KR20190055538A - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
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- KR20190055538A KR20190055538A KR1020170152373A KR20170152373A KR20190055538A KR 20190055538 A KR20190055538 A KR 20190055538A KR 1020170152373 A KR1020170152373 A KR 1020170152373A KR 20170152373 A KR20170152373 A KR 20170152373A KR 20190055538 A KR20190055538 A KR 20190055538A
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- 150000002894 organic compounds Chemical class 0.000 title claims description 6
- 239000010410 layer Substances 0.000 claims abstract description 105
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 11
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- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000005647 linker group Chemical group 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
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- 238000010345 tape casting Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- H01L51/0067—
-
- H01L51/5012—
-
- H01L51/5048—
-
- H01L51/5088—
-
- 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
-
- 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
-
- 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]
- H10K50/14—Carrier transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
Abstract
Description
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 바람직하게는 전자 수송능 및 발광능이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same and more preferably to a compound having excellent electron transporting ability and light emitting ability and by incorporating it into one or more organic layers to improve characteristics such as luminous efficiency, And an organic electroluminescent device.
1950년대 베르나노스(Bernanose)의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent) 소자에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.A study on organic electroluminescent devices which resulted in blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film emission of Bernanose in the 1950s was carried out by Tang in 1987 by the function of hole layer and luminescent layer An organic electroluminescent device having a laminated structure divided into layers has been proposed. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광물질, 정공주입 물질, 정공수송 물질, 전자수송 물질, 전자주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.
유기 전계 발광 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.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. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다.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. The development of such a phosphorescent material can theoretically improve luminescence efficiency up to four times as compared with that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층에 사용되는 물질로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광물질로는 안트라센 유도체들이 보고되고 있다. 특히, 발광물질로 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq 3 and the like are widely known as materials used in the hole blocking layer and the electron transporting layer, and anthracene derivatives are reported as luminescent materials. Particularly, a metal complex compound containing Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like having advantages in terms of efficiency improvement as a light emitting material has a blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.
그러나, 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 우수한 성능을 가지는 유기물층 재료의 개발이 요구되고 있다.However, conventional organic material layers have advantages in terms of light emission characteristics, but their glass transition temperature is low and their thermal stability is not very good, so that they are not satisfactory in terms of lifetime in an organic electroluminescent device. Therefore, development of an organic material layer having excellent performance is required.
본 발명은 내열성, 캐리어 수송능, 발광능 등이 우수하여 유기 전계 발광 소자의 유기물 층 재료, 구체적으로 발광층 재료, 수명 개선층 재료, 발광 보조층 재료, 또는 전자 수송층 재료 등으로 사용될 수 있는 신규 화합물을 제공하는 것을 목적으로 한다.The present invention relates to a novel compound capable of being used for an organic material layer material of an organic electroluminescence device, specifically a light emitting layer material, a life improving layer material, a light emitting auxiliary layer material, or an electron transporting layer material, And to provide the above objects.
또, 본 발명은 상기 신규 화합물을 포함하여 구동전압이 낮고, 발광 효율이 높으며, 수명이 향상된 유기 전계 발광 소자를 제공하는 것도 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the novel compound, which has low driving voltage, high luminous efficiency, and improved lifetime.
상기 목적을 달성하기 위하여, 본 발명의 일례는 하기 화학식 1로 표시되는 화합물을 제공한다.In order to accomplish the above object, an example of the present invention provides a compound represented by the following general formula (1).
하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):
상기 화학식 1에서,In Formula 1,
X1 내지 X3은 질소 또는 탄소이며, 적어도 두 개 이상의 질소를 포함하고,X 1 to X 3 are nitrogen or carbon, and contain at least two or more nitrogen atoms,
Y1 내지 Y4 중 하나는 질소이며, 나머지는 탄소이고,One of Y 1 to Y 4 is nitrogen and the other is carbon,
n은 1 내지 3의 정수이며,n is an integer of 1 to 3,
L은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,L is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,
R1은 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C6~C60의 아릴기로 이루어진 군에서 선택되거나, R1이 복수인 경우 인접한 기와 결합하여 축합 고리를 형성하며;R 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C 1 to C 40 alkyl group, C 6 to C 60 aryl group, or when R 1 is plural, bonding with adjacent groups to form a condensed ring;
a는 0 내지 4의 정수이고,a is an integer of 0 to 4,
A는 하기 화학식 2 또는 화학식 3으로 표시되며,A is represented by the following general formula (2) or (3)
상기 화학식 2 내지 화학식 3에서,In the above Chemical Formulas 2 to 3,
Z1 내지 Z3은 질소 또는 탄소이며, 적어도 두 개 이상의 질소를 포함하고,Z 1 to Z 3 are nitrogen or carbon, and contain at least two or more nitrogen atoms,
Z4 내지 Z6은 N(R4) 또는 탄소이며, 적어도 두 개 이상의 질소를 포함하며,Z 4 to Z 6 are N (R 4 ) or carbon, and contain at least two or more nitrogen atoms,
Ar1 내지 Ar4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기에서 선택되고,Ar 1 to Ar 4 are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cyclo An alkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkyl group, 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 , is selected from an arylamine group of C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 of,
R2 내지 R4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시 클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,R 2 to R 4 are the same or different and 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 cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkynyl 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 the arylboronic group, C 6 ~ C 60 aryl phosphine group, and selected from the group consisting of C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,
*는 상기 화학식 1과 결합이 이루어지는 부분을 의미하고,* Represents a moiety bonded to Formula 1,
상기 R1의 알킬기, 아릴기와, 상기 Ar1 내지 Ar4, R2 내지 R4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 포스핀기, 포스핀옥사이드기, 아릴아민기와, 상기 L의 아릴렌기, 헤테로아릴렌기는, 각각 독립적으로 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C40의 포스핀기, C1~C40의 포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 상기 치환기가 복수일 경우 복수의 치환기는 서로 동일하거나 상이하다.Alkyl group of the R 1, the aryl group, said Ar 1 to Ar 4, R 2 an alkyl group of 1 to R 4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy The aryl group and the heteroarylene group of L each independently represent a group selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, an alkoxy group, an aryloxy group, An amino group, 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 heteroaryl group having 3 to 40 nuclear atoms A cycloalkyl group, 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 alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 1 ~ C 40 of the phosphine group, C 1 ~ C 40 phosphine of Ox Group and a C 6 ~ is unsubstituted or substituted by one or more substituents selected from the group consisting of an aryl amine of the C 60, when the substituent is a plurality a plurality of substituents are the same or different from each other.
또한, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하고, 상기 1층 이상의 유기물 층에서 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다. 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자수송 보조층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택될 수 있다. 이때, 상기 화학식 1로 표시되는 화합물은 전자 수송층 및 전자 수송 보조층의 전자 수송 재료로 사용될 수 있다.In addition, the present invention provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes a compound represented by Formula 1 A light emitting device is provided. The organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, and an electron injecting layer. At this time, the compound represented by Formula 1 may be used as an electron transporting material for the electron transporting layer and the electron transporting layer.
