KR101366492B1 - Novel compound and organic electroluminescent device comprising the same - Google Patents
Novel compound and organic electroluminescent device comprising the same Download PDFInfo
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- KR101366492B1 KR101366492B1 KR1020120066360A KR20120066360A KR101366492B1 KR 101366492 B1 KR101366492 B1 KR 101366492B1 KR 1020120066360 A KR1020120066360 A KR 1020120066360A KR 20120066360 A KR20120066360 A KR 20120066360A KR 101366492 B1 KR101366492 B1 KR 101366492B1
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- South Korea
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- unsubstituted
- substituted
- compound
- aryl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 224
- 239000011368 organic material Substances 0.000 claims abstract description 17
- 238000002347 injection Methods 0.000 claims abstract description 15
- 239000007924 injection Substances 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000004429 atom Chemical group 0.000 claims description 25
- 125000005264 aryl amine group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- -1 R 21 Chemical compound 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 125000005104 aryl silyl group Chemical group 0.000 claims description 15
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YGHBDHOLBYSDEM-UHFFFAOYSA-N (3-nitropyridin-2-yl)boronic acid Chemical compound OB(O)C1=NC=CC=C1[N+]([O-])=O YGHBDHOLBYSDEM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
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- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
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- 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
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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- 125000001041 indolyl group Chemical group 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
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- 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 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
- 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 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
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 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
- 125000005580 triphenylene 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- H10K2101/00—Properties of the organic materials covered by group H10K85/00
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- 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
Abstract
본 발명은 정공 주입 및 수송능, 발광능 등이 우수한 신규 아크리딘계 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel acridine-based compound having excellent hole injection and transport ability, light emitting ability, and the like and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the same in at least one organic material layer.
Description
본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 정공 주입능, 정공 수송능, 발광능 등이 우수한 신규 아크리딘계 화합물 및 상기 화합물을 유기물층의 재료로서 포함하여 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel compound and an organic electroluminescent device comprising the same, and more specifically, a novel acridine-based compound having excellent hole injection ability, hole transport ability, light emission ability, and the like, and including the compound as a material of an organic material layer to emit light The present invention relates to an organic EL device having improved characteristics such as efficiency, driving voltage, and lifetime.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광 (electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후, 유기 EL 소자의 효율 및 수명을 향상시키기 위하여, 소자 내 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 또한 이에 사용되는 특화된 물질의 개발로 이어졌다. A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film emission of Bernanose in the 1950s In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to improve the efficiency and lifetime of the organic EL device, the organic EL device has been developed to introduce a characteristic organic material layer in the device, and the development of specialized materials used thereon has been continued.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이, 음극에서는 전자가 각각 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥 상태로 떨어질 때 빛이 나게 된다. 유기물층으로 사용되는 물질은 그 기능에 따라 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 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 and holes are injected into the organic layer, respectively. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. A material used as an organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있기 때문에, 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해서도 관심이 집중되고 있다. The luminescent material may be classified into blue, green, and red luminescent materials depending on the luminescent color. In addition, it can be classified into yellow and orange light emitting materials necessary for realizing a 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. 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 phosphorescent materials can theoretically improve luminescence efficiency up to four times that of fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로사용되는 물질로는, 하기 화학식으로 표시되는 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 물질로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히, 발광 물질 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 있고, 이들은 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq 3 and the like represented by the following chemical formulas are widely known as materials used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, there are metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 , , And is used as a red dopant material. So far, CBP has shown excellent properties as a phosphorescent host material.
그러나, 종래 발광 물질들은 발광 특성 측면에서 양호하나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 EL 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. 따라서, 우수한 성능을 가지는 발광 물질의 개발이 요구되고 있다.However, conventional luminescent materials are good in terms of luminescence characteristics, but have low thermal stability due to their low glass transition temperature, and thus are not satisfactory in terms of lifetime in organic EL devices. Therefore, development of a luminescent material having excellent performance is required.
본 발명은 정공 주입능, 정공 수송능, 발광능 등이 모두 우수하여 발광층 재료, 정공 수송층 재료, 정공 주입층 재료로 사용될 수 있는 신규 화합물을 제공하는 것을 목적으로 한다. An object of the present invention is to provide a novel compound that can be used as a light emitting layer material, a hole transporting layer material, a hole injection layer material having excellent hole injection ability, hole transporting ability, light emitting ability and the like.
또, 본 발명은 상기 신규 화합물을 포함하여 구동전압이 낮고, 발광 효율이 높으며, 수명이 향상된 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the novel compound having a low driving voltage, high luminous efficiency, and an improved lifetime.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).
(상기 화학식 1에서,(In the formula 1,
X1 내지 X8은 각각 독립적으로 CR11 또는 N이고, 이때 복수개의 CR11은 서로 동일하거나 상이하며;X 1 to X 8 are each independently CR 11 or N, wherein a plurality of CR 11 are the same as or different from each other;
R11은 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 C3~C40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이때 이들은 인접한 기와 축합(fused)하여 방향족 고리 또는 헤테로방향족 고리를 형성하거나 또는 비형성하고;R 11 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 Alkynyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted C 3 to C 40 heterocycloalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted Heteroaryl group having 5 to 60 carbon atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 1 to An alkylsilyl group of C 40 , a substituted or unsubstituted C 6 -C 60 arylsilyl group, and a substituted or unsubstituted C 6 -C 60 arylamine group, wherein they are fused with adjacent groups Thereby forming or not forming an aromatic ring or heteroaromatic ring;
단, X1 내지 X8 중 적어도 하나는 인접한 기와 하기 화학식 2로 표시되는 축합(fused) 고리를 형성하며;Provided that at least one of X 1 to X 8 forms a fused ring represented by Formula 2 with an adjacent group;
상기 화학식 2 에서,In Formula 2,
Y1 내지 Y4는 각각 독립적으로 CR12 또는 N이고, 이때 복수개의 CR12는 서로 동일하거나 상이하며;Y 1 to Y 4 are each independently CR 12 or N, wherein a plurality of CR 12 are the same as or different from each other;
R12은 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 C3~C40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이때 이들은 인접한 기와 축합(fused)하여 방향족 고리 또는 헤테로방향족 고리를 형성하거나 또는 비형성하고;R 12 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 Alkynyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted C 3 to C 40 heterocycloalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted Heteroaryl group having 5 to 60 carbon atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 1 to An alkylsilyl group of C 40 , a substituted or unsubstituted C 6 -C 60 arylsilyl group, and a substituted or unsubstituted C 6 -C 60 arylamine group, wherein they are fused with adjacent groups Thereby forming or not forming an aromatic ring or heteroaromatic ring;
Ar1 및 Ar2은 각각 독립적으로 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 C3~C40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이때 이들은 인접한 기와 축합(fused) 고리를 형성하거나 또는 비형성하며;Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 1 ~ C 40 alkyl group, a substituted or unsubstituted C 2 ~ C 40 alkenyl group, a substituted or unsubstituted C 2 ~ C 40 alkynyl group, Substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted C 3 to C 40 heterocycloalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted nuclear atom A substituted or unsubstituted C 1 -C 40 alkyloxy group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 1 -C 40 group An alkylsilyl group, a substituted or unsubstituted C 6 -C 60 arylsilyl group, and a substituted or unsubstituted C 6 -C 60 arylamine group, wherein they form a fused ring with an adjacent group Or non-formal;
R21 및 R22는 각각 독립적으로 수소, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되며;R 21 and R 22 are each independently hydrogen, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted nuclear atom having 5 to 60 atoms. Heteroaryl groups are selected from the group consisting of;
상기 R11, R12, R21, R22, Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기 및 아릴아민기에 각각 도입될 수 있는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 니트릴기, 니트로기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C1~C40의 아미노기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 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, 이때 복수개의 치환기는 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkyl of R 11 , R 12, R 21 , R 22 , Ar 1 and Ar 2 One or more substituents that can be introduced to each of the silyl, arylsilyl and arylamine groups are each independently deuterium, halogen, nitrile, nitro, cyano, C 1 -C 40 alkyl, C 2 -C 40 alkenes group, C 1 ~ C 40 alkoxy group, C 1 ~ C 40 of the amino group, C of 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 40 aryl group, a nuclear atom Heteroaryl group of 5 to 60, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ arylamine group of C 60 of In the county And a plurality of substituents may be the same or different from each other.
또한, 본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화합물을 포함하는 것이 특징인 유기 전계 발광 소자를 제공한다. In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises the compound. Provided is an organic electroluminescent device.
상기 화합물을 포함하는 1층 이상의 유기물층은 정공 수송층, 정공 주입층 및 발광층으로 이루어진 군에서 선택되며, 바람직하게는 정공 수송층 및/또는 발광층이며, 보다 바람직하게는 발광층이다. 특히, 상기 화합물이 발광층에 포함될 경우, 상기 화합물은 인광 호스트 재료로 사용된다.At least one organic material layer including the compound is selected from the group consisting of a hole transporting layer, a hole injection layer and a light emitting layer, preferably a hole transporting layer and / or a light emitting layer, more preferably a light emitting layer. In particular, when the compound is included in the light emitting layer, the compound is used as a phosphorescent host material.
본 발명에 따른 화합물은 내열성, 정공 주입능, 정공 수송능, 발광능 등이 우수하기 때문에, 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 정공 주입층 재료, 정공 수송층 재료 또는 발광층 재료로 사용될 수 있다.Since the compound according to the present invention is excellent in heat resistance, hole injecting ability, hole transporting ability, and light emitting ability, it can be used as an organic material layer of an organic electroluminescent device, preferably as a hole injecting layer material, a hole transporting layer material, .
또한, 본 발명에 따른 화합물을 정공 주입층, 정공 수송층 및/또는 발광층에 포함하는 유기 EL 소자는 발광 성능, 구동전압, 수명, 효율 등의 측면이 크게 향상될 수 있고, 나아가 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic EL device including the compound according to the present invention in the hole injection layer, the hole transport layer, and / or the light emitting layer may greatly improve aspects such as light emission performance, driving voltage, lifespan, efficiency, and the like. Can be applied effectively.
이하, 본 발명에 대해 설명한다.Hereinafter, the present invention will be described.
