KR20150045295A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- KR20150045295A KR20150045295A KR20130124833A KR20130124833A KR20150045295A KR 20150045295 A KR20150045295 A KR 20150045295A KR 20130124833 A KR20130124833 A KR 20130124833A KR 20130124833 A KR20130124833 A KR 20130124833A KR 20150045295 A KR20150045295 A KR 20150045295A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- aryl
- alkyl
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 147
- 239000002019 doping agent Substances 0.000 claims abstract description 37
- 239000010410 layer Substances 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000463 material Substances 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- -1 4,6-difluorophenylpyridyl Chemical group 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000005281 excited state Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
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- 229940125904 compound 1 Drugs 0.000 description 3
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- 238000004020 luminiscence type Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 0 *(C1CC2)C3C=CCCC3C1C=C2C(CCC12)CC1C1C=CCCC1N2C1CC=CCC1 Chemical compound *(C1CC2)C3C=CCCC3C1C=C2C(CCC12)CC1C1C=CCCC1N2C1CC=CCC1 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
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- JNIGFUXIZVCEED-UHFFFAOYSA-N 3-(9h-carbazol-2-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C(C5=CC=CC=C5N4)=CC=3)C=C2C2=CC=CC=C21 JNIGFUXIZVCEED-UHFFFAOYSA-N 0.000 description 1
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- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
본 발명은 도판트 화합물 및 호스트 화합물을 함유하는 발광층을 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent device including a light emitting layer containing a dopant compound and a host compound.
전계 발광 소자(electroluminescence device: EL 소자)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 다이아민과 알루미늄 착물을 이용하는 유기 EL 소자를 처음으로 개발하였다[참조: Appl. Phys. Lett. 51, 913, 987].An electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company first developed an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a light emitting layer forming material (Appl. Phys. Lett. 51, 913, 987].
유기 EL 소자는 통상 애노드 및 캐소드와 이들 사이에 유기물층을 포함하는 구조를 가진다. 유기 EL 소자의 유기물층은 정공주입층, 정공전달층, 전자차단층, 발광층, 정공차단층, 전자전달층, 전자주입층 등으로 이루어질 수 있으며, 이러한 유기 EL 소자에서는 전압 인가에 의해 애노드에서 정공이, 캐소드에서 전자가 발광층에 주입되고, 정공과 전자의 재결합에 의해 에너지가 높은 엑시톤이 형성된다. 이 에너지에 의해 발광 유기 화합물이 여기 상태로 되며, 발광 유기 화합물의 여기 상태가 기저 상태로 돌아가면서 에너지를 빛으로 방출하여 발광하게 된다. An organic EL element usually has a structure including an anode and a cathode and an organic layer between them. The organic material layer of the organic EL device may be composed of a hole injection layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer and an electron injecting layer. In such an organic EL device, , Electrons are injected from the cathode into the light emitting layer, and excitons with high energy are formed by recombination of holes and electrons. This energy causes the light-emitting organic compound to be in an excited state, and the excited state of the light-emitting organic compound is returned to the ground state, and energy is emitted to the light to emit light.
유기 EL 소자의 발광 재료는 소자의 발광 효율을 결정하는 가장 중요한 요인으로서, 발광 재료는 양자 효율이 높고 전자와 정공의 이동도가 커야 하고, 발광 재료에 의해 형성된 발광층은 균일하고 안정해야 한다. 이러한 발광 재료는 발광색에 따라 청색, 녹색 또는 적색 발광 재료로 나뉘고, 추가로 노란색 또는 주황색 발광 재료도 있다. 또한, 발광 재료는 기능적인 측면에서 호스트 재료와 도판트 재료로 구분될 수 있는데 일반적으로 EL 특성이 가장 우수한 소자 구조로는 호스트에 도판트를 도핑하여 발광층을 만드는 것으로 알려져 있다. 또한, 발광 재료는 여기 상태에 따라 형광 발광 재료(일중항 여기상태) 및 인광 발광 재료(삼중항 여기상태)로 분류된다. 초기의 유기 EL 소자는 형광 발광 재료를 주로 사용하였으나, 인광 발광 재료가 형광 재료에 비해 전기를 빛으로 바꾸는 효율(발광 효율)이 4배 이상 높고 소비전력 절감이 가능해 상대적으로 수명이 길어지는 효과가 있다는 점에서 인광 발광 재료의 개발 연구가 널리 수행되고 있다.The light emitting material of the organic EL device is the most important factor for determining the light emitting efficiency of the device. The light emitting material has high quantum efficiency and high electron and hole mobility, and the light emitting layer formed by the light emitting material must be uniform and stable. Such a light emitting material is divided into a blue, green or red light emitting material depending on a luminescent color, and further, there is a yellow or orange light emitting material. In addition, the light emitting material can be divided into a host material and a dopant material from the viewpoint of function. Generally, it is known that an EL material has the best EL structure to form a light emitting layer by doping a host with a dopant. Further, the light emitting material is classified into a fluorescent light emitting material (singlet excited state) and a phosphorescent light emitting material (triplet excited state) according to the excited state. Although the initial organic EL device is mainly made of a fluorescent material, a phosphorescent material has a fourfold higher efficiency (luminous efficiency) for converting electricity into light as compared with a fluorescent material, and the power consumption can be reduced, The development of phosphorescent materials has been widely carried out.