본 발명의 일례에 따른 화학식 1로 표시되는 화합물은 내열성, 캐리어 수송능, 발광능 등이 우수하기 때문에, 유기 전계 발광 소자의 유기물층 재료로 사용될 수 있다The compound represented by the formula (1) according to an example of the present invention is excellent in heat resistance, carrier transport ability, and light emitting ability, and can be used as an organic material layer material of an organic electroluminescent device
또한, 본 발명의 일례에 따른 화합물을 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상될 수 있고, 따라서 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound according to an example of the present invention can significantly improve aspects such as light emitting performance, driving voltage, lifetime, and efficiency, and thus can be effectively applied to a full color display panel and the like.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 유기 화합물1. Organic compounds
본 발명에 따른 신규 유기 화합물은 트리아진 또는 피리미딘에 피리딘 화합물이 결합되어 있는 전자끌개기(Electron-Withdrawing Group, EWG)에 2개 이상의 질소(N)가 포함된 전자끌개기(EWG)가 연결기(linker)를 통해 비대칭으로 연결된 구조를 기본 골격으로 하며, 이때 2개 이상의 질소가 포함된 전자끌개기는 트리아진, 피리미딘, 트리아졸로피리딘이다. 이러한 기본 골격에 다양한 치환기가 도입된 화합물은 상기 화학식 1로 표시된다.A novel organic compound according to the present invention includes an electron-withdrawing group (EWG) in which two or more nitrogen (N) is contained in an electron-withdrawing group (EWG) in which pyridine compound is bonded to triazine or pyrimidine, and a linker to form an asymmetrically connected structure. In this case, electron-donating groups containing two or more nitrogen atoms are triazine, pyrimidine, and triazolopyridine. Compounds having various substituents introduced into these basic skeletons are represented by the above formula (1).
상기 화학식 1로 표시되는 화합물은 종래 유기 EL 소자용 재료에 비해 강한 전자 수송 능력을 가져 상대적으로 높은 발광 효율을 나타낼 수 있고, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 발광능 등이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자가 포함할 경우, 소자의 구동전압, 효율, 수명 등이 향상될 수 있다.The compound represented by the formula (1) has a higher electron transporting ability than the conventional organic EL device materials and can exhibit a relatively high luminous efficiency. The compound represented by the formula (1) has a high glass transition temperature and thus is excellent in thermal stability, It is excellent. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.
또한 상기 화합물은 전자 이동성이 특히 우수할 뿐만 아니라 높은 유리 전이온도 및 열적 안정성이 우수하다. 이로 인해, 본 발명의 화학식 1로 표시되는 화합물은 전자 수송 능력 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 유기물층인 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나의 재료로 사용될 수 있다. 바람직하게는 그린 인광의 발광층, 전자 수송층 및 전자 수송층에 추가로 적층되는 전자수송 보조층 중 어느 하나의 재료로 사용될 수 있다. 또한, 전자 수송 보조층의 역할로는 높은 삼중항 에너지를 갖고 있기 때문에 TTF(triplet-triplet fusion) 효과로 인한 우수한 효율 상승을 나타낼 수 있다. 또한, 발광층에서 생성된 엑시톤이 발광층에 인접하는 전자수송층 또는 정공수송층으로 확산되는 것을 방지할 수 있다. 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있고, 소자의 내구성 및 안정성이 향상되어 소자의 수명이 효율적으로 증가될 수 있다. 개발된 재료들이 대부분 저전압 구동이 가능하여 이로 인한 수명이 개선되는 물리적 특징들을 나타낸다.In addition, the compound is not only excellent in electron mobility but also excellent in high glass transition temperature and thermal stability. Accordingly, the compound represented by the general formula (1) of the present invention is excellent in electron transporting ability and light emitting property, and therefore, it is preferable that the compound represented by the general formula (1) It can be used as a material. Preferably an electron transporting auxiliary layer laminated on the light emitting layer of green phosphorescence, the electron transporting layer and the electron transporting layer. In addition, since the electron transporting layer has high triplet energy, it can exhibit excellent efficiency due to the triplet-triplet fusion (TTF) effect. Further, it is possible to 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. The number of the excitons contributing to light emission in the light emitting layer can be increased to improve the light emitting efficiency of the device and the durability and stability of the device can be improved and the lifetime of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that can be driven at low voltage, thereby improving lifetime.
따라서, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자에 사용할 경우, 우수한 열적 안정성 및 캐리어 수송능(특히, 전자 수송능 및 발광능)을 기대할 수 있을 뿐만 아니라 소자의 구동전압, 효율, 수명 등이 향상될 수 있다.Accordingly, when the compound represented by Formula 1 is used in an organic electroluminescent device, excellent thermal stability and carrier transport ability (in particular, electron transporting ability and light emitting ability) can be expected, and the driving voltage, Can be improved.
또한, 상기 화학식 1로 표시되는 화합물은 전자 수송에 매우 유리할 뿐만 아니라 장수명 특성을 보여준다. 이러한 화합물의 우수한 전자수송 능력은 유기 전계 발광 소자에서 높은 효율과 빠른 이동성(mobility)을 가질 수 있고, 치환기의 방향이나 위치에 따라 HOMO 및 LUMO 에너지 레벨을 조절이 용이하다. 그러므로, 이러한 화합물을 사용한 유기 전계 발광 소자에서 높은 전자 수송성을 나타낼 수 있다.Further, the compound represented by the above formula (1) is not only very advantageous for electron transport, but also exhibits long life characteristics. The excellent electron transporting ability of such a compound can have high efficiency and fast mobility in an organic electroluminescent device, and it is easy to control HOMO and LUMO energy levels according to the direction or position of a substituent. Therefore, high electron transportability can be exhibited in the organic electroluminescent device using such a compound.
구체적으로, 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화학식 4 내지 화학식 8 중 어느 하나로 표시될 수 있다.Specifically, the compound represented by the formula (1) according to the present invention can be represented by any one of the following formulas (4) to (8).
상기 화학식 4 내지 화학식 8에서, X1 내지 X3, Y1 내지 Y4, L, A, n은 각각 화학식 1에서 정의한 바와 같다.X 1 to X 3 , Y 1 to Y 4 , L, A and n are as defined in formula (1).
바람직하게는, 상기 화학식 1에서 L은 단일 결합 또는 하기 L-1 내지 L-5로 표시되는 구조로 이루어진 군에서 선택될 수 있다.Preferably, L in the formula (1) may be a single bond or a structure represented by the following formulas L-1 to L-5.
바람직하게는, 상기 화학식 1에서 A는 하기 A-1 내지 A-12로 표시되는 구조로 이루어진 군에서 선택될 수 있다.Preferably, A in the formula (1) may be selected from the group consisting of the structures represented by the following A-1 to A-12.
바람직하게는, 상기 화학식 1에서 A는 하기 A-13 내지 A-26으로 표시되는 구조로 이루어진 군에서 선택될 수 있다.Preferably, A in the formula (1) may be selected from the group consisting of the structures represented by the following A-13 to A-26.
바람직하게는, 상기 Ar1 내지 Ar4는 각각 독립적으로 하기 구조에서 선택되는 아릴기일 수 있다.Preferably, Ar 1 to Ar 4 may each independently be an aryl group selected from the following structures.
