WO2019143108A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

Info

Publication number
WO2019143108A1
WO2019143108A1 PCT/KR2019/000611 KR2019000611W WO2019143108A1 WO 2019143108 A1 WO2019143108 A1 WO 2019143108A1 KR 2019000611 W KR2019000611 W KR 2019000611W WO 2019143108 A1 WO2019143108 A1 WO 2019143108A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
aryl
formula
different
same
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2019/000611
Other languages
English (en)
Korean (ko)
Inventor
한송이
엄민식
홍진석
박정근
손효석
이용환
박우재
심재의
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Doosan Corp
Original Assignee
Doosan Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020180165795A external-priority patent/KR102792712B1/ko
Application filed by Doosan Corp filed Critical Doosan Corp
Publication of WO2019143108A1 publication Critical patent/WO2019143108A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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

Definitions

  • the present invention relates to an organic electroluminescent device having improved characteristics such as high luminous efficiency, low driving voltage and long life time by using at least one kind of host material having an electronic characteristic and at least one kind of host material having a hole characteristic as a light emitting layer component .
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.
  • the light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color.
  • yellow and orange light emitting materials are also used as light emitting materials for realizing better color.
  • a host / dopant system can be used as a light emitting material.
  • the dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as materials used for the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer, and the anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material .
  • Ir as a phosphorescent material that has a great advantage in improving the efficiency aspects of the light-emitting material (ppy) 3, (acac) Ir (btp) 2
  • Ir metal complex compound is a blue, green and red host material that includes such as . So far, CBP has shown excellent properties as a phosphorescent host material.
  • Patent Document 1 Japanese Laid-Open Patent Publication No. 2001-160489
  • the present invention has been conceived in order to solve the above-described problems, and more specifically, a host material having electron characteristics and a host material having hole characteristics as a light emitting layer component are mixed to exhibit high luminous efficiency and low driving voltage, And an object of the present invention is to provide an organic electroluminescent device.
  • a negative electrode disposed opposite to the positive electrode; And a light-emitting layer interposed between the anode and the cathode, wherein the light-emitting layer comprises at least one first compound represented by the following general formula (1); And at least one second compound represented by the following general formula (2).
  • X 1 and X 2 are the same as or different from each other and each independently O or S,
  • Y 1 to Y 16 are the same as or different from each other, and each independently CR 8 or N, provided that when there are a plurality of CR 8 s , the plurality of R 8 s are the same as or different from each other,
  • Z 1 to Z 3 are the same or different and each independently CR 5 or N, at least one of them is N,
  • Ar 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cycloalkyl, A C 6 to C 60 aryl group,
  • n are each an integer of 0 to 3, m + n? 1,
  • a and B are the same or different from each other and are each independently any one of the substituents represented by the following formulas (1a) to (1c);
  • X 3 is a single bond, or O or S,
  • L is a single bond or an arylene group having 6 to 40 carbon atoms
  • Ar 2 and Ar 3 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ , or selected from the group consisting of C 60 aryl amine, with or adjacent groups bonded may form a condensed ring,
  • a, c, and f are each an integer of 0 to 3
  • b, d and e are each an integer of 0 to 4, wherein b + m? 4, d + n? 4,
  • R 1 to R 8 are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 An alkynyl group, a C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyl A C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting of an
  • L 1 and L 2 are the same or different and are each independently a single bond or a group selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms,
  • Ar 21 and Ar 22 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group A C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine pingi, C 6 ⁇ C 60 aryl phosphine oxide is selected from the group and a C 6 ⁇ C 60 aryl amine group of;
  • R 21 and R 22 are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ⁇ heteroaryl group of C 60 aryl group, the nuclear atoms of 5 to 60, C 1 ⁇ alkyloxy of C 40, C 6 ⁇ C 60 of the aryloxy group, an alkyl boronic of C 1 ⁇ C 40 alkyl silyl group, the group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 group, C 6 ⁇ An aryl boron group of C 60 , a phosphine group of C 1 to C 40 , a phosphine oxide group of C 1 to
  • n are each independently an integer of 0 to 4,
  • the present invention provides an organic electroluminescent device having high light emitting characteristics, low driving voltage and long life characteristics at the same time by mixing a host having excellent electron transporting ability and injecting ability as a light emitting layer component, and a host having a hole transporting ability and an excellent injection ability can do. Further, a full color display panel having improved performance and lifetime can be manufactured.
  • FIG. 1 is a cross-sectional view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.
  • organic electroluminescent device A organic layer
  • the present invention relates to a positive electrode; cathode; And at least one organic compound layer interposed between the anode and the cathode, the organic compound layer including a hole transporting region, a light emitting layer and an electron transporting region, wherein at least one first compound represented by Formula 1 and the second compound represented by Formula 2 < / RTI > of at least one second compound.
  • excitons are generated while electrons generated at the cathode and holes generated at the anode meet and recombine, and light is emitted while the exciton transitions to the ground state. Since the luminous efficiency of the organic electroluminescent device is proportional to the number of the excitons formed in the light emitting layer, in order to maximize the luminous efficiency of the device, it is required that as many excitons as possible exist in the light emitting layer.
  • the present invention is characterized in that at least two kinds of hosts (for example, a first host) having a specific structure having an electronic characteristic and a host having a hole characteristic (for example, a second host) do.
