KR20230047988A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents
Organic light-emitting compound and organic electroluminescent device using the same Download PDFInfo
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- KR20230047988A KR20230047988A KR1020230040601A KR20230040601A KR20230047988A KR 20230047988 A KR20230047988 A KR 20230047988A KR 1020230040601 A KR1020230040601 A KR 1020230040601A KR 20230040601 A KR20230040601 A KR 20230040601A KR 20230047988 A KR20230047988 A KR 20230047988A
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 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
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 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
- 238000011160 research Methods 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
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 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
- 125000004306 triazinyl group Chemical group 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D209/56—Ring systems containing three or more rings
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- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- 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
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- H10K50/00—Organic light-emitting devices
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Abstract
Description
본 발명은 신규한 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 유기 전계 발광 소자의 유기물층에 사용되는 화합물에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device including the same, and more particularly, to a compound used in an organic material layer of an organic electroluminescent device.
1950년대 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 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 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Research on organic electroluminescent (EL) devices, which began with Bernanose’s observation of light emission in organic thin films in the 1950s and led to blue electroluminescence using anthracene single crystal in 1965, was conducted by Tang in 1987. An organic electroluminescent device having a laminated structure divided into functional layers of a light emitting layer has been proposed. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
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 the two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the material used as the organic layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.
유기 전계 발광 소자의 발광층 형성 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그 밖에, 보다 나은 천연색을 구현하기 위한 발광 재료로 노란색 및 주황색 발광 재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있어 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다.Materials for forming the light emitting layer of the organic electroluminescent device may be classified into blue, green, and red light emitting materials according to the light emitting color. In addition, yellow and orange light emitting materials are also used as light emitting materials for implementing better natural colors. In addition, in order to increase color purity and increase light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The dopant material may be divided into a phosphorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, the development of phosphorescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층 재료로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 재료는 안트라센 유도체들이 형광 도펀트/호스트 재료로서 보고되고 있다. 특히, 발광 재료 중 효율 향상 측면에서 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색의 도펀트 재료로 사용되고 있다. 현재까지는 CBP(4,4-dicarbazolybiphenyl)가 인광 호스트 재료로 우수한 특성을 나타내고 있다.Until now, hole injection layer, hole transport layer. As materials for the hole blocking layer and electron transport layer, NPB, BCP, Alq 3 , and the like represented by the following chemical formula are widely known, and anthracene derivatives have been reported as fluorescent dopant/host materials for light emitting materials. In particular, phosphorescent materials having advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , and (acac)Ir(btp) 2 as blue, green, and red dopant materials. is being used as Until now, CBP (4,4-dicarbazolybiphenyl) has shown excellent properties as a phosphorescent host material.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 좋지 않아 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다.However, conventional materials, although advantageous in terms of light emitting properties, have low glass transition temperatures and poor thermal stability, so they are not satisfactory in terms of lifespan of organic light emitting devices.
상기한 문제점을 해결하기 위해, 본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 열적 안적성 및 발광 특성 등이 우수한 신규 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, an object of the present invention is to provide a novel compound that can be applied to an organic electroluminescent device and has excellent thermal stability and light emitting properties.
또한 본 발명은 상기 신규 화합물을 포함하여 낮은 구동 전압과 높은 발광 효율을 나타내며 수명이 향상된 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In addition, an object of the present invention is to provide an organic electroluminescent device exhibiting a low driving voltage and high luminous efficiency and having an improved lifetime, including the novel compound.
상기한 목적을 달성하기 위해 본 발명은, 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
A 고리는 단일환 또는 다환의 방향족 고리이고;Ring A is a monocyclic or polycyclic aromatic ring;
X는 -O-, -S-, 또는 -C(R5R6)- 이며;X is -O-, -S-, or -C(R 5 R 6 )-;
L1 및 L2는 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 and L 2 are a single bond, or selected from the group consisting of a C 6 ~ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Ar1은 하기 화학식 2 내지 화학식 4 중 어느 하나로 표시되고,Ar 1 is represented by any one of Formulas 2 to 4 below;
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에서, *은 결합이 이루어지는 부분을 의미하고,In Chemical Formulas 2 to 4, * means a part where a bond is formed,
Y1 내지 Y17은 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R7)에서 선택되고, 이때 R7이 복수인 경우, 복수의 R7은 서로 같거나 또는 상이하며,Y 1 to Y 17 are the same as or different from each other, and are each independently selected from N or C (R 7 ), wherein when R 7 is plural, a plurality of R 7 are the same as or different from each other;
상기 화학식 3에서 L1에 결합되는 Y6 내지 Y9 중 어느 하나는 C(R7)이고,In Formula 3, any one of Y 6 to Y 9 bonded to L 1 is C(R 7 ),
Z1은 N 또는 C(R7)이며,Z 1 is N or C(R 7 );
R1 내지 R4 및 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 1 to R 4 and R 7 are each independently hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group And C 6 ~ C 60 It is selected from the group consisting of an arylamine group,
R5 및 R6는 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 서로 결합하여 축합 고리를 형성하며,R 5 and R 6 are hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 aryl Silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group and C 6 ~ C 60 Is selected from the group consisting of an arylamine group of, or bonded to each other to form a condensed ring,
R1 내지 R7의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며,An alkyl group of R 1 to R 7 , a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, Arylphosphine oxide group and arylamine group are each independently selected from deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~C 40 alkyloxy group, C 6 ~C 60 aryloxy group, C 3 ~C 40 alkylsilyl group, C 6 ~C 60 arylsilyl group, C 1 ~C 40 alkylboron group, C 6 ~C 60 arylboron group, C 6 ~C 60 arylphosphine group, C 6 ~C 60 arylphosphine oxide group, and Substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ~ C 60 arylamine groups;
a 내지 d는 각각 1 내지 4의 정수이다.a to d are integers of 1 to 4, respectively.