최근에 고효율 및 장수명의 유기 EL 소자의 개발이 시급한 과제로 대두되고 있는데, 특히 중대형 OLED 패널에서 요구하고 있는 EL 특성 수준을 고려해 볼 때 기존의 발광 재료에 비해 매우 우수한 재료의 개발이 시급한 실정이다. Recently, development of high-efficiency and long-life organic EL devices has become an urgent task. Especially, considering the EL characteristic level required for medium to large-sized OLED panels, it is urgent to develop materials superior to existing light emitting materials.
현재까지 이리듐(III) 착물 계열이 인광 발광 재료의 도판트로 널리 알려져 있으며, 각각의 적색, 녹색 및 청색 발광별로 (acac)Ir(btp)2(비스(2-(2'-벤조티에닐)-피리디네이토-N,C-3')이리듐(아세틸아세토네이트)), Ir(ppy)3(트리스(2-페닐피리딘)이리듐) 및 Firpic(비스(4,6-다이플루오로페닐피리디네이토-N,C2)피콜리네이토이리듐) 등의 재료가 알려져 있다.Until now, the iridium (III) complex series has been widely known as a dopant of phosphorescent light emitting materials. Ir (btp) 2 (bis (2- (2'-benzothienyl) Iridium (acetylacetonate)), Ir (ppy) 3 (tris (2-phenylpyridine) iridium) and Firpic (bis (4,6-difluorophenylpyridyl) Nato-N, C2) picolinatoimidiridium) are known.
또한, 호스트 재료는 발광 소자의 효율과 성능에 큰 영향을 미치므로, 그 선택이 중요하다. 종래 기술에서, 인광용 호스트 재료로는 4,4',N,N'-다이카바졸-바이페닐(CBP)가 가장 널리 알려져 있었다. 최근에는, 일본의 파이오니어 등이 정공차단층의 재료로 사용되던 바토큐프로인(Bathocuproine, BCP) 및 알루미늄(III)비스(2-메틸-8-퀴놀리네이트)(4-페닐페놀레이트)(Balq) 등을 호스트 재료로 이용해 고성능의 유기 EL 소자를 개발한 바 있다.In addition, since the host material greatly affects the efficiency and performance of the light emitting device, its selection is important. In the prior art, 4,4 ', N, N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. In recent years, Pioneer et al. Of Japan have been using bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenyl phenolate) Balq) as a host material to develop a high-performance organic EL device.
그러나, 기존의 이러한 인광용 호스트 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 다음과 같은 단점이 있다: (1) 유리 전이 온도가 낮고 열적 안정성이 낮아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변한다. (2) 유기 EL 소자에서 전력 효율 = [(π/전압)×전류 효율]의 관계에 있으므로 전력 효율은 전압에 반비례한다. 인광용 호스트 재료를 사용한 유기 EL 소자는 형광 호스트 재료를 사용한 유기 EL 소자에 비해 전류 효율(cd/A)은 높으나, 구동 전압 역시 상당히 높기 때문에 전력 효율(lm/w) 면에서 큰 이점이 없다. (3) 유기 EL 소자에 사용할 경우, 작동 수명 측면에서도 만족스럽지 못하며, 발광 효율도 여전히 개선이 요구된다.However, the conventional phosphorescent host materials are advantageous from the viewpoint of luminescence properties, but they have the following disadvantages: (1) when the glass transition temperature is low and the thermal stability is low, the material undergoes a high temperature deposition process under vacuum, It changes. (2) In the organic EL device, the power efficiency is inversely proportional to the voltage since it is in the relationship of power efficiency = [(pi / voltage) x current efficiency]. The organic EL device using the host material for phosphorescence has a higher current efficiency (cd / A) than the organic EL device using the fluorescent host material, but has a large driving voltage as well, so there is no great advantage in power efficiency (lm / w). (3) When it is used in an organic EL device, it is unsatisfactory in terms of operating life, and luminous efficiency is still required to be improved.
