WO2017104994A1 - Composition pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé - Google Patents

Composition pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé Download PDF

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WO2017104994A1
WO2017104994A1 PCT/KR2016/013480 KR2016013480W WO2017104994A1 WO 2017104994 A1 WO2017104994 A1 WO 2017104994A1 KR 2016013480 W KR2016013480 W KR 2016013480W WO 2017104994 A1 WO2017104994 A1 WO 2017104994A1
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ring
layer
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organic
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장재완
김슬기
김원삼
박보람
최승원
하종진
이학영
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DukSan Neolux Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to the light emitting colors.
  • a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • Efficiency, lifespan, and driving voltage are related to each other, and as the efficiency increases, the driving voltage is relatively decreased, and as the result, the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases. It shows a tendency to increase the life.
  • simply improving the organic material layer does not maximize the efficiency. This is because a long lifetime and high efficiency can be simultaneously achieved when an optimal combination of energy level and T 1 value between each organic material layer, intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved. Therefore, there is a need for the development of a light emitting material capable of achieving an efficient charge balance in the light emitting layer.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • a stable and efficient material is supported by a stable and efficient material. It should be preceded, but the development of a stable and efficient organic material layer for an organic electric device has not been made enough. Therefore, the development of new materials is continuously required, and in particular, the development of the host material of the light emitting layer is urgently required.
  • An object of the present invention is to provide a compound capable of lowering the driving voltage of the device and improving the luminous efficiency, color purity and lifetime of the device, an organic electric device using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • the compound according to the embodiment of the present invention not only can the driving voltage of the device be lowered, but the luminous efficiency, color purity, and lifetime of the device can be greatly improved.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • first, second, A, B, (a), and (b) can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It should be understood that the elements may be “connected”, “coupled” or “connected”.
  • a component such as a layer, film, region, plate, etc.
  • it is not only when the other component is “on top of” but also another component in between. It is to be understood that this may also include cases.
  • a component is said to be “directly above” another part, it should be understood to mean that there is no other part in the middle.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • fluorenyl group or “fluorenylene group” means a monovalent or divalent functional group in which R, R 'and R “are all hydrogen in the following structures, unless otherwise stated, and" Substituted fluorenyl group “or” substituted fluorenylene group “means that at least one of the substituents R, R ', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a carbon It includes the case of forming a compound by spying together.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • the aryl group or arylene group includes monocyclic, ring aggregate, conjugated ring system, spiro compound and the like.
  • heterocyclic group includes not only aromatic rings, such as “heteroaryl groups” or “heteroarylene groups,” but also non-aromatic rings, and each carbon number includes one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom refers to N, O, S, P or Si unless otherwise indicated, and heterocyclic groups are monocyclic, ring aggregates, conjugated multiple ring systems, spies, including heteroatoms. Means a compound or the like.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • ring includes monocyclic and polycyclic rings, includes hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and nonaromatic rings.
  • polycyclic includes ring assemblies, fused multiple ring systems and spiro compounds, such as biphenyl, terphenyl, and the like, including aromatics as well as nonaromatics, hydrocarbons
  • the ring as well includes heterocycles comprising at least one heteroatom.
  • ring assemblies means that two or more ring systems (single or conjugated ring systems) are directly connected to each other through a single bond or a double bond and directly between such rings. It means that the number of linkages is one less than the total number of ring systems in this compound. Ring aggregates may have the same or different ring systems directly connected to each other via a single bond or a double bond.
  • conjugated multiple ring systems refers to a covalently fused ring form of at least two atoms, including a ring system in which two or more hydrocarbons are fused together and at least one heteroatom. And heterocyclic systems having at least one conjugated form. These conjugated several ring systems can be aromatic rings, heteroaromatic rings, aliphatic rings or combinations of these rings.
  • spiro compound has a "spiro union", and a spiro linkage means a linkage formed by two rings sharing one atom only.
