be arranged in a horizontal direction from the first electrode to the second electrode direction.

根据本说明书的一实施方式,上述蓝色荧光发光层包含主体和掺杂剂,上述主体可以为选自下述结构中的任一个。According to an embodiment of the present specification, the blue fluorescent light-emitting layer includes a host and a dopant, and the host may be any one selected from the following structures.

Figure BDA0002736434820001011
Figure BDA0002736434820001011

Figure BDA0002736434820001021
Figure BDA0002736434820001021

本说明书的有机发光器件除了第一或第二有机物层中的1层以上包含本说明书的化合物,即由上述化学式1和3表示的化合物以外,可以利用该技术领域中已知的材料和方法进行制造。The organic light-emitting device of the present specification can be fabricated using materials and methods known in the technical field, except that one or more layers of the first or second organic layer contain the compounds of the present specification, that is, compounds represented by the above-mentioned Chemical Formulas 1 and 3. manufacture.

上述有机发光器件包括复数层第一或第二有机物层时,上述有机物层可以由相同的物质或不同的物质形成。When the above-mentioned organic light-emitting device includes a plurality of first or second organic material layers, the above-mentioned organic material layers may be formed of the same substance or different substances.

本说明书的有机发光器件除了第一或第二有机物层中的1层以上包含上述化合物,即由上述化学式1和3中的任一个表示的化合物以外,可以利用该技术领域中已知的材料和方法进行制造。The organic light-emitting device of the present specification can utilize materials known in the technical field and other than the compound represented by any one of the above-mentioned Chemical Formulas 1 and 3, except that one or more layers of the first or second organic substance layer contain the above-mentioned compound. method to manufacture.

例如,本说明书的有机发光器件可以通过在基板上依次层叠第一电极、第一和第二有机物层、以及第二电极而制造。这时,可以如下制造:利用溅射法(sputtering)或电子束蒸发法(e-beam evaporation)之类的PVD(physical Vapor Deposition:物理气相沉积)方法,在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极,然后在该阳极上形成包含空穴注入层、空穴传输层、发光层和电子传输层的有机物层,之后在该有机物层上蒸镀可用作阴极的物质而制造。除了这种方法以外,也可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件。For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, first and second organic substance layers, and a second electrode on a substrate. In this case, it can be produced by depositing a metal or having conductivity on a substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. metal oxides or their alloys to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer is formed on the anode, and then vapor deposition on the organic layer can be used as Made from the cathode material. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

另外,上述化学式1和3的化合物在制造有机发光器件时不仅可以利用真空蒸镀法,还可以利用溶液涂布法来形成有机物层。在这里,所谓溶液涂布法是指旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但不仅限于此。In addition, the compounds of the above-mentioned Chemical Formulas 1 and 3 can be used not only by a vacuum evaporation method but also by a solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the solution coating method refers to a spin coating method, a dip coating method, a blade coating method, an ink jet printing method, a screen printing method, a spray method, a roll coating method, or the like, but is not limited thereto.

除了这些方法以外,还可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件(国际专利申请公开第2003/012890号)。但是,制造方法并不限定于此。In addition to these methods, an organic light-emitting device can be produced by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited to this.

在本说明书的一实施方式中,上述第一电极为阳极,上述第二电极为阴极。In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

在另一实施方式中,上述第一电极为阴极,上述第二电极为阳极。In another embodiment, the first electrode is a cathode, and the second electrode is an anode.

作为上述阳极物质,通常为了使空穴能够顺利地注入,优选为功函数大的物质。作为可以在本发明中使用的阳极物质的具体例,有钒、铬、铜、锌、金等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:Al或SnO2:Sb等金属与氧化物的组合;聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等,但不仅限于此。The anode material is preferably a material with a large work function in order to allow smooth injection of holes in general. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO) Metal oxides such as ZnO:Al or SnO 2 :Sb and other metals and oxides; poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, etc., but not limited thereto.

作为上述阴极物质,通常为了使电子容易地注入,优选为功函数小的物质。作为阴极物质的具体例,有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅等金属或它们的合金;LiF/Al或LiO2/Al等多层结构物质等,但不仅限于此。As the cathode material, generally, in order to facilitate electron injection, a material having a small work function is preferable. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; LiF/Al, LiO 2 /Al, etc. Layer structure substances, etc., but not limited to this.

上述空穴注入物质是注入来自电极的空穴的层,作为空穴注入物质,优选为如下化合物:具有传输空穴的能力,具有注入来自阳极的空穴的效果,具有对于发光层或发光材料的优异的空穴注入效果,防止发光层中所生成的激子向电子注入层或电子注入材料迁移,而且薄膜形成能力优异的化合物。优选空穴注入物质的HOMO(最高占有分子轨道,highest occupied molecular orbital)介于阳极物质的功函数与周围有机物层的HOMO之间。作为空穴注入物质的具体例,有金属卟啉(porphyrin)、低聚噻吩、芳基胺系有机物、六腈六氮杂苯并菲系有机物、喹吖啶酮(quinacridone)系有机物、苝(perylene)系有机物、蒽醌及聚苯胺和聚噻吩系导电性高分子等,但不仅限于此。The hole-injecting substance is a layer that injects holes from the electrode, and the hole-injecting substance is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, and has the effect of injecting holes from the anode, and having the ability to transport holes in the light-emitting layer or the light-emitting material. It has excellent hole injection effect, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and is a compound with excellent thin film forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole-injecting substance include porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, perylene ( perylene) organic compounds, anthraquinone, polyaniline and polythiophene-based conductive polymers, etc., but not limited to this.

上述空穴传输层是接收来自空穴注入层的空穴并将空穴传输至发光层的层,空穴传输物质是能够接收来自阳极或空穴注入层的空穴并将其转移至发光层的物质,对空穴的迁移率大的物质是合适的。作为具体例,有芳基胺系有机物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等,但不仅限于此。The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport substance is a layer capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer A material with high mobility for holes is suitable. Specific examples include arylamine-based organic substances, conductive polymers, and block copolymers in which both a conjugated portion and a non-conjugated portion are present, but the present invention is not limited thereto.