한국공개특허 KR 10-2011-0130475 A는 유기 전계 발광 소자의 도판트 화합물로서 이리듐 착체를 개시하면서, 해당 이리듐 착체에 적합한 호스트 화합물로서 트리페닐렌 부분과 디벤조티오펜 부분을 포함하는 화합물을 제시하고 있다. 또한, 한국공개특허 KR 10-2011-0015836 A는 카바졸 부분을 포함하는 유기 발광 화합물을 개시하면서, 해당 화합물과 Ir(ppy)3 또는 (piq)2Ir(acac)[비스-(1-페닐이소퀴놀릴)이리듐(III)아세틸아세토네이트]의 조합을 제시한다. Korean Published Patent Application No. 10-2011-0130475 A discloses an iridium complex as a dopant compound of an organic electroluminescent device and presents a compound containing a triphenylene moiety and a dibenzothiophene moiety as a host compound suitable for the iridium complex . In addition, KR 10-2011-0015836 A discloses an organic luminescent compound containing a carbazole moiety, and discloses an organic electroluminescent compound comprising Ir (ppy) 3 or (piq) 2 Ir (acac) [bis- Isoquinolyl) iridium (III) acetylacetonate].
그러나 기존의 도판트 화합물과 호스트 화합물을 함유하는 발광재료를 유기 전계 발광 소자에 적용하는 경우, 구동 전압, 발광 효율, 전력 효율 등의 측면에서 여전히 만족스럽지 못하였다.However, when a light emitting material containing an existing dopant compound and a host compound is applied to an organic electroluminescent device, it is still unsatisfactory in terms of driving voltage, luminous efficiency, and power efficiency.
본 발명자들은 특정의 이리듐 착체와 특정의 카바졸 포함 화합물을 조합하여 발광 재료로 사용하였을 때, 낮은 구동전압에서도 뛰어난 발광효율과 전력효율을 발휘하는 유기 전계 발광 소자가 얻어질 수 있음을 발견하여 본 발명을 완성하였다. The present inventors have found that an organic electroluminescent device exhibiting excellent luminescent efficiency and power efficiency even at a low driving voltage can be obtained when a specific iridium complex and a specific carbazole-containing compound are used as a light emitting material Thereby completing the invention.
따라서 본 발명의 목적은 발광 효율, 전력 효율 및 수명 특성이 개선되고 구동 전압이 낮은 유기 전계 발광 소자를 제공하는 것이다.Accordingly, an object of the present invention is to provide an organic electroluminescent device with improved luminous efficiency, power efficiency, and lifetime characteristics and a low driving voltage.
상기의 목적을 달성하기 위하여, 본 발명은 애노드와 캐소드 사이에 유기물층이 삽입된 유기 전계 발광 소자에 있어서, 상기 유기물층은 하기 화학식 1로 표시되는 도판트 화합물 하나 이상과 하기 화학식 2로 표시되는 호스트 화합물 하나 이상이 함유된 발광층을 포함하는, 유기 전계 발광 소자를 제공한다.According to an aspect of the present invention, there is provided an organic electroluminescent device including an organic compound layer interposed between an anode and a cathode, wherein the organic compound layer comprises at least one dopant compound represented by the following general formula (1) And at least one light-emitting layer containing at least one light-emitting layer.