또한, 본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물 층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 An organic electroluminescent device comprising the compound is provided.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물 층의 재료로 사용될 수 있다. 특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 열적 안정성, 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.Since the compound represented by Chemical Formula 1 of the present invention has excellent thermal stability and light emitting properties, it can be used as a material for an organic layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having thermal stability, excellent light emitting performance, low driving voltage, high efficiency and long lifespan can be prepared compared to conventional host materials. Furthermore, a full color display panel with improved performance and lifespan can be manufactured.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
<신규 유기 화합물><New organic compounds>
본 발명은 카바졸과 디벤조 모이어티가 결합되어 기본 골격을 형성하고, 상기 기본 골격에 전자 흡습성이 큰 전자 끌개기(electron-withdrawing group; EWG)가 도입된 화합물로, 상기 화학식 1로 표시된다.The present invention is a compound in which a carbazole and a dibenzo moiety are bonded to form a basic skeleton, and an electron-withdrawing group (EWG) having high electron absorption is introduced into the basic skeleton, and is represented by Formula 1 above. .
구체적으로, 본 발명의 화학식 1로 표시되는 화합물은 카바졸의 질소(N)에 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기(예를 들어, 트리아진기, 피리딘기, 트라이졸로피리딘기 등)와 같은 전자 흡습성이 큰 전자 끌개기(EWG)가 도입되어 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에, 이를 유기 전계 발광 소자의 유기물층에 적용할 경우 정공과 전자의 결합력을 높일 수 있다.Specifically, the compound represented by Formula 1 of the present invention is a substituted or unsubstituted aryl group on nitrogen (N) of carbazole, or a substituted or unsubstituted heteroaryl group (eg, triazine group, pyridine group, tri Since an electron withdrawing group (EWG) with high electron hygroscopicity such as a zolopyridine group is introduced and the entire molecule has a bipolar characteristic, when applied to the organic layer of an organic electroluminescent device, the bonding force between holes and electrons can be increased. can
이와 같이, 상기 화학식 1로 표시되는 화합물은 전자 이동성이 우수할 뿐 아니라 높은 유리 전이온도(Tg) 및 열적 안정이 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 발광층, 전자 수송층 및 전자 수송층에 추가로 적층되는 전자수송 보조층 중 어느 하나의 재료로 사용될 수 있다.As such, the compound represented by Chemical Formula 1 has excellent electron mobility as well as high glass transition temperature (Tg) and excellent thermal stability. For this reason, since the compound represented by Chemical Formula 1 of the present invention has excellent electron transport ability and light emitting characteristics, it is suitable for any one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer, which are the organic material layers of the organic electroluminescent device. material can be used. Preferably, it may be used as a material for any one of the light emitting layer, the electron transport layer, and the electron transport auxiliary layer additionally stacked on the electron transport layer.
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, diffusion of excitons generated in the light emitting layer to an electron transport layer or a hole transport layer adjacent to the light emitting layer can be prevented. The number of excitons contributing to light emission in the light emitting layer is increased so that the light emitting efficiency of the device can be improved, and the lifespan of the device can be effectively increased by improving durability and stability of the device. Most of the developed materials are capable of low-voltage driving, thereby exhibiting physical characteristics that improve lifespan.
상기 화학식 1로 표시되는 화합물에서, A 고리는 단일환 또는 다환의 방향족 고리이고, X는 -O-, -S-, 또는 -C(R5R6)- 이며, L1 및 L2는 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택된다.In the compound represented by Formula 1, ring A is a monocyclic or polycyclic aromatic ring, X is -O-, -S-, or -C(R 5 R 6 )-, and L 1 and L 2 are single It is selected from the group consisting of a bond or a C 6 ~ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms.
본 발명의 바람직한 일례를 들면, Ar1은 하기 화학식 2 내지 화학식 4 중 어느 하나로 표시된다.For a preferred example of the present invention, Ar 1 is represented by any one of Formulas 2 to 4 below.
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에서,In Formulas 2 to 4,
*은 결합이 이루어지는 부분을 의미하고,* indicates the part where the coupling is made,
Y1 내지 Y17은 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R7)에서 선택되고, 이때 R7이 복수인 경우, 복수의 R7은 서로 같거나 또는 상이할 수 있다.Y 1 to Y 17 are the same as or different from each other, and are each independently selected from N or C(R 7 ). In this case, when R 7 is plural, a plurality of R 7 may be the same as or different from each other.
상기 화학식 3에서, L1에 결합되는 Y6 내지 Y9 중 어느 하나는 C(R7)인 것이 바람직하다.In Formula 3, any one of Y 6 to Y 9 bonded to L 1 is preferably C(R 7 ).
상기 화학식 4에서, Z1은 N 또는 C(R7)일 수 있다.In Formula 4, Z 1 may be N or C(R 7 ).
R1 내지 R4 및 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된다. 바람직하게는 상기 R1 내지 R4는 모두 수소인 경우이다.R 1 to R 4 and R 7 are each independently hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group And C 6 ~ C 60 It is selected from the group consisting of an arylamine group. Preferably, all of R 1 to R 4 are hydrogen.
R5 및 R6는 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 서로 결합하여 축합 고리를 형성할 수 있다. 바람직하게는, 상기 R5 및 R6는 각각 독립적으로, 수소, C1~C40의 알킬기 및 C6~60의 아릴기로 이루어진 군에서 선택된다.R 5 and R 6 are hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 aryl Silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group and C 6 ~ C 60 It is selected from the group consisting of an arylamine group, or may be bonded to each other to form a condensed ring. Preferably, R 5 and R 6 are each independently selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, and a C 6 to 60 aryl group.
R1 내지 R7의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되될 수 있다.An alkyl group of R 1 to R 7 , a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, Arylphosphine oxide group and arylamine group are each independently selected from deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~C 40 alkyloxy group, C 6 ~C 60 aryloxy group, C 3 ~C 40 alkylsilyl group, C 6 ~C 60 arylsilyl group, C 1 ~C 40 alkylboron group, C 6 ~C 60 arylboron group, C 6 ~C 60 arylphosphine group, C 6 ~C 60 arylphosphine oxide group, and It may be substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ~ C 60 arylamine groups.
a 내지 d는 각각 1 내지 4의 정수이다.a to d are integers of 1 to 4, respectively.
본 발명의 화학식 1로 표시되는 화합물은, L2가 페닐 또는 비페닐 등을 포함하는 아릴기인 경우에 하기 화학식 5의 화합물로 보다 구체화될 수 있다.The compound represented by Formula 1 of the present invention, when L 2 is an aryl group including phenyl or biphenyl, may be further embodied as a compound represented by Formula 5 below.