본 발명에 따른 신규 화합물은 아크리딘 모이어티(acridine moiety)에 인돌 유도체 모이어티가 융합(fused)되어 기본 골격을 이루며, 이러한 기본 골격에 다양한 치환체가 결합되어 있는 아크리딘계 화합물로서, 상기 화학식 1로 표시되는 것을 특징으로 한다. 이러한 화학식 1로 표시되는 화합물은 종래 유기 EL 소자용 재료[예: 4,4-dicarbazolybiphenyl (이하, 'CBP'라 함)]보다 큰 분자량을 가져 열적 안정성이 높을 뿐만 아니라, 정공 주입능, 정공 수송능, 발광능 등이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자가 포함할 경우, 소자의 구동 전압, 효율, 수명 등이 향상될 수 있다.The novel compound according to the present invention is an acridine-based compound in which an indole derivative moiety is fused to an acridine moiety to form a basic skeleton, and various substituents are bonded to the basic skeleton. It is characterized by being displayed as 1. The compound represented by the formula (1) has a higher molecular weight than the conventional organic EL device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')) has a high thermal stability, hole injection ability, hole number It is excellent in the ability to transmit power and light emission. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
상기 화학식 1로 표시되는 화합물은 아크리딘계 모이어티와 인돌 유도체 모이어티가 융합(축합)되어 이루어진 인돌로아크리딘(indoloacridine) 기본 골격에 알킬기, 아릴기, 헤테로아릴기 등의 다양한 치환체가 연결되어 있고, 또 방향족 고리 또는 헤테로방향족 고리, 바람직하게는 헤레토방향족 고리가 축합되어 있음으로써, 에너지 레벨이 조절되어 넓은 밴드갭 (sky blue ~ red)을 가질 수 있다. 이러한 화합물은 소자의 인광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있고, 또한 도입되는 치환체의 종류에 따라 전자 수송 능력 등도 향상시킬 수 있다. 따라서, 상기 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(인광 호스트 재료), 정공 수송층 재료 및 정공 주입층 재료, 보다 바람직하게는 발광층 재료로 사용될 수 있다. 또한, 상기 화학식 1의 화합물은 선택적으로 적절한 치환체를 도입함으로써, 전자 수송층 재료 등으로도 사용될 수 있다. 특히, 상기 화학식 1의 화합물은 인돌로아크리딘계 기본골격으로 인해 넓은 밴드갭을 가지면서, 정공과 전자의 결합력을 향상시킬 수 있기 때문에, 종래 CBP에 비해 발광층 재료, 특히 인광 호스트 재료로서 우수한 특성을 발휘할 수 있다.The compound represented by Formula 1 has various substituents such as alkyl group, aryl group, heteroaryl group, etc., connected to indoloacridine base skeleton formed by fusion (condensation) of acridine-based moiety and indole derivative moiety. And by condensation of an aromatic ring or a heteroaromatic ring, preferably a heretoaromatic ring, the energy level can be controlled to have a wide bandgap (sky blue to red). Such a compound can improve the phosphorescence property of the device, and can also improve the hole injection / transport capacity, the luminous efficiency, the driving voltage, the lifespan characteristics, and the like, and also improve the electron transport ability and the like depending on the type of substituents to be introduced. . Therefore, the compound of Formula 1 may be used as an organic material layer material, preferably a light emitting layer material (phosphorescent host material), a hole transport layer material and a hole injection layer material, more preferably a light emitting layer material of the organic electroluminescent device. In addition, the compound of Formula 1 may optionally be used as an electron transporting layer material by introducing an appropriate substituent. In particular, the compound of Formula 1 has a wide bandgap due to the indolo acridine-based skeleton, and can improve the binding force between the hole and the electron, it has excellent properties as a light emitting layer material, especially a phosphorescent host material compared to the conventional CBP Can be exercised.
또한, 상기 화학식 1로 표시되는 화합물은 인돌로아크리딘계 기본 골격에 다양한 치환체, 특히 아릴기 및/또는 헤테로아릴기가 도입되어 화합물의 분자량이 유의적으로 증대됨으로써, 유리 전이온도가 향상되고, 이로 인해 종래 CBP보다 높은 열적 안정성을 가질 수 있다. 따라서, 본 발명의 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자는 내구성 및 수명 특성이 크게 향상될 수 있다. In addition, the compound represented by the formula (1) is introduced into a variety of substituents, especially aryl groups and / or heteroaryl groups in the indolo acridine-based skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby It may have a higher thermal stability than conventional CBP. Therefore, the organic electroluminescent device including the compound represented by Chemical Formula 1 of the present invention may greatly improve durability and lifespan characteristics.
아울러, 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 정공 주입/수송층, 청색, 녹색 및/또는 적색의 인광 호스트 재료로 채택할 경우, 종래 CBP 대비 효율 및 수명 측면에서 월등히 우수한 효과를 발휘할 수 있다. 따라서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 성능 개선 및 수명 향상에 크게 기여할 수 있으며, 나아가 유기 전계 발광 소자의 수명 향상은 풀 칼라 유기 발광 패널의 성능을 극대화시킬 수 있다.In addition, when the compound represented by Chemical Formula 1 is adopted as a hole injection / transport layer, a blue, green and / or red phosphorescent host material of an organic EL device, it may exhibit an excellent effect in terms of efficiency and lifetime compared to conventional CBP. have. Therefore, the compound according to the present invention can greatly contribute to improvement of the performance and lifetime of the organic electroluminescent device, and further, the lifetime of the organic electroluminescent device can maximize the performance of the full-color organic electroluminescent panel.
본 발명에 따른 화학식 1로 표시되는 화합물에서, X1 내지 X8는 각각 독립적으로 CR11 또는 질소(N)이고, 이때 복수개의 CR11은 서로 동일하거나 상이할 수 있다.In the compound represented by Formula 1 according to the present invention, X 1 to X 8 are each independently CR 11 or nitrogen (N), wherein a plurality of CR 11 may be the same or different from each other.
상기 R11은 수소, 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 것이 바람직하다. R 11 is hydrogen, halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted nuclear atom having 5 to 60 atoms It is preferably selected from the group consisting of a heteroaryl group and a substituted or unsubstituted C 6 ~ C 60 arylamine group.
이때, 상기 R11의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있고, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.At this time, the alkyl group, aryl group, heteroaryl group and arylamine group of R 11 are each independently deuterium, halogen, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, heteroatoms of 3 to 40 hetero atoms Cycloalkyl group, C 6 ~ C 60 aryl group, C 5 ~ C 60 heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkyl Silyl 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 arylphosphine group, C 6 ~ C 60 aryl It may be substituted with one or more substituents selected from the group consisting of a phosphine oxide group and a C 6 ~ C 60 arylamine group, a plurality of substituents may be the same or different from each other.
다만, 상기 화학식 1의 화합물에서, 상기 X1 내지 X8 중 적어도 하나, 바람직하게는 X5 내지 X8 중 적어도 하나는 인접한 기와 상기 화학식 2로 표시되는 축합 고리를 형성한다. However, in the compound of Formula 1, at least one of X 1 to X 8 , preferably at least one of X 5 to X 8 forms a condensed ring represented by Formula 2 with an adjacent group.
상기 화학식 2로 표시되는 축합 고리에 있어서, Y1 내지 Y4는 각각 독립적으로 CR12 또는 질소(N)이고, 이때 복수개의 CR12는 서로 동일하거나 상이할 수 있다.In the condensed ring represented by Formula 2, Y 1 to Y 4 are each independently CR 12 or nitrogen (N), and a plurality of CR 12 may be the same or different from each other.
상기 R12는 수소, 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 것이 바람직하다. R 12 is hydrogen, halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted nuclear atom having 5 to 60 atoms It is preferably selected from the group consisting of a heteroaryl group and a substituted or unsubstituted C 6 ~ C 60 arylamine group.
이때, 상기 R12의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있고, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.At this time, the alkyl group, aryl group, heteroaryl group and arylamine group of R 12 are each independently deuterium, halogen, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, heteronuclear atoms of 3 to 40 Cycloalkyl group, C 6 ~ C 60 aryl group, C 5 ~ C 60 heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkyl Silyl 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 arylphosphine group, C 6 ~ C 60 aryl It may be substituted with one or more substituents selected from the group consisting of a phosphine oxide group and a C 6 ~ C 60 arylamine group, a plurality of substituents may be the same or different from each other.
바람직하게는, 본 발명의 화합물에서, 상기 X1 내지 X8, 및 Y1 내지 Y4 중 적어도 하나가 N일 수 있다. 상기 X1 내지 X8, 및 Y1 내지 Y4 중 적어도 하나가 N일 경우, C와 N의 이중결합으로 인해서 소자의 구동전압이 낮아지는 효과가 있다.Preferably, in the compound of the present invention, at least one of X 1 to X 8 , and Y 1 to Y 4 may be N. When at least one of X 1 to X 8 and Y 1 to Y 4 is N, the driving voltage of the device is lowered due to a double bond of C and N.
또, 상기 화학식 1로 표시되는 화합물에서, Ar1 및 Ar2가 각각 독립적으로 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택된 것일 경우, 보다 넓은 밴드갭을 가질 수 있으며, 또한 유리전이온도가 보다 향상되어 열적 안정성이 보다 더 향상될 수 있어 바람직하다.In addition, in the compound represented by Formula 1, Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6 ~ C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms When selected from the group, it may have a wider bandgap, it is also preferable because the glass transition temperature can be further improved and the thermal stability is further improved.
상기 Ar1 및Ar2의 아릴기 및 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노, 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다. 이때, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.The Ar aryl groups 1 and Ar 2, and heteroaryl groups each independently selected from deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ~ C 60 aryl group, nuclear atom 5 ~ 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ 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 It may be substituted with one or more substituents selected from the group consisting of an oxide group and a C 6 ~ C 60 arylamine group. Here, the plurality of substituents may be the same or different from each other.
일례로, 본 발명의 Ar1 및 Ar2 에서, 상기 아릴기 또는 헤테로아릴기는 페닐, 나프틸, 인덴, 안트라센, 페난트렌, 파이렌, 트리페닐렌, 피리딘, 피리미딘, 피라진, 트리아진, 퀴놀린, 이소퀴놀린, 퀴녹살린, 플루오렌, 카바졸, 디벤조싸이오펜, 디벤조퓨란, 아크리딘, 인돌, 벤조퓨란, 벤조싸이오펜, 벤즈이미다졸, 벤조싸이아졸, 퓨린 등일 수 있다.For example, in Ar 1 and Ar 2 of the present invention, the aryl group or heteroaryl group is phenyl, naphthyl, indene, anthracene, phenanthrene, pyrene, triphenylene, pyridine, pyrimidine, pyrazine, triazine, quinoline , Isoquinoline, quinoxaline, fluorene, carbazole, dibenzothiophene, dibenzofuran, acridine, indole, benzofuran, benzothiophene, benzimidazole, benzothiazole, purine and the like.