상기 화학식 1에서, In Formula 1,
L1 내지 L3은 각각 독립적으로 하기의 구조에서 선택되고,L 1 to L 3 are each independently selected from the following structures,
단, L1 내지 L3 중 적어도 하나는 A-1, A-2 또는 A-3의 구조를 가져야 하며;Provided that at least one of L 1 to L 3 has a structure of A-1, A-2 or A-3;
X는 O 또는 S이고;X is O or S;
R1 내지 R11은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-30)알킬, 치환 또는 비치환된 (C3-30)시클로알킬, 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며;R 1 to R 11 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-30) alkyl, substituted or unsubstituted (C3-30) cycloalkyl, substituted or unsubstituted -30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;
a 내지 h는 각각 독립적으로 0 내지 4의 정수이고, a 내지 h가 2이상인 정수의 경우, 각각의 R1 내지 R8는 서로 동일하거나 상이할 수 있고;each of a to h is independently an integer of 0 to 4, and when a to h are an integer of 2 or more, each of R 1 to R 8 may be the same or different from each other;
상기 화학식 2에서,In Formula 2,
Y1은 O, S, -NR31 또는 -CR32R33이고,Y 1 is O, S, -NR 31 or -CR 32 R 33 ,
L4 및 L5은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며,L 4 and L 5 are each independently a single bond, substituted or unsubstituted (C6-30) aryl, or substituted or unsubstituted (5-30 membered heteroaryl)
R21 내지 R24은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-30)알킬, 치환 또는 비치환된 (C6-30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 실릴, 또는 치환 또는 비치환된 아미노이거나, 인접한 치환체와 서로 결합하여 (3-30원)의 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지방족 또는 방향족 환의 탄소원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;R 21 to R 24 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-30) alkyl, substituted or unsubstituted (C6-30) aryl, substituted or unsubstituted (5- Or a substituted or unsubstituted amino, or may combine with adjacent substituents to form a (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring, , The carbon atom of the aliphatic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
Ar1은 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원) 헤테로아릴이며;Ar 1 is substituted or unsubstituted (C6-30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;
R31 내지 R33은 각각 독립적으로 수소, 치환 또는 비치환된(C1-30)알킬, 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이거나, 인접한 치환체와 서로 결합하여 (3-30원) 단일환 또는 다환의 지방족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지방족 또는 방향족 환의 탄소원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R 31 to R 33 are each independently hydrogen, substituted or unsubstituted (C1-30) alkyl, substituted or unsubstituted (C6-30) aryl, or substituted or unsubstituted (5-30 membered) (3-30 members) to form a monocyclic or polycyclic aliphatic or aromatic ring, and the carbon atom of the aliphatic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be;
o 및 p은 각각 독립적으로 0 내지 4의 정수이며, o 또는 p가 2이상인 정수의 경우, 각각의 R21 또는 각각의 R22은 서로 동일하거나 상이할 수 있고, o and p are each independently an integer of 0 to 4, and when o or p is an integer of 2 or more, each R 21 or each R 22 may be the same or different from each other,
q 및 r은 각각 독립적으로 0 내지 3의 정수이며, q 또는 r이 2이상인 정수의 경우 각각의 R23 또는 각각의 R24은 서로 동일하거나 상이할 수 있고,q and r are each independently an integer of 0 to 3, and when q or r is an integer of 2 or more, each R 23 or each R 24 may be the same or different from each other,
상기 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.The heteroaryl comprises at least one heteroatom selected from B, N, O, S, P (= O), Si and P.
본 발명에 따른 유기 전계 발광 소자는 수명, 발광 효율, 전력 효율이 우수하면서도 구동 전압이 낮은 장점이 있다. The organic electroluminescent device according to the present invention is advantageous in terms of lifetime, luminous efficiency, power efficiency, and low driving voltage.
이하에서 본 발명을 더욱 상세히 설명하나, 이는 설명을 위한 것으로 본 발명의 범위를 제한하는 방법으로 해석되어서는 안 된다.The present invention will now be described in more detail, but this should not be construed as limiting the scope of the present invention.
본 발명은 상기 화학식 1로 표시되는 도판트 화합물 하나 이상과 상기 화학식 2 로 표시되는 호스트 화합물 하나 이상이 함유된 발광층을 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent device comprising at least one dopant compound represented by the general formula (1) and at least one host compound represented by the general formula (2).
먼저, 상기 화학식 1로 표시되는 도판트 화합물에 대해 구체적으로 설명하면 다음과 같다.First, the dopant compound represented by Formula 1 will be described in detail.
상기 화학식 1로 표시되는 도판트 화합물 하나 이상은 하기 화학식 3 내지 5로 표시되는 화합물 중 하나 이상일 수 있다.At least one dopant compound represented by the formula (1) may be at least one of the compounds represented by the following formulas (3) to (5).
상기 화학식 3 내지 5에서,In the above formulas 3 to 5,
R1 내지 R6, a 내지 f, X, L2, 및 L3은 앞서 화학식 1에서 정의한 바와 같다.R 1 to R 6 , a to f, X, L 2 , and L 3 have the same meanings as defined in formula (1).
또한, 상기 화학식 1로 표시되는 도판트 화합물은 바람직하게는 상기 화학식 3 으로 표시되는 구조를 가질 수 있다. Also, the dopant compound represented by Formula 1 may have a structure represented by Formula 3 above.