  • a first host having a specific structure having an electronic characteristic
  • a host having a hole characteristic for example, a second host
  • the ability to receive electrons and holes from each host is relatively large, and thus exciton generation is performed more smoothly.
  • the more the excitons are formed in the light emitting layer the more effective the device and the lifetime are increased.
  • the organic electroluminescent device using one kind of host or two kinds of host compared with the organic electroluminescent device including the conventional light emitting host material (for example, CBP) can be manufactured. Further, a full color display panel having improved high efficiency and long life characteristics can also be manufactured.
  • An organic electroluminescent device includes a light emitting layer comprising at least one first compound represented by Formula 1 and at least one second compound represented by Formula 2.
  • the first compound and the second compound are mixed in a host material (phosphorescent host) of the light emitting layer.
  • FIG. 1 is a view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode 10; A cathode 20; And a light emitting layer 40 positioned between the anode 10 and the cathode 20.
  • the organic electroluminescent device 100 includes a hole transport region 30 disposed between the anode 10 and the light emitting layer 40; And an electron transporting region 50 disposed between the light emitting layer 40 and the cathode 20 and preferably includes at least one of a hole transporting region 30 and an electron transporting region 50 .
  • the anode 10 serves to inject holes into the organic material layer A.
  • the material forming the anode 10 is not particularly limited, and those known in the art can be used.
  • Non-limiting examples thereof include metals such as vanadium, chromium, copper, zinc and gold; Alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al, SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; And carbon black.
  • metals such as vanadium, chromium, copper, zinc and gold
  • Alloys thereof Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al, SnO 2: a combination of a metal and an oxide such as S
  • the method for producing the anode 10 is not particularly limited, and can be produced according to a conventional method known in the art. For example, a method of coating a positive electrode material on a substrate made of a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film can be mentioned.
  • the cathode 20 injects electrons into the organic material layer A.
  • the material forming the cathode 20 is not particularly limited, and those known in the art can be used. Non-limiting examples thereof include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Alloys thereof; And multilayer structured materials such as LiF / Al and LiO 2 / Al.
  • the method for producing the cathode 20 is not particularly limited, and can be produced by a method known in the art.
  • the organic layer (A) included in the organic electroluminescent device according to the present invention can be used without limitation in a conventional structure used as an organic layer of a conventional organic EL device.
  • the hole transport region 30, the light emitting layer 40, And a transport region 50 can be included in the organic electroluminescent device according to the present invention.
  • the hole transporting region 30 included in the organic material layer A of the present invention serves to move the holes injected from the anode 10 to the light emitting layer 40.
  • the hole transporting region 30 may include at least one selected from the group consisting of a hole injecting layer 31 and a hole transporting layer 32. At this time, in consideration of the characteristics of the organic electroluminescent device, it is preferable that both the hole injection layer 31 and the hole transport layer 32 are included.
  • the material forming the hole injection layer 31 and the hole transport layer 32 is not particularly limited as long as the material has a low hole injection barrier and a high hole mobility and the hole injection layer / Can be used. At this time, the materials constituting the hole injection layer (31) and the hole transport layer (32) may be the same or different.
  • the hole injecting material may be any of the hole injecting materials known in the art.
  • usable hole injection materials include phthalocyanine compounds such as copper phthalocyanine; (N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine, m- , 4 "-tris (3-methylphenylphenylamino) triphenylamine), TDATA (4,4'4" -Tris (N, N-diphenylamino) triphenylamine), 2TNATA (naphthyl) -N-phenylamino ⁇ -triphenylamine, PEDOT / PSS, poly (4-styrenesulfonate), PANI / DBSA sulfonicacid, PANI / PSS (polyaniline) / poly (4-styrenesulfonate), etc.
  • the hole transporting material may be any one of known hole transporting materials.
  • usable hole transport materials include carbazole-based derivatives such as phenylcarbazole and polyvinylcarbazole, fluorene-based derivatives, N, N'-bis (3-methylphenyl) Triphenylamine derivatives such as N'-diphenyl- [1,1-biphenyl] -4,4'-diamine and TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine) , N'-di (1-naphthyl) -N, N'-diphenylbenzidine) and TAPC (4,4'-Cyclohexylidene bis [N, Or two or more of them may be mixed.
  • the hole transporting region 30 may be manufactured by a conventional method known in the art. For example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • a vacuum deposition method for example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • the light emitting layer 40 included in the organic material layer A of the present invention is a layer in which excitons are formed by the combination of holes and electrons and the color of the light emitted by the organic electroluminescent device depends on the material constituting the light emitting layer 40 It can be different.
  • the material forming the light emitting layer (40) includes at least one first compound represented by Formula (1) and at least one second compound represented by Formula (2). At this time, the first compound and the second compound may be used as a phosphorescent host material of the light emitting layer, respectively.
  • the compound represented by Formula 1 is a host material having electronic characteristics. More specifically a core having a nitrogen heteroaromatic ring (e.g., azine) and two dibenzo-based moieties (e.g., dibenzofuran or dibenzothiophene) bonded on both sides thereof, Has a basic skeleton in which at least one phenyl group of two dibenzo-based moieties is connected to an electron donating group (EDG) having a conventional electron donor in the art.
  • EDG electron donating group
  • the compound of the formula (1) has a dibenzo-type moiety (e.g., dibenzofuran (DBF), dibenzothiophene (DBT)) having both physicochemical properties for holes and electrons and an electron attracting moiety Pyrazine, triazine), which is a kind of azo group of the EWG group (e.g., pyridine, pyrazine, triazine), and the dibenzo series moietiesecabazole, indolocarbazole, phenoxazine, phenothiazine, aryl An electron donor group such as amine is connected.