  • atoms shared by the two rings are called spiro atoms, and according to the number of spiro atoms in a compound, they are respectively referred to as 'monospyro-', 'diespyro-' and 'trispyro-' It is called a compound.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group
  • an alkenyl group substituted with an arylcarbonyl group is used herein.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • substituted in the term “substituted or unsubstituted” refers to deuterium, halogen, amino groups, nitrile groups, nitro groups, C 1 -C 20 alkyl groups, C 1 -C 20 alkoxy group, C 1 -C 20 alkylamine group, C 1 -C 20 alkylthiophene group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl group, C 6 -C 20 aryl group, of a C 6 -C 20 aryl group substituted with a heavy hydrogen, C 8 -C 20 aryl alkenyl group, a silane group, a boron Substituted by at least one substituent selected from the group consisting of a group, a germanium group, and a C 2 -C 20
  • the group name corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified in each symbol and examples of the substituents in this specification may describe 'the name of the group reflecting the singer', but is described as 'the parent compound name'. You may. For example, in the case of phenanthrene, which is a kind of aryl group, the monovalent group is phenanthryl and the divalent group may be grouped with a singer, such as phenanthryl, to describe the group name. Regardless, it may be described as the parent compound name 'phenanthrene'.
  • pyrimidine it may be described as 'pyrimidine' irrespective of the valence, or as the 'name of the group' of the singer, such as pyrimidinyl group in the case of monovalent and pyrimidinylene in the case of divalent. have.
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • an organic electric device 100 may include a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110.
  • An organic material layer including the compound according to the present invention is provided between the two electrodes 180.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence.
  • at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like. It may also serve as a hole blocking layer.
  • the organic electronic device further includes a protective layer or a light efficiency improving layer formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer. can do.
  • Compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170, a host or dopant material of the light emitting layer 150, or a material of the light efficiency improving layer.
  • the compound of the present invention may be used as the material of the light emitting layer 150, the hole transport layer 140 and / or the light emitting auxiliary layer 151, preferably may be used as a material of the light emitting layer 150.
  • the intrinsic properties (mobility, interfacial characteristics, etc.) of the organic organic device can improve the service life and efficiency at the same time.
  • the organic electroluminescent device may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD.
  • the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130 thereon.
  • the organic material layer including a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170 By forming an organic material layer including a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170, and then depositing a material that can be used as the cathode 180 thereon have.
  • the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150
  • an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
  • the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to an embodiment of the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the organic electroluminescent device may be one of an organic electroluminescent device, an organic solar cell, an organic photosensitive member, an organic transistor, a monochromatic or white illumination device.
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • X 1 is S, O, C (R 4 ) (R 5 ) or Si (R ′) (R ′′).
  • R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An alkyl group of C 1 -C 50 ; A fused ring group of an aromatic ring of C 6 -C 60 and an aliphatic ring of C 3 -C 60 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And combinations thereof may be selected from the group.
  • R 1 to R 3 is an aryl group, preferably an aryl group of C 6 -C 30 , more preferably an aryl group of C 6 -C 18 , and exemplarily phenyl, biphenyl, naphthyl, triphenyl Ren and the like.
  • R 1 to R 3 are heterocyclic groups, preferably C 2 -C 30 heterocyclic group, more preferably C 2 -C 12 It may be a heterocyclic group, for example pyridine, pyrimidine, quinazoline , Benzoquinazolin, carbazole, benzocarbazole, dibenzocarbazole, dibenzofuran, dibenzothiophene, benzofurypyrimidine, benzophenanthrothiophene, benzophenanthrofuran, benzothiopyrimidine, etc. have.
  • R 1 to R 3 When R 1 to R 3 is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorene, if halogen may be fluorine, if alkyl group may be tert-butyl group, if it is an alkenyl group ethene It may be a diary or, in the case of an alkoxy group, may be methoxy.
  • R 1 to R 3 may independently form neighboring groups or R 2 and R 3 may be bonded to each other to form at least one ring. That is, adjacent R 1 , adjacent R 2 , adjacent R 3 , or R 2 and R 3 may be bonded to each other to form a ring, wherein the formed ring is a C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; And combinations thereof. For example, they may be bonded to each other to form a ring such as benzene or naphthalene, and in particular, R 2 and R 3 may be bonded to each other to form benzene or naphthalene.
  • R ⁇ 1> -R ⁇ 3> may be the same or different, respectively.
  • R 4 , R 5 , R 'and R'' Are independently of each other, hydrogen; heavy hydrogen; An alkyl group of C 1 -C 50 ; Of C 2 -C 30 Alkenyl groups; An alkynyl group of C 2 -C 30 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; Silyl groups of C 1 -C 30 ; C 6 -C 60 aryl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl group; And -L'-N (R a ) (R b ).