[화학식 5][Formula 5]
상기 화학식 5에서, L1은 단일결합 또는 하기 구조에서 선택되는 아릴렌일 수 있으며, n은 0 내지 2의 정수이다.In Formula 5, L 1 may be a single bond or an arylene selected from the following structures, and n is an integer from 0 to 2.
한편 본 발명에 따른 화학식 1로 표시되는 화합물에서, L1은 단일결합이고, Ar1은 화학식 2 또는 3으로 표시되며, 여기서 Y1 내지 Y5, 및 Y6 내지 Y9 중에서 2 이상은 N이고, 상기 L2는 메타 위치 결합을 갖는 C6~C18의 아릴렌기인 것이 바람직하다.Meanwhile, in the compound represented by Formula 1 according to the present invention, L 1 is a single bond, Ar 1 is represented by Formula 2 or 3, wherein Y 1 to Y 5 , and Y 6 to Y 9 , at least two of which are N, and , L 2 is preferably a C 6 to C 18 arylene group having a meta-position bond.
구체적으로, 상기 화학식 2 및 3으로 표시되는 치환체는 하기 화학식 S1 내지 S5로 표시되는 치환체로 이루어진 군에서 선택되는 것이 바람직하다.Specifically, the substituents represented by Formulas 2 and 3 are preferably selected from the group consisting of substituents represented by Formulas S1 to S5 below.
이러한 본 발명의 화학식 1로 표시되는 화합물은 하기 화합물 1 내지 330으로 구체화될 수 있으나, 이들로 한정되는 것은 아니다.The compound represented by Formula 1 of the present invention may be embodied in the following compounds 1 to 330, but is not limited thereto.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, 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. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkenyl" refers to 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 thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.
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. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkynyl" refers to 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 thereof include, but are not limited to, ethynyl and 2-propynyl.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 40의 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.In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed 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 40의 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.In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and furthermore, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl and the like, but are not limited thereto.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. can include Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 "아릴아민"은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미한다.In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 40 carbon atoms.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are N, O, S or a heteroatom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 40의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" refers to silyl substituted with aryl having 5 to 40 carbon atoms.
본 발명에서 "축합고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
<유기 전계 발광 소자><Organic electroluminescent device>
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)를 제공한다.The present invention provides an organic electroluminescent device (organic EL device) including the compound represented by Formula 1 above.
보다 구체적으로, 본 발명의 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 of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes the compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 수명 개선층, 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, 전자수송층 및 전자 수송층에 추가로 적층되는 전자수송 보조층으로 구성된 군에서 선택될 수 있으며, 발광층인 것이 바람직하다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a lifespan improvement layer, an electron transport layer, and an electron injection layer, and at least one organic material layer among them is a compound represented by Formula 1 above. can include Specifically, the organic material layer including the compound of Formula 1 may be selected from the group consisting of a light emitting layer, an electron transport layer, and an electron transport auxiliary layer additionally stacked on the electron transport layer, and is preferably a light emitting layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트를 포함할 수 있는데, 이때 호스트로서 상기 화학식 1로 표시되는 화합물을 단독으로 포함하거나 상기 화학식 1로 표시되는 화합물과 함께 다른 화합물을 호스트로 포함할 수 있다.The light emitting layer of the organic electroluminescent device of the present invention may include a host. In this case, the compound represented by Formula 1 may be included alone as a host, or another compound together with the compound represented by Formula 1 may be included as a host. .
상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 청색, 녹색, 적색의 인광 호스트 재료로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 구체적으로 상기 화학식 1로 표시되는 화합물은 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 전계 발광 소자에 포함되는 것이 바람직하다. 특히, 본 발명의 화학식 1로 표시되는 화합물은 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료인 것이 바람직하며, 발광층의 적색 인광 호스트인 것이 더욱 바람직하다.When the compound represented by Formula 1 is included as a material for the light emitting layer of the organic light emitting device, preferably as a blue, green, or red phosphorescent host material, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency of the organic light emitting device is increased. (luminous efficiency and power efficiency), lifespan, luminance, driving voltage, etc. can be improved. Specifically, the compound represented by Formula 1 is preferably included in an organic electroluminescent device as a green and/or red phosphorescent host, a fluorescent host, or a dopant material. In particular, the compound represented by Formula 1 of the present invention is preferably a phosphorescent host, fluorescent host or dopant material of the light emitting layer, more preferably a red phosphorescent host of the light emitting layer.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 상기 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층, 전자수송층 및 전자 수송층에 추가로 적층되는 전자수송 보조층이 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 injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. At least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, preferably in addition to the light emitting layer, the electron transport layer and the electron transport layer. The stacked electron transport auxiliary layer may include the compound represented by Formula 1 above.
본 발명의 유기 전계 발광 소자의 구조는 전극(음극, 또는 양극)과 유기물층의 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between an electrode (cathode or anode) and an organic material layer.
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.The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
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 layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but may be a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet.
또, 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.In addition, as the anode material, 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); combinations of metals and oxides such as ZnO:Al or SnO 2 :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 is not limited thereto.
또, 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.In addition, as the negative electrode material, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; and multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and conventional materials known in the art may 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 through examples. However, the following examples are only to illustrate the present invention, and the present invention is not limited by the following examples.
[준비예 1] CD1의 합성[Preparation Example 1] Synthesis of CD1
<단계 1> 10-(3-클로로페닐)-7H-벤조[c]카바졸의 합성<Step 1> Synthesis of 10-(3-chlorophenyl)-7H-benzo[c]carbazole
질소 기류 하에서 10-브로모-7H-벤조[c]카바졸 (20 g, 81.3 mmol), (3-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)에 400 ml/100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 10-(3-클로로페닐)-7H-벤조[c]카바졸 (19.4 g, 수율 86 %)을 얻었다.10-Bromo-7H-benzo[c]carbazole (20 g, 81.3 mmol), (3-chlorophenyl)boronic acid (15.3 g, 97.5 mmol), Pd(PPh 3 ) 4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added with 400 ml/100 ml of THF/H 2 O and stirred at 80° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the filtered organic layer, it was purified by column chromatography to obtain the target compound, 10-(3-chlorophenyl)-7H-benzo[c]carbazole (19.4 g, yield 86%).