또, 상기 R21 및 R22는 각각 독립적으로 수소, 할로겐, 시아노, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C6~C60의 아릴아민기로 이루어진 군에서 선택된 것이 바람직하다.In addition, the R 21 and R 22 are each independently hydrogen, halogen, cyano, alkyl group of C 1 ~ C 40 , C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 6 ~ It is preferably selected from the group consisting of C 60 arylamine groups.
이때, 상기 R21 및 R22의 알킬기, 아릴기, 헤테로아릴기, 아릴아민기는 각각 독립적으로 중수소, 할로겐, C1~C40의 알킬기, C3~C40의 시클로알킬기, C3~C40의 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, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있고, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.At this time, the alkyl group, aryl group, heteroaryl group, arylamine group of R 21 and R 22 are each independently deuterium, halogen, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 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 1 ~ 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 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl phosphine oxide group and a C 6 ~ C 60 arylamine group, a plurality of substituents may be the same or different from each other.
보다 바람직하게는, 상기 R21 및 R22는 각각 독립적으로 메틸 또는 페닐일 수 있다.More preferably, R 21 and R 22 may each independently be methyl or phenyl.
본 발명에 따른 화학식 1의 화합물에서, 상기 R11, R12, Ar1 및 Ar2는 각각 독립적으로 수소, 및 하기 치환기 S1 내지 S166로 이루어진 군에서 선택될 수 있는데, 이에 한정되는 것은 아니다. In the compound of Formula 1 according to the present invention, R 11 , R 12, Ar 1 and Ar 2 may be each independently selected from the group consisting of hydrogen and the following substituents S1 to S166, but is not limited thereto.
본 발명에 따른 화학식 1로 표시되는 화합물의 예로는 하기 화학식 3으로 표시되는 화합물, 화학식 4로 표시되는 화합물 등이 있는데, 이에 한정되지 않는다.Examples of the compound represented by Formula 1 according to the present invention include a compound represented by Formula 3, a compound represented by Formula 4, and the like, but is not limited thereto.
상기 화학식 3 및 4에서, In the above formulas (3) and (4)
X1 내지 X5, 및 X8은 각각 독립적으로 CR11 또는 N이고, 이때 복수개의 CR11은 서로 동일하거나 상이하고;X 1 to X 5 , and X 8 are each independently CR 11 or N, wherein a plurality of CR 11 are the same as or different from each other;
Y1 내지 Y4는 각각 독립적으로 CR12 또는 N이고, 이때 복수개의 CR12는 서로 동일하거나 상이하며;Y 1 to Y 4 are each independently CR 12 or N, wherein a plurality of CR 12 are the same as or different from each other;
단, X1 내지 X5, X8 및 Y1 내지 Y4 중 적어도 하나는 N이고;Provided that at least one of X 1 to X 5 , X 8 and Y 1 to Y 4 is N;
R11, R12, R21, R22, Ar1 및 Ar2는 각각 화학식 1에서 정의한 바와 동일하다.R 11 , R 12 , R 21 , R 22 , Ar 1 and Ar 2 are the same as defined in Chemical Formula 1, respectively.
또, 본 발명에 따른 화학식 1로 표시되는 화합물의 예로는 하기 화학식 5로 표시되는 화합물 내지 화학식 8로 표시되는 화합물 등이 있는데, 이에 한정되지 않는다.In addition, examples of the compound represented by Formula 1 according to the present invention include a compound represented by the following formula (5) to a compound represented by the formula (8), but is not limited thereto.
상기 화학식 5 내지 8에서,In the above formulas 5 to 8,
상기 X1 내지 X8, Y1 내지 Y4, R21, R22, Ar1, 및 Ar2는 각각 화학식 1에서 정의한 바와 동일하다.X 1 to X 8, Y 1 to Y 4 , R 21 , R 22 , Ar 1 , and Ar 2 are the same as defined in Formula 1, respectively.
상기 화학식 1로 표시되는 화합물의 구체적인 예로는 하기 예시된 것들이 있는데, 이에 한정되는 것은 아니다. 하기 화합물의 구조식에서, Ar1 및 Ar2는 각각 독립적으로 화학식 1에서 정의한 바와 동일하다.Specific examples of the compound represented by Chemical Formula 1 include those exemplified below, but are not limited thereto. In the structural formula of the following compound, Ar 1 And Ar 2 are each independently the same as defined in Formula 1.
본 발명에서 사용되는 "비치환된 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. As used herein, "unsubstituted 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, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
또, 본 발명에서 "비치환된 알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있으며, 이에 한정되는 것은 아니다.In the present invention, "unsubstituted alkenyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. do. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
또, 본 발명에서 "비치환된 알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이의 예로는 에타인일(ethynyl), 2-프로파인일(2-propynyl) 등이 있는데, 이에 제한되는 것은 아니다.In the present invention, "unsubstituted alkynyl" means a monovalent functional group obtained by removing a hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond do. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
또, 본 발명에서 "비치환된 시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이러한 시클로알킬의 예로는 시클로프로필, 시클로펜틸, 시클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine)등이 있는데, 이에 한정되지 않는다.In the present invention, "unsubstituted cycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
또, 본 발명에서 "비치환된 헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미하며, 이때 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O 또는 S와 같은 헤테로 원자로 치환된다. 이의 비-제한적인 예로는 모르폴린, 피페라진 등이 있다.In the present invention, "unsubstituted 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, wherein at least one of the rings Carbon, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.
또, 본 발명에서 "비치환된 아릴"은 단독 고리 혹은 2 이상의 고리가 조합된, 탄소수 6 내지 60의 방향족 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이때, 2 이상의 고리는 서로 단순 부착(pendant)되거나 축합된(fused) 형태로 부착될 수 있다. 이의 비제한적인 예로는 페닐, 비페닐, 터페닐(terphenyl), 나프틸, 페난트릴, 안트릴 등이 있다.In the present invention, "unsubstituted aryl" means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In this case, the two or more rings may be attached to each other in a simple or fused form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.
또, 본 발명에서 "비치환된 헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기로서, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 질소(N), 산소(O), 황(S) 또는 셀레늄(Se)과 같은 헤테로원자로 치환된다. 이때, 헤테로아릴은 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된(fused) 형태로 부착될 수 있고, 나아가 아릴기와의 축합된 형태도 포함한다. 이러한 헤테로아릴의 비제한적인 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 고리를 포함하고, 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등도 포함하는 것으로 해석한다.In the present invention, "unsubstituted heteroaryl" is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and preferably at least one carbon in the ring, preferably Preferably 1 to 3 carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). In this case, heteroaryl may be attached in a form in which two or more rings are simply attached or fused to each other, and also include a condensed form with an aryl group. Non-limiting examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. Includes rings and is also meant to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.
또, 본 발명에서 "비치환된 알킬옥시"는 RO-로 표시되는 1가의 작용기를 의미하며, 이때 상기 R은 탄소수 1 내지 40개의 알킬로서, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 포함될 수 있으며 이에 한정되지는 않는다. In the present invention, "unsubstituted alkyloxy" means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, which may be linear, branched or cyclic cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
또, 본 발명에서 "비치환된 아릴옥시"는 R'O-로 표시되는 1가의 작용기를 의미하며, 이때 상기 R'는 탄소수 6 내지 60의 아릴이다. 아릴옥시의 비제한적인 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있다.In the present invention, "unsubstituted aryloxy" means a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
또, 본 발명에서 "비치환된 알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, "비치환된 아릴실릴"은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미하고, "비치환된 아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.In the present invention, "unsubstituted alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms, and " Unsubstituted arylamine "means an amine substituted with aryl having 6 to 60 carbon atoms.
또한, 본 발명에서 "축합(fused) 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, "fused ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
본 발명에 따른 화학식 1로 표시되는 화합물은 일반적인 합성방법에 따라 합성될 수 있다 [Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조]. 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.
The compound represented by Chemical Formula 1 according to the present invention may be synthesized according to a general synthetic method [ Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995)). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
한편, 본 발명은 전술한 화학식 1로 표시되는 화합물(바람직하게는 화학식 3 내지 8 중 어느 하나로 표시되는 화합물)을 포함하는 유기 전계 발광 소자를 제공한다.On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1) (preferably a compound represented by any one of formulas 3 to 8).
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 화합물(바람직하게는 화학식 3 내지 8 중 어느 하나로 표시되는 화합물)을 1종 이상 포함하는 것을 특징으로 하는 한다.Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, and at least one of the at least one organic material layer. Is characterized in that it comprises at least one compound represented by Formula 1 (preferably a compound represented by any one of Formulas 3 to 8).
상기 1층 이상의 유기물층으로는 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등이 있는데, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 바람직하게는 상기 화학식 1의 화합물을 포함하는 1층 이상의 유기물층은 정공 수송층, 정공 주입층 또는 발광층일 수 있으며, 보다 바람직하게는 발광층 또는 정공 수송층일 수 있고, 보다 더욱 바람직하게는 발광층일 수 있다.The at least one organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, at least one organic material layer including the compound of Formula 1 may be a hole transport layer, a hole injection layer or a light emitting layer, more preferably a light emitting layer or a hole transport layer, even more preferably a light emitting layer.
일례로, 본 발명에 따른 유기 전계 발광 소자의 발광층은 호스트 재료 및/또는 도펀트 재료를 포함한다. 이때, 상기 화학식 1로 표시되는 화합물(바람직하게는 화학식 3 내지 8 중 어느 하나로 표시되는 화합물)을 발광층의 인광 호스트 재료 또는 형광 호스트나, 이의 도펀트 재료로 사용할 수 있다. 바람직하게는, 상기 화학식 1로 표시되는 화합물이 청색, 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 발광 소자에 포함될 수 있다. 이 경우, 상기 화합물로 인해 소자의 발광효율, 휘도, 전력효율, 열적 안정성 및 수명이 향상될 수 있다. For example, the light emitting layer of the organic electroluminescent device according to the present invention includes a host material and / or a dopant material. In this case, the compound represented by Chemical Formula 1 (preferably, the compound represented by any one of Chemical Formulas 3 to 8) may be used as a phosphorescent host material, a fluorescent host, or a dopant material thereof. Preferably, the compound represented by Formula 1 may be included in the organic light emitting device as a blue, green and / or red phosphorescent host, a fluorescent host, or a dopant material. In this case, the luminous efficiency, luminance, power efficiency, thermal stability and lifespan of the device may be improved due to the compound.
본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 비제한적인 예로는 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 선택적으로, 전자수송층 위에는 전자주입층이 추가로 적층될 수도 있다. 또한, 본 발명에 따른 유기 전계 발광 소자는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조로 이루어질 수도 있다.The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. Optionally, an electron injection layer may be further stacked on the electron transport layer. In addition, the organic electroluminescent device according to the present invention may have a structure in which an anode, one or more organic layers and an anode are sequentially stacked, and an insulating layer or an adhesive layer is interposed between the electrodes and the organic layer.