上述发光物质是能够从空穴传输层和电子传输层分别接收空穴和电子并使它们结合而发出可见光区域的光的物质,优选为对于荧光或磷光的量子效率高的物质。作为具体例,有8-羟基喹啉铝配合物(Alq3)、咔唑系化合物、二聚苯乙烯基(dimerized styryl)化合物;BAlq;10-羟基苯并喹啉-金属化合物;苯并

Figure BDA0002736434820001041
唑、苯并噻唑及苯并咪唑系化合物;聚(对亚苯基亚乙烯基)(PPV)系高分子;螺环(spiro)化合物;聚芴;红荧烯等,但不仅限于此。The light-emitting substance is a substance that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq 3 ), carbazole-based compound, dimerized styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compound;
Figure BDA0002736434820001041
azoles, benzothiazoles, and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene, etc., but not limited thereto.

上述电子传输物质是接收来自电子注入层的电子并将电子传输至发光层的层。The above-mentioned electron transport material is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.

上述电子注入层是注入来自电极的电子的层,优选为如下化合物:具有传输电子的能力,具有注入来自阴极的电子的效果,具有对于发光层或发光材料的优异的电子注入效果,防止发光层中所生成的激子向空穴注入层迁移,而且薄膜形成能力优异的化合物。具体而言,有芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、

Figure BDA0002736434820001042
唑、
Figure BDA0002736434820001043
二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等和它们的衍生物、金属配位化合物、以及含氮五元环衍生物等,但并不限定于此。The above-mentioned electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injection effect to the light-emitting layer or light-emitting material, and prevents the light-emitting layer The excitons generated in the compound migrate to the hole injection layer and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide,
Figure BDA0002736434820001042
azole,
Figure BDA0002736434820001043
Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylene methanes, anthrone, etc., their derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but not limited thereto.

作为上述金属配位化合物,有8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯化镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但并不限定于此。Examples of the aforementioned metal complex include lithium 8-quinolinate, bis(8-quinolinolato)zinc, bis(8-quinolinolato)copper, bis(8-quinolinolato)manganese, tris(8-hydroxyquinoline) Quinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxyl) Benzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl) yl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but not limited thereto.

上述空穴阻挡层是阻止空穴到达阴极的层,是调节到达发光层的电子的层,可以成为电子调节层。此外,上述电子电荷生成层为生成电子电荷的层。The above-mentioned hole blocking layer is a layer that prevents holes from reaching the cathode, is a layer that regulates electrons reaching the light-emitting layer, and can be an electron regulating layer. In addition, the above-mentioned electron charge generation layer is a layer that generates electron charge.

根据所使用的材料,根据本说明书的有机发光器件可以为顶部发光型、底部发光型或双向发光型。The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type or a bidirectional emission type according to the materials used.

实施发明的方式way of implementing the invention

包含由上述化学式1和3表示的化合物的有机发光器件的制造在以下实施例中具体地进行说明。但是,下述实施例是用于例示本说明书,本说明书的范围并不限定于此。The production of the organic light-emitting device including the compounds represented by the above-mentioned Chemical Formulas 1 and 3 is specifically described in the following Examples. However, the following examples are for illustrating the present specification, and the scope of the present specification is not limited thereto.

制造例1:化合物EC1的制造Production Example 1: Production of Compound EC1

Figure BDA0002736434820001051
Figure BDA0002736434820001051

将上述化合物EC1-A(10g,26.6mmol)和上述化合物EC1-B(12.3g,26.6mmol)完全溶解于四氢呋喃(100mL)后,将碳酸钾(11.0g,79.7mmol)溶解于50mL的水而进行添加。加入四(三苯基膦)钯(0.92g,0.797mmol)后,加热搅拌8小时。将温度降至常温而结束反应后,去除碳酸钾溶液并过滤白色固体。将过滤的白色固体用四氢呋喃和乙酸乙酯分别洗涤2次,从而制造了化合物EC1(15.4g,收率81%)。After the above-mentioned compound EC1-A (10 g, 26.6 mmol) and the above-mentioned compound EC1-B (12.3 g, 26.6 mmol) were completely dissolved in tetrahydrofuran (100 mL), potassium carbonate (11.0 g, 79.7 mmol) was dissolved in 50 mL of water to obtain a solution. to add. After adding tetrakis(triphenylphosphine)palladium (0.92 g, 0.797 mmol), the mixture was heated and stirred for 8 hours. After the temperature was lowered to normal temperature to complete the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to prepare compound EC1 (15.4 g, yield 81%).

MS[M+H]+=716MS[M+H] + = 716

制造例2:化合物EC2的制造Production Example 2: Production of Compound EC2

Figure BDA0002736434820001052
Figure BDA0002736434820001052

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC2表示的化合物。The compound represented by the above-mentioned chemical formula EC2 was produced by the same method as the production method of EC1 of Production Example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=553MS[M+H] + = 553

制造例3:化合物EC3的制造Production Example 3: Production of Compound EC3

Figure BDA0002736434820001061
Figure BDA0002736434820001061

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC3表示的化合物。The compound represented by the above-mentioned chemical formula EC3 was produced by the same method as the production method of EC1 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=640MS[M+H] + = 640

制造例4:化合物EC4的制造Production Example 4: Production of Compound EC4

Figure BDA0002736434820001062
Figure BDA0002736434820001062

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC4表示的化合物。The compound represented by the above-mentioned chemical formula EC4 was produced by the same method as the production method of EC1 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=640MS[M+H] + = 640

制造例5:化合物EC5的制造Production Example 5: Production of Compound EC5

Figure BDA0002736434820001063
Figure BDA0002736434820001063

将上述化合物EC5-A(10g,17.1mmol)和上述化合物EC5-B(9.2g,34.2mmol)完全溶解于四氢呋喃(100mL)后,将碳酸钾(7.1g,51.3mmol)溶解于50mL的水而进行添加。加入四(三苯基膦)钯(0.59g,0.513mmol)后,加热搅拌8小时。将温度降至常温而结束反应后,去除碳酸钾溶液并过滤白色固体。将过滤的白色固体用四氢呋喃和乙酸乙酯分别洗涤2次,从而制造了化合物EC5(9.5g,收率70%)。After the above-mentioned compound EC5-A (10 g, 17.1 mmol) and the above-mentioned compound EC5-B (9.2 g, 34.2 mmol) were completely dissolved in tetrahydrofuran (100 mL), potassium carbonate (7.1 g, 51.3 mmol) was dissolved in 50 mL of water to obtain a solution. to add. After adding tetrakis(triphenylphosphine)palladium (0.59 g, 0.513 mmol), the mixture was heated and stirred for 8 hours. After the temperature was lowered to normal temperature to complete the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to prepare compound EC5 (9.5 g, yield 70%).