  • a dibenzo-type moiety e.g., dibenzofuran (DBF), dibenzothiophene (DBT) having both physicochemical properties for holes and electrons and an electron attracting moiety Pyrazine, triazine
  • EWG group e.g., pyridine, pyrazine, triazine
  • the compound of Formula 1 is a bipolar compound, the recombination of holes and electrons is high, so that the hole injecting / transporting ability, luminous efficiency, driving voltage, lifetime characteristics, durability and the like can be improved. Accordingly, when the compound of Chemical Formula 1 is applied as a green phosphorescent material, not only can it have excellent luminous efficiency characteristics, but also can be driven at a low voltage and exhibit lifetime increasing effect, and can exhibit thermal stability, high glass transition temperature characteristics, (morphology). Since the organic EL device is also effective in inhibiting crystallization of the organic material layer, the performance and lifetime characteristics of the organic EL device including the compound can be greatly improved.
  • the planarity and stereoscopic property of the compound can be realized according to the bonding positions of two dibenzofurans or dibenzothiophene moieties bonded to azine groups.
  • the electron transporting ability is improved, and the driving and efficiency of the device to which these compounds are applied can be expected to be increased.
  • the dibenzofuran moiety or the dibenzothiophene moiety is more excellent in electron and hole stability than an aryl group, lifetime characteristics of a device to which such a compound is applied can be further improved.
  • EDG electron donor groups
  • carbazole groups indolocarbazoles, phenoxazines, phenothiazines, arylamine groups and the like
  • the HOMO level of the compound can be freely controlled.
  • the carbazole group is electrochemically stable and has a deep HOMO level by conjugation with other amines EDG.
  • the polycyclic electron donor (EDG) having a condensed ring and / or fused ring form has excellent thermal stability and electrochemical stability, has a high glass transition temperature (Tg) and excellent carrier transporting ability.
  • Tg glass transition temperature
  • the electron and hole transport mobility is very excellent, and the balance of the carriers in the light emitting layer is very excellent.
  • the host material should have a triplet energy gap higher than the dopant of the host. That is, in order to effectively provide phosphorescent emission from the dopant, the lowest excitation state of the host must be higher energy than the lowest emission state of the dopant.
  • the compound represented by Formula 1 has a high triplet energy and can be used as a host material because the energy level can be controlled higher than that of the dopant.
  • the compound represented by the formula (1) can prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Accordingly, the luminous efficiency of the device can be improved by increasing the number of the excitons contributing to the light emission in the light emitting layer, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased.
  • the compound represented by the general formula (1) of the present invention has a core comprising an azine group and two dibenzo-based moieties (dibenzofuran or dibenzothiophene moiety) connected to both sides thereof, An aryl group and / or a heteroaryl group in which at least one electron donor group (EDG) is bonded to any one of six-membered rings in the core and substituted with at least one deuterium (D)
  • EDG electron donor group
  • X 1 and X 2 are the same as or different from each other and each independently O or S. At this time, when d is 0, dibenzofuran moiety is formed, and in case of S, dibenzothiophene moiety can be formed.
  • Y 1 to Y 16 are the same as or different from each other, and each independently CR 8 or N; In this case, when there are a plurality of CR 8 s , the plurality of R 8 s may be the same or different.
  • the remaining is CR 8 ;
  • At least one of Y 13 to Y 16 is N, the remaining is CR 8 ;
  • At least one of Y 1 to Y 4 is N, and at least one of Y 9 to Y 12 is N, the remainder is CR 8 ;
  • At least one of Y 5 to Y 8 is N, and at least one of Y 13 to Y 16 is N, the remainder is CR 8 ;
  • At least one of Y 1 to Y 4 is N, and when one of Y 13 to Y 16 is N, the remaining is CR 8 ;
  • Y 1 to Y 16 may all be CR 8 (see the following formulas 11 to 15).
  • R 8 is hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, an alkynyl group of C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ C 60 aryloxy group, C group 1 ⁇ C 40 alkyl silyl, C 6 ⁇ C 60 aryl silyl group, a alkyl boronic of C 1 ⁇ C 40, an aryl boronic a C 6 ⁇ C 60, C 1 ⁇ C 40 phosphine groups, C 1 to C 40 phosphine oxide groups, and C 6 to C 60
  • R 8 is a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 of the A cycloalkyl group, and a C 6 to C 60 aryl group.
  • Z 1 to Z 3 are the same or different and are each independently CR 5 or N, and at least one of them is N. In one preferred embodiment, from 1 to 3 of Z 1 to Z 3 may be N, for example, pyridine, pyrimidine, triazine. More preferably, all of Z 1 to Z 3 are N and triazine is electron-withdrawing.
  • Ar 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cycloalkyl, A C 6 to C 60 aryl group, and the like.
  • Ar 1 is preferably an aryl group of C 6 to C 60 , and may be, for example, a phenyl group, a biphenyl group, a naphthyl group, a triphenyl group, an anthryl group, a phenanthryl group and the like.
  • Ar 1 can be selected from the group of substituents represented by the following structural formulas. At this time, any hydrogen included in the following substituents may be substituted with at least one or more deuterium (D), or may be unsubstituted.
  • D deuterium
  • Ar 1 may be substituted with at least one substituent group known in the art (for example, the same definition as R 6 ).
  • a and c are each an integer of 0 to 3
  • b and d are an integer of 0 to 4, respectively.
  • hydrogen means not substituted with R 1 to R 4
  • a to d are each an integer of 1 or more, one or more hydrogen atoms are substituted with R 1 to R 4 . it means.
  • R 1 to R 5 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the An alkynyl group, a C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyl A C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6
  • R 1 to R 5 each are plural, they are the same as or different from each other. Specifically, R 1 to R 5 are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 An alkynyl group of C 40 to C 40 , a cycloalkyl group of C 3 to C 40 , and an aryl group of C 6 to C 60 .
  • m and n are each an integer of 0 to 3, and m + n? 1.
  • m or n 0, it means that hydrogen is not substituted with A or B.
  • m and n are each an integer of 1 or more, it means that at least one hydrogen is substituted with A and B, respectively.