본 발명에 따른 유기 전계 발광 소자는 상기 유기물층 중 1층 이상(예컨대, 발광층, 정공수송층 및/또는 전자수송층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device according to the present invention is not limited to the organic electroluminescent device according to the present invention, except that at least one of the organic layers (for example, a light emitting layer, a hole transporting layer and / or an electron transporting layer) Can be produced by forming other organic layers and electrodes using known materials and methods.
상기 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에만 한정되지 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 발명에서 사용 가능한 기판으로는 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 사용될 수 있는데, 이에 한정되지 않는다.As the substrate usable in the present invention, a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, etc. may be used, but is not limited thereto.
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 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이에 한정되지 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 and polyaniline; Or 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; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; Layer structure 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, 당업계에 알려진 통상의 물질이 사용될 수 있다.
The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional 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 illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예 1] 화합물 IMC-1의 합성Preparation Example 1 Synthesis of Compound IMC-1
<단계 1> 9,9-dimethyl-2-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine의 합성Step 1 Synthesis of 9,9-dimethyl-2- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine
질소 기류 하에서 18.21 g (50.0 mmol)의 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine, 9.18 g (55.0 mmol)의 2-nitrophenylboronic acid, 6.00 g (150.0 mmol)의 NaOH과 200 ml/100 ml의 THF/H2O를 넣고, 교반하여 반응 혼합물을 얻었다. 이후, 40 ℃에서 2.90 g (5 mol%)의 Pd(PPh3)4를 넣고, 80 ℃에서 12시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 추출한 다음, MgSO4를 넣고 필터링하였다. 이후, 필터링된 유기층에서 용매를 제거한 다음, 컬럼크로마토그래피를 이용하여 9,9-dimethyl-2-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine 16.67 g (yield: 82 %)을 얻었다.18.21 g (50.0 mmol) of 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine, 9.18 g (55.0 mmol) of 2-nitrophenylboronic acid, 6.00 g (150.0 mmol) of NaOH under a nitrogen stream And 200 ml / 100 ml of THF / H 2 O were added and stirred to obtain a reaction mixture. Then, 2.90 g (5 mol%) of Pd (PPh 3 ) 4 was added at 40 ° C., and stirred at 80 ° C. for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride and then filtered with MgSO 4 . Thereafter, the solvent was removed from the filtered organic layer, and then 16.67 g (yield: 82%) of 9,9-dimethyl-2- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine was obtained using column chromatography. .
1H-NMR: δ 1.75 (s, 6H), 6.68 (m, 6H), 7.00 (m, 2H), 7.24 (m, 3H), 7.66 (m, 2H), 8.01 (m, 3H) 1 H-NMR: δ 1.75 (s, 6H), 6.68 (m, 6H), 7.00 (m, 2H), 7.24 (m, 3H), 7.66 (m, 2H), 8.01 (m, 3H)
<단계 2> 화합물 ≪ Step 2 > IMCIMC -1의 합성Synthesis of -1
질소 기류 하에서 준비예 1의 <단계 1>에서 얻은 9,9-dimethyl-2-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine 7.76 g (19.10 mmol)를 triphenylphosphine 12.52 g (47.72 mmol), 및 1,2-dichlorobenzene 50 ml와 혼합한 다음, 12시간 교반하였다. 반응 종료 후, 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하여 유기층을 얻었다. 이후, MgSO4로 추출된 유기층에서 물을 제거한 다음, 컬럼크로마토그래피를 이용하여 화합물 IMC-1 2.86 g (yield: 40 %)을 획득하였다. Under nitrogen stream, 7.76 g (19.10 mmol) of 9,9-dimethyl-2- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine obtained in <Step 1 of Preparation Example 1> 12.52 g (47.72 mmol) of triphenylphosphine , And 50 ml of 1,2-dichlorobenzene were mixed and then stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and extraction was performed with dichloromethane to obtain an organic layer. Thereafter, water was removed from the organic layer extracted with MgSO 4, and then 2.86 g (yield: 40%) of Compound IMC-1 was obtained using column chromatography.
1H-NMR: δ 1.75 (s, 6H), 6.69 (m, 6H), 7.01 (m, 2H), 7.26 (m, 3H), 7.68 (m, 3H), 8.12 (d, 1H), 10.44 (s, 1H)
1 H-NMR: δ 1.75 (s, 6H), 6.69 (m, 6H), 7.01 (m, 2H), 7.26 (m, 3H), 7.68 (m, 3H), 8.12 (d, 1H), 10.44 ( s, 1 H)
[준비예 2] 화합물 IMC-2 및 화합물 IMC-3의 합성Preparation Example 2 Synthesis of Compound IMC-2 and Compound IMC-3
<단계 1> 9,9-dimethyl-2-(3-nitropyridin-2-yl)-10-phenyl-9,10-dihydroacridine의 합성Step 1 Synthesis of 9,9-dimethyl-2- (3-nitropyridin-2-yl) -10-phenyl-9,10-dihydroacridine
준비예 1의 <단계 1>에서 사용된 2-nitrophenylboronic acid 대신 3-nitropyridin-2-ylboronic acid 25.19 g (150 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 9,9-dimethyl-2-(3-nitropyridin-2-yl)-10-phenyl-9,10-dihydroacridine을 얻었다.Perform the same procedure as in <Step 1> of Preparation Example 1, except that 25.19 g (150 mmol) of 3-nitropyridin-2-ylboronic acid was used instead of 2-nitrophenylboronic acid used in <Step 1> of Preparation Example 1. To 9,9-dimethyl-2- (3-nitropyridin-2-yl) -10-phenyl-9,10-dihydroacridine.
1H-NMR: δ 1.75 (s, 6H), 6.66 (m, 6H), 7.03 (m, 2H), 7.24 (m, 3H), 7.87 (d, 1H), 8.19 (m, 2H), 8.89 (d, 1H) 1 H-NMR: δ 1.75 (s, 6H), 6.66 (m, 6H), 7.03 (m, 2H), 7.24 (m, 3H), 7.87 (d, 1H), 8.19 (m, 2H), 8.89 ( d, 1H)
<단계 2> 화합물 ≪ Step 2 > IMCIMC -2 및 화합물 -2 and compound IMCIMC -3의 합성Synthesis of -3
준비예 1의 <단계 2>에서 사용된 9,9-dimethyl-2-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine 대신 준비예 2의 <단계 1>에서 얻은 9,9-dimethyl-2-(3-nitropyridin-2-yl)-10-phenyl-9,10-dihydroacridine 7.78 g (19.10 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 화합물 IMC-2 및 화합물 IMC-3을 얻었다.9,9-dimethyl obtained in <Step 1> of Preparation Example 2 instead of 9,9-dimethyl-2- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine used in <Step 2> of Preparation Example 1 Compound was prepared in the same manner as in <Step 2> of Preparation Example 1, except that 7.78 g (19.10 mmol) of 2- (3-nitropyridin-2-yl) -10-phenyl-9,10-dihydroacridine was used. IMC-2 and compound IMC-3 were obtained.
IMC-2 의 1H-NMR: δ 1.75 (s, 6H), 6.68 (m, 6H), 7.02 (m, 2H), 7.23 (m, 3H), 7.80 (m, 2H), 8.44 (d, 1H), 10.42 (s, 1H) 1 H-NMR of IMC-2: δ 1.75 (s, 6H), 6.68 (m, 6H), 7.02 (m, 2H), 7.23 (m, 3H), 7.80 (m, 2H), 8.44 (d, 1H ), 10.42 (s, 1 H)
IMC-3 의 1H-NMR: δ 1.75 (s, 6H), 6.67 (m, 6H), 7.02 (m, 2H), 7.23 (m, 3H), 7.84 (m, 2H), 8.45 (d, 1H), 10.41 (s, 1H)
1 H-NMR of IMC-3: δ 1.75 (s, 6H), 6.67 (m, 6H), 7.02 (m, 2H), 7.23 (m, 3H), 7.84 (m, 2H), 8.45 (d, 1H ), 10.41 (s, 1 H)
[준비예 3] 화합물 IMC-4 의 합성 Preparation Example 3 Synthesis of Compound IMC-4
<단계 1> 9,9-dimethyl-3-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine의 합성Step 1 Synthesis of 9,9-dimethyl-3- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine
준비예 1의 <단계 1>에서 사용된 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine 대신 3-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine 18.21 g (50.0 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 9,9-dimethyl-3-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine을 얻었다.3-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine used in <Step 1> of Preparation Example 1 9,9-dimethyl-3- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine in the same manner as in <Step 1> of Preparation Example 1, except that 18.21 g (50.0 mmol) was used. Got.
1H-NMR: δ 1.75 (s, 6H), 6.68 (m, 7H), 7.01 (m, 2H), 7.22 (m, 3H), 7.64 (t, 1H), 7.99 (m, 3H) 1 H-NMR: δ 1.75 (s, 6H), 6.68 (m, 7H), 7.01 (m, 2H), 7.22 (m, 3H), 7.64 (t, 1H), 7.99 (m, 3H)
<단계 2> 화합물 ≪ Step 2 > IMCIMC -4의 합성Synthesis of -4
준비예 1의 <단계 2>에서 사용된 9,9-dimethyl-2-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine 대신 준비예 3의 <단계 1>에서 얻은 9,9-dimethyl-3-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine 15.48 g (38.0 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 화합물 IMC-4를 얻었다.9,9-dimethyl obtained in <Step 1> of Preparation Example 3 instead of 9,9-dimethyl-2- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine used in <Step 2> of Preparation Example 1 Compound IMC-4 was carried out in the same manner as in <Step 2> of Preparation Example 1, except that 15.48 g (38.0 mmol) of -3- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine was used. Got it.