MS[M+H]+=795MS[M+H] + = 795

制造例6:化合物EC6的制造Production Example 6: Production of Compound EC6

Figure BDA0002736434820001071
Figure BDA0002736434820001071

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC6表示的化合物。The compound represented by the above-mentioned chemical formula EC6 was produced by the same method as the production method of EC1 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=807MS[M+H] + = 807

制造例7:化合物EC7的制造Production Example 7: Production of Compound EC7

Figure BDA0002736434820001072
Figure BDA0002736434820001072

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC7表示的化合物。The compound represented by the above-mentioned chemical formula EC7 was produced by the same method as the production method of EC1 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=654MS[M+H] + = 654

制造例8:化合物EC8的制造Production Example 8: Production of Compound EC8

Figure BDA0002736434820001073
Figure BDA0002736434820001073

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC8表示的化合物。The compound represented by the above-mentioned chemical formula EC8 was produced by the same method as the production method of EC1 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=821MS[M+H] + = 821

制造例9:化合物EC9的制造Production Example 9: Production of Compound EC9

Figure BDA0002736434820001081
Figure BDA0002736434820001081

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC9表示的化合物。The compound represented by the above-mentioned chemical formula EC9 was produced by the same method as the production method of EC1 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=848MS[M+H] + = 848

制造例10:化合物EC10的制造Production Example 10: Production of Compound EC10

Figure BDA0002736434820001082
Figure BDA0002736434820001082

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC1的制造方法相同的方法制造了由上述化学式EC10表示的化合物。The compound represented by the above-mentioned chemical formula EC10 was produced by the same method as the production method of EC1 of Production Example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=537MS[M+H] + = 537

制造例11:化合物ET1的制造Production Example 11: Production of Compound ET1

Figure BDA0002736434820001083
Figure BDA0002736434820001083

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC5的制造方法相同的方法制造了由上述化学式ET1表示的化合物。The compound represented by the above-mentioned chemical formula ET1 was produced by the same method as the production method of EC5 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=799MS[M+H] + = 799

制造例12:化合物ET2的制造Production Example 12: Production of Compound ET2

Figure BDA0002736434820001091
Figure BDA0002736434820001091

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC5的制造方法相同的方法制造了由上述化学式ET2表示的化合物。The compound represented by the above-mentioned chemical formula ET2 was produced by the same method as the production method of EC5 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=743MS[M+H] + =743

制造例13:化合物ET3的制造Production Example 13: Production of Compound ET3

Figure BDA0002736434820001092
Figure BDA0002736434820001092

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC5的制造方法相同的方法制造了由上述化学式ET3表示的化合物。The compound represented by the above-mentioned chemical formula ET3 was produced by the same method as the production method of EC5 of Production Example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=763MS[M+H] + = 763

制造例14:化合物ET4的制造Production Example 14: Production of Compound ET4

Figure BDA0002736434820001093
Figure BDA0002736434820001093

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC5的制造方法相同的方法制造了由上述化学式ET4表示的化合物。The compound represented by the above-mentioned chemical formula ET4 was produced by the same method as the production method of EC5 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=591MS[M+H] + = 591

制造例15:化合物ET5的制造Production Example 15: Production of Compound ET5

Figure BDA0002736434820001101
Figure BDA0002736434820001101

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC5的制造方法相同的方法制造了由上述化学式ET5表示的化合物。The compound represented by the above-mentioned chemical formula ET5 was produced by the same method as the production method of EC5 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=791MS[M+H] + = 791

制造例16:化合物ET6的制造Production Example 16: Production of Compound ET6

Figure BDA0002736434820001102
Figure BDA0002736434820001102

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC5的制造方法相同的方法制造了由上述化学式ET6表示的化合物。The compound represented by the above-mentioned chemical formula ET6 was produced by the same method as the production method of EC5 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=759MS[M+H] + = 759

制造例17:化合物ET7的制造Production Example 17: Production of Compound ET7

Figure BDA0002736434820001103
Figure BDA0002736434820001103

如上述反应式那样使用各起始物质,除此以外,通过与制造例1的EC5的制造方法相同的方法制造了由上述化学式ET7表示的化合物。The compound represented by the above-mentioned chemical formula ET7 was produced by the same method as the production method of EC5 of Production Example 1 except that each starting material was used as in the above-mentioned reaction formula.

MS[M+H]+=699MS[M+H] + = 699

实施例1-1Example 1-1

将ITO(氧化铟锡,indium tin oxide)以

Figure BDA0002736434820001111
的厚度被涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中,利用超声波进行洗涤。这时,洗涤剂使用菲希尔公司(Fischer Co.)制品,蒸馏水使用了利用密理博公司(Millipore Co.)制造的过滤器(Filter)过滤两次的蒸馏水。将ITO洗涤30分钟后,用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后,用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后,输送至等离子体清洗机。此外,利用氧等离子体,将上述基板清洗5分钟后,将基板输送至真空蒸镀机。ITO (indium tin oxide, indium tin oxide) with
Figure BDA0002736434820001111
The thickness of the glass substrate coated as a thin film is put into distilled water in which detergent is dissolved, and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered twice by a Millipore Co. filter was used for the distilled water. After washing with ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropanol, acetone, and methanol, followed by drying, and then transported to a plasma cleaning machine. Moreover, after the said board|substrate was wash|cleaned for 5 minutes by oxygen plasma, the board|substrate was conveyed to a vacuum vapor deposition machine.

在这样准备的ITO透明电极上,将下述HI-A化合物以

Figure BDA0002736434820001112
的厚度进行热真空蒸镀而形成空穴注入层。在上述空穴注入层上,依次真空蒸镀下述HAT化合物
Figure BDA0002736434820001113
和下述HT-A化合物
Figure BDA0002736434820001114
而形成空穴传输层。On the thus prepared ITO transparent electrode, the following HI-A compound was prepared as
Figure BDA0002736434820001112
A hole injection layer was formed by thermal vacuum evaporation. On the above hole injection layer, the following HAT compounds were sequentially vacuum-deposited
Figure BDA0002736434820001113
and the following HT-A compounds
Figure BDA0002736434820001114
A hole transport layer is formed.