  • m and n may each be an integer of 0 to 2.
  • b + m and d + n may be an integer of 0 to 4, respectively.
  • a and B are electron donating substituents each of which serves to provide electrons.
  • an electron donating group (EDG) known in the art can be used without limitation.
  • a and B are each a carbazole group, a condensed ring or a fused ring type of a polyvalent carbazole-based moiety (e.g., condensed carbazole, indolocarbazole, biscarbazole), phenoxazine, phenothiazine, Amine group, and the like.
  • a and B are the same as or different from each other, and each independently can be any of the substituents represented by the above formulas (1a) to (1c).
  • X 3 is a single bond or may be selected from the group consisting of O, or S.
  • X 3 may be a carbazole group, a condensed ring and / or a polycyclic carbazole-based moiety in the form of a fused ring (for example, a condensed carbazole, an indolocarbazole, or the like) Of a bis-carbazole.
  • X < 3 > is O or S, phenoxazine or phenothiazine can be formed.
  • e is an integer of 0 to 4
  • f is an integer of 0 to 3.
  • hydrogen means not substituted by R 6 and R 7
  • e and f are each an integer of 1 or more, at least one hydrogen is substituted with R 6 and R 7 respectively .
  • R 6 and R 7 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C A C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkenyl group, C 6 -C 60 aryloxy groups, C 1 -C 40 alkylsilyl groups, C 6 -C 60 arylsilyl groups, C 1 -C 40 alkylboron groups, C 6 -C 60 a group of the arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the
  • R 6 and R 7 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 A C 3 to C 40 cycloalkyl group, and a C 6 to C 60 aryl group, or may be bonded to adjacent groups to form a condensed ring.
  • adjacent groups may be one R 6 and one R 6 , one R 6 and one Ar 2 , one R 7 and another R 7 , one R 7, and one Ar 2 .
  • L may be a divalent group linker known in the art. Specifically, L is a single bond or an arylene group having 6 to 40 carbon atoms. When L is a C 6 to C 40 arylene group, it may be a phenylene group, a biphenylene group, a naphthylene group, a triphenylene group or the like, preferably a phenylene group or a biphenylene group.
  • Ar 2 and Ar 3 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, group, C 3 ⁇ C 40 cycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ , or selected from the group consisting of an aryl amine of the C 60, or adjacent groups combined To form a condensed ring.
  • said Ar 2 and Ar 3 are the same or different from each other, and each independently C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ the group consisting of an aryl amine of the C 60 . ≪ / RTI >
  • a and B are the same as or different from each other, and each independently can be any one selected from the group of substituents represented by the following structural formulas.
  • any hydrogen contained in the following substituents may be substituted with at least one deuterium (D) or may be unsubstituted.
  • E is selected from the group consisting of O, S, NR 11 , CR 12 R 13 , and SiR 14 R 15 ,
  • a halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a substituted or unsubstituted alkyl group having 5 to 5 nucleus atoms, wherein R 11 to R 15 are the same or different and each independently represents hydrogen, deuterium, Lt; / RTI > to 60, and < RTI ID 0.0 >
  • Ar 11 is hydrogen or a C 6 to C 60 aryl group
  • the compound represented by Formula 1 may include an aryl group and / or a heteroaryl group substituted with at least one deuterium (D) in the molecular structure.
  • at least one of Ar 1 , A and B in Formula 1 is a C 6 to C 60 aryl group substituted with at least one deuterium (D), or a heteroaryl group having 5 to 50 nucleus atoms Group.
  • the number of deuterium (D) substituted in the compound is not particularly limited, and may be, for example, at least 1, preferably 4 or more. Specifically, it may be 1 to 18.
  • the compound containing a plurality of deuterium (D) can maximize the color purity of green more than the compounds having the same structure without deuterium, and further increase the intramolecular bonding force between the weakened carbon- Can be significantly improved.
  • the nitrogen-containing heterocycle having an EWG properties such as, Z 1 ⁇ Z 3 containing ring
  • EWG properties such as, Z 1 ⁇ Z 3 containing ring
  • X 1 hamyuhwan and X Symmetry or asymmetry structure depending on the carbon bond positions of the carbon-carbon double bonds.
  • the bonding position of one of Y 1 to Y 4 of the X 1 containing ring connected to the Z 1 to Z 3 containing ring and the bonding position of one of Y 9 to Y 12 of the X 2 containing ring are symmetrical or asymmetric Structure.
  • the carbon position of the X 1 -containing ring bonded to the azine group is Y 1
  • the X 2 -containing The carbon position of the ring may be any of Y 10 to Y 12 except Y 9 (see Chemical Formula 5 below).
  • the asymmetric structure of two dibenzo-based moieties respectively linked to the nitrogen-containing heterocycle may be represented by any one of the following formulas (3) to (6).
  • the ring containing Z 1 to Z 3 in Formula 3 is bonded to any one of Y 10 to Y 12 (provided that the Z 1 to Z 3 containing ring is not bonded to Y 9 )
  • the ring containing Z 1 to Z 3 in Formula 4 is bonded to any one of Y 9 and Y 11 to Y 12 (provided that the ring containing Z 1 to Z 3 is not bonded to Y 10 )
  • the ring containing Z 1 to Z 3 in Formula 5 is bonded to any one of Y 9 , Y 10, and Y 12 (provided that the Z 1 to Z 3 containing ring is not bonded to Y 11 )
  • the ring containing Z 1 to Z 3 in the above formula (6) is bonded to any one of Y 9 to Y 11 (provided that the ring containing Z 1 to Z 3 is not bonded to Y 12 ).
  • X 1 , X 2 , Y 1 to Y 16 , Z 1 to Z 3 , Ar 1 , m, n, A, B, a to d and R 1 to R 4 are as defined in Formula 1, respectively.
  • asymmetric compound In the case of the above-mentioned asymmetric compound, it is relatively easy to control the intermolecular distance as compared with the compound having a symmetric structure. That is, due to the nature of the dibenzo-based moiety capable of bonding at the 1,2,3,4-position, a structural disorder between the hydrogen of triazine and the dibenzo-based moiety occurs at the 1,4-bond, The distance will be farther away, which will also increase the T1 value. By using the above-mentioned characteristics, it is possible to adjust the HOMO-LUMO and T1 and S1 values of the organic material layer through the asymmetry of the chemical structure.
  • the compound represented by Formula 3 may be further represented by any one of Formulas 3a to 3c.
  • the compound represented by Formula 4 may be further represented by any one of Formulas 4a to 4c.
  • the compound represented by Formula 5 may be further represented by any one of Formulas 5a to 5c.
  • the compound represented by Formula 6 may be further represented by any one of Formulas 6a to 6c.