1H-NMR: δ 7.38 (d, 1H), 7.46 (m, 6H), 7.61 (m, 2H), 7.77 (d, 1H), 8.03 (s, 1H), 8.15 (d, 2H), 10.30 (s, 1H) 1H -NMR: δ 7.38 (d, 1H), 7.46 (m, 6H), 7.61 (m, 2H), 7.77 (d, 1H), 8.03 (s, 1H), 8.15 (d, 2H), 10.30 ( s, 1H)
<단계 2> CD1의 합성<Step 2> Synthesis of CD1
질소 기류 하에서 10-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]싸이오페-4-닐보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.10-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]thiophe-4-nylboronic acid (15.4 g, 64.8 mmol) under nitrogen stream , Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol %) and 1,4-dioxane/H 2 O (400 ml/100 ml) and stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD1 (18.4 g, 수율 78%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD1 (18.4 g, yield 78%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.88 (d, 3H), 8.13 (d, 1H), 10.3 (s, 1H) 1H -NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.88 (d, 3H), 8.13 (d, 1H), 10.3 (s, 1H)
[준비예 2] CD2의 합성[Preparation Example 2] Synthesis of CD2
<단계 1> 9-(3-클로로페닐)-7H-벤조[c]카바졸의 합성<Step 1> Synthesis of 9-(3-chlorophenyl)-7H-benzo[c]carbazole
질소 기류 하에서 9-브로모-7H-벤조[c]카바졸 (20 g, 81.3 mmol), (3-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)에 400 ml/100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피로 이용하여 목적 화합물인 9-(3-클로로페닐)-7H-벤조[c]카바졸 (18.4 g, 수율 82 %)을 얻었다.9-Bromo-7H-benzo[c]carbazole (20 g, 81.3 mmol), (3-chlorophenyl)boronic acid (15.3 g, 97.5 mmol), Pd(PPh 3 ) 4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added with 400 ml/100 ml of THF/H 2 O and stirred at 80° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 9-(3-chlorophenyl)-7H-benzo[c]carbazole (18.4 g, yield 82%).
1H-NMR: δ 7.40 (d, 1H), 7.44 (m, 5H), 7.48 (d, 1H) 7.60 (m, 2H), 7.74 (d, 1H), 8.01 (s, 1H), 8.12 (d, 2H), 10.11 (s, 1H)1H-NMR: δ 7.40 (d, 1H), 7.44 (m, 5H), 7.48 (d, 1H) 7.60 (m, 2H), 7.74 (d, 1H), 8.01 (s, 1H), 8.12 (d, 2H), 10.11 (s, 1H)
<단계 2> CD2의 합성<Step 2> Synthesis of CD2
질소 기류 하에서 9-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]싸이오페-4-닐보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.9-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]thiophe-4-nylboronic acid (15.4 g, 64.8 mmol) under nitrogen stream , Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol %) and 1,4-dioxane/H 2 O (400 ml/100 ml) and stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD2 (17.8 g, 수율 76%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD2 (17.8 g, yield 76%).
1H-NMR: δ 7.01 (t, 3H), 7.44 (d, 2H), 7.60 (m, 10H), 7.75 (s, 1H), 7.88 (d, 3H), 8.13 (d, 1H), 10.22 (s, 1H) 1H -NMR: δ 7.01 (t, 3H), 7.44 (d, 2H), 7.60 (m, 10H), 7.75 (s, 1H), 7.88 (d, 3H), 8.13 (d, 1H), 10.22 ( s, 1H)
[준비예 3] CD3의 합성[Preparation Example 3] Synthesis of CD3
<단계 1> 8-(3-클로로페닐)-7H-벤조[c]카바졸의 합성<Step 1> Synthesis of 8-(3-chlorophenyl)-7H-benzo[c]carbazole
질소 기류 하에서 8-브로모-7H-벤조[c]카바졸 (20 g, 81.3 mmol), (3-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)에 400 ml/100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 8-(3-클로로페닐)-7H-벤조[c]카바졸 (15.3 g, 수율 71 %)을 얻었다.8-Bromo-7H-benzo[c]carbazole (20 g, 81.3 mmol), (3-chlorophenyl)boronic acid (15.3 g, 97.5 mmol), Pd(PPh 3 ) 4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added with 400 ml/100 ml of THF/H 2 O and stirred at 80° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the filtered organic layer, it was purified by column chromatography to obtain the target compound, 8-(3-chlorophenyl)-7H-benzo[c]carbazole (15.3 g, yield 71%).
1H-NMR: δ 7.33 (d, 1H), 7.41 (m, 5H), 7.48 (d, 1H) 7.60 (m, 2H), 7.74 (d, 1H), 8.01 (s, 1H), 8.31 (d, 1H) 8.42 (d, 1H), 10.76 (s, 1H)1H-NMR: δ 7.33 (d, 1H), 7.41 (m, 5H), 7.48 (d, 1H) 7.60 (m, 2H), 7.74 (d, 1H), 8.01 (s, 1H), 8.31 (d, 1H) 8.42 (d, 1H), 10.76 (s, 1H)
<단계 2> CD3의 합성<Step 2> Synthesis of CD3
질소 기류 하에서 8-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]싸이오페-4-닐보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.8-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]thiophe-4-nylboronic acid (15.4 g, 64.8 mmol) under nitrogen stream , Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol %) and 1,4-dioxane/H 2 O (400 ml/100 ml) and stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD3 (15.8 g, 수율 70%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD3 (15.8 g, yield 70%).