이상에서 설명한 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 예시되는 화합물 1 내지 160 중 어느 하나로 표시되는 화합물로 보다 구체화될 수 있다. 그러나, 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by formula (1) according to the present invention may be further represented by any of compounds 1 to 160 shown below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미하며, 이의 비제한적인 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있다.In the present invention, "alkyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl , Pentyl, iso-amyl, hexyl, and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알케닐의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서"알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알키닐의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, " alkynyl " means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 "아릴"은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.&Quot; Aryl " in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.&Quot; Heteroaryl " in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 "아릴옥시"는 R"O-로 표시되는 1가의 작용기를 의미하며, 상기 R"는 탄소수 6 내지 60의 아릴이다. 이러한 아릴옥시의 비제한적인 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있다.In the present invention, "aryloxy" means a monovalent functional group represented by R "O-, and R" is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 작용기를 의미하며, 상기 R'은 탄소수 1 내지 40의 알킬로서, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 비제한적인 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있다.In the present invention, " alkyloxy " means a monovalent functional group represented by R'O-, and R 'is alkyl having 1 to 40 carbon atoms, which may be linear, branched or cyclic . ≪ / RTI > Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이의 비제한적인 예로는 시클로프로필, 시클로펜틸, 시클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine)등이 있다."Cycloalkyl" in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3의 탄소가 N, O 또는 S와 같은 헤테로 원자로 치환된다. 이의 비제한적인 예로는 모르폴린, 피페라진 등이 있다.In the present invention, "heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and includes at least one carbon atom in the ring, preferably 1 Lt; RTI ID = 0.0 > N, < / RTI > O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, "아릴실릴"은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미하고, "알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미하며, "아릴포스핀기"는 탄소수 1 내지 60의 아릴로 치환된 포스핀기를 의미하며, "아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.&Quot; Alkylsilyl " means silyl substituted with alkyl having 1 to 40 carbon atoms, " arylsilyl " means silyl substituted with aryl having 6 to 60 carbon atoms, Quot; means a boron group substituted with aryl having 6 to 60 carbon atoms, " arylphosphine group " means a phosphine group substituted with aryl having 1 to 60 carbon atoms, &Quot; arylamine " means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
이와 같은 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 실시예의 합성과정을 참고하여 다양한 합성할 수 있다. 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.The compound represented by formula (1) according to the present invention can be synthesized in various ways by referring to the synthesis process of the following examples. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
2. 유기 전계 발광 소자2. Organic electroluminescent device
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).
보다 구체적으로, 본 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자수송 보조층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층, 전자수송 보조층 및 전자 수송층인 것이 바람직하다.The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer. ≪ / RTI > compounds. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 is a light emitting layer, an electron transporting auxiliary layer and an electron transporting layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료(바람직하게는, 인광 호스트 재료)를 포함할 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 발광층은 상기 화학식 1의 화합물 이외의 화합물을 호스트로 포함할 수 있다.The light emitting layer of the organic electroluminescence device of the present invention may include a host material (preferably, a phosphorescent host material). The light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공 주입층, 정공 수송층, 발광 보조층, 발광층 및 전자 수송층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층 또는 전자수송층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 여기서, 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 구조는 전극과 전술한 유기물층과 함께 전자수송 보조층이 추가된 구조일 수 있다. 이때, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자수송 보조층 및 전자 수송층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층, 전자수송 보조층 또는 전자수송층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially stacked . At least one of the hole injecting layer, the hole transporting layer, the light-emitting auxiliary layer, the light emitting layer, and the electron transporting layer may include the compound represented by the formula (1), and preferably the light emitting layer or the electron transporting layer comprises the compound represented by the formula . ≪ / RTI > Here, an electron injection layer may be further stacked on the electron transport layer. Further, the structure of the organic electroluminescent device of the present invention may be a structure in which an electrode and an electron transporting auxiliary layer are added together with the organic material layer described above. At this time, at least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting supporting layer and the electron transporting layer may include the compound represented by the above formula (1) The transport layer may contain a compound represented by the above formula (1).
한편, 본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.
또한, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or 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 or polyaniline; And carbon black, but are not limited thereto.
또한, 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 들 수 있으나, 이에 한정되지는 않는다.Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
또한, 정공 주입층, 정공 수송층 및 발광 보조층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.The hole injecting layer, the hole transporting layer, and the light emitting auxiliary layer are not particularly limited, and ordinary materials known in the art can be used.
이하, 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
[[ 준비예Preparation Example 1] One] PPYPPY -1의 합성Synthesis of -1
<단계 1> <Step 1> PPYPPY -1의 합성Synthesis of -1
4,6-디클로로-2-페닐피리미딘 45.0 g 및 (4-(피리딘-3-일)페닐)보로닉산 40.0 g, 테트라키스(트리페닐포스핀)팔라듐(0) 6.0 g, K2CO3 42 g을 톨루엔 800 ㎖, 에탄올 200 ㎖, 물 200 ㎖에 넣고 2시간 가열 환류 교반하였다. 반응 종결 후 충분량의 물로 실활한 뒤, 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PPY-1 39.8 g(수율 58%)을 얻었다.4,6-Dichloro-2-phenyl-pyrimidine and 45.0 g (4- (pyridin-3-yl) phenyl) Boro acid 40.0 g, tetrakis (triphenylphosphine) palladium (0) 6.0 g, K 2 CO 3 42 g was added to 800 ml of toluene, 200 ml of ethanol and 200 ml of water and the mixture was refluxed with stirring for 2 hours. After completion of the reaction, the reaction solution was deactivated with a sufficient amount of water. Then, the solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried with magnesium sulfate, concentrated and purified by column chromatography to obtain 39.8 g of PPY- ≪ / RTI >
1H-NMR: δ 9.24 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 5H), 7.57-7.50 (m, 4H), 7.25 (d, 2H) 7.03 (s, 1H)1H), 7.25 (d, 2H) 7.03 (s, IH), 7.70 (d, IH)
Mass: [(M+H)+] : 344Mass: [(M + H) < + & gt ; ]: 344
[준비예 2] PPY-2 ~ 4의 합성[Preparation Example 2] Synthesis of PPY-2 to 4
<단계 1> (E)-1-(4-<Step 1> Synthesis of (E) -1- (4- 브로모페닐Bromophenyl )-3-(4-피리딘-3-일)페닐)프로-2-펜-1-온의 합성) -3- (4-pyridin-3-yl) phenyl) prop-2-en-
4-(피리딘-3-일)벤잘데하이드 50.0g 및 1-(4-브로모페닐)에탄-1-온 49.1 g, 소듐메톡사이드 18.2 g을 에탄올 800 ㎖에 넣고 8시간 교반하였다. 반응 종결 후 실온에서 1시간 교반한 뒤, 아세트산에틸로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 (E)-1-(4-브로모페닐)-3-(4-피리딘-3-일)페닐)프로-2-펜-1-온 36.4 g(수율 72%)을 얻었다.50.0 g of 4- (pyridin-3-yl) benzaldehyde, 49.1 g of 1- (4-bromophenyl) ethan-1-one and 18.2 g of sodium methoxide were placed in 800 ml of ethanol and stirred for 8 hours. After completion of the reaction, the mixture was stirred at room temperature for 1 hour, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain (E) -1- (4-bromophenyl) - (4-pyridin-3-yl) phenyl) prop-2-en-1-one 36.4 g (yield 72%).
1H-NMR: δ 9.24 (s, 1H), 8.50 (d, 1H), 8.38 (d, 1H), 8.08-8.01 (m, 3H), 7.75 (d, 2H), 7.60-7.45 (m, 6H)(D, 2H), 7.60-7.45 (m, 6H), 8.08-8.01 (m, 3H)
Mass: [(M+H)+] : 364Mass: [(M + H) < + & gt ; ]: 364
<단계 2> <Step 2> PPYPPY -2의 합성Synthesis of -2
(E)-1-(4-브로모페닐)-3-(4-피리딘-3-일)페닐)프로-2-펜-1-온 36.4 g 및 벤지미다미드 하이드로클로라이드 24.1 g, 소듐하이드록사이드 14.2 g을 에탄올 500 ㎖에 넣고 4시간 가열 환류 교반하였다. 반응 종결 후 반응물을 250 ㎖까지 감압 농축한 후, 충분량의 물로 실활한 뒤 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PPY-2 36.2 g(수율 79%)을 얻었다.(4-bromophenyl) -3- (4-pyridin-3-yl) phenyl) prop-2-en-1-one and 24.1 g of benzimidamide hydrochloride, 14.2 g of the side was placed in 500 ml of ethanol, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to a volume of 250 ml and then deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain PPY -2 36.2 g (yield 79%).