  • X 1 , X 2 , Y 1 to Y 16 , Z 1 to Z 3 , Ar 1 , m, n, A, B, a to d and R 1 to R 4 are as defined in claim 1, respectively.
  • X 1 -containing ring bonded to the azine group for example, a ring containing Z 1 to Z 3
  • X 2 containing ring may be Y 9 (see Chemical Formula 7 below).
  • the symmetrical structure of two dibenzo-based moieties respectively linked to the nitrogen-containing heterocycle may be represented by any one of the following formulas (7) to (10).
  • X 1 , X 2 , Y 1 to Y 16 , Z 1 to Z 3 , Ar 1 , m, n, A, B, a to d and R 1 to R 4 are as defined in Formula 1, respectively.
  • the degree of symmetry affects the HOMO-LUMO overlap. This can affect the T1 and S1 values, and if this difference is large, it also affects the TTA and singlet fission, so it is important to adjust it appropriately.
  • dibenzo-based moieties such as dibenzofurane or dibenzothiophene moiety may be further represented by any one of the following formulas (11) to (15).
  • X 1 , X 2 , Z 1 to Z 3 , Ar 1 , n, A and B are as defined in the above formula (1).
  • each of X 1 and X 2 is independently O or S, and Z 1 to Z 3 are each independently CR 5 or N, a is N, Ar 1 is an aryl group of C 6 ⁇ C 60. At least one of A and B may be selected from the substituent groups of A and B exemplified above.
  • the compound represented by the formula (1) according to the present invention may be further represented by any of the following formulas (1) to (678).
  • the compounds represented by formula (1) of the present invention are not limited by the following examples.
  • the other material of the light emitting layer 40 according to the present invention is a compound represented by the above formula (2) and is a host material having hole characteristics.
  • the compound represented by Formula 2 has a 3,3'-biscarbazole basic skeleton, and various types of C 6 -C 60 aryl and / or heteroaryl groups may be substituted thereon.
  • the carbazole skeleton has electron donating group characteristics, which are electron donating and hole transporting properties. Accordingly, when two carbazole skeletons are included in the molecule as shown in Formula 2, they have high hole transportability, and the molecular weight is significantly increased as compared with one carbazole skeleton, resulting in high thermal stability.
  • the basic skeleton in the form of 3,3'-bonded biscarbazole is the main binding site of carbazole, which can firmly link two carbazoles to enhance the thermal and electrical stability of the molecule itself.
  • L 1 and L 2 may be divalent groups of linkers known in the art. Specifically, L 1 and L 2 are the same or different and are each independently a single bond or a group selected from the group consisting of C 6 to C 18 arylene groups and heteroarylene groups having 5 to 18 nuclear atoms .
  • L 1 and L 2 include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, indenylene group, pyranthrenylene group, carbazolylene group, thiophenylene group, indolylene group, , A quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a pyridinylene group, and a pyrimidinylene group. More specifically, it is preferable that L 1 and L 2 are a single bond, a phenylene group, or a biphenylene group.
  • Ar 21 and Ar 22 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 of the heteroaryl group, C 1 ⁇ C 40 alkyloxy group of, C of 6 ⁇ C 60 aryl oxy group, C 1 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic in, aryl of C 6 ⁇ C 60 phosphine group may be selected from the aryl phosphine oxide group and an arylamine group of C 6 ⁇ C 60 of a C 6 ⁇
  • Ar 21 and Ar 22 may be the same or different and each independently selected from the group of substituents represented by the following structural formulas.
  • Ar 23 to Ar 27 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 6 to C 60 aryl, 60 heteroaryl groups.
  • Ar 21 and Ar 22 may be substituted with at least one substituent (for example, the same definition as R 6 ) known in the art.
  • R 21 and R 22 may be substituted for any of the phenyl groups of the carbazole skeleton of Formula 2.
  • R 21 and R 22 are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, alkynyl of C 2 ⁇ C 40, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, a C A C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C group of 6 to arylboronic of C 60, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40
  • R 21 and R 22 are the same or different and each independently represents hydrogen, deuterium, a halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, Lt; / RTI > to 60 heteroaryl groups.
  • the substituents such as the alkyl group and the aryl group described above may exhibit an effect of strengthening the electron donating group characteristic in the molecule by having an electron donor and a hole transporting property.
  • n and n each independently represent an integer of 0 to 4; When m and n are each 0, hydrogen is not substituted with R 21 and R 22 , and when m and n are each an integer of 1 or more, at least one hydrogen is substituted with R 21 and R 22 respectively .
  • the compound represented by the formula (2) according to the present invention may be further represented by any one of the following formulas (B-1) to (B-96).
  • the compounds represented by formula (2) according to the present invention are not limited by the following examples.
  • the compound represented by the above-described formula (1) or (2) can be produced without limitation by methods known in the art. For example, they can be synthesized in various ways with reference to the synthetic process of the following examples.
  • the light emitting layer 40 of the present invention comprises a host and a dopant doped to the host. In this way, the energy efficiency can be improved in the process of energy transfer from the host to the dopant.
  • the host comprises a first host represented by Formula 1; And a second host represented by Formula 2 above.
  • the mixing ratio between the first host and the second host is not particularly limited, and can be appropriately adjusted within the range known in the art.
  • the mixing ratio of the first host to the second host may be 20-80: 80-20, preferably 30-70: 70-30.
  • the host comprises a first host represented by Formula 1; A second host represented by Formula 2; And a third host, which is represented by Formula 1 and is different from the first host.
  • the mixing ratio between the first host and the third host is not particularly limited.
  • a host e.g., a first host and a third host
  • the host e.g., the second host
  • the mixing ratio between the first host, the second host and the third host may be 5 to 45:10 to 90: 5 to 45, preferably 10 to 40:20 to 80:10 to 40: Lt; / RTI >
  • the light emitting layer 40 of the present invention may further include a host material known in the art.
  • a host material known in the art.
  • usable host materials include alkali metal complexes; Alkaline earth metal complex compounds; Or condensed aromatic ring derivatives.