  • R 4 , R 5 , R 'and R'' Are independently of each other, hydrogen; heavy hydrogen; C 1 -C 30 alkyl group; C 6 -C 30 aryloxy group; Aryl group of C 6 -C 30 ; C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And fluorenyl groups; And the like.
  • R 4 , R 5 , R 'and R'' May independently be hydrogen, a methyl group, a phenyl group, a fluorenyl group, or the like.
  • R 4 and R 5 may be bonded to each other to form a ring, and R ′ and R ′′ may also be bonded to each other to form a ring.
  • L ' is a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; And a C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P.
  • R a and R b are each independently a C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An alkyl group of C 1 -C 50 ; A fused ring group of an aromatic ring of C 6 -C 60 and an aliphatic ring of C 3 -C 60 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; And an aryloxy group of C 6 -C 30 It can be selected from the group consisting of.
  • a ring formed by bonding, and a ring formed by bonding of R 2 and R 3 to each other is deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Of C 6 -C 20 Aryl group; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -C 20 hetero
  • Formula 1 may be represented by the following formula (2) or (3).
  • R 1 to R 3 , 1, m, n and X 1 are the same as defined in Chemical Formula 1.
  • s and u are each an integer of 0-4, t and v are each an integer of 0-6, s + t is an integer of 1 or more, u + v is an integer of 1 or more.
  • L 2 to L 5 are independently of each other, a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; And a C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; And combinations thereof may be selected from the group.
  • L 2 to L 5 are independently of each other a single bond; C 6 -C 30 arylene group; Fluorenylene groups; And a C 2 -C 30 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; And the like.
  • L 2 to L 5 is a single bond, phenyl, biphenyl, fluorene, carbazole, pyridine, pyrimidine, triazine, benzocarbazole, dibenzocarbazole, quinazoline, acenaphthobenzofuran, acenaph Tobenzothiophene and the like.
  • X 2 and X 3 may be independently of each other N, NL 1 -Ar 1 , O, S, C (R 10 ) (R 11 ) or Si (R 18 ) (R 19 ).
  • X 2 when X 2 is N, it may be connected to L 2
  • X 3 when X 3 is N, it may be connected to L 3 .
  • R 6 to R 9 , and R 12 to R 17 are each independently hydrogen; heavy hydrogen; halogen; C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An alkyl group of C 1 -C 50 ; A fused ring group of an aromatic ring of C 6 -C 60 and an aliphatic ring of C 3 -C 60 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; -L'-N (R a ) (R b ); And combinations thereof may be selected from the group.
  • R 6 to R 9 and R 12 to R 17 may combine with each other to form at least one ring.
  • a, b, c, d, e, f, o, p, q, and r are each an integer of 0-4.
  • L 1 is a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And combinations thereof may be selected from the group.
  • L 1 is a single bond independently from each other; C 6 -C 30 arylene group; Fluorenylene groups; And a C 2 -C 30 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; And the like.
  • L 1 is a single bond, phenyl, biphenyl, fluorene, carbazole, pyridine, pyrimidine, triazine, benzocarbazole, dibenzocarbazole, quinazoline, acenaphthobenzofuran, acenaphthobenzocyse Ore, etc.
  • Ar 1 is a C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; -L'-N (R a ) (R b ); An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And combinations thereof may be selected from the group.
  • an aryl group of C 6 -C 30 Fluorenyl group; C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; -L'-N (R a ) (R b ); And the like.
  • Ar 1 is a phenyl group, biphenyl group, triphenylene group, ferenyl group, phenanthryl group, fluorenyl group, spirofluorenyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinazolyl group, benzoquinazolyl group , Dibenzoquinazolyl group, dibenzothienyl group, dibenzofuryl group, benzofuropyrimidyl group, naphthopuropyrimidyl group, benzothienopyrimidyl group, carbazole group, benzocarbazole group and the like.
  • R 10 , R 11 , R 18 and R 19 are each independently hydrogen; heavy hydrogen; An alkyl group of C 1 -C 50 ; Of C 2 -C 30 Alkenyl groups; An alkynyl group of C 2 -C 30 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; Silyl groups of C 1 -C 30 ; C 6 -C 60 aryl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl group; -L'-N (R a ) (R b ); And combinations thereof may be selected from the group.
  • R 10 , R 11 , R 18 and R 19 are, independently from each other, hydrogen; heavy hydrogen; C 1 -C 30 alkyl group; C 6 -C 30 aryloxy group; Aryl group of C 6 -C 30 ; C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And fluorenyl groups; And the like.