1H-NMR: δ 9.21 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 6H), 7.76 (d, 2H), 7.59-7.55 (m, 6H), 7.25 (d, 2H)2H), 7.59-7.55 (m, 6H), 7.25 (d, 2H), 7.76 (d, 2H)
Mass: [(M+H)+] : 464Mass: [(M + H) < + & gt ; ]: 464
<단계 3> <Step 3> PPYPPY -3의 합성Synthesis of -3
PPY-2 15.0 g 및 (3-클로로페닐)보로닉산 6.1 g, 테트라키스(트리페닐포스핀)팔라듐(0) 0.9 g, K2CO3 7.0 g을 톨루엔 300 ㎖, 에탄올 60 ㎖, 물 60 ㎖에 넣고 2시간 가열 환류 교반하였다. 반응 종결 후 충분량의 물로 실활한 뒤, 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PPY-3 10.9 g(수율 68%)을 얻었다.PPY-2 15.0 g, and (3-chlorophenyl) Boro acid 6.1 g, tetrakis (triphenylphosphine) palladium (0), 0.9 g, K 2 CO 3 7.0 g 300 ㎖ a toluene, ethanol ㎖ 60, water 60 ㎖ And the mixture was refluxed with stirring for 2 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 10.9 g (yield: 68%) of PPY- ≪ / RTI >
1H-NMR: δ 9.21 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 6H), 7.97 (s, 1H), 7.76 (d, 2H), 7.59-7.55 (m, 6H), 7.48 (m, 2H), 7.39 (d, 1H), 7.25 (d, 2H)(M, 6H), 7.97 (s, IH), 7.76 (d, 2H), 7.59-7. 55 (m, 6H) , 7.48 (m, 2 H), 7.39 (d, 1 H), 7.25 (d, 2 H)
Mass: [(M+H)+] : 496Mass: [(M + H) < + & gt ; ]: 496
[준비예 3] PPY-4 ~ 6의 합성[Preparation Example 3] Synthesis of PPY-4 to 6
<단계 1> (E)-1-(3-<Step 1> Synthesis of (E) -1- (3- 브로모페닐Bromophenyl )-3-(4-피리딘-3-일)페닐)프로-2-펜-1-온의 합성) -3- (4-pyridin-3-yl) phenyl) prop-2-en-
4-(피리딘-3-일)벤잘데하이드 50.0 g 및 1-(3-브로모페닐)에탄-1-온 49.1 g, 소듐메톡사이드 18.2 g을 에탄올 800 ㎖에 넣고 8시간 교반하였다. 반응 종결 후 실온에서 1시간 교반한 뒤, 아세트산에틸로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 (E)-1-(3-브로모페닐)-3-(4-피리딘-3-일)페닐)프로-2-펜-1-온 38.2 g(수율 74%)을 얻었다.50.0 g of 4- (pyridin-3-yl) benzaldehyde and 49.1 g of 1- (3-bromophenyl) ethan-1-one and 18.2 g of sodium methoxide were placed in 800 ml of ethanol and stirred for 8 hours. After completion of the reaction, the reaction mixture was stirred at room temperature for 1 hour and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain (E) -1- (3- - (4-pyridin-3-yl) phenyl) prop-2-en-1-one 38.2 g (yield 74%).
1H-NMR: δ 9.24 (s, 1H), 8.50 (d, 1H), 8.38 (d, 1H), 8.08-8.01 (m, 3H), 7.82 (d, 1H), 7.60-7.45 (m, 7H)(D, IH), 8.08-8.01 (m, 3H), 7.82 (d, IH), 7.60-7. 45 (m, 7H)
Mass: [(M+H)+] : 364Mass: [(M + H) < + & gt ; ]: 364
<단계 2> <Step 2> PPYPPY -4의 합성Synthesis of -4
(E)-1-(3-브로모페닐)-3-(4-피리딘-3-일)페닐)프로-2-펜-1-온 38.2 g 및 벤지미다미드 하이드로클로라이드 25.0 g, 소듐하이드록사이드 14.8 g을 에탄올 500 ㎖에 넣고 4시간 가열 환류 교반하였다. 반응 종결 후 반응물을 250 ㎖까지 감압 농축한 후, 충분량의 물로 실활한 뒤 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PPY-4 34.2 g(수율 75%)을 얻었다.38.2 g of (E) -1- (3-bromophenyl) -3- (4-pyridin-3- yl) phenyl) 14.8 g of the side was placed in 500 ml of ethanol, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to a volume of 250 ml and then deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain PPY -4 (34.2 g, yield 75%).
1H-NMR: δ 9.24 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 6H), 7.78 (d, 1H), 7.67 (d, 1H) 7.50-7.43 (m, 6H), 7.25 (d, 2H)(D, IH), 7.67 (d, IH), 7.50-7.43 (m, 6H) 7.25 (d, 2 H)
Mass: [(M+H)+] : 464Mass: [(M + H) < + & gt ; ]: 464
<단계 3> <Step 3> PPYPPY -5의 합성Synthesis of -5
PPY-4 15.0 g 및 (3-클로로페닐)보로닉산 6.1 g, 테트라키스(트리페닐포스핀)팔라듐(0) 0.9 g, K2CO3 7.0 g을 톨루엔 300 ㎖, 에탄올 60 ㎖, 물 60 ㎖에 넣고 2시간 가열 환류 교반하였다. 반응 종결 후 충분량의 물로 실활한 뒤, 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PPY-5 10.1 g(수율 67%)을 얻었다.PPY-4 15.0 g, and (3-chlorophenyl) Boro acid 6.1 g, tetrakis (triphenylphosphine) palladium (0), 0.9 g, K 2 CO 3 7.0 g 300 ㎖ a toluene, ethanol ㎖ 60, water 60 ㎖ And the mixture was refluxed with stirring for 2 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 10.1 g of PPY- ≪ / RTI >
1H-NMR: δ 9.24 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 6H), 7.97 (s, 1H), 7.78 (d, 1H), 7.67 (d, 1H) 7.50-7.43 (m, 8H), 7.35 (d, 1H), 7.25 (d, 2H)1H), 7.67 (d, 1H), 7.67 (d, 1H), 7.50-7.30 (m, 7.43 (m, 8 H), 7.35 (d, 1 H), 7.25 (d, 2 H)
Mass: [(M+H)+] : 496Mass: [(M + H) < + & gt ; ]: 496
<단계 4> <Step 4> PPYPPY -6의 합성Synthesis of -6
PPY-5 10.0 g 및 (3-클로로페닐)보로닉산 4.1 g, Pd(OAc)2 0.1 g, XPhos 0.4 g, Cs2CO3 4.5 g, 톨루엔 200 ㎖, 에탄올 40 ㎖, 물 40 ㎖에 넣고 2시간 가열 환류 교반하였다. 반응 종결 후 충분량의 물로 실활한 뒤, 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PPY-6 6.7 g(수율 66%)을 얻었다.PPY-5 10.0 g, and (3-chlorophenyl) Boro acid 4.1 g, Pd (OAc) 2 0.1 g, XPhos 0.4 g, Cs 2 CO 3 4.5 g, placed in a 200 ㎖ toluene, ethanol 40 ㎖, water 40 ㎖ 2 And the mixture was refluxed with stirring for a time. After completion of the reaction, the reaction solution was deactivated with sufficient water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried with magnesium sulfate, concentrated and purified by column chromatography to obtain 6.7 g (yield 66%) of PPY- ≪ / RTI >