  • the host material may be at least one selected from the group consisting of an aluminum complex compound, a beryllium complex compound, an anthracene derivative, a pyrene derivative, a triphenylene derivative, a carbazole derivative, a dibenzofuran derivative, Thiophene derivatives, or a combination of at least two of them.
  • the dopant included in the light emitting layer 40 of the present invention is not particularly limited as long as it is well known in the art, and examples thereof include an anthracene derivative, a pyrene derivative, an arylamine derivative, iridium (Ir) ), And the like.
  • the dopant may be classified into a red dopant, a green dopant, and a blue dopant.
  • the red dopant, the green dopant, and the blue dopant commonly known in the art can be used without particular limitation.
  • red dopant examples include PtOEP (Pt (II) octaethylporphine: Pt (II) octaethylporphine), Ir (piq) 3 (tris (2-phenylisoquinoline) iridium: (2'-benzothienyl) -pyridinato-N, C3 ') iridium (acetylacetonate): Bis (2- N, C3 ') iridium (acetylacetonate)), or a mixture of two or more thereof.
  • PtOEP Pt (II) octaethylporphine
  • Ir (piq) 3 tris (2-phenylisoquinoline) iridium: (2'-benzothienyl) -pyridinato-N, C3 ') iridium (acet
  • green dopant examples include Ir (ppy) 3 (tris (2-phenylpyridine) iridium: tris (2-phenylpyridine) iridium), Ir (ppy) (Acetylacetonato) iridium (III): bis (2-phenylpyridine) (acetylacetato) iridium (III)), Ir (mppy) (2-benzothiazolyl) -1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- [1] benzopyrano [ 6,7,8-ij] -quinolizin-11-one: 10- (2-benzothiazolyl) -1,1,7,7-tetramethyl-2,3,6,7, -tetrahydro- 5H, 11H- [1] benzopyrano [6,7,8-ij] -quinolizine-11-one), or a mixture of two or more thereof.
  • Nonlimiting examples of the blue dopant include bis [3,5-difluoro-2- (2-pyridyl) phenyl] (picolinato) iridium (III) (2-pyridyl) phenyl (picolinato) iridium (III)), (F2ppy) 2Ir (tmd), Ir (dfppz) 3, DPVBi (4,4'- yl) biphenyl: 4,4'-bis (2,2'-diphenylethen-1-yl) biphenyl), DPAVBi (4,4'-Bis [4- (diphenylamino) styryl] biphenyl: Bis (4-diphenylaminostyryl) biphenyl), TBPe (2,5,8,11-tetra-tert-butyl perylene: 2,5,8,11-tetra- Or a mixture of two or more of these.
  • the mixing ratio between the host and the dopant is not particularly limited and can be appropriately adjusted within the range known in the art.
  • the host may be included in the range of 70 to 99.9 wt%, and the dopant may be included in the range of 0.1 to 30 wt%. More specifically, when the light emitting layer 40 is blue fluorescence, green fluorescence, or red fluorescence, the host may be contained in the range of 80 to 99.9 wt%, and the dopant may be included in the range of 0.1 to 20 wt%.
  • the host may be included in the range of 70 to 99 wt% and the dopant may be included in the range of 1 to 30 wt%.
  • the light emitting layer 40 includes a red light emitting layer including a red phosphorescent material; A green light emitting layer including a green phosphorescent material; Or a blue light-emitting layer containing a blue phosphor or a blue phosphor.
  • a light emitting layer containing a green phosphorescent material Preferably a light emitting layer containing a green phosphorescent material.
  • the above-described light emitting layer 40 may be a single layer or a plurality of layers of two or more layers.
  • the organic electroluminescent device can emit light of various colors.
  • the present invention can provide an organic electroluminescent device having a plurality of luminescent layers made of different materials in series to form a mixed color.
  • the driving voltage of the device is increased, while the current value in the organic light emitting device is constant, thereby providing an organic electroluminescent device having improved luminous efficiency by the number of light emitting layers.
  • the electron transporting region 50 included in the organic material layer A serves to move electrons injected from the cathode 20 to the light emitting layer 40.
  • the electron transport region 50 may include at least one selected from the group consisting of the electron transport layer 51 and the electron injection layer 52. In consideration of the characteristics of the organic electroluminescent device, it is preferable to include both the electron transport layer 51 and the electron injection layer 52 described above.
  • the electron injection layer 52 can use an electron injection material which is easy to inject electrons and has a high electron mobility, without limitation.
  • usable electron injecting materials include the above-mentioned bipolar compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes and the like. Specifically, LiF, Li2O, BaO, NaCl, CsF; Lanthanum metals such as Yb and the like; Or metal halides such as RbCl, RbI and the like, which may be used alone or in combination of two or more.
  • the electron transporting region 50 of the present invention may be co-deposited with an n-type dopant to facilitate the injection of electrons from the cathode.
  • the n-type dopant can be used without limitation in the alkali metal complexes known in the art, and examples thereof include alkali metals, alkaline earth metals and rare earth metals.
  • the electron transport region 50 can be manufactured by a conventional method known in the art. For example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • a vacuum deposition method for example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • the organic light emitting device 100 of the present invention may further include a light emitting auxiliary layer (not shown) disposed between the hole transporting region 30 and the light emitting layer 40.
  • the light emission assisting layer serves to regulate the thickness of the organic layer (A) while serving to transport holes, which are moved from the hole transporting region (30), to the light emitting layer (40).
  • This luminescent auxiliary layer has a high LUMO value and prevents electrons from migrating to the hole transport layer 32 and has a high triplet energy to prevent the exciton of the luminescent layer 40 from diffusing into the hole transport layer 32.
  • This luminescent auxiliary layer may include a hole transporting material and may be made of the same material as the hole transporting region. Further, the light-emission-assisting layers of the red, green, and blue organic light-emitting devices may be made of the same material.
  • the light-emitting auxiliary layer material is not particularly limited, and examples thereof include carbazole derivatives and arylamine derivatives.
  • Non-limiting examples of usable luminescent auxiliary layers include NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine), TPD (N, N'-bis- (3-methylphenyl) phenyl-benzidine, s-TAD, and 4,4 ', 4 "-tris (N-3-methylphenyl-Nphenyl-amino) -triphenylamine. These may be used alone or in combination of two or more.
  • the light-emitting auxiliary layer may include a p-type dopant in addition to the above-described materials. As the p-type dopant, well-known p-type dopants used in the related art can be used.