接着,在上述空穴传输层上,以膜厚度

Figure BDA0002736434820001115
将BH化合物和下述BD化合物以25:1的重量比进行真空蒸镀而形成发光层。Next, on the above-mentioned hole transport layer, a film thickness of
Figure BDA0002736434820001115
The light-emitting layer was formed by vacuum-evaporating the BH compound and the following BD compound at a weight ratio of 25:1.

在上述发光层上,真空蒸镀上述化合物EC1,从而以

Figure BDA0002736434820001116
的厚度形成空穴阻挡层。在上述空穴阻挡层上,将上述化合物ET1和下述LiQ化合物以1:1的重量比进行真空蒸镀,从而以
Figure BDA0002736434820001117
的厚度形成电子注入和传输层。在上述电子注入和传输层上,依次将氟化锂(LiF)以
Figure BDA0002736434820001118
的厚度、将铝以
Figure BDA0002736434820001119
的厚度进行蒸镀,从而形成阴极。On the above-mentioned light-emitting layer, the above-mentioned compound EC1 was vacuum-evaporated to form a
Figure BDA0002736434820001116
thickness to form a hole blocking layer. On the above-mentioned hole blocking layer, the above-mentioned compound ET1 and the following LiQ compound were vacuum-evaporated at a weight ratio of 1:1, so as to obtain a
Figure BDA0002736434820001117
The thickness of the electron injection and transport layer is formed. On the above electron injection and transport layer, lithium fluoride (LiF) was sequentially
Figure BDA0002736434820001118
thickness, aluminum to
Figure BDA0002736434820001119
The thickness is evaporated to form a cathode.

在上述过程中,有机物的蒸镀速度维持0.4至

Figure BDA00027364348200011110
阴极的氟化锂维持
Figure BDA00027364348200011111
的蒸镀速度,铝维持
Figure BDA00027364348200011112
的蒸镀速度,在蒸镀时,真空度维持1×10-7至5×10-5托,从而制造了有机发光器件。During the above process, the evaporation rate of organic matter is maintained from 0.4 to
Figure BDA00027364348200011110
Lithium fluoride maintenance of the cathode
Figure BDA00027364348200011111
The evaporation rate of aluminum maintains
Figure BDA00027364348200011112
The vapor deposition rate is 100%, and the vacuum degree is maintained at 1×10 -7 to 5×10 -5 Torr during the vapor deposition, thereby fabricating an organic light-emitting device.

Figure BDA0002736434820001121
Figure BDA0002736434820001121

实施例1-2至1-18和比较例1-1至1-18Examples 1-2 to 1-18 and Comparative Examples 1-1 to 1-18

使用下述表1的化合物代替上述实施例1-1的化合物EC1和ET1,除此以外,通过与实施例1-1相同的方法制作了有机发光器件。An organic light-emitting device was produced by the same method as in Example 1-1, except that the compounds of the following Table 1 were used in place of the compounds EC1 and ET1 of the above-mentioned Example 1-1.

对上述实施例1-1至1-18和比较例1-1至1-18中制造的有机发光器件,在10mA/cm2的电流密度下测定了驱动电压和发光效率,在20mA/cm2的电流密度下测定了相对于初始亮度成为90%所需的时间(T90)。将上述结果示于下述表1。For the organic light-emitting devices manufactured in the above-mentioned Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-18, the driving voltage and the luminous efficiency were measured at a current density of 10 mA/cm 2 , and at 20 mA/cm 2 The time required to reach 90% of the initial brightness (T90) was measured at a current density of . The above results are shown in Table 1 below.

[表1][Table 1]

Figure BDA0002736434820001131
Figure BDA0002736434820001131

Figure BDA0002736434820001141
Figure BDA0002736434820001141

Figure BDA0002736434820001151
Figure BDA0002736434820001151

在上述表1中,如果将实施例1-1至1-18与比较例1-1至1-18进行比较,则适用了根据本说明书的化学式1和化学式3的有机发光器件,与只适用了化学式1或化学式3的有机发光器件相比,在寿命方面显著优异。In Table 1 above, if Examples 1-1 to 1-18 are compared with Comparative Examples 1-1 to 1-18, the organic light-emitting devices according to Chemical Formula 1 and Chemical Formula 3 of the present specification are applied, and only Compared with the organic light-emitting device of Chemical Formula 1 or Chemical Formula 3, it is remarkably excellent in lifetime.

实施例2-1Example 2-1

将ITO(氧化铟锡)以

Figure BDA0002736434820001152
的厚度被涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中,利用超声波进行洗涤。这时,洗涤剂使用菲希尔公司制品,蒸馏水使用了利用密理博公司制造的过滤器过滤两次的蒸馏水。将ITO洗涤30分钟后,用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后,用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后,输送至等离子体清洗机。此外,利用氧等离子体,将上述基板清洗5分钟后,将基板输送至真空蒸镀机。ITO (Indium Tin Oxide)
Figure BDA0002736434820001152
The thickness of the glass substrate coated as a thin film is put into distilled water in which detergent is dissolved, and washed with ultrasonic waves. At this time, a product of Fischer Co., Ltd. was used for the detergent, and distilled water that was filtered twice by a filter made by Millipore Co., Ltd. was used for the distilled water. After washing with ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropanol, acetone, and methanol, followed by drying, and then transported to a plasma cleaning machine. Moreover, after the said board|substrate was wash|cleaned for 5 minutes by oxygen plasma, the board|substrate was conveyed to a vacuum vapor deposition machine.

在这样准备的ITO透明电极上,将下述HI-A化合物以

Figure BDA0002736434820001157
的厚度进行热真空蒸镀而形成第一空穴注入层。在上述第一空穴注入层上,依次真空蒸镀下述HAT化合物
Figure BDA0002736434820001153
和下述HT-A化合物
Figure BDA0002736434820001154
而形成第一空穴传输层。On the thus prepared ITO transparent electrode, the following HI-A compound was prepared as
Figure BDA0002736434820001157
The thickness of the first hole injection layer is formed by thermal vacuum evaporation. On the above-mentioned first hole injection layer, the following HAT compounds were sequentially vacuum-deposited
Figure BDA0002736434820001153
and the following HT-A compounds
Figure BDA0002736434820001154
Thus, a first hole transport layer is formed.