1H-NMR: δ 9.24 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 6H), 7.97 (s, 1H), 7.90 (s, 1H), 7.78 (d, 1H), 7.67 (d, 1H) 7.50-7.40 (m, 10H), 7.35 (d, 2H), 7.25 (d, 2H)(D, IH), 7.67 (d, IH), 7.70 (d, IH) (d, IH), 7.50-7.40 (m, IH), 7.35 (d, 2H), 7.25
Mass: [(M+H)+] : 572Mass: [(M + H) < + & gt ; ]: 572
[[ 준비예Preparation Example 4] 4] PTZPTZ -1 ~ 2의 합성Synthesis of -1 to 2
<단계 1> <Step 1> PTZPTZ -1의 합성Synthesis of -1
2,4-디클로로-6-페닐-1,3,5-트리아진 45.0 g 및 (4-(피리딘-3-일)페닐)보로닉산 39.2 g, 테트라키스(트리페닐포스핀)팔라듐(0) 6.0 g, K2CO3 42 g을 톨루엔 800 ㎖, 에탄올 200 ㎖, 물 200 ㎖에 넣고 2시간 가열 환류 교반하였다. 반응 종결 후 충분량의 물로 실활한 뒤, 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PTZ-1 36.2 g(수율 53%)을 얻었다.45.0 g of 2,4-dichloro-6-phenyl-1,3,5-triazine and 39.2 g of (4- (pyridin-3-yl) phenyl) boronic acid, tetrakis (triphenylphosphine) palladium 6.0 g and K 2 CO 3 ( 42 g) were added to toluene (800 ml), ethanol (200 ml) and water (200 ml), and the mixture was refluxed with stirring for 2 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 36.2 g of PTZ- ≪ / RTI >
1H-NMR: δ 9.24 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 3H), 7.96 (d, 2H), 7.57-7.50 (m, 4H), 7.25 (d, 2H)2H), 7.57-7.50 (m, 4H), 7.25 (d, 2H), 7.96 (d,
Mass: [(M+H)+] : 345Mass: [(M + H) < + & gt ; ]: 345
<단계 2> <Step 2> PTZPTZ -2의 합성Synthesis of -2
PTZ-1 10.0 g 및 (3-클로로페닐)보로닉산 4.1 g, 테트라키스(트리페닐포스핀)팔라듐(0) 0.6 g, K2CO3 4.7 g을 톨루엔 200 ㎖, 에탄올 40 ㎖, 물 40 ㎖에 넣고 2시간 가열 환류 교반하였다. 반응 종결 후 충분량의 물로 실활한 뒤, 용액을 분액 깔때기에 옮겨서 메틸렌클로라이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 PTZ-2 8.7 g(수율 71%)을 얻었다.(Tetrakis (triphenylphosphine) palladium (0) 0.6 g and K 2 CO 3 4.7 g) were dissolved in toluene (200 ml), ethanol (40 ml) and water (40 ml) And the mixture was refluxed with stirring for 2 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 8.7 g (71% ≪ / RTI >
1H-NMR: δ 9.24 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 3H), 8.16 (s, 1H), 7.96-7.95 (m, 3H), 7.50-7.43 (m, 6H), 7.25 (d, 2H)(S, 1H), 7.96-7.95 (m, 3H), 7.50-7.43 (m, 3H), 8.42-8.30 6H), < / RTI > 7.25 (d, 2H)
Mass: [(M+H)+] : 421Mass: [(M + H) < + & gt ; ]: 421
[[ 준비예Preparation Example 5] ID-1의 합성 5] Synthesis of ID-1
<단계 1> [(2-≪ Step 1 > [(2- 피리디닐아미노Pyridinylamino )) 싸이옥소메틸Thioxomethyl ]-, 에틸 에스터 (] -, ethyl ester ( 9CI9CI )의 합성) Synthesis of
2-아미노피리딘 100 g에 디클로로메테인(DCM) 500 ㎖를 가하였다. 0로 냉각하고 에톡시카보닐 아이소싸이오시아네이트 139.3 g을 15분에 걸쳐 천천히 적가하였다. 반응액을 상온으로 올리고 20시간 교반하였다. 감압증류하여 용매를 적절히 제거하고 여과하였다. 훈풍 건조 후 [(2-피리디닐아미노)싸이옥소메틸]-, 에틸 에스터(215 g, 수율 90%)을 얻었다.To 100 g of 2-aminopyridine was added 500 ml of dichloromethane (DCM). 0 and 139.3 g ethoxycarbonylisothiocyanate was slowly added dropwise over 15 minutes. The reaction solution was warmed to room temperature and stirred for 20 hours. The solvent was appropriately removed by distillation under reduced pressure and the mixture was filtered. After drying with warm air, [(2-pyridinylamino) thioxomethyl] -, ethyl ester (215 g, yield 90%) was obtained.
<단계 2> <Step 2> [1,2,4]트리아졸로[1,5-a]피리딘[1,2,4] triazolo [1,5-a] pyridine -2--2- 아민의Amine 합성 synthesis
하이드록실아민 하이드로클로라이드 298 g에 에탄올/메탈올(1:1, 2.15 L) 혼합용매를 가하였다. 트리에틸아민 399 ㎖를 반응액에 가하고 1시간 교반하였다. 상기에서 합성된 [(2-피리디닐아미노)싸이옥소메틸]-, 에틸 에스터 215 g을 첨가하고 서서히 온도를 올려주어 3시간 동안 가열 환류하였다. 온도를 상온으로 냉각하고 생성된 고체를 여과하였다. 얻어진 고체 생성물을 합하여 정제수, 에탄올/메탄올 혼합용매 및 n-헥산으로 세척하고 훈풍 건조하여 [1,2,4]트리아졸로[1,5-a]피리딘-2-아민(115 g, 수율 90%)을 얻었다.A mixed solvent of ethanol / methanol (1: 1, 2.15 L) was added to 298 g of hydroxylamine hydrochloride. 399 ml of triethylamine was added to the reaction solution and stirred for 1 hour. 215 g of [(2-pyridinylamino) thioxomethyl] -, ethyl ester synthesized above was added and the temperature was gradually raised, and the mixture was heated to reflux for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered. The obtained solid products were combined and washed with purified water, an ethanol / methanol mixed solvent and n-hexane, and dried under a warm air stream to obtain [l, 2,4] triazolo [l, 5- a] pyridin- ).