  • the organic electroluminescent device 100 of the present invention may further include an electron transporting layer (not shown) disposed between the electron transporting region 50 and the light emitting layer 40.
  • the electron transporting layer can prevent the excitons or holes generated in the light emitting layer from diffusing into the electron transporting region.
  • the electron transporting layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (e.g., BCP), a heterocyclic derivative including nitrogen, and the like.
  • the electron transporting auxiliary layer may be formed by vacuum deposition, spin coating, casting, Langmuir-Blodgett, inkjet printing, laser printing, laser induced thermal imaging (LITI) ), But the present invention is not limited thereto.
  • the organic electroluminescent device 100 of the present invention may further include a capping layer (not shown) disposed on the cathode 20 described above.
  • the capping layer functions to protect the organic light emitting device and efficiently emit light generated in the organic layer to the outside.
  • the capping layer may be formed of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis (6 '- (2' N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-bis [N- (1-naphthyl) biphenyl-4,4'-diamine (TPD), 1,1'-bis (di-4-tolylaminophenyl) cyclohexane (TAPC).
  • TPD 1,1'-bis (di-4-tolylaminophenyl) cyclohexane
  • TAPC 1,1'-bis (di-4-tolylaminophenyl) cyclohexane
  • Such a capping layer may be a single layer, but may include two or more layers having different refractive indexes so that the refractive index gradually changes while passing through the two or more layers.
  • the capping layer may be formed by a conventional method known in the art. For example, various methods such as a vacuum deposition method, a spin coating method, a casting method, or a Langmuir-Blodgett (LB) method may be used.
  • various methods such as a vacuum deposition method, a spin coating method, a casting method, or a Langmuir-Blodgett (LB) method may be used.
  • the organic light emitting device of the present invention including the above-described configuration can be manufactured according to a conventional method known in the art.
  • an organic light emitting device can be manufactured by vacuum-depositing a cathode material on a substrate, then vacuum-depositing a hole transporting material, a light emitting layer material, an electron transporting material, and a cathode material on the anode in this order .
  • the organic electroluminescent device 100 has a structure in which an anode 10, an organic material layer A and a cathode 20 are sequentially laminated and a structure is formed between the anode 10 and the organic material layer A or between the anode 20 ) And the organic material layer (A).
  • lifetime characteristics can be excellent because the lifetime of the initial brightness is increased while maintaining the maximum luminous efficiency.
  • 6-phenyl-1,3,5-triazine (4.0 g, 11.2 mmol) and 2-chloro-4- (dibenzo [b, d] furan- Pd (PPh 3 ) 4 (0.3 g, 0.2 mmol) and K 2 CO 3 (3.7 g, 26.9 mmol) were added to toluene 30 ml and H 2 O 15 ml and stirred at 110 ° C for 8 hours. The solids formed after the reaction were filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain Compound 2 (6.9 g, yield 84%).
  • a glass substrate coated with ITO (Indium tin oxide) thin film having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
  • ITO Indium tin oxide
  • a green organic EL device was fabricated in the same manner as in Example 1 except that CBP was used instead of Compound 1 and B-5 as a luminescent host material in forming the light emitting layer.
  • a green organic EL device was fabricated in the same manner as in Example 1 except that B-5 was used instead of Compound 1 and B-5 as a luminescent host material in forming the light emitting layer.
  • a green organic EL device was fabricated in the same manner as in Example 1 except that CBP and B-5 were used in place of Compound 1 and B-5 as a luminescent host material in forming the light emitting layer.
  • Example 1 One B-5 1: 1 5.32 514 57.4
  • Example 2 2 B-10 1: 1 4.89 516 56.9
  • Example 3 4 B-51 1: 1 4.21 515 62.5
  • Example 4 337 B-18 1: 1 5.13 515 51.4
  • Example 5 385 B-37 1: 1 5.24 514 52.1
  • Example 6 434 B-44 1: 1 5.45 516 55.4
  • Example 7 481 B-6 1: 1 4.96 516 49.5
  • Example 9 652 B-10 1: 1 4.18 514 59.2
  • Example 10 2 B-6 1: 1 4.58 515 52.6
  • Example 11 4 B-5 1: 1 4.84 516 56.4
  • Example 12 4 B-10 1: 1: 1 5.12 514 51.8
  • Example 13 652 B-5 1: 1: 1 4.94 515 48.4
  • Example 14 337 B-44 3: 7 5.28 514 55.7
  • Example 10 2 B-6 1:
  • the green organic EL device of Example 1-16 using the compound according to the present invention as a light emitting layer was prepared in the same manner as in Comparative Examples 1 and 2 using only CBP and B-5, -5 in comparison with the green organic EL device of Comparative Example 3 in which the light emitting layer component was used in combination as the light emitting layer component.
  • a glass substrate coated with ITO Indium Tin Oxide
  • ITO Indium Tin Oxide
  • the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
  • a solvent such as isopropyl alcohol, acetone, or methanol
  • Example 17 One B-5 2 35:50:15 5.21 515 54.3
  • Example 18 2 B-10 337 15:50:35 4.78 515 56.4
  • Example 19 4 B-51 652 35:50:15 4.15 516 61.8
  • Example 20 337 B-18 434 15:50:35 5.58 514 52.1
  • Example 21 385 B-37 4 40:50:10 5.62 514 51.8
  • Example 22 434 B-44 646 10:50:40 5.43 516 58.4
  • Example 23 481 B-6 One 20:60:20 5.73 516 54.7
  • Example 25 652 B-10 2 30:40:30 4.96 514 55.6 Comparative Example 1 CBP - - 6.93 516 38.2 Comparative Example 3 CBP B-5 - 1: 1: 0
  • the green organic EL device of Example 17-25 using the compound according to the present invention as a light emitting layer was prepared in the same manner as in Comparative Example 1 using CBP alone as a light emitting layer and CBP and B- It was found that the organic EL device of the present invention exhibited better performance in terms of efficiency and driving voltage as compared with the green organic EL device of Comparative Example 3 which was used in combination.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention peut fournir un dispositif électroluminescent organique dans lequel au moins un type de matériau hôte ayant des propriétés électroniques, et au moins un type de matériau hôte ayant des propriétés de trou sont combinés et utilisés en tant que composant de couche électroluminescente, et par conséquent le dispositif électroluminescent organique présente des propriétés améliorées telles qu'une efficacité d'émission de lumière élevée, une faible tension de commande et une longue durée de vie.
PCT/KR2019/000611 2018-01-16 2019-01-15 Dispositif électroluminescent organique Ceased WO2019143108A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20180005765 2018-01-16
KR10-2018-0005765 2018-01-16
KR1020180165795A KR102792712B1 (ko) 2018-01-16 2018-12-20 유기 전계 발광 소자
KR10-2018-0165795 2018-12-20