接着,在上述第一空穴传输层上,以膜厚度

Figure BDA0002736434820001155
将BH化合物和下述BD化合物以25:1的重量比进行真空蒸镀而形成第一发光层。Next, on the above-mentioned first hole transport layer, a film thickness of
Figure BDA0002736434820001155
The first light-emitting layer was formed by vacuum-evaporating the BH compound and the following BD compound at a weight ratio of 25:1.

在上述第一发光层上,将上述化合物EC1进行真空蒸镀,从而以

Figure BDA0002736434820001156
的厚度形成第一空穴阻挡层。在上述第一空穴阻挡层上,将上述化合物ET1与下述LiQ化合物以1:1的重量比进行真空蒸镀,从而以
Figure BDA0002736434820001161
的厚度形成第一电子注入和传输层。On the above-mentioned first light-emitting layer, the above-mentioned compound EC1 is vacuum-evaporated to obtain a
Figure BDA0002736434820001156
The thickness of the first hole blocking layer is formed. On the above-mentioned first hole blocking layer, the above-mentioned compound ET1 and the following LiQ compound were vacuum-evaporated in a weight ratio of 1:1, so as to obtain a
Figure BDA0002736434820001161
of thickness to form the first electron injection and transport layer.

在上述第一电子注入和传输层上,以膜厚度

Figure BDA0002736434820001162
将化合物ET-C和锂化合物以100:2的重量比进行真空蒸镀而形成电子电荷生成层。在上述电子电荷生成层上,将HI-A化合物以
Figure BDA0002736434820001163
的厚度进行热真空蒸镀而形成第二空穴注入层。On the above-mentioned first electron injection and transport layer, with a film thickness
Figure BDA0002736434820001162
The electron charge generation layer was formed by vacuum-evaporating the compound ET-C and the lithium compound at a weight ratio of 100:2. On the above-mentioned electron charge generation layer, the HI-A compound is
Figure BDA0002736434820001163
The thickness of the second hole injection layer is formed by thermal vacuum evaporation.

在上述第二空穴注入层上,依次真空蒸镀下述HAT化合物

Figure BDA0002736434820001164
和下述HT-A化合物
Figure BDA0002736434820001165
而形成第二空穴传输层。On the second hole injection layer described above, the following HAT compounds were sequentially vacuum-deposited
Figure BDA0002736434820001164
and the following HT-A compounds
Figure BDA0002736434820001165
And the second hole transport layer is formed.

接着,在上述第二空穴传输层上,以膜厚度

Figure BDA0002736434820001166
将BH化合物和下述BD化合物以25:1的重量比进行真空蒸镀而形成第二发光层。Next, on the above-mentioned second hole transport layer, a film thickness of
Figure BDA0002736434820001166
The second light-emitting layer was formed by vacuum-evaporating the BH compound and the following BD compound at a weight ratio of 25:1.

在上述第二发光层上,将化合物EC1进行真空蒸镀,从而以

Figure BDA0002736434820001167
的厚度形成空穴阻挡层。在上述第二空穴阻挡层上,将上述化合物ET1和下述LiQ化合物以1:1的重量比进行真空蒸镀,从而以
Figure BDA0002736434820001168
的厚度形成第二电子注入和传输层。在上述第二电子注入和传输层上,依次将氟化锂(LiF)以
Figure BDA0002736434820001169
的厚度、将铝以
Figure BDA00027364348200011610
的厚度进行蒸镀,从而形成阴极。On the second light-emitting layer, the compound EC1 was vacuum-evaporated to
Figure BDA0002736434820001167
thickness to form a hole blocking layer. On the above-mentioned second hole blocking layer, the above-mentioned compound ET1 and the following LiQ compound were vacuum-evaporated at a weight ratio of 1:1, so as to obtain a
Figure BDA0002736434820001168
A second electron injection and transport layer is formed. On the above-mentioned second electron injection and transport layer, lithium fluoride (LiF) was sequentially added to
Figure BDA0002736434820001169
thickness, aluminum to
Figure BDA00027364348200011610
The thickness is evaporated to form a cathode.

在上述过程中,有机物的蒸镀速度维持0.4至

Figure BDA00027364348200011611
阴极的氟化锂维持
Figure BDA00027364348200011612
的蒸镀速度,铝维持
Figure BDA00027364348200011613
的蒸镀速度,在蒸镀时,真空度维持1×10-7至5×10-5托,从而制造了有机发光器件。During the above process, the evaporation rate of organic matter is maintained from 0.4 to
Figure BDA00027364348200011611
Lithium fluoride maintenance of the cathode
Figure BDA00027364348200011612
The evaporation rate of aluminum maintains
Figure BDA00027364348200011613
The vapor deposition rate is 100%, and the vacuum degree is maintained at 1×10 -7 to 5×10 -5 Torr during the vapor deposition, thereby fabricating an organic light-emitting device.

Figure BDA0002736434820001171
Figure BDA0002736434820001171

实施例2-2至2-18和比较例2-1至2-18Examples 2-2 to 2-18 and Comparative Examples 2-1 to 2-18

使用下述表1的化合物代替上述实施例2-1的化合物EC1和ET1,除此以外,通过与实施例2-1相同的方法制作了有机发光器件。An organic light-emitting device was produced by the same method as in Example 2-1, except that the compounds of the following Table 1 were used in place of the compounds EC1 and ET1 of the above-mentioned Example 2-1.

对上述实施例2-2至2-18和比较例2-1至2-18中制造的有机发光器件,在10mA/cm2的电流密度下测定了驱动电压和发光效率,在20mA/cm2的电流密度下测定了相对于初始亮度成为90%所需的时间(T90)。将上述结果示于下述表2。For the organic light-emitting devices manufactured in the above-mentioned Examples 2-2 to 2-18 and Comparative Examples 2-1 to 2-18, the driving voltage and the luminous efficiency were measured at a current density of 10 mA/cm 2 , and at 20 mA/cm 2 The time required to reach 90% of the initial brightness (T90) was measured at a current density of . The above results are shown in Table 2 below.