1H-NMR (in DMSO): δ 8.50 (dd, 1H), 7.39 (t, 1H), 7.29 (dd, 1H), 6.81 (t, 1H), 5.97 (s, 2H)(D, 1H), 6.97 (s, 2H), 7.90 (d, 1H)
Mass: [(M+H)+] : 134Mass: [(M + H) < + & gt ; ]: 134
<단계 3> 2-<Step 3> 2- 브로모Bromo -- [1,2,4]트리아졸로[1,5-a]피리딘[1,2,4] triazolo [1,5-a] pyridine 의 합성 Synthesis of
상기에서 합성된 [1,2,4]트리아졸로[1,5-a]피리딘-2-아민 115 g 에 CuBr2 57.5 g과 테트라하이드로퓨란(THF) 1.2 L를 가하였다. 반응액을 0로 냉각하고 HBr 1.2 L를 천천히 첨가하고 수산화나트륨 177 g을 정제수 600 ㎖에 용해시켜 천천히 적가하였다. 반응액을 상온에서 12시간 교반하였다. 반응액에 수산화나트륨수용액 500 ㎖를 가하고 1 시간 교반 후 혼합액을 에틸 아세테이트(EA) 2 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 2-브로모-[1,2,4]트리아졸로[1,5-a]피리딘(102 g, 수율 60%)을 얻었다.To 115 g of the [1,2,4] triazolo [1,5-a] pyridin-2-amine synthesized above was added 57.5 g of CuBr 2 and 1.2 L of tetrahydrofuran (THF). The reaction solution was cooled to 0, 1.2 L of HBr was slowly added, and 177 g of sodium hydroxide was dissolved in 600 ml of purified water and slowly added dropwise. The reaction solution was stirred at room temperature for 12 hours. To the reaction mixture was added 500 ml of an aqueous solution of sodium hydroxide. After stirring for 1 hour, the mixture was extracted with 2 L of ethyl acetate (EA) and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure and purified by silica gel column chromatography to obtain 2-bromo- [1,2,4] triazolo [1,5-a] pyridine (102 g, yield 60% ≪ / RTI >
1H-NMR (in DMSO): δ 8.92 (dd, 1H), 7.78 (dd, 1H), 7.72 (td, [0110] 1H), 7.23 (td, 1H)(Dd, 1H), 7.72 (td, 1H), 7.23 (td, 1H)
Mass: [(M+H)+] : 198Mass: [(M + H) < + & gt ; ]: 198
<단계 4> ID-1의 합성<Step 4> Synthesis of ID-1
상기에서 합성된 2-브로모-[1,2,4]트리아졸로[1,5-a]피리딘 102 g, 4,4,4',4',5,5,5',5'-옥타메틸-2,2'-바이(1,3,2-디옥사보로란) 58.8 g에 1,4-다이옥산 1.5 L를 가하였다. Pd(dppf)Cl2 7.8 g, 아세트산칼륨 57.1 g을 반응액에 첨가하였다. 혼합액을 130에서 12시간 동안 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 1.5 L로 반응을 종결시켰다. 혼합액을 EA 2.5 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 황산마그네슘으로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 ID-1(31.1 g, 수율 25%)을 얻었다.102 g of the 2-bromo- [1,2,4] triazolo [1,5-a] pyridine synthesized above, 4 g of 4,4,4 ', 4', 5,5,5 ' To 58.8 g of methyl-2,2'-bi (1,3,2-dioxaborolane) was added 1.5 L of 1,4-dioxane. 7.8 g of Pd (dppf) Cl 2 and 57.1 g of potassium acetate were added to the reaction solution. The mixture was heated to reflux at 130 for 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 1.5 L of aqueous ammonium chloride solution. The mixture was extracted with 2.5 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous magnesium sulfate, distilled under reduced pressure, and purified by silica gel column chromatography to obtain ID-1 (31.1 g, yield 25%).
Mass: [(M+H)+] : 246Mass: [(M + H) < + & gt ; ]: 246
[[ 합성예Synthetic example 1] 화합물 1의 합성 1] Synthesis of Compound 1
PPY-1 3.0 g 및 (4-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 3.4 g, 테트라키스(트리페닐포스핀)팔라듐(0) 500 mg, 2M 포타슘 카보네이트 수용액 15 ㎖을 톨루엔 60 ㎖, 에탄올 12 ㎖와 물 12 ㎖에 넣고 2시간 가열 환류 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 인산칼륨 용액을 제거하여 층분리하여 감압증류하고 실리카겔 컬럼크로마토그래피 (메틸렌클로라이드 단독 사용)로 정제하여 화합물 1(2.3 g, 수율 55%)을 제조하였다.3.0 g of PPY-1 and 3.4 g of (4- (4,6-diphenyl-1,3,5-triazine-2-yl) phenyl) boronic acid, tetrakis (triphenylphosphine) palladium mg of 2M potassium carbonate aqueous solution (15 ml) were added to toluene (60 ml), ethanol (12 ml) and water (12 ml), and the mixture was refluxed with stirring for 2 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium phosphate solution was removed, the layers were separated, vacuum distilled, and purified by silica gel column chromatography (using methylene chloride alone) to give Compound 1 (2.3 g, yield 55%).
Mass: [(M+H)+] : 617Mass: [(M + H) < + & gt ; ]: 617
[[ 합성예Synthetic example 2] 화합물 3의 합성 2] Synthesis of Compound 3
상기 합성예 1에서 PPY-1 대신 PTZ-1를 사용한 것을 제외하고는 동일한 방법으로 화합물 3(2.7 g, 수율 53%)을 제조하였다.Compound 3 (2.7 g, yield 53%) was prepared in the same manner as in Synthesis Example 1, except that PTZ-1 was used instead of PPY-1.
Mass: [(M+H)+] : 618Mass: [(M + H) < + & gt ; ]: 618
[[ 합성예Synthetic example 3] 화합물 6의 합성 3] Synthesis of Compound 6
상기 합성예 1에서 PPY-1 대신 PPY-2를 사용하였고, (4-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 ID-1을 사용한 것을 제외하고는 동일한 방법으로 화합물 6(2.9 g, 수율 56%)을 제조하였다.PPY-2 was used instead of PPY-1 in Synthesis Example 1 and ID-1 was used instead of (4- (4,6-diphenyl-1,3,5-triazin- Compound 6 (2.9 g, yield 56%) was prepared in the same manner except that
Mass: [(M+H)+] : 503Mass: [(M + H) < + & gt ; ]: 503
[[ 합성예Synthetic example 4] 화합물 11의 합성 4] Synthesis of Compound 11
상기 합성예 1에서 (4-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산을 사용한 것을 제외하고는 동일한 방법으로 화합물 11(2.3 g, 수율 51%)을 제조하였다.(3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenylboronic acid was used in place of (4- -Triazin-2-yl) phenyl) boronic acid, the compound 11 (2.3 g, yield 51%) was prepared.
Mass: [(M+H)+] : 617Mass: [(M + H) < + & gt ; ]: 617
[[ 합성예Synthetic example 5] 화합물 13의 합성 5] Synthesis of Compound 13
상기 합성예 4에서 PPY-1 대신 PTZ-1을 사용한 것을 제외하고는 동일한 방법으로 화합물 13(2.3 g, 수율 50%)를 제조하였다.Compound 13 (2.3 g, yield 50%) was prepared in the same manner as in Synthesis Example 4, except that PTZ-1 was used instead of PPY-1.
Mass: [(M+H)+] : 618Mass: [(M + H) < + & gt ; ]: 618
[[ 합성예Synthetic example 6] 화합물 16의 합성 6] Synthesis of Compound 16
상기 합성예 3에서 PPY-2 대신 PPY-4를 사용한 것을 제외하고는 동일한 방법으로 화합물 16(3.1 g, 수율 59%)를 제조하였다.Compound 16 (3.1 g, yield 59%) was prepared in the same manner as in Synthesis Example 3, except that PPY-4 was used instead of PPY-2.
Mass: [(M+H)+] : 503Mass: [(M + H) < + & gt ; ]: 503
[[ 합성예Synthetic example 7] 화합물 21의 합성 7] Synthesis of Compound 21
상기 합성예 2에서 PTZ-1 대신 PPY-2를 사용한 것을 제외하고는 동일한 방법으로 화합물 21(2.6 g, 수율 54%)를 제조하였다.Compound 21 (2.6 g, yield: 54%) was prepared in the same manner as in Synthesis Example 2, except that PPY-2 was used instead of PTZ-1.