Publications (1)

Publication Number Publication Date
WO2019143108A1 true WO2019143108A1 (fr) 2019-07-25

Family

ID=67302342

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2019/000611 Ceased WO2019143108A1 (fr) 2018-01-16 2019-01-15 Dispositif électroluminescent organique

Country Status (1)

Country Link
WO (1) WO2019143108A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210184131A1 (en) * 2018-07-27 2021-06-17 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
KR20170086211A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20170113469A (ko) * 2016-03-30 2017-10-12 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20170113321A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
KR20170113320A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
WO2018174679A1 (fr) * 2017-03-24 2018-09-27 희성소재(주) Élément électroluminescent organique et composition pour couche de matériau organique dans l'élément électroluminescent organique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
KR20170086211A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20170113321A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
KR20170113320A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
KR20170113469A (ko) * 2016-03-30 2017-10-12 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2018174679A1 (fr) * 2017-03-24 2018-09-27 희성소재(주) Élément électroluminescent organique et composition pour couche de matériau organique dans l'élément électroluminescent organique

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210184131A1 (en) * 2018-07-27 2021-06-17 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same
US12453283B2 (en) * 2018-07-27 2025-10-21 Lg Chem, Ltd. Compound and organic light emitting device comprising the same

Similar Documents

Publication Publication Date Title
WO2016089080A1 (fr) Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
WO2015041428A1 (fr) Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé
WO2016148425A2 (fr) Composé pour dispositif électrique organique, dispositif électrique organique utilisant ce composé, et dispositif électronique correspondant
WO2016105165A2 (fr) Composé électroluminescent organique et dispositif électroluminescent organique l'utilisant
WO2015156580A2 (fr) Composé organique et élément électroluminescent organique le contenant
WO2016108596A2 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020159019A1 (fr) Composé électroluminescent organique, et dispositif électroluminescent organique l'utilisant
WO2011055932A9 (fr) Composé organique, dispositif électronique organique l'utilisant et borne associée
WO2015099438A1 (fr) Composé organique électroluminescent, et élément organique électroluminescent l'utilisant
WO2021154041A1 (fr) Composé, composition de revêtement le comprenant, dispositif électroluminescent organique l'utilisant, et procédé de fabrication associé
WO2014027814A1 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
WO2022005249A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2024014866A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2023214829A1 (fr) Composition pour dispositif électroluminescent organique et dispositif électroluminescent organique la comprenant
WO2022005251A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2019013503A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2023013900A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2020209602A1 (fr) Composé organique, et élément électroluminescent organique l'utilisant
WO2023214820A1 (fr) Composition pour élément électroluminescent organique, et élément électroluminescent organique la comprenant
WO2024144190A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2024205127A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2024035190A1 (fr) Diode électroluminescente organique et composé organique
WO2019143108A1 (fr) Dispositif électroluminescent organique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19740844

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19740844

Country of ref document: EP

Kind code of ref document: A1