1H-NMR: δ 7.11 (t, 3H), 7.48 (d, 2H), 7.63 (m, 10H), 7.75 (d, 1H), 7.88 (d, 3H), 8.19 (d, 1H), 10.83 (s, 1H) 1H -NMR: δ 7.11 (t, 3H), 7.48 (d, 2H), 7.63 (m, 10H), 7.75 (d, 1H), 7.88 (d, 3H), 8.19 (d, 1H), 10.83 ( s, 1H)
[준비예 4] CD4의 합성[Preparation Example 4] Synthesis of CD4
질소 기류 하에서 [준비예 1] <단계 1>에서 합성한, 10-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]싸이오페-3-닐보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.10-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]thiophene, synthesized in [Preparation Example 1] <Step 1> under a nitrogen stream -3-Nylboronic acid (15.4 g, 64.8 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol %) and 1,4-dioxane/H 2 O (400 ml/100 ml) and then stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD4 (17.2 g, 수율 75%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD4 (17.2 g, yield 75%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H) 1H -NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 ( s, 1H)
[준비예 5] CD5의 합성[Preparation Example 5] Synthesis of CD5
질소 기류 하에서 [준비예 1] <단계 1>에서 합성한, 10-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]퓨란-4-닐보로닉산 (15.4 g, 64.6 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.10-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]furan- 4-nylboronic acid (15.4 g, 64.6 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane/H2O (400 ml/100 ml) was mixed and then stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD5 (17.2 g, 수율 75%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD5 (17.2 g, yield 75%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H)1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s , 1H)
[준비예 6] CD6의 합성[Preparation Example 6] Synthesis of CD6
질소 기류 하에서 [준비예 2] <단계 1>에서 합성한, 9-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]퓨란-4-닐보로닉산 (15.4 g, 64.6 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 9-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]furan- 4-nylboronic acid (15.4 g, 64.6 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane/H2O (400 ml/100 ml) was mixed and then stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD6 (18.7 g, 수율 79%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD6 (18.7 g, yield 79%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H)1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s , 1H)
[준비예 7] CD7의 합성[Preparation Example 7] Synthesis of CD7
질소 기류 하에서 [준비예 3] <단계 1>에서 합성한, 8-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]퓨란-4-닐보로닉산 (15.4 g, 64.6 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.8-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]furan, synthesized in [Preparation Example 3] <Step 1> under a nitrogen stream 4-nylboronic acid (15.4 g, 64.6 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane/H2O (400 ml/100 ml) was mixed and then stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD7 (18.7 g, 수율 79%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD7 (18.7 g, yield 79%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H)1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s , 1H)
[준비예 8] CD8의 합성[Preparation Example 8] Synthesis of CD8
질소 기류 하에서 [준비예 1] <단계 1>에서 합성한, 10-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]퓨란-3-닐보로닉산 (15.4 g, 64.6 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.10-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]furan- 3-Nylboronic acid (15.4 g, 64.6 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane/H 2 O (400 ml/100 ml) was mixed and stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD8 (18.7 g, 수율 79%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD8 (18.7 g, yield 79%).
*1591H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H)*1591H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 ( s, 1H)
[준비예 9] CD9의 합성[Preparation Example 9] Synthesis of CD9
질소 기류 하에서 [준비예 1] <단계 1>에서 합성한, 10-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.6 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.10-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluorene, synthesized in [Preparation Example 1] <Step 1> under a nitrogen stream -2-yl)boronic acid (15.4 g, 64.6 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol%) ) and 1,4-dioxane/H2O (400 ml/100 ml) and stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD9 (18.7 g, 수율 79%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD9 (18.7 g, yield 79%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H)1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s , 1H)
[준비예 10] CD10의 합성[Preparation Example 10] Synthesis of CD10
질소 기류 하에서 [준비예 2] <단계 1>에서 합성한, 9-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]퓨란-3-닐보로닉산 (15.4 g, 64.6 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.9-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]furan- 3-Nylboronic acid (15.4 g, 64.6 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane/H2O (400 ml/100 ml) was mixed and then stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과하여 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD10 (18.7 g, 수율 79%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the organic layer obtained by filtration, it was purified by column chromatography to obtain CD10 (18.7 g, yield 79%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H)1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s , 1H)
[준비예 11] CD11의 합성[Preparation Example 11] Synthesis of CD11
질소 기류 하에서 [준비예 3] <단계 1>에서 합성한, 8-(3-클로로페닐)-7H-벤조[c]카바졸 (15 g, 54.01 mmol), 디벤조[b,d]퓨란-3-닐보로닉산 (15.4 g, 64.6 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2 (0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다.8-(3-chlorophenyl)-7H-benzo[c]carbazole (15 g, 54.01 mmol), dibenzo[b,d]furan, synthesized in [Preparation Example 3] <Step 1> under a nitrogen stream 3-Nylboronic acid (15.4 g, 64.6 mmol), Cs 2 CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane/H2O (400 ml/100 ml) was mixed and then stirred at 120° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CD11 (18.7 g, 수율 79%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the obtained organic layer, it was purified by column chromatography to obtain CD11 (18.7 g, yield 79%).
1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s, 1H)1H-NMR: δ 7.32 (t, 3H), 7.58 (m, 11H), 7.75 (s, 2H), 7.86 (d, 2H), 7.98 (s, 1H), 8.09 (d, 1H), 10.31 (s , 1H)
[합성예 1] 화합물 1의 합성[Synthesis Example 1] Synthesis of Compound 1
CD1 (10 g, 22.9 mmol)와 2-클로로-4,6-디페닐-1,3,5-트리아진 (6.8 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol)을 150 ml 톨루엔에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 여과된 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물 1 (11.6 g, 수율 75%)을 얻었다.CD1 (10 g, 22.9 mmol) with 2-chloro-4,6-diphenyl-1,3,5-triazine (6.8 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol); P(t-Bu) 3 (0.9 g, 4.6 mmol) and sodium tert-butoxide (4.4 g, 45.9 mmol) were added to 150 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto, followed by filtration. After removing the solvent from the filtered organic layer, it was purified by column chromatography to obtain the target compound 1 (11.6 g, yield 75%).
Mass: [(M+H)+] : 707Mass: [(M+H) + ] : 707
[합성예 2] 화합물 6의 합성[Synthesis Example 2] Synthesis of Compound 6
CD1 대신 CD4(10 g, 22.9 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 6 (11.2 g, 수율 74%)를 얻었다.The target compound 6 (11.2 g, yield 74%) was obtained in the same manner as in Synthesis Example 1, except that CD4 (10 g, 22.9 mmol) was used instead of CD1.
Mass: [(M+H)+] : 707Mass: [(M+H) + ] : 707
[합성예 3] 화합물 171의 합성[Synthesis Example 3] Synthesis of Compound 171
CD1 대신 CD2(10 g, 22.9 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 171 (10.8 g, 수율 72%)를 얻었다.Except for using CD2 (10 g, 22.9 mmol) instead of CD1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound 171 (10.8 g, yield 72%).