[表2][Table 2]

Figure BDA0002736434820001181
Figure BDA0002736434820001181

Figure BDA0002736434820001191
Figure BDA0002736434820001191

Figure BDA0002736434820001201
Figure BDA0002736434820001201

在上述表2中,如果将实施例2-1至2-18与比较例2-1至2-18进行比较,则适用了根据本说明书的化学式1和化学式3的有机发光器件,与只适用了化学式1或化学式3的有机发光器件相比,在寿命方面显著优异。In Table 2 above, if Examples 2-1 to 2-18 are compared with Comparative Examples 2-1 to 2-18, the organic light-emitting devices according to Chemical Formula 1 and Chemical Formula 3 of the present specification are applied, and only Compared with the organic light-emitting device of Chemical Formula 1 or Chemical Formula 3, it is remarkably excellent in lifetime.

实施例3Example 3

将根据本说明书的一实施方式的化合物EC1至EC10、ET1至ET7、以及ET-A至ET-B的电子亲和势(eV)值示于下述表3。Electron affinity (eV) values of compounds EC1 to EC10, ET1 to ET7, and ET-A to ET-B according to an embodiment of the present specification are shown in Table 3 below.

[表3][table 3]

化合物compound 电子亲和势(eV)Electron Affinity (eV) EC1EC1 1.381.38 EC2EC2 1.261.26 EC3EC3 1.421.42 EC4EC4 1.321.32 EC5EC5 1.671.67 EC6EC6 1.601.60 EC7EC7 1.361.36 EC8EC8 1.381.38 EC9EC9 1.561.56 EC10EC10 1.171.17 ET1ET1 1.851.85 ET2ET2 1.71.7 ET3ET3 1.531.53 ET4ET4 1.691.69 ET5ET5 1.551.55 ET6ET6 1.741.74 ET7ET7 1.681.68 ET-AET-A 1.451.45 ET-BET-B 1.411.41

上述电子亲和势(eV)是利用美国高斯(Gaussian)公司制造的量子化学计算程序高斯03来进行的,并且利用密度泛函理论(DFT),作为泛函数利用B3LYP、作为基函数利用6-31G*,对最佳的结构,通过时变密度泛函理论(TD-DFT),求得计算值。上述表3的用于空穴阻挡层的上述化学式1的化合物与用于电子注入和传输层的上述化学式3的化合物的电子亲和势(eV)关系中具有EEt>EEc关系的有机发光器件中,作为空穴阻挡层(或电子调节层)化合物的上述化学式1适当地控制从作为电子注入和传输化合物的上述化学式3传递的电子量,从而提高有机发光器件的效率、寿命。The above-mentioned electron affinity (eV) was carried out by using the quantum chemical calculation program Gauss 03 manufactured by Gaussian Corporation in the United States, and by using density functional theory (DFT), B3LYP was used as a functional function, and 6- was used as a basis function. 31G*, for the optimal structure, the calculated value was obtained by time-varying density functional theory (TD-DFT). Organic luminescence having a relationship of E Et > E Ec in the electron affinity (eV) relationship of the compound of the above Chemical Formula 1 for the hole blocking layer and the compound of the above Chemical Formula 3 for the electron injection and transport layer of the above Table 3 In the device, the above-mentioned Chemical Formula 1 as the hole blocking layer (or electron regulating layer) compound appropriately controls the amount of electrons transferred from the above-mentioned Chemical Formula 3 as the electron injecting and transporting compound, thereby improving the efficiency and lifetime of the organic light-emitting device.

Claims (13)