또한, 상기 화학식 1 및 3 내지 5에서, 바람직하게는, R1 내지 R11은 각각 독립적으로 수소, 치환 또는 비치환된 (C1-C10)알킬, 치환 또는 비치환된 (C3-C10)시클로알킬, 치환 또는 비치환된 (C6-C20)아릴, 또는 치환 또는 비치환된 (5-20원)헤테로아릴이고, a 내지 h는 각각 독립적으로 0 내지 2의 정수이다.In the above general formulas (1) and (3) to (5), preferably, R 1 to R 11 each independently represent hydrogen, substituted or unsubstituted (C 1 -C 10) alkyl, substituted or unsubstituted (C 3 -C 10) cycloalkyl , Substituted or unsubstituted (C6-C20) aryl, or substituted or unsubstituted (5-20 membered heteroaryl), and a to h are each independently an integer of 0 to 2.
상기 화학식 3으로 표시되는 화합물은 보다 구체적으로는 하기의 화합물로 예시될 수 있으나, 하기 화합물에 한정되는 것은 아니다.More specifically, the compound represented by the formula (3) may be exemplified by the following compounds, but is not limited to the following compounds.
또한, 상기 화학식 4로 표시되는 화합물은 보다 구체적으로는 하기의 화합물로 예시될 수 있으나, 하기 화합물에 한정되는 것은 아니다.The compound represented by the formula (4) is more specifically exemplified by the following compounds, but is not limited to the following compounds.
또한, 상기 화학식 5로 표시되는 화합물은 보다 구체적으로는 하기의 화합물로 예시될 수 있으나, 하기 화합물에 한정되는 것은 아니다.In addition, the compound represented by the formula (5) may be more specifically exemplified by the following compounds, but is not limited to the following compounds.
상기 화학식 3 내지 5의 화합물을 비롯한 상기 화학식 1의 화합물은 당업계에 공지된 합성 방법에 의해 제조할 수 있다. 예를 들어, 한국공개특허 KR 10-2011-0130476 A에 개시된 방법에 의해 제조될 수 있다.The compound of Formula 1 including the compounds of Formulas 3 to 5 may be prepared by a synthesis method known in the art. For example, by the method disclosed in Korean Patent Laid-Open Publication No. 10-2011-0130476 A.
다음으로, 상기 화학식 2로 표시되는 호스트 화합물에 대해 구체적으로 설명한다.Next, the host compound represented by Formula 2 will be described in detail.
상기 화학식 2로 표시되는 호스트 화합물 하나 이상은 하기 화학식 6 내지 12로 표시되는 화합물 중 하나 이상일 수 있다. At least one of the host compounds represented by the formula (2) may be one or more of the compounds represented by the following formulas (6) to (12).
상기 화학식 6 내지 12에서,In the above formulas (6) to (12)
R21 내지 R24, Y1, L4, L5, Ar1, o, p, q 및 r은 앞서 정의한 바와 같다.R 21 to R 24 , Y 1 , L 4 , L 5 , Ar 1 , o, p, q and r are as defined above.
바람직하게는, 상기 화학식2로 표시되는 호스트 화합물 하나 이상은 상기 화학식 6, 9 및 10으로 표시되는 화합물 중 하나 이상일 수 있다.Preferably, at least one of the host compounds represented by Formula 2 may be one or more of the compounds represented by Formulas 6, 9, and 10.
상기 화학식 2 또는 6 내지 12에서, 상기 L4 및 L5는 바람직하게는, 각각 독립적으로 단일 결합, 치환 또는 비치환된 (C6-20)아릴, 또는 치환 또는 비치환된 (5-20원)헤테로아릴이며;Wherein L 4 and L 5 are each independently a single bond, a substituted or unsubstituted (C 6-20) aryl, or a substituted or unsubstituted (5-20 member) Heteroaryl;
R21 내지 R24는 각각 독립적으로, 수소, 치환 또는 비치환된 (C1-C10)알킬, 치환 또는 비치환된 (C6-C20)아릴, 치환 또는 비치환된 (5-20원)헤테로아릴이거나, 인접한 치환체와 서로 결합하여 (3-30원) 단일환 또는 다환의 지방족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지방족 또는 방향족 환의 탄소원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R 21 to R 24 each independently represent hydrogen, substituted or unsubstituted (C 1 -C 10) alkyl, substituted or unsubstituted (C 6 -C 20) aryl, substituted or unsubstituted (5-20 membered) (3-30 members) to form a monocyclic or polycyclic aliphatic or aromatic ring, and the carbon atom of the aliphatic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be;