Mass: [(M+H)+] : 707Mass: [(M+H) + ] : 707
[합성예 4] 화합물 191의 합성[Synthesis Example 4] Synthesis of Compound 191
CD1 대신 CD3(10 g, 22.9 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 191 (13.3 g, 수율 79%)를 얻었다.The target compound 191 (13.3 g, yield 79%) was obtained in the same manner as in Synthesis Example 1, except that CD3 (10 g, 22.9 mmol) was used instead of CD1.
Mass: [(M+H)+] : 707Mass: [(M+H) + ] : 707
[합성예 5] 화합물 51의 합성[Synthesis Example 5] Synthesis of Compound 51
CD1 대신 CD5(10 g, 21.7 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 51 (12.1 g, 수율 76%)를 얻었다.The target compound 51 (12.1 g, yield 76%) was obtained in the same manner as in Synthesis Example 1, except that CD5 (10 g, 21.7 mmol) was used instead of CD1.
Mass: [(M+H)+] : 691Mass: [(M+H) + ] : 691
[합성예 6] 화합물 56의 합성[Synthesis Example 6] Synthesis of Compound 56
CD1 대신 CD8(10 g, 21.7 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 56 (13.5 g, 수율 79%)를 얻었다.Except for using CD8 (10 g, 21.7 mmol) instead of CD1, the target compound 56 (13.5 g, yield 79%) was obtained in the same manner as in Synthesis Example 1.
Mass: [(M+H)+] : 691Mass: [(M+H) + ] : 691
[합성예 7] 화합물 231의 합성[Synthesis Example 7] Synthesis of Compound 231
CD1 대신 CD6(10 g, 21.7 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 231 (11.2 g, 수율 74%)를 얻었다.Except for using CD6 (10 g, 21.7 mmol) instead of CD1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound 231 (11.2 g, yield 74%).
Mass: [(M+H)+] : 691Mass: [(M+H) + ] : 691
[합성예 8] 화합물 251의 합성[Synthesis Example 8] Synthesis of Compound 251
CD1 대신 CD7(10 g, 21.7 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 251 (12.9 g, 수율 77%)를 얻었다.The target compound 251 (12.9 g, yield 77%) was obtained in the same manner as in Synthesis Example 1, except that CD7 (10 g, 21.7 mmol) was used instead of CD1.
Mass: [(M+H)+] : 691Mass: [(M+H) + ] : 691
[합성예 9] 화합물 106의 합성[Synthesis Example 9] Synthesis of Compound 106
CD1 대신 CD9(10 g, 20.6 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 106 (12.1 g, 수율 76%)를 얻었다.Except for using CD9 (10 g, 20.6 mmol) instead of CD1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound 106 (12.1 g, yield 76%).
Mass: [(M+H)+] : 717Mass: [(M+H) + ] : 717
[합성예 10] 화합물 296의 합성[Synthesis Example 10] Synthesis of Compound 296
CD1 대신 CD10(10 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 296 (13.4 g, 수율 79%)를 얻었다.Except for using CD10 (10 g, 20.6 mmol) instead of CD1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound 296 (13.4 g, yield 79%).
Mass: [(M+H)+] : 717Mass: [(M+H) + ] : 717
[합성예 11] 화합물 316의 합성[Synthesis Example 11] Synthesis of Compound 316
CD1 대신 CD11(10 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 316 (11.2 g, 수율 74%)를 얻었다.Except for using CD11 (10 g, 20.6 mmol) instead of CD1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound 316 (11.2 g, yield 74%).
Mass: [(M+H)+] : 717Mass: [(M+H) + ] : 717
[합성예 12] 화합물 5의 합성[Synthesis Example 12] Synthesis of Compound 5
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-클로로-4-페닐퀴나졸린 (6.3 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 5 (10.9 g, 수율 73%)를 얻었다.The same procedure as in Synthesis Example 1 was performed except that 2-chloro-4-phenylquinazoline (6.3 g, 22.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. This was carried out to obtain the target compound 5 (10.9 g, yield 73%).
Mass: [(M+H)+] : 680Mass: [(M+H) + ] : 680
*223[합성예 13] 화합물 10의 합성 *223 [Synthesis Example 13] Synthesis of Compound 10
CD1 대신 CD4(10 g, 22.9 mmol)를 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 10 (13.5 g, 수율 79%)를 얻었다.Except for using CD4 (10 g, 22.9 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 10 (13.5 g, yield 79%).
Mass: [(M+H)+] : 680Mass: [(M+H) + ] : 680
[합성예 14] 화합물 175의 합성[Synthesis Example 14] Synthesis of Compound 175
CD1 대신 CD2(10 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 175 (11.2 g, 수율 74%)를 얻었다.Except for using CD2 (10 g, 22.9 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 175 (11.2 g, yield 74%).
Mass: [(M+H)+] : 680Mass: [(M+H) + ] : 680
[합성예 15] 화합물 195의 합성[Synthesis Example 15] Synthesis of Compound 195
CD1 대신 CD3(10 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 195 (11.2 g, 수율 74%)를 얻었다.Except for using CD3 (10 g, 22.9 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 195 (11.2 g, yield 74%).
Mass: [(M+H)+] : 680Mass: [(M+H) + ] : 680
[합성예 16] 화합물 55의 합성[Synthesis Example 16] Synthesis of Compound 55
CD1 대신 CD5(10 g, 21.7 mmol)를 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 55 (11.2 g, 수율 74%)를 얻었다.Except for using CD5 (10 g, 21.7 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 55 (11.2 g, yield 74%).
Mass: [(M+H)+] : 664Mass: [(M+H) + ] : 664
[합성예 17] 화합물 60의 합성[Synthesis Example 17] Synthesis of Compound 60
CD1 대신 CD8(10 g, 21.7 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 60 (12.1 g, 수율 76%)를 얻었다.Except for using CD8 (10 g, 21.7 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 60 (12.1 g, yield 76%).