1.一种有机发光器件,其中,包括:第一电极、与所述第一电极对置而具备的第二电极、以及具备在所述第一电极与所述第二电极之间的第一有机物层和第二有机物层,1. An organic light-emitting device comprising: a first electrode, a second electrode provided opposite to the first electrode, and a first electrode provided between the first electrode and the second electrode an organic layer and a second organic layer, 其中所述第一有机物层包含由下述化学式1表示的化合物,以及wherein the first organic layer contains a compound represented by the following Chemical Formula 1, and 所述第二有机物层包含由下述化学式3表示的化合物:The second organic layer includes a compound represented by the following Chemical Formula 3: 化学式1Chemical formula 1
Figure FDA0002736434810000011
Figure FDA0002736434810000011
在化学式1中,In Chemical Formula 1, X为O或S,X is O or S, R1至R4彼此相同或不同,并且各自独立地为氢、氘、卤素基团、氰基、硝基、取代或未取代的烷基、取代或未取代的卤代烷基、取代或未取代的卤代烷氧基、取代或未取代的环烷基、取代或未取代的烯基、取代或未取代的芳基、或者取代或未取代的杂环基,或者相邻的基团彼此结合而形成取代或未取代的环,R1 to R4 are the same or different from each other and are each independently hydrogen, deuterium, halogen group, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted haloalkyl, substituted or unsubstituted haloalkoxy substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, or adjacent groups combined with each other to form a substituted or unsubstituted substituted ring, R1至R4中的至少一个由下述化学式2A或2B表示,At least one of R1 to R4 is represented by the following chemical formula 2A or 2B, n1至n4各自独立地为1至4的整数,n1 to n4 are each independently an integer of 1 to 4, 化学式2AChemical formula 2A
Figure FDA0002736434810000021
Figure FDA0002736434810000021
化学式2BChemical formula 2B
Figure FDA0002736434810000022
Figure FDA0002736434810000022
在化学式2A和2B中,In Chemical Formulas 2A and 2B, A1至A3中的至少一个为N,并且其余为CH,或者与L1、L2、L3、Ar4和Ar5中的相邻的基团结合而形成取代或未取代的环,At least one of A1 to A3 is N, and the rest are CH, or combined with adjacent groups in L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring, L1至L3彼此相同或不同,并且各自独立地为直接键合、取代或未取代的亚芳基、或者取代或未取代的2价的杂环基,或者与A1至A3中的相邻的基团结合而形成取代或未取代的环,L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, or a group adjacent to A1 to A3 group together to form substituted or unsubstituted rings, Ar4和Ar5彼此相同或不同,并且各自独立地为氢、氘、取代或未取代的芳基、或者取代或未取代的杂环基,或者与A1至A3中的相邻的基团结合而形成取代或未取代的环,Ar4 and Ar5 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group, or formed by combining with adjacent groups among A1 to A3 substituted or unsubstituted rings, Ar6为氢、氘、取代或未取代的芳基、或者取代或未取代的杂环基,a为0至5的整数,Ar6 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, a is an integer from 0 to 5, 化学式3chemical formula 3
Figure FDA0002736434810000023
Figure FDA0002736434810000023
在化学式3中,In Chemical Formula 3, Ar1和Ar2各自为取代或未取代的芳基、或者取代或未取代的杂环基,Ar1 and Ar2 are each a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, Ar3为取代或未取代的2至4价的烷基、取代或未取代的2至4价的芳基、或者取代或未取代的2至4价的环烷基,Ar3 is a substituted or unsubstituted 2- to 4-valent alkyl group, a substituted or unsubstituted 2- to 4-valent aryl group, or a substituted or unsubstituted 2- to 4-valent cycloalkyl group, X1至X3中的至少一个为N,其余为CH,At least one of X1 to X3 is N, the rest are CH, L为直接键合、或者取代或未取代的亚芳基,L is a direct bond, or a substituted or unsubstituted arylene group, n5为2至4的整数,n5 is an integer from 2 to 4, 在所述化学式1至3中,所述a和n1至n5各自独立地为2以上时,括号内的取代基彼此相同或不同。In the chemical formulae 1 to 3, when the a and n1 to n5 are each independently 2 or more, the substituents in parentheses are the same or different from each other.
2.根据权利要求1所述的有机发光器件,其中,所述化学式1由下述化学式1-1至化学式1-5中的任一个表示:2. The organic light-emitting device of claim 1, wherein the Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-5: 化学式1-1Chemical formula 1-1
Figure FDA0002736434810000031
Figure FDA0002736434810000031
化学式1-2Chemical formula 1-2
Figure FDA0002736434810000041
Figure FDA0002736434810000041
化学式1-3Chemical formula 1-3
Figure FDA0002736434810000042
Figure FDA0002736434810000042
化学式1-4Chemical formula 1-4
Figure FDA0002736434810000043
Figure FDA0002736434810000043
化学式1-5Chemical formula 1-5
Figure FDA0002736434810000051
Figure FDA0002736434810000051
在所述化学式1-1至化学式1-5中,In the Chemical Formula 1-1 to Chemical Formula 1-5, X、R1至R4、L1至L3、A1至A3、Ar4、Ar5和n1至n4的定义与权利要求1中的定义相同,L1'、L2'、L3'、A1'、A2'、A3'、Ar4'和Ar5'各自与所述L1、L2、L3、A1、A2、A3、Ar4和Ar5的定义相同。The definitions of X, R1 to R4, L1 to L3, A1 to A3, Ar4, Ar5 and n1 to n4 are the same as those in claim 1, L1', L2', L3', A1', A2', A3', Ar4' and Ar5' each have the same definitions as described for L1, L2, L3, A1, A2, A3, Ar4 and Ar5.
3.根据权利要求1所述的有机发光器件,其中,所述Ar3为取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的2价的菲基、或者取代或未取代的2价的环烷基。3. The organic light-emitting device according to claim 1, wherein the Ar3 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent phenanthrenyl group, or a substituted or unsubstituted divalent cycloalkyl. 4.根据权利要求1所述的有机发光器件,其中,所述化学式1选自下述结构式:4. The organic light-emitting device of claim 1, wherein the chemical formula 1 is selected from the following structural formulas:
Figure FDA0002736434810000061
Figure FDA0002736434810000061
Figure FDA0002736434810000071
Figure FDA0002736434810000071
Figure FDA0002736434810000081
Figure FDA0002736434810000081
Figure FDA0002736434810000091
Figure FDA0002736434810000091
Figure FDA0002736434810000101
Figure FDA0002736434810000101
Figure FDA0002736434810000111
Figure FDA0002736434810000111
Figure FDA0002736434810000121
Figure FDA0002736434810000121
Figure FDA0002736434810000131
Figure FDA0002736434810000131
Figure FDA0002736434810000141
Figure FDA0002736434810000141
Figure FDA0002736434810000151
Figure FDA0002736434810000151
Figure FDA0002736434810000161
Figure FDA0002736434810000161
Figure FDA0002736434810000171
Figure FDA0002736434810000171
Figure FDA0002736434810000181
Figure FDA0002736434810000181
Figure FDA0002736434810000191
Figure FDA0002736434810000191
Figure FDA0002736434810000201
Figure FDA0002736434810000201
Figure FDA0002736434810000211
Figure FDA0002736434810000211
Figure FDA0002736434810000221
Figure FDA0002736434810000221
Figure FDA0002736434810000231
Figure FDA0002736434810000231
Figure FDA0002736434810000241
Figure FDA0002736434810000241
Figure FDA0002736434810000251
Figure FDA0002736434810000251
Figure FDA0002736434810000261
Figure FDA0002736434810000261
Figure FDA0002736434810000271
Figure FDA0002736434810000271
Figure FDA0002736434810000281
Figure FDA0002736434810000281
Figure FDA0002736434810000291
Figure FDA0002736434810000291
Figure FDA0002736434810000301