IMC-4 의 1H-NMR: δ 1.75 (s, 6H), 6.69 (m, 5H), 7.01 (m, 2H), 7.23 (m, 4H), 7.54 (m, 3H), 8.12 (d, 1H), 10.44 (s, 1H)
1 H-NMR of IMC-4: δ 1.75 (s, 6H), 6.69 (m, 5H), 7.01 (m, 2H), 7.23 (m, 4H), 7.54 (m, 3H), 8.12 (d, 1H ), 10.44 (s, 1 H)
[준비예 4] 화합물 IMC-5 의 합성 Preparation Example 4 Synthesis of Compound IMC-5
<단계 1> 9,9-dimethyl-3-(3-nitropyridin-2-yl)-10-phenyl-9,10-dihydroacridine의 합성Step 1 Synthesis of 9,9-dimethyl-3- (3-nitropyridin-2-yl) -10-phenyl-9,10-dihydroacridine
준비예 1의 <단계 1>에서 사용된 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine 대신 3-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine 18.21 g (50.0 mmol)을 사용하고, 2-nitrophenylboronic acid 대신 3-nitropyridin-2-ylboronic acid 9.24 g (55.0 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 9,9-dimethyl-3-(3-nitropyridin-2-yl)-10-phenyl-9,10-dihydroacridine을 얻었다.3-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine used in <Step 1> of Preparation Example 1 18.21 g (50.0 mmol) is used, Except for using 9.24 g (55.0 mmol) of 3-nitropyridin-2-ylboronic acid instead of 2-nitrophenylboronic acid, 9,9-dimethyl-3- (3 -nitropyridin-2-yl) -10-phenyl-9,10-dihydroacridine was obtained.
1H-NMR: δ 1.75 (s, 6H), 6.68 (m, 5H), 7.01 (m, 2H), 7.24 (m, 5H), 7.58 (d, 1H), 8.32 (d, 1H), 8.89 (d, 1H) 1 H-NMR: δ 1.75 (s, 6H), 6.68 (m, 5H), 7.01 (m, 2H), 7.24 (m, 5H), 7.58 (d, 1H), 8.32 (d, 1H), 8.89 ( d, 1H)
<단계 2> 화합물 ≪ Step 2 > IMCIMC -5의 합성Synthesis of -5
준비예 1의 <단계 2>에서 사용된 9,9-dimethyl-2-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine 대신 준비예 4의 <단계 1>에서 얻은 9,9-dimethyl-3-(3-nitropyridin-2-yl)-10-phenyl-9,10-dihydroacridine 15.69 g (38.5 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 화합물 IMC-5를 얻었다.9,9-dimethyl obtained in <Step 1> of Preparation Example 4 instead of 9,9-dimethyl-2- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine used in <Step 2> of Preparation Example 1 Compound was prepared in the same manner as in <Step 2> of Preparation Example 1, except that 15.69 g (38.5 mmol) of -3- (3-nitropyridin-2-yl) -10-phenyl-9,10-dihydroacridine was used. IMC-5 was obtained.
IMC-5 의 1H-NMR: δ 1.75 (s, 6H), 6.68 (m, 5H), 7.01 (m, 2H), 7.23 (m, 5H), 7.98 (d, 1H), 8.43 (d, 1H), 10.42 (s, 1H)
1 H-NMR of IMC-5: δ 1.75 (s, 6H), 6.68 (m, 5H), 7.01 (m, 2H), 7.23 (m, 5H), 7.98 (d, 1H), 8.43 (d, 1H ), 10.42 (s, 1 H)
[준비예 5] 화합물 IMC-6 의 합성 Preparation Example 5 Synthesis of Compound IMC-6
<단계 1> 2-(3-nitropyridin-2-yl)-9,9,10-triphenyl-9,10-dihydroacridine의 합성Step 1 Synthesis of 2- (3-nitropyridin-2-yl) -9,9,10-triphenyl-9,10-dihydroacridine
준비예 1의 <단계 1>에서 사용된 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine 대신 2-bromo-9,9,10-triphenyl-9,10-dihydroacridine 24.42 g (50.0 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 2-(3-nitropyridin-2-yl)-9,9,10-triphenyl-9,10-dihydroacridine을 얻었다.24.42 g of 2-bromo-9,9,10-triphenyl-9,10-dihydroacridine instead of 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine used in <Step 1> of Preparation Example 1 Except for using (50.0 mmol), 2- (3-nitropyridin-2-yl) -9,9,10-triphenyl-9,10-dihydroacridine in the same manner as in <Step 1> of Preparation Example 1 Got.
1H-NMR: δ 1.75 (s, 6H), 6.68 (m, 11H), 7.01 (m, 2H), 7.24 (m, 9H), 7.58 (d, 1H), 8.27 (d, 1H), 8.89 (d, 1H) 1 H-NMR: δ 1.75 (s, 6H), 6.68 (m, 11H), 7.01 (m, 2H), 7.24 (m, 9H), 7.58 (d, 1H), 8.27 (d, 1H), 8.89 ( d, 1H)
<단계 2> 화합물 ≪ Step 2 > IMCIMC -6의 합성Synthesis of -6
준비예 1의 <단계 2>에서 사용된 9,9-dimethyl-2-(2-nitrophenyl)-10-phenyl-9,10-dihydroacridine 대신 준비예 5의 <단계 1>에서 얻은 2-(3-nitropyridin-2-yl)-9,9,10-triphenyl-9,10-dihydroacridine 17.54 g (33.0 mmol)을 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 화합물 IMC-6를 얻었다.2- (3-) obtained in <Step 1> of Preparation Example 5 instead of 9,9-dimethyl-2- (2-nitrophenyl) -10-phenyl-9,10-dihydroacridine used in <Step 2> of Preparation Example 1 Compound IMC- was prepared in the same manner as in <Step 2> of Preparation Example 1, except that 17.54 g (33.0 mmol) of nitropyridin-2-yl) -9,9,10-triphenyl-9,10-dihydroacridine was used. 6 was obtained.
IMC-6 의 1H-NMR: δ 1.75 (s, 6H), 6.68 (m, 11H), 7.01 (m, 2H), 7.23 (m, 9H), 7.98 (d, 1H), 8.38 (d, 1H), 10.43 (s, 1H)
1 H-NMR of IMC-6: δ 1.75 (s, 6H), 6.68 (m, 11H), 7.01 (m, 2H), 7.23 (m, 9H), 7.98 (d, 1H), 8.38 (d, 1H ), 10.43 (s, 1 H)
[[ 합성예Synthetic example 1] One] ACAC -1의 합성Synthesis of -1
질소 기류 하에서 준비예 1에서 합성된 화합물 IMC-1 (4.98 g, 13.29 mmol)을, 3,3'-(5-bromo-1,3-phenylene)dipyridine (8.27 g, 26.57 mmol), Cu powder(0.17 g, 2.66 mmol), K2CO3(3.66 g, 26.57 mmol), Na2SO4(3.78 g, 26.57 mmol) 및 nitrobenzene(100 ml)와 혼합하고, 190 ℃에서 12시간 동안 교반하였다. Compound IMC-1 (4.98 g, 13.29 mmol) synthesized in Preparation Example 1, under nitrogen stream, 3,3 '-(5-bromo-1,3-phenylene) dipyridine (8.27 g, 26.57 mmol) and Cu powder 0.17 g, 2.66 mmol), K 2 CO 3 (3.66 g, 26.57 mmol), Na 2 SO 4 (3.78 g, 26.57 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 h.
반응이 종결된 후, nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음, MgSO4를 이용하여 유기층에서 물을 제거하였다. 유기층에서 용매를 제거한 후, 컬럼크로마토그래피로 정제하여 화합물 AC-1 (5.06 g, 수율: 63 %)을 얻었다. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO 4 . The solvent was removed from the organic layer, and then purified by column chromatography to obtain the compound AC-1 (5.06 g, yield: 63%).
Exact Mass: 604 g/molExact Mass: 604 g / mol
Elemental Analysis: C, 85.40; H, 5.33; N, 9.26
Elemental Analysis: C, 85.40; H, 5. 33; N, 9.26
[합성예 2] 화합물 AC-2의 합성Synthesis Example 2 Synthesis of Compound AC-2
합성예 1에서 사용된 3,3'-(5-bromo-1,3-phenylene)dipyridine 대신 2-bromo-4,6-diphenylpyridine 6.24 g (20.12 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-2 (4.78 g, 수율: 59 %)을 얻었다.Synthesis Example 1 except that 6.24 g (20.12 mmol) of 2-bromo-4,6-diphenylpyridine was used instead of 3,3 '-(5-bromo-1,3-phenylene) dipyridine used in Synthesis Example 1. Compound AC-2 (4.78 g, yield: 59%) was obtained in the same manner as the same.
Exact Mass: 603 g/molExact Mass: 603 g / mol
Elemental Analysis: C, 87.53; H, 5.51; N, 6.96
Elemental Analysis: C, 87.53; H, 5.51; N, 6.96
[합성예 3] 화합물 AC-3의 합성Synthesis Example 3 Synthesis of Compound AC-3
질소 기류 하에서 준비예 1에서 합성된 화합물 IMC-1 (2.19 g, 5.85 mmol)를, 2-chloro-4,6-diphenylpyrimidine (2.09 g, 7.85 mmol), NaH (2.11 g, 8.78 mmol) 및 DMF(80 ml)와 혼합한 다음, 상온에서 3 시간 동안 교반하였다. 반응이 종결된 후, 물을 넣고 고체 화합물을 필터링한 다음, 컬럼 크로마토그래피로 정제하여 화합물 AC-3 (2.86 g, 수율: 81 %)를 얻었다.Compound IMC-1 (2.19 g, 5.85 mmol), synthesized in Preparation Example 1 under nitrogen stream, 2-chloro-4,6-diphenylpyrimidine (2.09 g, 7.85 mmol), NaH (2.11 g, 8.78 mmol) and DMF ( 80 ml) and then stirred at room temperature for 3 hours. After the reaction was terminated, water was added, the solid compound was filtered and purified by column chromatography to give the compound AC-3 (2.86 g, yield: 81%).
Exact Mass: 604 g/molExact Mass: 604 g / mol
Elemental Analysis: C, 85.40; H, 5.33; N, 9.26
Elemental Analysis: C, 85.40; H, 5. 33; N, 9.26
[합성예 4] 화합물 AC-4의 합성Synthesis Example 4 Synthesis of Compound AC-4
합성예 3에서 사용된 2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 1.49 g (8.37 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-4 (3.01 g, 수율: 89 %)을 얻었다.Synthesis Example 3 except that 1.49 g (8.37 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 3. Compound AC-4 (3.01 g, yield: 89%) was obtained in the same manner as the same.
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[합성예 5] 화합물 AC-5의 합성Synthesis Example 5 Synthesis of Compound AC-5
합성예 3에서 사용된 2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.78 g (9.02 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-5 (2.73 g, 수율: 75 %)을 얻었다.3.78 g (9.02 mmol) of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 3 Except for the same as in Synthesis Example 3, the compound AC-5 (2.73 g, yield: 75%) was obtained.