Y1은 O, S 또는 -NR31이며, R31은 치환 또는 비치환된 (C1-C10)알킬, 또는 치환 또는 비치환된 (C6-20)아릴이며;Y 1 is O, S or -NR 31 , R 31 is Substituted or unsubstituted (C1-C10) alkyl, or substituted or unsubstituted (C6-20) aryl;
Ar1은 치환 또는 비치환된 (C6-20)아릴, 또는 헤테로원자로서 1 내지 3개의 질소를 포함하는 치환 또는 비치환된 (5-20원)헤테로아릴이고, 여기서, 상기 Ar1의 치환 (C6-18)아릴 및 치환 (5-20원)헤테로아릴의 치환체는 각각 독립적으로, 할로겐 또는 (C1-10)알킬로 치환되거나 비치환된 (C6-20)아릴, (C1-10)알킬로 치환되거나 비치환된 (5-20원)헤테로아릴, 트리(C6-20)아릴실릴, 디(C1-10)알킬(C6-20)아릴실릴, (C1-10)알킬디(C6-20)아릴실릴, 모노 또는 디(C6-20)아릴아미노, 및 (C1-10)알킬(C6-20)아릴아미노로 이루어진 군에서 선택되는 1종 이상일 수 있다. Ar 1 is a substituted or unsubstituted (C6-20) aryl, or a substituted heteroatom, which contain from 1 to 3 nitrogen and unsubstituted (5-20 membered) heteroaryl, wherein the substitution of Ar 1 ( C6-18) aryl and substituted (5-20 membered) heteroaryl are each independently selected from the group consisting of (C6-20) aryl, (C1-10) alkyl optionally substituted by halogen or (C1-10) (C6-20) arylsilyl, di (C1-10) alkyl (C6-20) arylsilyl, (C1-10) alkyldi (C6-20) (C6-20) arylamino, aryloxy, arylsilyl, mono or di (C6-20) arylamino, and (C1-10) alkyl (C6-20) arylamino.
상기 Ar1은 하기 B-1 내지 B-7로 표시되는 구조에서 선택되는 것이 바람직하다.It is preferable that Ar 1 is selected from the structures represented by the following B-1 to B-7.
상기 B-1 내지 B-7에서,In the above B-1 to B-7,
A는 중수소, 할로겐, 치환 또는 비치환된 (C1-30)알킬, (C1-30)알콕시, 치환 또는 비치환된 (C6-30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, (C3-30)시클로알킬, (5-7원)헤테로시클로알킬, 트리(C1-30)알킬실릴, 트리(C6-30)아릴실릴, 디(C1-30)알킬(C6-30)아릴실릴, (C1-30)알킬디(C6-30)아릴실릴, (C2-30)알케닐, (C2-30)알키닐, 시아노, 모노 또는 디(C1-30)알킬아미노, 모노 또는 디(C6-30)아릴아미노, (C1-30)알킬(C6-30)아릴아미노, 디(C6-30)아릴보로닐, 디(C1-30)알킬보로닐, (C1-30)알킬(C6-30)아릴보로닐, (C6-30)아르(C1-30)알킬, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 1종 이상이고, m은 0 내지 4의 정수이고, m이 2 이상일 경우, 각각의 A는 서로 동일하거나 상이할 수 있고, *은 결합 사이트이다. 상기 A는 바람직하게는 할로겐 또는 (C1-10) 알킬로 치환되거나 비치환된 (C6-20)아릴, (C1-10) 알킬로 치환되거나 비치환된 (5-20원)헤테로아릴, 트리(C6-20)아릴실릴, 디(C1-10)알킬(C6-20)아릴실릴, (C1-10)알킬디(C6-20)아릴실릴, 모노 또는 디(C6-20)아릴아미노, 및 (C1-10)알킬(C6-20)아릴아미노로 이루어진 군으로부터 선택되는 1종 이상일 수 있고, m은 바람직하게는 0 내지 2의 정수이거나 0 또는 1일 수 있다.A is selected from deuterium, halogen, substituted or unsubstituted (C1-30) alkyl, (C1-30) alkoxy, substituted or unsubstituted (C6-30) aryl, substituted or unsubstituted (5-30 membered) (C3-30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-30) alkylsilyl, tri (C6-30) arylsilyl, di (C1-30) (C1-30) alkylsilyl, (C2-30) alkenyl, (C2-30) alkynyl, cyano, mono or di (C1-30) alkylamino, mono or di (C6-30) arylamino, (C1-30) alkyl (C6-30) arylamino, di (C6-30) arylboronyl, di (C1-30) alkylboronyl, (C6-30) aryl, (C6-30) aryl (C1-30) alkyl, carboxyl, nitro and hydroxy, m is an integer of 0-4, When m is 2 or more, each A may be the same as or different from each other, and * is a binding site. A is preferably (C6-20) aryl optionally substituted with halogen or (C1-10) alkyl, (5-20) heteroaryl optionally substituted with (C1-10) alkyl, tri (C6-20) arylsilyl, mono or di (C6-20) arylamino, and (C6-20) arylsilyl, di (C1-10) (C1-C10) alkyl (C6-20) arylamino, and m is preferably an integer of 0 to 2, or 0 or 1.