  • R 10 , R 11 , R 18 and R 19 are each independently of the other hydrogen; Methyl group, phenyl group, fluorenyl group and the like.
  • R 10 and R 11 may be bonded to each other to form a ring, wherein spiro compounds may be formed together with carbon (C) to which they are bonded.
  • R 18 and R 19 may be bonded to each other to form a ring, and at this time, a spiro compound may be formed together with silicon (Si) to which they are bonded.
  • L ′, R a and R b are the same as defined in Chemical Formula 1.
  • Ar 1 may be one of the following structural formulas Z-1 to Z-8.
  • Z 1 to Z 70 may be each independently C, C (R c ) or N, wherein C in Z 1 to Z 70 is bonded to L 1 of Formula 2 Can be.
  • one of Z 1 to Z 6 of formula Z-1 may be C, at least the other may be N, one of Z 7 to Z 14 of formula Z-2 is C, and at least the other is N And one of Z 15 to Z 24 of Formula Z-3 may be C, and at least the other may be N, one of Z 25 to Z 34 of Formula Z-4 is C, and at least the other is N And one of Z 35 to Z 44 of Formula Z-5 may be C, and at least the other may be N.
  • One of Z 45 to Z 56 of Formula Z-6 is C, and at least the other is N And one of Z 57 to Z 62 of Formula Z-7 may be C, and at least the other may be N.
  • One of Z 63 to Z 70 of Formula Z-8 is C, and at least the other is N Can be.
  • R c is hydrogen; heavy hydrogen; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 30 ; An alkynyl group of C 2 -C 30 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; A silyl group of C 1 -C 30; C 6 -C 60 aryl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl group; -L'-N (R a ) (R b ); And combinations thereof.
  • R c is an aryl group of C 6 -C 30 ; C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And fluorenyl groups; And the like.
  • R c is a phenyl group, naphthyl group, biphenyl group, pyrenyl group, pyridyl group, pyrimidinyl group, triazineyl group, indole group, dibenzothienyl group, carbazole group, dibenzofuryl group, dibenzoquinazolyl group, benzo Quinazolyl group, fluorenyl group, spirobifluorenyl group, and the like.
  • R c may be bonded to each other adjacent groups to form at least one ring selectively.
  • W 1 to W 3 may be selected from the group consisting of a single bond, C (R d ) (R e ), N-Ar 2 , O, S, and Si (R f ) (R g ).
  • R d to R g are each independently hydrogen; heavy hydrogen; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 30 ; An alkynyl group of C 2 -C 30 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; Silyl groups of C 1 -C 30 ; C 6 -C 60 aryl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl group; -L'-N (R a ) (R b ); And combinations thereof may be selected from the group.
  • R d to R g are each independently hydrogen; An alkyl group of C 1 -C 30 ; Aryl group of C 6 -C 30 ; And fluorenyl groups; And the like.
  • R d to R g may be each independently hydrogen, a methyl group, a phenyl group, a fluorenyl group, or the like.
  • R d and R e may be bonded to each other to form a ring, wherein a spiro compound may be formed together with carbon (C) to which they are bonded.
  • R f With R g May be bonded to each other to form a ring, and together with the silicon (Si) to which they are bonded, a spiro compound may be formed.
  • L ′, R a , and R b are the same as defined in Formula 1, and Ar 2 may be defined the same as Ar 1 defined in Formula 2.
  • the compound represented by Formula 1 may be one of the following compounds.
  • the present invention provides a compound for an organic electric device represented by Chemical Formula 1.
  • the present invention provides an organic electric device containing the compound represented by the formula (1).
  • the organic electric element includes a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode.
  • the organic material layer may include a compound represented by Chemical Formula 1, and Chemical Formula 1 may include a hole injection layer, a hole transport layer, a light emitting auxiliary layer, It may be contained in at least one layer of the light emitting layer, the electron transport auxiliary layer, the electron transport layer, it may be included as a component of one kind of a compound or two or more kinds. That is, the compound represented by Formula 1 may be used as a material of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer and / or an electron transport layer.
  • the compound represented by Formula 1 may be used as a phosphorescent host material of the light emitting layer.
  • the present invention is an optical efficiency improvement layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer It provides an organic electric element further comprising.