Mass: [(M+H)+] : 664Mass: [(M+H) + ] : 664
[합성예 18] 화합물 235의 합성[Synthesis Example 18] Synthesis of Compound 235
CD1 대신 CD6(10 g, 21.7 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 235 (12.6 g, 수율 76%)를 얻었다.Except for using CD6 (10 g, 21.7 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 235 (12.6 g, yield 76%).
Mass: [(M+H)+] : 664Mass: [(M+H) + ] : 664
[합성예 19] 화합물 255의 합성[Synthesis Example 19] Synthesis of Compound 255
CD1 대신 CD7(10 g, 21.7 mmol)를 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 255 (11.2 g, 수율 74%)를 얻었다.Except for using CD7 (10 g, 21.7 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 255 (11.2 g, yield 74%).
Mass: [(M+H)+] : 664Mass: [(M+H) + ] : 664
[합성예 20] 화합물 110의 합성[Synthesis Example 20] Synthesis of Compound 110
CD1 대신 CD9(10 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 110 (11.4 g, 수율 74%)를 얻었다.Except for using CD9 (10 g, 20.6 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 110 (11.4 g, yield 74%).
Mass: [(M+H)+] : 690Mass: [(M+H) + ] : 690
[합성예 21] 화합물 300의 합성[Synthesis Example 21] Synthesis of Compound 300
CD1 대신 CD10(10 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 300 (10.9 g, 수율 72%)를 얻었다.Except for using CD10 (10 g, 20.6 mmol) instead of CD1, the same procedure as in Synthesis Example 12 was performed to obtain the target compound 300 (10.9 g, yield 72%).
Mass: [(M+H)+] : 690Mass: [(M+H) + ] : 690
[합성예 22] 화합물 320의 합성[Synthesis Example 22] Synthesis of Compound 320
CD1 대신 CD11(10 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물 320 (11.4 g, 수율 74%)를 얻었다.The target compound 320 (11.4 g, yield 74%) was obtained in the same manner as in Synthesis Example 12, except that CD11 (10 g, 20.6 mmol) was used instead of CD1.
Mass: [(M+H)+] : 690Mass: [(M+H) + ] : 690
[실시예 1] 녹색 유기 전계 발광 소자의 제작[Example 1] Fabrication of green organic electroluminescent device
합성예 1에서 합성한 화합물 1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.After subjecting Compound 1 synthesized in Synthesis Example 1 to high purity sublimation purification by a commonly known method, a green organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 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 코팅된 유리 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it is ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned by using UV for 5 minutes and vacuum evaporator A glass substrate coated with was transferred.
이렇게 준비된 ITO 투명 유리 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90%의 화합물 1 + 10%의 Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 녹색 유기 전계 발광 소자를 제조하였다.m-MTDATA (60 nm) / TCTA (80 nm) / 90% of Compound 1 + 10% of Ir (ppy) 3 (30 nm) / BCP (10 nm) / Alq 3 on the prepared ITO transparent glass substrate (electrode) (30 nm)/LiF (1 nm)/Al (200 nm) were laminated in this order to prepare a green organic light emitting device.
[실시예 2 내지 11] 녹색 유기 전계 발광 소자의 제작[Examples 2 to 11] Fabrication of green organic electroluminescent device
녹색 발광 호스트 물질로서 화합물 1 대신 합성예 2~11에서 합성된 각각의 화합물을 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.A green organic electroluminescent device was prepared in the same manner as in Example 1, except for using each of the compounds synthesized in Synthesis Examples 2 to 11 instead of Compound 1 as a green light emitting host material.
[비교예 1] 녹색 유기 전계 발광 소자의 제작[Comparative Example 1] Production of green organic electroluminescent device
녹색 발광 호스트 물질로서 화합물 1 대신 CBP를 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.A green organic electroluminescent device was prepared in the same manner as in Example 1, except that CBP was used instead of Compound 1 as a green light emitting host material.
한편 실시예 1 내지 11 및 비교예 1에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.Meanwhile, the structures of m-MTDATA, TCTA, Ir(ppy) 3 , CBP and BCP used in Examples 1 to 11 and Comparative Example 1 are as follows.
[평가예 1][Evaluation Example 1]
실시예 1 내지 11 및 비교예 1에서 각각 제조된 녹색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For the green organic electroluminescent devices prepared in Examples 1 to 11 and Comparative Example 1, driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. .
(V)driving voltage
(V)
(nm)luminescence peak
(nm)
(cd/A)current efficiency
(cd/A)
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층의 재료로 사용한 실시예 1 내지 11의 녹색 유기 전계 발광 소자는, 종래 CBP를 발광층에 사용한 비교예 1의 녹색 유기 전계 발광 소자에 비해 전류효율 및 구동전압이 우수하다는 것을 알 수 있다. [실시예 12] 적색 유기 전계 발광 소자의 제조 As shown in Table 1, the green organic electroluminescent devices of Examples 1 to 11 using the compound according to the present invention as a material for the light emitting layer have current compared to the green organic light emitting device of Comparative Example 1 using conventional CBP for the light emitting layer. It can be seen that the efficiency and driving voltage are excellent. [Example 12] Preparation of red organic electroluminescent device
합성예 12에서 합성한 화합물 5를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기 과정에 따라 적색 유기 전계 발광 소자를 제조하였다.After subjecting the compound 5 synthesized in Synthesis Example 12 to high purity sublimation purification by a commonly known method, a red organic electroluminescent device was prepared according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 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 코팅된 유기 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it is ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned by using UV for 5 minutes and vacuum evaporator The organic substrate coated with was transferred.
이렇게 준비된 ITO 투명 유리 기판(전극) 위에, m-MTDATA (60 nm)/TCTA (80 nm)/ 90%의 화합물 5 + 10%의 (piq)2Ir(acac) (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 적색 유기 전계 발광 소자를 제조하였다.On the prepared ITO transparent glass substrate (electrode), m-MTDATA (60 nm)/TCTA (80 nm)/ 90% of compound 5 + 10% of (piq) 2 Ir(acac) (300 nm)/BCP (10 nm)/Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm) in this order to prepare a red organic light emitting device.
[실시예 13 내지 22] 적색 유기 전계 발광 소자의 제조[Examples 13 to 22] Preparation of red organic electroluminescent device
적색 발광 호스트 물질로서 화합물 5 대신 합성예 13~22에서 합성된 각각의 화합물을 사용하는 것을 제외하고는, 상기 실시예 12와 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다.A red organic electroluminescent device was prepared in the same manner as in Example 12, except for using each of the compounds synthesized in Synthesis Examples 13 to 22 instead of Compound 5 as a red light emitting host material.