Mass: [(M+H)+] : 693Mass: [(M + H) < + & gt ; ]: 693
[[ 합성예Synthetic example 8] 화합물 31의 합성 8] Synthesis of Compound 31
상기 합성예 4에서 PPY-1 대신 PPY-2를 사용한 것을 제외하고는 동일한 방법으로 화합물 31(2.3 g, 수율 52%)를 제조하였다.Compound 31 (2.3 g, yield 52%) was prepared in the same manner as in Synthesis Example 4, except that PPY-2 was used instead of PPY-1.
Mass: [(M+H)+] : 693Mass: [(M + H) < + & gt ; ]: 693
[[ 합성예Synthetic example 9] 화합물 36의 합성 9] Synthesis of Compound 36
PPY-3 3.0 g과 ID-1 2.1g 및 Cs2CO3 3.0 g을 섞고 톨루엔 60 ㎖와 에탄올 12 ㎖, 물 12 ㎖를 첨가한 뒤, Pd(OAc)2 55 mg과 Xphos 250 mg를 넣고 4시간동안 가열, 교반하였다. 반응 종료 후 상온으로 온도를 낮춘 후 여과하였다. 여과액을 물에 붓고 클로로포름으로 추출하고, 유기층을 MgSO4로 건조하였다. 감압 농축 시킨 뒤 THF:Hex = 1:3으로 컬럼하여 화합물 36(2.4 g, 수율 58%)를 제조하였다.2.0 g of PPY-3, 2.1 g of ID-1, 3.0 g of Cs 2 CO 3, 60 ml of toluene, 12 ml of ethanol and 12 ml of water were added, and then 55 mg of Pd (OAc) 2 and 250 mg of Xphos Lt; / RTI > for 1 hour. After completion of the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured into water and extracted with chloroform, dried the organic layer with MgSO 4. The mixture was concentrated under reduced pressure and then subjected to column chromatography with THF: Hex = 1: 3 to prepare Compound 36 (2.4 g, yield 58%).
Mass: [(M+H)+] : 579Mass: [(M + H) < + & gt ; ]: 579
[[ 합성예Synthetic example 10] 화합물 41의 합성 10] Synthesis of Compound 41
상기 합성예 4에서 PPY-1 대신 PPY-4를 사용한 것을 제외하고는 동일한 방법으로 화합물 41(1.9 g, 수율 45%)를 제조하였다.Compound 41 (1.9 g, yield 45%) was prepared in the same manner as in Synthesis Example 4, except that PPY-4 was used instead of PPY-1.
Mass: [(M+H)+] : 693Mass: [(M + H) < + & gt ; ]: 693
[[ 합성예Synthetic example 11] 화합물 43의 합성 11] Synthesis of Compound 43
상기 합성예 9에서 PPY-3 대신 PTZ-2를 사용했고, ID-1 대신 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산을 사용한 것을 제외하고는 동일한 방법으로 화합물 43(3.2 g, 수율 61%)를 제조하였다.PTZ-2 was used instead of PPY-3 in Synthesis Example 9, and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Compound 43 (3.2 g, yield 61%) was prepared in the same manner except for using the compound obtained in Preparation Example 1.
Mass: [(M+H)+] : 694Mass: [(M + H) < + & gt ; ]: 694
[[ 합성예Synthetic example 12] 화합물 46의 합성 12] Synthesis of Compound 46
상기 합성예 9에서 PPY-3 대신 PPY-5를 사용한 것을 제외하고는 동일한 방법으로 화합물 46(1.3 g, 수율 36%)를 제조하였다.Compound 46 (1.3 g, yield 36%) was prepared in the same manner as in Synthesis Example 9, except that PPY-5 was used instead of PPY-3.
Mass: [(M+H)+] : 579Mass: [(M + H) < + & gt ; ]: 579
[[ 합성예Synthetic example 13] 화합물 71의 합성 13] Synthesis of Compound 71
상기 합성예 11에서 PTZ-2 대신 PPY-5를 사용한 것을 제외하고는 동일한 방법으로 화합물 71(1.8 g, 수율 33%)를 제조하였다.Compound 71 (1.8 g, yield 33%) was prepared in the same manner as in Synthesis Example 11, except that PPY-5 was used instead of PTZ-2.
Mass: [(M+H)+] : 769Mass: [(M + H) < + & gt ; ]: 769
[[ 합성예Synthetic example 14] 화합물 76의 합성 14] Synthesis of Compound 76
상기 합성예 9에서 PPY-3 대신 PPY-6을 사용한 것을 제외하고는 동일한 방법으로 화합물 76(2.1 g, 수율 41%)을 제조하였다.Compound 76 (2.1 g, yield 41%) was prepared in the same manner as in Synthesis Example 9, except that PPY-6 was used instead of PPY-3.
Mass: [(M+H)+] : 655Mass: [(M + H) < + & gt ; ]: 655
[실시예 1 내지 14] 청색 유기 전계 발광 소자의 제작[Examples 1 to 14] Fabrication of blue organic electroluminescent device
합성예에서 합성된 화합물 1, 3, 6, 11, 13, 16, 21, 31, 36, 41, 43, 46, 71, 76을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제작하였다.Compounds 1, 3, 6, 11, 13, 16, 21, 31, 36, 41, 43, 46, 71 and 76 synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, Thereby preparing an organic electroluminescent device.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (㈜두산전자, 30 nm)/표 1의 전자 수송층 재료 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.(15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / electron transport layer material (Table 1) on the ITO transparent electrode prepared above 30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.
[비교예 1] 청색 유기 전계 발광 소자의 제작[Comparative Example 1] Fabrication of a blue organic electroluminescent device
전자 수송층 재료로서 화합물 1 대신 Alq3을 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that Alq 3 was used instead of Compound 1 as the electron transport layer material.
[비교예 2] 청색 유기 전계 발광 소자의 제작[Comparative Example 2] Fabrication of blue organic electroluminescent device
전자 수송층 물질로서 화합물 1을 사용하지 않은 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that Compound 1 was not used as an electron transport layer material.
상기 실시예 1 내지 14 및 비교예 1, 2에서 사용된 NPB, AND 및 Alq3의 구조는 하기와 같다.The structures of NPB, AND and Alq3 used in Examples 1 to 14 and Comparative Examples 1 and 2 are as follows.
[평가예 1][Evaluation Example 1]
실시예 1 내지 14 및 비교예 1, 2에서 제작된 각각의 청색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 1에 나타내었다.Each of the blue organic electroluminescent devices fabricated in Examples 1 to 14 and Comparative Examples 1 and 2 was measured for driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm 2, Respectively.
(V)Driving voltage
(V)
(nm)Emission peak
(nm)
(cd/A)Current efficiency
(cd / A)
상기 표 1에 나타낸 바와 같이, 상기 합성예에서 합성된 화합물 1, 3, 6, 11, 13, 16, 21, 31, 36, 41, 43, 46, 71, 76을 전자 수송층에 사용한 청색 유기 전계 발광 소자(실시예 1 내지 14)는 종래의 Alq3를 전자 수송층에 사용한 청색 유기 전계 발광 소자(비교예 1) 및 전자 수송층이 없는 청색 유기 전계 발광 소자(비교예 2)에 비해 구동전압, 발광피크 및 전류효율 면에서 우수한 성능을 나타내는 것을 알 수 있었다.As shown in the above Table 1, the blue organic electric field of Compound 1, 3, 6, 11, 13, 16, 21, 31, 36, 41, 43, 46, 71, Compared to the blue organic electroluminescent device using the conventional Alq 3 as the electron transporting layer (Comparative Example 1) and the blue organic electroluminescent device without the electron transporting layer (Comparative Example 2) using the conventional Alq 3 , the light emitting devices (Examples 1 to 14) Peak and current efficiency.