Exact Mass: 757 g/molExact Mass: 757 g / mol
Elemental Analysis: C, 85.57; H, 5.19; N, 9.24
Elemental Analysis: C, 85.57; H, 5.19; N, 9.24
[[ 합성예Synthetic example 6] 화합물 6] compound ACAC -6의 합성Synthesis of -6
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 2에서 합성된 화합물 IMC-2 3.04 g (9.78 mmol)를 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-6 (2.37 g, 수율: 60 %)을 얻었다.Compound AC-6 (2.37 g) was prepared in the same manner as in Synthesis Example 1, except that 3.04 g (9.78 mmol) of Compound IMC-2 synthesized in Preparation Example 2 was used instead of Compound IMC-1 used in Synthesis Example 1. , Yield: 60%).
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[[ 합성예Synthetic example 7] 화합물 7] compound ACAC -7의 합성Synthesis of -7
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 2에서 합성된 화합물 IMC-2 2.4 g (6.40 mmol)을 사용하고, 3,3'-(5-bromo-1,3-phenylene)dipyridine 대신 2-bromo-4,6-diphenylpyridine 2.98 g (9.60 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일하게 수행하여 화합물 AC-7 (2.40 g, 수율: 62 %)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 1, 2.4 g (6.40 mmol) of compound IMC-2 synthesized in Preparation Example 2 was used, and 3,3 '-(5-bromo-1,3-phenylene) dipyridine was used instead of 2 Compound AC-7 (2.40 g, yield: 62%) was obtained in the same manner as in Synthesis Example 1 except that 2.98 g (9.60 mmol) of -bromo-4,6-diphenylpyridine was used.
Exact Mass: 604 g/molExact Mass: 604 g / mol
Elemental Analysis: C, 85.40; H, 5.33; N, 9.26
Elemental Analysis: C, 85.40; H, 5. 33; N, 9.26
[[ 합성예Synthetic example 8] 화합물 8] compound ACAC -8의 합성Synthesis of -8
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 2에서 합성된 화합물 IMC-2 2.32 g (8.71 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-8 (2.99 g, 수율 85%)을 얻었다.Compound AC-8 (2.99 g) was prepared in the same manner as in Synthesis Example 3, except that 2.32 g (8.71 mmol) of Compound IMC-2 synthesized in Preparation Example 2 was used instead of Compound IMC-1 used in Synthesis Example 3. , Yield 85%) was obtained.
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[[ 합성예Synthetic example 9] 화합물 9] Compound ACAC -9의 합성Synthesis of -9
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 2에서 합성된 화합물 IMC-2 2.14 g (5.71 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 2.29 g (8.57 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-9 (3.05 g, 수율 88%)를 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 2.14 g (5.71 mmol) of compound IMC-2 synthesized in Preparation Example 2 were used, and 2-chloro-4,6-diphenyl instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-9 (3.05 g, yield 88%) was obtained in the same manner as Synthesis Example 3, except that 2.29 g (8.57 mmol) of -1,3,5-triazine was used.
Exact Mass: 606 g/molExact Mass: 606 g / mol
Elemental Analysis: C, 81.16; H, 4.98; N, 13.85
Elemental Analysis: C, 81.16; H, 4.98; N, 13.85
[합성예 10] 화합물 AC-10의 합성Synthesis Example 10 Synthesis of Compound AC-10
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 2에서 합성된 화합물 IMC-2 1.69 g (4.50 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 2.83 g (6.75 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-10 (2.87 g, 수율 84%)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 1.69 g (4.50 mmol) of compound IMC-2 synthesized in Preparation Example 2 was used, and 2,4-di (biphenyl-3) instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-10 (2.87 g, Yield 84%) was carried out in the same manner as in Synthesis Example 3, except that 2.83 g (6.75 mmol) of -yl) -6-chloro-1,3,5-triazine was used. Got it.
Exact Mass: 758 g/molExact Mass: 758 g / mol
Elemental Analysis: C, 83.88; H, 5.05; N, 11.07
Elemental Analysis: C, 83.88; H, 5.05; N, 11.07
[[ 합성예Synthetic example 11] 화합물 11] compound ACAC -11의 합성Synthesis of -11
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 3에서 합성된 화합물 IMC-3 3.03 g (9.73 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-11 (2.75 g, 수율: 70 %)을 얻었다.Compound AC-11 (2.75 g) was prepared in the same manner as in Synthesis Example 1, except that 3.03 g (9.73 mmol) of Compound IMC-3 synthesized in Preparation Example 3 was used instead of Compound IMC-1 used in Synthesis Example 1. , Yield: 70%) was obtained.
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[[ 합성예Synthetic example 12] 화합물 12] compounds ACAC -12의 합성Synthesis of -12
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 3에서 합성된 화합물 IMC-3 2.38 g (6.35 mmol)을 사용하고, 3,3'-(5-bromo-1,3-phenylene)dipyridine 대신 2-bromo-4,6-diphenylpyridine 2.96 g (9.53 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-12 (2.61 g, 수율 68%)를 얻었다.Instead of compound IMC-1 used in Synthesis Example 1, 2.38 g (6.35 mmol) of compound IMC-3 synthesized in Preparation Example 3 were used, and 2, instead of 3,3 '-(5-bromo-1,3-phenylene) dipyridine, was used. Compound AC-12 (2.61 g, yield 68%) was obtained in the same manner as in Synthesis Example 1 except that 2.96 g (9.53 mmol) of -bromo-4,6-diphenylpyridine was used.
Exact Mass: 604 g/molExact Mass: 604 g / mol
Elemental Analysis: C, 85.40; H, 5.33; N, 9.26
Elemental Analysis: C, 85.40; H, 5. 33; N, 9.26
[[ 합성예Synthetic example 13] 화합물 13] compound ACAC -13의 합성Synthesis of -13
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 3에서 합성된 화합물 IMC-3 1.55 g (5.82 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-13 (3.03 g, 수율 86%)을 얻었다.Compound AC-13 (3.03 g) was prepared in the same manner as in Synthesis Example 3, except that 1.55 g (5.82 mmol) of Compound IMC-3 synthesized in Preparation Example 3 was used instead of Compound IMC-1 used in Synthesis Example 3. , Yield 86%).
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[[ 합성예Synthetic example 14] 화합물 14] Compound ACAC -14의 합성Synthesis of -14
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 3에서 합성된 화합물 IMC-3 2.24 g (5.97 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 2.40 g (8.96 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-14 (3.19 g, 수율 88%)를 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 2.24 g (5.97 mmol) of compound IMC-3 synthesized in Preparation Example 3 were used, and 2-chloro-4,6-diphenyl instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-14 (3.19 g, yield 88%) was obtained in the same manner as Synthesis Example 3, except that 2.40 g (8.96 mmol) of -1,3,5-triazine was used.
Exact Mass: 606 g/molExact Mass: 606 g / mol
Elemental Analysis: C, 81.16; H, 4.98; N, 13.85
Elemental Analysis: C, 81.16; H, 4.98; N, 13.85
[[ 합성예Synthetic example 15] 화합물 15] compound ACAC -15의 합성Synthesis of -15
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 3에서 합성된 화합물 IMC-3 1.82 g (4.85 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.05 g (7.28 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-15 (3.09 g, 수율 84%)를 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 1.82 g (4.85 mmol) of compound IMC-3 synthesized in Preparation Example 3 was used, and 2,4-di (biphenyl-3) instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-15 (3.09 g, Yield 84%) was carried out in the same manner as in Synthesis Example 3, except that 3.05 g (7.28 mmol) of -yl) -6-chloro-1,3,5-triazine was used. Got it.
Exact Mass: 758 g/molExact Mass: 758 g / mol
Elemental Analysis: C, 83.88; H, 5.05; N, 11.07
Elemental Analysis: C, 83.88; H, 5.05; N, 11.07
[[ 합성예Synthetic example 16] 화합물 16] compound ACAC -16의 합성Synthesis of -16
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 4에서 합성된 화합물 IMC-4 2.56 g (6.84 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-16 (2.40 g, 수율 58%)을 얻었다.Compound AC-16 (2.40 g) was prepared in the same manner as in Synthesis Example 1, except that 2.56 g (6.84 mmol) of Compound IMC-4 synthesized in Preparation Example 4 was used instead of Compound IMC-1 used in Synthesis Example 1. , Yield 58%).
Exact Mass: 604 g/molExact Mass: 604 g / mol
Elemental Analysis: C, 85.40; H, 5.33; N, 9.26
Elemental Analysis: C, 85.40; H, 5. 33; N, 9.26
[[ 합성예Synthetic example 17] 화합물 17] Compound ACAC -17의 합성Synthesis of -17
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 4에서 합성된 화합물 IMC-4 2.75 g (7.34 mmol)을 사용하고, 3,3'-(5-bromo-1,3-phenylene)dipyridine 대신 2-bromo-4,6-diphenylpyridine 3.42 g (11.01 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-17 (2.66 g, 수율: 60 %)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 1, 2.75 g (7.34 mmol) of compound IMC-4 synthesized in Preparation Example 4 were used, and 3,3 '-(5-bromo-1,3-phenylene) dipyridine was used instead of 2 Compound AC-17 (2.66 g, yield: 60%) was obtained in the same manner as in Synthesis Example 1, except that 3.42 g (11.01 mmol) of -bromo-4,6-diphenylpyridine was used.
Exact Mass: 603 g/molExact Mass: 603 g / mol
Elemental Analysis: C, 87.53; H, 5.51; N, 6.96
Elemental Analysis: C, 87.53; H, 5.51; N, 6.96
[합성예 18] 화합물 AC-18의 합성Synthesis Example 18 Synthesis of Compound AC-18
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 4에서 합성된 화합물 IMC-4 2.26 g (6.05 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-18 (3.07 g, 수율: 84 %)을 얻었다.Compound AC-18 (3.07 g) was prepared in the same manner as in Synthesis Example 3, except that 2.26 g (6.05 mmol) of Compound IMC-4 synthesized in Preparation Example 4 was used instead of Compound IMC-1 used in Synthesis Example 3. , Yield: 84%).
Exact Mass: 604 g/molExact Mass: 604 g / mol
Elemental Analysis: C, 85.40; H, 5.33; N, 9.26
Elemental Analysis: C, 85.40; H, 5. 33; N, 9.26
[[ 합성예Synthetic example 19] 화합물 19] Compound ACAC -19의 합성-19 Synthesis
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 4에서 합성된 화합물 IMC-4 2.26 g (6.04 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 2.43 g (9.06 mol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-19 (3.00 g, 수율: 82 %)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 2.26 g (6.04 mmol) of compound IMC-4 synthesized in Preparation Example 4 was used, and 2-chloro-4,6-diphenyl instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-19 (3.00 g, yield: 82%) was obtained in the same manner as in Synthesis Example 3, except that 2.43 g (9.06 mol) of -1,3,5-triazine was used.