[비교예 2][Comparative Example 2]
적색 발광 호스트 물질로서 화합물 5 대신 CBP를 사용한 것을 제외하고는, 상기 실시예 12와 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다.A red organic electroluminescent device was prepared in the same manner as in Example 12, except that CBP was used instead of Compound 5 as a red light emitting host material.
한편 상기 실시예 12 내지 22 및 비교예 2에서 사용된 m-MTDATA, (piq)2Ir(acac), CBP 및 BCP의 구조는 하기와 같다.Meanwhile, the structures of m-MTDATA, (piq) 2 Ir(acac), CBP and BCP used in Examples 12 to 22 and Comparative Example 2 are as follows.
[평가예 2][Evaluation Example 2]
실시예 12 내지 22 및 비교예 2에서 각각 제조된 적색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하였고, 그 결과를 하기 표 2에 나타내었다.For the red organic EL devices prepared in Examples 12 to 22 and Comparative Example 2, driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below.
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층에 사용한 실시예 12 내지 22의 적색 유기 전계 발광 소자는, 종래 CBP를 발광층에 사용한 비교예 2의 적색 유기 전계 발광 소자에 비해 전류효율 및 구동전압이 우수하다는 것을 알 수 있다.As shown in Table 2, the red organic electroluminescent devices of Examples 12 to 22 using the compound according to the present invention in the light emitting layer have current efficiency and It can be seen that the driving voltage is excellent.
Claims (8)
[화학식 1]
상기 화학식 1에서,
A 고리는 단일환 또는 다환의 방향족 고리이고;
X는 -O-, -S-, 또는 -C(R5R6)- 이며;
L1 및 L2는 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고;
Ar1은 하기 화학식 2로 표시되고;
[화학식 2]
상기 화학식 2에서,
*은 결합이 이루어지는 부분을 의미하고;
Y1 내지 Y5은 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R7)에서 선택되고, 이때 R7이 복수인 경우, 복수의 R7은 서로 같거나 또는 상이하며;
상기 L2는 메타 위치 결합을 갖는 C6~C18의 아릴렌기이고;
R1 내지 R4 및 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, C6~C60의 아릴기로 이루어진 군에서 선택되고,
R1 내지 R4 및 R7의 알킬기, 시클로알킬기 및 아릴기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기 및 C6~C60의 아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고,
R5 및 R6는 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 서로 결합하여 축합 고리를 형성하며,
R5 내지 R6의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며,
a 내지 d는 각각 1 내지 4의 정수이다.A compound represented by Formula 1 below:
[Formula 1]
In Formula 1,
Ring A is a monocyclic or polycyclic aromatic ring;
X is -O-, -S-, or -C(R 5 R 6 )-;
L 1 and L 2 may be a single bond, or are selected from the group consisting of a C 6 ~ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Ar 1 is represented by Formula 2 below;
[Formula 2]
In Formula 2,
* indicates the part where the bond is made;
Y 1 to Y 5 are the same as or different from each other, and are each independently selected from N or C(R 7 ), wherein, when R 7 is plural, a plurality of R 7 are the same as or different from each other ;
L 2 is a C 6 ~ C 18 arylene group having a meta-position bond;
R 1 to R 4 and R 7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, C 6 ~ C 60 aryl group become,
The alkyl group, cycloalkyl group and aryl group of R 1 to R 4 and R 7 are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group and C 6 ~ C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups,
R 5 and R 6 are hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 aryl Silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group and C 6 ~ C 60 Is selected from the group consisting of an arylamine group of, or bonded to each other to form a condensed ring,
An alkyl group of R 5 to R 6 , a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, Arylphosphine oxide group and arylamine group are each independently selected from deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~C 40 alkyloxy group, C 6 ~C 60 aryloxy group, C 3 ~C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and Substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ~ C 60 arylamine groups;
a to d are integers of 1 to 4, respectively.
상기 화학식 1의 화합물은 하기 화학식 5로 표시되는 화합물:
[화학식 5]
상기 화학식 5에서,
L1은 단일결합 또는 하기 구조에서 선택되는 아릴렌이고;
n은 0 내지 2의 정수이며;
A, X, Ar1, R1 내지 R4, 및 a 내지 d는 각각 제1항에서 정의된 바와 같다.According to claim 1,
The compound of Formula 1 is a compound represented by Formula 5 below:
[Formula 5]
In Formula 5,
L 1 is a single bond or arylene selected from the following structures;
n is an integer from 0 to 2;
A, X, Ar 1 , R 1 to R 4 , and a to d are each as defined in claim 1.
상기 L1은 단일결합이고,
상기 Ar1은 화학식 2로 표시되고, 여기서 Y1 내지 Y5 중에서 2 이상은 N인 화합물.
According to claim 1,
L 1 is a single bond;
Wherein Ar 1 is represented by Formula 2, where at least 2 of Y 1 to Y 5 is N.
상기 화학식 2로 표시되는 치환체는 하기 화학식 S1 내지 S4로 표시되는 치환체로 이루어진 군에서 선택되는 화합물:
Substituents represented by Formula 2 are compounds selected from the group consisting of substituents represented by Formulas S1 to S4:
상기 R1 내지 R4는 모두 수소인 화합물.According to claim 1,
A compound wherein all of R 1 to R 4 are hydrogen.
상기 R5 및 R6는 각각 독립적으로, 수소, C1~C40의 알킬기 및 C6~60의 아릴기로 이루어진 군에서 선택되는 화합물.According to claim 1,
The R 5 and R 6 are each independently selected from the group consisting of hydrogen, a C 1 ~ C 40 alkyl group, and a C 6 ~ 60 aryl group.
상기 화합물을 포함하는 유기물층은 발광층, 전자 수송층 및 전자수송 보조층으로 구성된 군에서 선택되는 유기 전계 발광 소자.According to claim 7,
An organic electroluminescent device wherein the organic material layer containing the compound is selected from the group consisting of a light emitting layer, an electron transport layer, and an electron transport auxiliary layer.
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