Claims (10)
[화학식 1]
상기 화학식 1에서,
X1 내지 X3은 질소 또는 탄소이며, 적어도 두 개 이상의 질소를 포함하고,
Y1 내지 Y4 중 하나는 질소이며, 나머지는 탄소이고,
n은 1 내지 3의 정수이며,
L은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,
R1은 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C6~C60의 아릴기로 이루어진 군에서 선택되거나, R1이 복수인 경우 인접한 기와 결합하여 축합 고리를 형성하며;
a는 0 내지 4의 정수이고,
A는 하기 화학식 2 또는 화학식 3으로 표시되며,
[화학식 2]
[화학식 3]
상기 화학식 2 내지 화학식 3에서,
Z1 내지 Z3은 질소 또는 탄소이며, 적어도 두 개 이상의 질소를 포함하고,
Z4 내지 Z6은 N(R4) 또는 탄소이며, 적어도 두 개 이상의 질소를 포함하며,
Ar1 내지 Ar4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기에서 선택되고,
R2 내지 R4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시 클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,
*는 상기 화학식 1과 결합이 이루어지는 부분을 의미하고,
상기 R1의 알킬기, 아릴기와, 상기 Ar1 내지 Ar4, R2 내지 R4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 포스핀기, 포스핀옥사이드기, 아릴아민기와, 상기 L의 아릴렌기, 헤테로아릴렌기는, 각각 독립적으로 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C40의 포스핀기, C1~C40의 포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 상기 치환기가 복수일 경우 복수의 치환기는 서로 동일하거나 상이하다.A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
X 1 to X 3 are nitrogen or carbon, and contain at least two or more nitrogen atoms,
One of Y 1 to Y 4 is nitrogen and the other is carbon,
n is an integer of 1 to 3,
L is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,
R 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C 1 to C 40 alkyl group, C 6 to C 60 aryl group, or when R 1 is plural, bonding with adjacent groups to form a condensed ring;
a is an integer of 0 to 4,
A is represented by the following general formula (2) or (3)
(2)
(3)
In the above Chemical Formulas 2 to 3,
Z 1 to Z 3 are nitrogen or carbon, and contain at least two or more nitrogen atoms,
Z 4 to Z 6 are N (R 4 ) or carbon, and contain at least two or more nitrogen atoms,
Ar 1 to Ar 4 are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cyclo An alkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkyl group, 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 , is selected from an arylamine group of C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 of,
R 2 to R 4 are the same or different and 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 cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkynyl 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 the arylboronic group, C 6 ~ C 60 aryl phosphine group, and selected from the group consisting of C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,
* Represents a moiety bonded to Formula 1,
Alkyl group of the R 1, the aryl group, said Ar 1 to Ar 4, R 2 an alkyl group of 1 to R 4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy The aryl group and the heteroarylene group of L each independently represent a group selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, an alkoxy group, an aryloxy group, An amino group, 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 heteroaryl group having 3 to 40 nuclear atoms A cycloalkyl group, 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 alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 1 ~ C 40 of the phosphine group, C 1 ~ C 40 phosphine of Ox Group and a C 6 ~ is unsubstituted or substituted by one or more substituents selected from the group consisting of an aryl amine of the C 60, when the substituent is a plurality a plurality of substituents are the same or different from each other.
상기 화학식 1로 표시되는 화합물은 하기 화학식 4 내지 화학식 8 중 어느 하나로 표시되는 것인 화합물:
[화학식 4]
[화학식 5]
[화학식 6]
[화학식 7]
[화학식 8]
상기 화학식 4 내지 화학식 8에서,
X1 내지 X3, Y1 내지 Y4, L, A, n은 제1항에서 정의한 바와 같다.The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (4) to (8)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
[Chemical Formula 8]
In the above Chemical Formulas 4 to 8,
X 1 to X 3 , Y 1 to Y 4 , L, A and n are as defined in claim 1.
상기 화학식 1에서 L은 단일 결합 또는 하기 L-1 내지 L-5로 표시되는 구조로 이루어진 군에서 선택되는 것인 화합물.
L in Formula 1 is a single bond or a structure represented by the following formulas L-1 to L-5.
상기 화학식 1에서 A는 하기 A-1 내지 A-12로 표시되는 구조로 이루어진 군에서 선택되는 것인 화합물.
Wherein A in the above formula (1) is selected from the group consisting of the structures represented by the following A-1 to A-12.
상기 화학식 1에서 A는 하기 A-13 내지 A-26으로 표시되는 구조로 이루어진 군에서 선택되는 것인 화합물.
Wherein A in the above formula (1) is selected from the group consisting of the structures represented by the following A-13 to A-26.
상기 Ar1 내지 Ar4는 각각 독립적으로 하기 구조에서 선택되는 아릴기인 화합물.
Each of Ar 1 to Ar 4 is independently an aryl group selected from the following structures.
상기 화학식 1로 표시되는 화합물은 하기 화합물 1 내지 160 중 어느 하나인 화합물.
Wherein the compound represented by the formula (1) is any one of the following compounds (1) to (160).
상기 1층 이상의 유기물 층에서 적어도 하나는 제1항 내지 제7항 중 어느 한 항에 기재된 화합물을 포함하는 것인 유기 전계 발광 소자.1. An organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 7.
상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층, 전자수송 보조층 및 전자 주입층으로 이루어진 군에서 선택되는 것인 유기 전계 발광 소자.9. The method of claim 8,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer.
상기 화합물을 포함하는 유기물층은 전자 수송층 및 전자수송 보조층으로 이루어진 군에서 선택되는 것인 유기 전계 발광 소자.9. The method of claim 8,
Wherein the organic compound layer containing the compound is selected from the group consisting of an electron transporting layer and an electron transporting auxiliary layer.
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| CN111233776A (en) * | 2020-03-11 | 2020-06-05 | 吉林奥来德光电材料股份有限公司 | Organic photoelectric material containing heterocyclic structure, preparation method thereof and organic electroluminescent device comprising organic photoelectric material |
| WO2020116881A1 (en) * | 2018-12-03 | 2020-06-11 | 두산솔루스 주식회사 | Organic compound and organic electroluminescent element comprising same |
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| CN111909132A (en) * | 2019-05-07 | 2020-11-10 | 北京鼎材科技有限公司 | Organic material and organic electroluminescent device using same |
| CN111116562A (en) * | 2019-12-24 | 2020-05-08 | 吉林奥来德光电材料股份有限公司 | Organic light-emitting compound and preparation method and application thereof |
| CN111072637B (en) * | 2019-12-27 | 2023-04-07 | 吉林奥来德光电材料股份有限公司 | Organic light-emitting compound, preparation method thereof and organic light-emitting device |
| CN115536636A (en) * | 2021-06-29 | 2022-12-30 | 江苏三月科技股份有限公司 | Compound containing triazine structure and organic electroluminescent device containing compound |
| CN116283790A (en) * | 2021-12-07 | 2023-06-23 | 江苏三月科技股份有限公司 | Pyrimidine structure-containing compound and organic electroluminescent device prepared from same |
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