Figure FDA0002736434810000301
Figure FDA0002736434810000311
Figure FDA0002736434810000311
Figure FDA0002736434810000321
Figure FDA0002736434810000321
Figure FDA0002736434810000331
Figure FDA0002736434810000331
Figure FDA0002736434810000341
Figure FDA0002736434810000341
Figure FDA0002736434810000351
Figure FDA0002736434810000351
Figure FDA0002736434810000361
Figure FDA0002736434810000361
Figure FDA0002736434810000371
Figure FDA0002736434810000371
Figure FDA0002736434810000381
Figure FDA0002736434810000381
Figure FDA0002736434810000391
Figure FDA0002736434810000391
Figure FDA0002736434810000401
Figure FDA0002736434810000401
Figure FDA0002736434810000411
Figure FDA0002736434810000411
Figure FDA0002736434810000421
Figure FDA0002736434810000421
Figure FDA0002736434810000431
Figure FDA0002736434810000431
Figure FDA0002736434810000441
Figure FDA0002736434810000441
Figure FDA0002736434810000451
Figure FDA0002736434810000451
Figure FDA0002736434810000461
Figure FDA0002736434810000461
Figure FDA0002736434810000471
Figure FDA0002736434810000471
Figure FDA0002736434810000481
Figure FDA0002736434810000481
Figure FDA0002736434810000491
Figure FDA0002736434810000491
Figure FDA0002736434810000501
Figure FDA0002736434810000501
Figure FDA0002736434810000511
Figure FDA0002736434810000511
Figure FDA0002736434810000521
Figure FDA0002736434810000521
Figure FDA0002736434810000531
Figure FDA0002736434810000531
Figure FDA0002736434810000541
Figure FDA0002736434810000541
Figure FDA0002736434810000551
Figure FDA0002736434810000551
Figure FDA0002736434810000561
Figure FDA0002736434810000561
Figure FDA0002736434810000571
Figure FDA0002736434810000571
Figure FDA0002736434810000581
Figure FDA0002736434810000581
Figure FDA0002736434810000591
Figure FDA0002736434810000591
Figure FDA0002736434810000601
Figure FDA0002736434810000601
Figure FDA0002736434810000611
Figure FDA0002736434810000611
Figure FDA0002736434810000621
Figure FDA0002736434810000621
Figure FDA0002736434810000631
Figure FDA0002736434810000631
Figure FDA0002736434810000641
Figure FDA0002736434810000641
Figure FDA0002736434810000651
Figure FDA0002736434810000651
Figure FDA0002736434810000661
Figure FDA0002736434810000661
5.根据权利要求1所述的有机发光器件,其中,所述化学式3选自下述结构式:5. The organic light-emitting device according to claim 1, wherein the chemical formula 3 is selected from the following structural formulas:
Figure FDA0002736434810000671
Figure FDA0002736434810000671
Figure FDA0002736434810000681
Figure FDA0002736434810000681
Figure FDA0002736434810000691
Figure FDA0002736434810000691
Figure FDA0002736434810000701
Figure FDA0002736434810000701
Figure FDA0002736434810000711
Figure FDA0002736434810000711
Figure FDA0002736434810000721
Figure FDA0002736434810000721
Figure FDA0002736434810000731
Figure FDA0002736434810000731
Figure FDA0002736434810000741
Figure FDA0002736434810000741
Figure FDA0002736434810000751
Figure FDA0002736434810000751
Figure FDA0002736434810000761
Figure FDA0002736434810000761
Figure FDA0002736434810000771
Figure FDA0002736434810000771
Figure FDA0002736434810000781
Figure FDA0002736434810000781
Figure FDA0002736434810000791
Figure FDA0002736434810000791
Figure FDA0002736434810000801
Figure FDA0002736434810000801
Figure FDA0002736434810000811
Figure FDA0002736434810000811
Figure FDA0002736434810000821
Figure FDA0002736434810000821
Figure FDA0002736434810000831
Figure FDA0002736434810000831
Figure FDA0002736434810000841
Figure FDA0002736434810000841
Figure FDA0002736434810000851
Figure FDA0002736434810000851
6.根据权利要求1所述的有机发光器件,其中,由所述化学式1表示的化合物和由所述化学式3表示的化合物满足下述式1:6 . The organic light-emitting device according to claim 1 , wherein the compound represented by the chemical formula 1 and the compound represented by the chemical formula 3 satisfy the following formula 1: 式1Formula 1 EEt>EEc E Et >E Ec 在所述式1中,In the formula 1, EEt为由所述化学式3表示的化合物的电子亲和势(eV),EEc为由所述化学式1表示的化合物的电子亲和势(eV)。E Et is the electron affinity (eV) of the compound represented by the Chemical Formula 3, and E Ec is the electron affinity (eV) of the compound represented by the Chemical Formula 1. 7.根据权利要求1所述的有机发光器件,其中,所述第一有机物层为空穴阻挡层或电子调节层。7. The organic light-emitting device of claim 1, wherein the first organic layer is a hole blocking layer or an electron regulating layer. 8.根据权利要求1所述的有机发光器件,其中,所述第二有机物层为电子传输层或电子注入和传输层。8. The organic light-emitting device of claim 1, wherein the second organic layer is an electron transport layer or an electron injection and transport layer. 9.根据权利要求1所述的有机发光器件,其中,所述有机发光器件在所述第一电极与所述第二电极之间包括发射彼此不同的波长范围的光的2层以上的发光层。9 . The organic light-emitting device according to claim 1 , wherein the organic light-emitting device includes, between the first electrode and the second electrode, two or more light-emitting layers that emit light in wavelength ranges different from each other. 10 . . 10.根据权利要求1所述的有机发光器件,其中,所述有机发光器件在所述第一电极与所述第二电极之间包括2层以上的发光层,以及10. The organic light-emitting device of claim 1, wherein the organic light-emitting device comprises two or more light-emitting layers between the first electrode and the second electrode, and 各个发光层独立地包含荧光性掺杂剂或磷光性掺杂剂。Each light-emitting layer independently contains a fluorescent dopant or a phosphorescent dopant. 11.根据权利要求1所述的有机发光器件,其中,所述有机发光器件在所述第一电极与所述第二电极之间包括2层以上的发光层,以及11. The organic light-emitting device of claim 1, wherein the organic light-emitting device comprises two or more light-emitting layers between the first electrode and the second electrode, and 任一层发光层包含荧光性掺杂剂,并且另一层发光层包含磷光性掺杂剂。Either one of the light-emitting layers contains a fluorescent dopant, and the other light-emitting layer contains a phosphorescent dopant. 12.根据权利要求1所述的有机发光器件,其中,所述有机发光器件在所述第一电极与所述第二电极之间包括3层以上的发光层,以及12. The organic light-emitting device of claim 1, wherein the organic light-emitting device comprises three or more light-emitting layers between the first electrode and the second electrode, and 各个发光层包括蓝色荧光发光层。Each light-emitting layer includes a blue fluorescent light-emitting layer. 13.根据权利要求12所述的有机发光器件,其中,所述3层以上的发光层依次沿所述第一电极到所述第二电极的方向进行设置。13 . The organic light-emitting device according to claim 12 , wherein the three or more light-emitting layers are sequentially arranged along the direction from the first electrode to the second electrode. 14 .
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