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[[ 합성예Synthetic example 20] 화합물 20] compound ACAC -20의 합성Synthesis of -20
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 4에서 합성된 화합물 IMC-4 1.73 g (4.63 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 2.92 g (6.95 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-20 (3.12 g, 수율: 89 %)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 1.73 g (4.63 mmol) of compound IMC-4 synthesized in Preparation Example 4 was used, and 2,4-di (biphenyl-3) instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-20 (3.12 g, Yield: 89%) in the same manner as in Synthesis Example 3, except that 2.92 g (6.95 mmol) of -yl) -6-chloro-1,3,5-triazine was used. Got.
Exact Mass: 757 g/molExact Mass: 757 g / mol
Elemental Analysis: C, 85.57; H, 5.19; N, 9.24
Elemental Analysis: C, 85.57; H, 5.19; N, 9.24
[합성예 21] 화합물 AC-21의 합성Synthesis Example 21 Synthesis of Compound AC-21
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 5에서 합성된 화합물 IMC-5 4.99g (13.29 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-21 (5.55 g, 수율: 69 %)을 얻었다.Compound AC-21 (5.55 g) was prepared in the same manner as in Synthesis Example 1, except that 4.99 g (13.29 mmol) of Compound IMC-5 synthesized in Preparation Example 5 was used instead of Compound IMC-1 used in Synthesis Example 1. , Yield: 69%).
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[[ 합성예Synthetic example 22] 화합물 22] compound ACAC -22의 합성Synthesis of -22
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 5에서 합성된 화합물 IMC-5 4.98 g (13.29 mmol)을 사용하고, 3,3'-(5-bromo-1,3-phenylene)dipyridine 대신 2-bromo-4,6-diphenylpyridine 6.18 g (19.94 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-22 (6.26 g, 수율: 78 %)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 1, 4.98 g (13.29 mmol) of compound IMC-5 synthesized in Preparation Example 5 were used, and 3,3 '-(5-bromo-1,3-phenylene) dipyridine was used instead of 2 Compound AC-22 (6.26 g, yield: 78%) was obtained in the same manner as in Synthesis Example 1, except that 6.18 g (19.94 mmol) of -bromo-4,6-diphenylpyridine was used.
Exact Mass: 604 g/molExact Mass: 604 g / mol
Elemental Analysis: C, 85.40; H, 5.33; N, 9.26
Elemental Analysis: C, 85.40; H, 5. 33; N, 9.26
[[ 합성예Synthetic example 23] 화합물 23] compound ACAC -23의 합성Synthesis of -23
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 5에서 합성된 화합물 IMC-5 2.20 g (5.85 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-23 (3.08 g, 수율: 87 %)을 얻었다.Compound AC-23 (3.08 g) was prepared in the same manner as in Synthesis Example 3, except that 2.20 g (5.85 mmol) of Compound IMC-5 synthesized in Preparation Example 5 was used instead of Compound IMC-1 used in Synthesis Example 3. , Yield: 87%).
Exact Mass: 605 g/molExact Mass: 605 g / mol
Elemental Analysis: C, 83.28; H, 5.16; N, 11.56
Elemental Analysis: C, 83.28; H, 5. 16; N, 11.56
[합성예 24] 화합물 AC-24의 합성Synthesis Example 24 Synthesis of Compound AC-24
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 5에서 합성된 화합물 IMC-5 2.20 g (5.85 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 2.64 g (9.85 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-24 (3.30 g, 수율: 93 %)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 2.20 g (5.85 mmol) of compound IMC-5 synthesized in Preparation Example 5 were used, and 2-chloro-4,6-diphenyl instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-24 (3.30 g, yield: 93%) was obtained in the same manner as in Synthesis Example 3, except that 2.64 g (9.85 mmol) of -1,3,5-triazine was used.
Exact Mass: 606 g/molExact Mass: 606 g / mol
Elemental Analysis: C, 81.16; H, 4.98; N, 13.85
Elemental Analysis: C, 81.16; H, 4.98; N, 13.85
[[ 합성예Synthetic example 25] 화합물 25] compound ACAC -25의 합성Synthesis of -25
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 5에서 합성된 화합물 IMC-5 2.20 g (5.85 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 4.12 g (9.85 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-25 (4.08 g, 수율: 92 %)를 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 2.20 g (5.85 mmol) of compound IMC-5 synthesized in Preparation Example 5 was used, and 2,4-di (biphenyl-3) instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-25 (4.08 g, Yield: 92%) in the same manner as in Synthesis Example 3, except that 4.12 g (9.85 mmol) of -yl) -6-chloro-1,3,5-triazine was used. Got.
Exact Mass: 758 g/molExact Mass: 758 g / mol
Elemental Analysis: C, 83.88; H, 5.05; N, 11.07
Elemental Analysis: C, 83.88; H, 5.05; N, 11.07
[[ 합성예Synthetic example 26] 화합물 26] compound ACAC -26의 합성Synthesis of -26
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 6에서 합성된 화합물 IMC-6 6.64 (13.29 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-26 (6.30 g, 수율: 65 %)을 얻었다.Except for using the compound IMC-6 6.64 (13.29 mmol) synthesized in Preparation Example 6 instead of the compound IMC-1 used in Synthesis Example 1, the compound AC-26 (6.30 g, Yield: 65%).
Exact Mass: 729 g/molExact Mass: 729 g / mol
Elemental Analysis: C, 85.57; H, 4.83; N, 9.60
Elemental Analysis: C, 85.57; H, 4.83; N, 9.60
[[ 합성예Synthetic example 27] 화합물 27] compound ACAC -27의 합성-27
합성예 1에서 사용된 화합물 IMC-1 대신 준비예 6에서 합성된 화합물 IMC-6 6.64 (13.29 mmol)을 사용하고, 3,3'-(5-bromo-1,3-phenylene)dipyridine 대신 2-bromo-4,6-diphenylpyridine 8.24 g (26.57 mmol)을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 화합물 AC-27 (6.39 g, 수율: 66 %)를 얻었다.Instead of compound IMC-1 used in Synthesis Example 1, compound IMC-6 6.64 (13.29 mmol) synthesized in Preparation Example 6 was used, and 2- instead of 3,3 '-(5-bromo-1,3-phenylene) dipyridine was used. Compound AC-27 (6.39 g, yield: 66%) was obtained in the same manner as in Synthesis Example 1 except that 8.24 g (26.57 mmol) of bromo-4,6-diphenylpyridine was used.
Exact Mass: 728 g/molExact Mass: 728 g / mol
Elemental Analysis: C, 87.33; H, 4.98; N, 7.69
Elemental Analysis: C, 87.33; H, 4.98; N, 7.69
[[ 합성예Synthetic example 28] 화합물 28] compound ACAC -28의 합성-28 Synthesis
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 6에서 합성된 화합물 IMC-6 2.92 g (5.85 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-28 (3.50 g, 수율: 82 %)을 얻었다.Compound AC-28 (3.50 g) was prepared in the same manner as in Synthesis Example 3, except that 2.92 g (5.85 mmol) of Compound IMC-6 synthesized in Preparation Example 6 was used instead of Compound IMC-1 used in Synthesis Example 3. , Yield: 82%) was obtained.
Exact Mass: 729 g/molExact Mass: 729 g / mol
Elemental Analysis: C, 85.57; H, 4.83; N, 9.60
Elemental Analysis: C, 85.57; H, 4.83; N, 9.60
[[ 합성예Synthetic example 29] 화합물 29] compound ACAC -29의 합성Synthesis of -29
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 6에서 합성된 화합물 IMC-6 2.92 g (5.85 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 2.64 g (9.85 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-29 (3.72 g, 수율 87%)를 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 2.92 g (5.85 mmol) of compound IMC-6 synthesized in Preparation Example 6 were used, and 2-chloro-4,6-diphenyl instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-29 (3.72 g, yield 87%) was obtained in the same manner as Synthesis Example 3, except that 2.64 g (9.85 mmol) of -1,3,5-triazine was used.
Exact Mass: 730 g/molExact Mass: 730 g / mol
Elemental Analysis: C, 83.81; H, 4.69; N, 11.50
Elemental Analysis: C, 83.81; H, 4.69; N, 11.50
[[ 합성예Synthetic example 30] 화합물 30] Compound ACAC -30의 합성Synthesis of -30
합성예 3에서 사용된 화합물 IMC-1 대신 준비예 6에서 합성된 화합물 IMC-6 2.92 g (5.85 mmol)을 사용하고, 2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 4.14 g (9.85 mmol)을 사용하는 것을 제외하고는, 합성예 3과 동일하게 수행하여 화합물 AC-30 (4.85 g, 수율: 94%)을 얻었다.Instead of compound IMC-1 used in Synthesis Example 3, 2.92 g (5.85 mmol) of compound IMC-6 synthesized in Preparation Example 6 were used, and 2,4-di (biphenyl-3) instead of 2-chloro-4,6-diphenylpyrimidine was used. Compound AC-30 (4.85 g, Yield: 94%) in the same manner as in Synthesis Example 3, except that 4.14 g (9.85 mmol) of -yl) -6-chloro-1,3,5-triazine was used. Got.
Exact Mass: 882 g/molExact Mass: 882 g / mol
Elemental Analysis: C, 85.69; H, 4.79; N, 9.52
Elemental Analysis: C, 85.69; H, 4.79; N, 9.52
[[ 실시예Example 1] 녹색 유기 1] Green organic ELEL 소자의 제작 Device fabrication
합성예 1에서 합성된 화합물 AC-1를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 하기 과정에 따라 녹색 유기 EL 소자를 제조하였다.Compound AC-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
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.Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60 nm) / TCTA (80 nm) / 화합물 AC-10 + 10 % Ir(ppy)3 (300nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) 순으로 적층하여 유기 EL 소자를 제조하였다. On the ITO transparent electrode prepared as above, m-MTDATA (60 nm) / TCTA (80 nm) / compound AC-10 + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30 nm) ) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP used are as follows.
[실시예 2 ~ 30] 녹색 유기 EL 소자의 제조Example 2 to 30 Fabrication of Green Organic EL Device
실시예 1에서 발광층 형성시 호스트 물질로 사용된 화합물 AC-1 대신 합성예 2 내지 30에서 각각 합성된 화합물 AC-1 ~ AC-30을 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 EL 소자를 제조하였다.
In the same manner as in Example 1 except for using the compounds AC-1 to AC-30 synthesized in Synthesis Examples 2 to 30 instead of the compound AC-1 used as a host material when forming the emission layer in Example 1 A green organic EL device was manufactured.