  • the compounds (final products) according to the present invention are prepared using Sub 2 as in Scheme 1, but are not limited thereto.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Triphenylen-2-ylboronic acid (3.0 g, 11.04 mmol), Sub 2-I-56 (7.80 g, 11.04 mmol), Pd (PPh 3 ) 4 (0.38 g, 0.33 mmol), K 2 CO 3 (4.58 g, 33.11 mmol), THF (49 mL) and water (24 mL) were obtained using 6.79 g of the product using the synthesis method of M 1-I-1 (yield: 72%).
  • the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto.
  • the compound belonging to Sub 2 may be the following compounds, but is not limited thereto.
  • Table 1 shows FD-MS values of some compounds belonging to Sub 2.
  • An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention as a light emitting host material of a light emitting layer.
  • a 4,4 ', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine (abbreviated as "2-TNATA”) film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate.
  • a 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviated as "NPD”) membrane was formed as a hole transport compound on the hole injection layer to a thickness of 60 nm.
  • Vacuum deposition was performed to form a hole transport layer.
  • Compound 1-14 of the present invention was used as a host on the hole transport layer, and bis- (1-phenylisoquinoline) iridium (III) acetylacetonate (abbreviated as "(piq) 2 Ir (acac)”) was used as a dopant material.
  • the light emitting layer was deposited to a thickness of 30 nm by doping at a weight ratio of 5: 5.
  • BAlq (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum
  • BAlq 2-methyl-8-quinolinolato
  • Alq 3 8-hydroxyquinoline aluminum
  • LiF which is an alkali metal halide
  • Al was deposited to a thickness of 150 nm to prepare an organic electroluminescent device.
  • Examples 2 to 20 are the same as in Example 1 except that each compound of the present invention shown in Table 3 is used instead of compound 1-14 according to the embodiment of the present invention as a red host material of the emission layer.
  • An organic electroluminescent device was manufactured by the method.
  • Comparative Examples 1 to 3 are organic in the same manner as in Example 1, except for using the following Comparative Compound 1 to Comparative Compound instead of Compound 1-14 according to the Example of the present invention as a host material of the emission layer. An electroluminescent device was prepared.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 1 to 20 and Comparative Examples 1 to 3 of the present invention
  • the T95 lifetime was measured using a McScience Life Measurement Equipment at 2500 cd / m 2 reference luminance, and the measurement results are shown in Table 3 below.
  • the organic electroluminescent device using the compound according to an embodiment of the present invention as a phosphorescent host material can significantly improve the luminous efficiency, driving voltage and lifetime.
  • a compound having a core having the same structure as that of Comparative Compound 2 or 3 showed better device results than that of Comparative Compound 1, which is CBP, which is used as a general host material.
  • Compounds according to an embodiment of the present invention showed the best device results with the lowest driving voltage, maximizing efficiency and lifetime.
  • the LUMO energy value is relatively low, thereby easily receiving electrons into the electron transporting layer. It is believed that improving the charge balance results in lower driving voltages, higher efficiency and longer lifetime. Therefore, this suggests that while the heterocyclic group having the ET property is substituted in the core of the present invention, the chemical and physical properties may be significantly changed.
  • An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention as a light emitting host material of a light emitting layer.
  • a 2-TNATA film is vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm.
  • the NPD film is vacuum-deposited at a thickness of 60 nm as a hole transport compound on the hole injection layer.
  • a transport layer was formed.
  • Compound 1-1 of the present invention was used as a host on the hole transport layer, and a dopant material was doped with tris (2-phenylpyridine) -iridium (abbreviated as "Ir (ppy) 3 ") at a 95: 5 weight ratio of 30 nm thick.
  • the light emitting layer was deposited by.
  • BAlq was vacuum-deposited to a thickness of 10 nm with a holdoff layer, and Alq 3 was formed into a thickness of 40 nm with an electron transport layer.
  • LiF which is an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to prepare an organic electroluminescent device.
  • Examples 22 to 38 are the same as in Example 21, except that each compound of the present invention shown in Table 4 was used instead of Compound 1-1 according to the embodiment of the present invention as a green host material of the emission layer.
  • An organic electroluminescent device was manufactured by the method.
  • Comparative Examples 4 to 6 were organic in the same manner as in Example 21, except that Comparative Compound 1 to Comparative Compound were used instead of Compound 1-1 according to the Example of the present invention, respectively, as a host material of the emission layer.