[비교예 1] 녹색 유기 EL 소자의 제작[Comparative Example 1] Production of green organic EL device
실시예 1에서 발광층 형성시 호스트 물질로 사용된 화합물 AC-1 대신 CBP(4,4-dicarbazolybiphenyl)를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 EL 소자를 제조하였다.
A green organic EL device was manufactured in the same manner as in Example 1, except that CBP (4,4-dicarbazolybiphenyl) was used instead of the compound AC-1 used as a host material in forming the emission layer in Example 1.
[평가예][Evaluation example]
실시예 1 내지 30, 및 비교예 1에서 각각 제조된 녹색 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.The driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured for green organic EL devices prepared in Examples 1 to 30 and Comparative Example 1, respectively, and the results are shown in Table 1 below.
실험 결과, 상기 표1에서 알 수 있는 바와 같이, 본 발명에 따른 화합물(화합물 AC-1 ~ 화합물 AC-30)을 발광층의 호스트 물질로 사용한 실시예 1 내지 30에서 각각 제조된 녹색 유기 EL 소자는, 종래 호스트 물질인 CBP를 사용한 녹색 유기 EL 소자(비교예1)에 비해 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As a result of the experiment, as shown in Table 1, the green organic EL device manufactured in Examples 1 to 30 using the compound (compound AC-1 to compound AC-30) according to the present invention as a host material of the light emitting layer In comparison with the green organic EL device (Comparative Example 1) using CBP, which is a conventional host material, it was found to exhibit better performance in terms of efficiency and driving voltage.
Claims (9)
[화학식 1]
(상기 화학식 1에서,
X1 내지 X8은 각각 독립적으로 CR11 또는 N이고, 이때 복수개의 CR11은 서로 동일하거나 상이하며;
R11은 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 C3~C40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이때 이들은 인접한 기와 축합(fused)하여 방향족 고리 또는 헤테로방향족 고리를 형성하거나 또는 비형성하고;
단, X1 내지 X8 중 적어도 하나는 인접한 기와 하기 화학식 2로 표시되는 축합(fused) 고리를 형성하며;
[화학식 2]
상기 화학식 2 에서,
Y1 내지 Y4는 각각 독립적으로 CR12 또는 N이고, 이때 복수개의 CR12는 서로 동일하거나 상이하며;
R12은 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 C3~C40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이때 이들은 인접한 기와 축합(fused)하여 방향족 고리 또는 헤테로방향족 고리를 형성하거나 또는 비형성하고;
Ar1 및 Ar2은 각각 독립적으로, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 C3~C40의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 치환 또는 비치환된 C6~C60의 아릴실릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 이때 이들은 인접한 기와 축합(fused) 고리를 형성하거나 또는 비형성하며;
R21 및 R22는 각각 독립적으로 수소, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되며;
상기 R11, R12, R21, R22, Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기 및 아릴아민기에 각각 도입될 수 있는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 니트릴기, 니트로기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C1~C40의 아미노기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 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, 이때 복수개의 치환기는 서로 동일하거나 상이할 수 있음).A compound represented by the following formula (1):
[Chemical Formula 1]
(In Formula 1,
X 1 to X 8 are each independently CR 11 or N, wherein a plurality of CR 11 are the same as or different from each other;
R 11 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 Alkynyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted C 3 to C 40 heterocycloalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted Heteroaryl group having 5 to 60 carbon atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 1 to An alkylsilyl group of C 40 , a substituted or unsubstituted C 6 -C 60 arylsilyl group, and a substituted or unsubstituted C 6 -C 60 arylamine group, wherein they are fused with adjacent groups Thereby forming or not forming an aromatic ring or heteroaromatic ring;
Provided that at least one of X 1 to X 8 forms a fused ring represented by Formula 2 with an adjacent group;
(2)
In Chemical Formula 2,
Y 1 to Y 4 are each independently CR 12 or N, wherein a plurality of CR 12 are the same as or different from each other;
R 12 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 Alkynyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted C 3 to C 40 heterocycloalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted Heteroaryl group having 5 to 60 carbon atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 1 to An alkylsilyl group of C 40 , a substituted or unsubstituted C 6 -C 60 arylsilyl group, and a substituted or unsubstituted C 6 -C 60 arylamine group, wherein they are fused with adjacent groups Thereby forming or not forming an aromatic ring or heteroaromatic ring;
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group , A substituted or unsubstituted C 3 ~ C 40 cycloalkyl group, a substituted or unsubstituted C 3 ~ C 40 heterocycloalkyl group, a substituted or unsubstituted C 6 ~ C 60 aryl group, a substituted or unsubstituted nucleus Heteroaryl group having 5 to 60 atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 1 to C 40 Alkylsilyl group, substituted or unsubstituted C 6 ~ C 60 arylsilyl group and substituted or unsubstituted C 6 ~ C 60 arylamine group selected from the group consisting of a fused ring with an adjacent group Form or non-form;
R 21 and R 22 are each independently hydrogen, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted nuclear atom having 5 to 60 atoms. Heteroaryl groups are selected from the group consisting of;
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkyl of R 11 , R 12, R 21 , R 22 , Ar 1 and Ar 2 One or more substituents that can be introduced to each of the silyl, arylsilyl and arylamine groups are each independently deuterium, halogen, nitrile, nitro, cyano, C 1 -C 40 alkyl, C 2 -C 40 alkenes group, C 1 ~ C 40 alkoxy group, C 1 ~ C 40 of the amino group, C of 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 40 aryl group, a nuclear atom Heteroaryl group of 5 to 60, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ arylamine group of C 60 of In the county Wherein the plurality of substituents may be the same or different from each other).
[화학식 3]
; 및
[화학식 4]
(상기 화학식 3 및 4에서,
X1 내지 X5, 및 X8은 각각 독립적으로 CR11 또는 N이고, 이때 복수개의 CR11은 서로 동일하거나 상이하고;
Y1 내지 Y4는 각각 독립적으로 CR12 또는 N이고, 이때 복수개의 CR12는 서로 동일하거나 상이하며;
단, X1 내지 X5, X8 및 Y1 내지 Y4 중 적어도 하나는 N이고;
R11, R12, R21, R22, Ar1 및 Ar2는 각각 제1항에서 정의한 바와 동일함).A compound according to claim 1, represented by the following formula (3) or (4):
(3)
; And
[Chemical Formula 4]
(In Chemical Formulas 3 and 4,
X 1 to X 5 , and X 8 are each independently CR 11 or N, wherein a plurality of CR 11 are the same as or different from each other;
Y 1 to Y 4 are each independently CR 12 or N, wherein a plurality of CR 12 are the same as or different from each other;
Provided that at least one of X 1 to X 5 , X 8 and Y 1 to Y 4 is N;
R 11 , R 12 , R 21 , R 22 , Ar 1 and Ar 2 are the same as defined in claim 1, respectively).
[화학식 5]
;
[화학식 6]
;
[화학식 7]
; 및
[화학식 8]
(상기 화학식 5 내지 8에서,
X1 내지 X8 , Y1 내지 Y4, R21, R22, Ar1, 및 Ar2는 각각 제1항에서 정의한 바와 동일함).The compound of claim 1, wherein the compound is represented by any one of Formulas 5 to 8:
[Chemical Formula 5]
;
[Chemical Formula 6]
;
(7)
; And
[Chemical Formula 8]
(In Chemical Formulas 5 to 8,
X 1 to X 8 , Y 1 to Y 4 , R 21 , R 22 , Ar 1 , and Ar 2 are the same as defined in claim 1 , respectively).
상기 Ar1 및 Ar2 는 각각 독립적으로C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되고,
상기 Ar1 및 Ar2의 아릴기 및 헤테로아릴기 각각에 도입될 수 있는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 니트릴기, 니트로기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C1~C40의 아미노기, 핵원자수 3 내지 40의 시클로알킬기, C3~C40의 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, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며, 이때 복수개의 치환기는 서로 동일하거나 상이할 수 있는 것이 특징인 화합물.4. The method according to any one of claims 1 to 3,
Ar 1 and Ar 2 are each independently selected from the group consisting of C 6 ~ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms,
One or more substituents that may be introduced into each of the aryl group and heteroaryl group of Ar 1 and Ar 2 are each independently deuterium, halogen, nitrile group, nitro group, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 1 to C 40 alkoxy group, C 1 to C 40 amino group, nuclear atom 3 to 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ C 40 of the alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ aryl of C 60 silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, and a C 6 ~ C 60 Is selected from the group consisting of an arylamine group, wherein the plurality of substituents is characterized in that the same or different from each other.
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제3항 중 어느 한 항에 기재된 화합물을 포함하는 것이 특징인 유기 전계 발광 소자. 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device, characterized in that it comprises the compound according to any one of claims 1 to 3.
상기 화합물을 포함하는 1층 이상의 유기물층은 정공 주입층, 정공 수송층 및 발광층으로 이루어진 군에서 선택되는 것이 특징인 유기 전계 발광 소자. The method of claim 5,
Wherein at least one organic compound layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer.
상기 화합물을 포함하는 유기물층은 발광층인 것이 특징인 유기 전계 발광 소자. The method of claim 5,
The organic material layer containing the compound is an organic electroluminescent device, characterized in that the light emitting layer.
상기 화합물은 인광 호스트인 것이 특징인 유기 전계 발광 소자.The method of claim 7, wherein
The compound is an organic electroluminescent device, characterized in that the phosphorescent host.
상기 화합물을 포함하는 유기물층은 정공수송층인 것이 특징인 유기 전계 발광 소자.The method of claim 5,
The organic material layer containing the compound is an organic electroluminescent device, characterized in that the hole transport layer.
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US8795848B2 (en) * | 2008-05-08 | 2014-08-05 | Nippon Steel & Sumikin Chemical Co., Ltd. | Indolocarbazole derivative with fused heterocyclic aromatic group for organic electroluminescent device and organic electroluminescent device containing same |
-
2012
- 2012-06-20 KR KR1020120066360A patent/KR101366492B1/en not_active IP Right Cessation
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2013
- 2013-03-06 WO PCT/KR2013/001821 patent/WO2013191355A1/en active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101101059B1 (en) | 2006-08-04 | 2011-12-29 | 캐논 가부시끼가이샤 | Fused heterocyclic compound and organic light emitting device |
KR20110028234A (en) * | 2009-09-11 | 2011-03-17 | 후지필름 가부시키가이샤 | Photoelectric conversion device, production method thereof, photosensor, imaging device and their drive methods |
Cited By (1)
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US11271169B2 (en) | 2017-08-24 | 2022-03-08 | Samsung Display Co., Ltd. | Nitrogen-containing compound and organic electroluminescence device including the same |
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KR20130142818A (en) | 2013-12-30 |
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