  • An electroluminescent device was prepared.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 21 to 38 and Comparative Examples 4 to 6 of the present invention
  • the T95 lifetime was measured using McScience's life measurement equipment at 5000 cd / m 2 reference luminance, and the measurement results are shown in Table 4 below.
  • the organic electroluminescent device using the organic light emitting device material of the present invention as a green phosphorescent host material has a lower driving voltage, higher luminous efficiency and longer life than Comparative Examples 4 to 6. I could confirm it.
  • Comparative Compound 2 or 3 showed better device results than Comparative Compound 1, which is a CBP used as a general host material, and the present invention is substituted with another substituent on the core of Comparative Compound 2 or 3.
  • Compounds according to the embodiment of the present invention showed the best device results with the lowest driving voltage, efficiency and lifetime are maximized.
  • the device characteristics were described in terms of the light emitting layer.
  • materials generally used as the light emitting layer include organic electron devices such as the electron transport layer, the electron injection layer, the hole injection layer, the hole transport layer, and the light emitting auxiliary layer. It can be used in combination with a single or other material as an organic layer of. Therefore, the compounds of the present invention can be used in a single or other materials mixed with other organic material layers, for example, electron transport layer, electron injection layer, hole injection layer, hole transport layer and light emitting auxiliary layer in addition to the light emitting layer.
  • a 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate as a hole injection layer to form a thickness of 60 nm.
  • an NPD film was vacuum deposited to a thickness of 60 nm as a hole transport compound on the hole injection layer to form a hole transport layer.
  • the light emitting layer was deposited to a thickness of 30 nm by doping the compound of the present invention as a host material on the hole transport layer with a weight ratio of 95: 5 of Ir (ppy) 3 as a dopant material. 1-44 was used by mixing in 50:50 weight ratio.
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and an electron transport layer having a thickness of 40 nm on Alq 3 was formed on the hole blocking layer.
  • LiF which is an alkali metal halide
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then, an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • Example 40 to [ Example 42] Green Organic Light Emitting Diode ( Light emitting layer Mixed phosphorescent host)
  • Examples 40 to 42 are organic electroluminescent in the same manner as in Example 39, except that each compound of the present invention shown in Table 5 is used instead of the compound 1-44 of the present invention as a host material of the emission layer. The device was manufactured.
  • Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 39 to 42 of the present invention, 5000cd / m 2
  • the T95 life was measured using McScience's life measurement equipment at the reference luminance, and the measurement results are shown in Table 5 below.
  • Table 5 shows the results of device measurements using Compound 1-11 of the present invention as two mixed phosphorescent host materials.
  • the compound of the present invention of the wide band gap-type of the present invention introduced the compound 1-11 (Example 23) of the low band gap-type and triphenylene group showed the most excellent device measurement results
  • the combination of -44, 1-45, 2-38, and 2-39 as two phosphorescent host materials resulted in greater efficiency and lifetime when two mixed host materials were used than when a single host material was used. It can be seen that it can be further improved.
  • the band gap and T1 values can be finely adjusted than in the case of a single host material, and thus, electrons and holes are efficiently transferred to the dopant, thereby increasing efficiency.
  • the lifespan also increases.

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Abstract

La présente invention concerne : un composé représenté par la formule chimique 1 ; un élément électronique organique comprenant une première électrode, une seconde électrode et une couche organique entre la première électrode et la seconde électrode ; et un dispositif électronique le comprenant, le composé représenté par la formule chimique 1 étant contenu dans la couche organique, ce qui permet de diminuer la tension de commande de l'élément électronique organique et d'améliorer l'efficacité lumineuse et la durée de vie.
PCT/KR2016/013480 2015-12-16 2016-11-22 Composition pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé Ceased WO2017104994A1 (fr)

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CN108864068A (zh) * 2018-07-27 2018-11-23 上海天马有机发光显示技术有限公司 一种化合物以及有机发光显示装置
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CN109988155A (zh) * 2019-01-16 2019-07-09 浙江华显光电科技有限公司 一种磷光主体化合物及其使用该化合物的有机电致发光器件
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CN115819410A (zh) * 2022-12-08 2023-03-21 长春海谱润斯科技股份有限公司 一种杂环衍生物及其有机发光器件
CN115819410B (zh) * 2022-12-08 2025-10-10 长春海谱润斯科技股份有限公司 一种杂环衍生物及其有机发光器件

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