상기 화학식 6 내지 12로 표시되는 화합물은 보다 구체적으로는 하기의 화합물로 예시될 수 있으나, 하기 화합물에 한정되는 것은 아니다.The compounds represented by the above formulas (6) to (12) are more specifically exemplified by the following compounds, but are not limited to the following compounds.
상기 화학식 6 내지 12의 화합물을 비롯한 상기 화학식 2의 화합물은 당업계에 공지된 합성 방법에 의해 제조할 수 있다. 예를 들어, 상기 화합물은 한국공개특허 KR 10-2011-0015836 A에 개시된 방법에 의해 제조될 수 있다.The compound of formula (2), including the compounds of formulas (6) to (12), can be prepared by a synthesis method known in the art. For example, the compound can be prepared by the method disclosed in Korean Patent Publication No. KR 10-2011-0015836 A.
본 명세서에서, "(C1-C30)알킬"은 탄소수가 1 내지 30개인 직쇄 또는 분지쇄 알킬을 의미하고, 여기에서 탄소수가 1 내지 20개인 것이 바람직하고, 1 내지 10개인 것이 더 바람직하다. 상기 알킬의 구체적인 예로서, 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸 및 tert-부틸 등이 있다. 본 명세서에서 "(C2-C30)알케닐"은 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알케닐을 의미하고, 여기에서 탄소수가 2 내지 20개인 것이 바람직하고, 2 내지 10개인 것이 더 바람직하다. 상기 알케닐의 구체적인 예로서, 비닐, 1-프로페닐, 2-프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 2-메틸부트-2-에닐 등이 있다. 본 명세서에서 본원에서 "(C2-C30)알키닐"은 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알키닐을 의미하고, 여기에서 탄소수가 2 내지 20개인 것이 바람직하고, 2 내지 10개인 것이 더 바람직하다. 상기 알키닐의 예로서, 에티닐, 1-프로피닐, 2-프로피닐, 1-부티닐, 2-부티닐, 3-부티닐, 1-메틸펜트-2-이닐 등이 있다. 본 명세서에서 본원에서 "(C3-C30)시클로알킬"은 탄소수가 3 내지 30개인 단일환 또는 다환 탄화수소를 의미하고, 여기에서 탄소수가 3 내지 20개인 것이 바람직하고, 3 내지 7개인 것이 더 바람직하다. 상기 시클로알킬의 예로서, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등이 있다. 본 명세서에서 "(5-7 원) 헤테로시클로알킬"은 환 골격 원자수가 5 내지 7개이고, B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자, 바람직하게는 O, S 및 N에서 선택되는 하나 이상의 헤테로원자를 포함하는 시클로알킬을 의미하고, 예를 들어, 테트라히드로푸란, 피롤리딘, 티올란, 테트라히드로피란 등이 있다. 본 명세서에서 "(C6-C30)아릴"은 탄소수가 6 내지 30개인 방향족 탄화수소에서 유래된 단일환 또는 융합환계 라디칼을 의미하고, 여기에서 환 골격 탄소수가 6 내지 20개인 것이 바람직하고, 6 내지 18개인 것이 더 바람직하다. 상기 아릴의 예로서 페닐, 비페닐, 터페닐, 나프틸, 비나프틸, 페닐나프틸, 나프틸페닐, 플루오레닐, 페닐플루오레닐, 벤조플루오레닐, 디벤조플루오레닐, 페난트레닐, 페닐페난트레닐, 안트라세닐, 인데닐, 인다닐, 트리페닐레닐, 피레닐, 테트라세닐, 페릴레닐, 크라이세닐, 나프타세닐, 플루오란테닐 등이 있다. 본 명세서에서 "(5-30 원) 헤테로아릴"은 환 골격 원자수가 5 내지 30개이고, B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자를 포함하는 아릴기를 의미한다. 여기에서 환 골격 원자수가 5 내지 20개인 것이 바람직하고, 5 내지 15개인 것이 더 바람직하다. 헤테로원자수는 바람직하게는 1 내지 4개이고, 단일 환계이거나 하나 이상의 벤젠환과 축합된 융합환계일 수 있으며, 부분적으로 포화될 수도 있다. 또한, 본원에서 상기 헤테로아릴은 하나 이상의 헤테로아릴 또는 아릴기가 단일 결합에 의해 헤테로아릴기와 연결된 형태도 포함한다. 상기 헤테로아릴의 예로서, 푸릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 푸라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단일 환계 헤테로아릴, 벤조푸란일, 벤조티오펜일, 이소벤조푸란일, 디벤조푸란일, 디벤조티오펜일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페녹사진일, 페난트리딘일, 벤조디옥솔릴 등의 융합 환계 헤테로아릴 등이 있다. 본 명세서에서 "할로겐"은 F, Cl, Br 및 I 원자를 포함한다. In the present specification, the term "(C 1 -C 30) alkyl" means straight chain or branched chain alkyl having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. In the present specification, "(C2-C30) alkenyl" means straight-chain or branched alkenyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, the term "(C2-C30) alkynyl" means straight chain or branched chain alkynyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms Do. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methylpent-2-onyl. As used herein, the term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7 . Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. The term "(5-7 membered) heterocycloalkyl" as used herein refers to a heterocycloalkyl group having 5 to 7 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, P (═O) , Preferably one or more heteroatoms selected from O, S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "(C6-C30) aryl" refers to a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 20, Personal is more desirable. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, For example, phenyl, naphthyl, phenyl, phenanthrenyl, anthracenyl, indenyl, indanyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, crycenyl, naphthacenyl and fluoranthenyl. In the present specification, the term "(5-30 membered heteroaryl") means a heteroaryl group having 5 to 30 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, P (═O) ≪ / RTI > Here, the number of the atoms of the ring skeleton is preferably 5 to 20, more preferably 5 to 15. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. The heteroaryls herein also include those wherein one or more heteroaryl or aryl groups are linked by a single bond to a heteroaryl group. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused heterocyclic heteroaryl such as norbornyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.
또한, 본 명세서에서 "치환 또는 비치환"이라는 기재에서 '치환'은 어떤 작용기에서 수소 원자가 다른 원자 또는 다른 작용기 (즉, 치환체)로 대체되는 것을 의미한다. 상기 화학식 1 및 2의 R1 내지 R7, R21 내지 R24, R31 내지 R33, L1, L2, 및 Ar1 에서 치환 (C1-30)알킬, 치환 (C3-30)시클로알킬, 치환 (C6-30)아릴, 치환 (5-30 원)헤테로아릴, 치환 실릴 및 치환 아미노의 치환체는 각각 독립적으로 중수소, 할로겐, 할로겐으로 치환되거나 비치환된 (C1-30)알킬, (C1-30)알콕시, (C1-30)알킬로 치환되거나 비치환된 (C6-30)아릴, (C1-30)알킬로 치환되거나 비치환된 (5-30원)헤테로아릴, (C3-30)시클로알킬, (5-7원)헤테로시클로알킬, 트리(C1-30)알킬실릴, 트리(C6-30)아릴실릴, 디(C1-30)알킬(C6-30)아릴실릴, (C1-30)알킬디(C6-30)아릴실릴, (C2-30)알케닐, (C2-30)알키닐, 시아노, 모노 또는 디(C1-30)알킬아미노, 모노 또는 디(C6-30)아릴아미노, (C1-30)알킬(C6-30)아릴아미노, 디(C6-30)아릴보로닐, 디(C1-30)알킬보로닐, (C1-30)알킬(C6-30)아릴보로닐, (C6-30)아르(C1-30)알킬, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 1종 이상일 수 있다. Also, in the specification of the term "substituted or unsubstituted" herein, "substituted" means that a hydrogen atom is replaced by another atom or another functional group (ie, a substituent) in a certain functional group. Formula 1 and 2 of R 1 to R 7, R 21 to R 24, R 31 to R 33, L 1, L substituted in the 2, and Ar 1, (C1-30) alkyl, substituted (C3-30) cycloalkyl , Substituted (C6-30) aryl, substituted (5-30 membered) heteroaryl, substituted silyl and substituted amino are each independently selected from deuterium, halogen, (C1-30) (C30-30) alkoxy, (C6-30) aryl optionally substituted with (C1-30) alkyl, (5-30) heteroaryl optionally substituted with (C1-30) (C6-30) arylsilyl, (C1-30) alkylsilyl, tri (C6-30) arylsilyl, di (C1-30) (C2-30) alkenyl, (C2-30) alkynyl, cyano, mono or di (C1-30) alkylamino, mono or di (C6-30) aryl (C1-30) alkyl (C6-30) arylamino, di (C6-30) arylboronyl, di (C1-30) alkylboronyl, (C6-30) ar (C1-30) alkyl, < RTI ID = 0.0 > One member selected from the group consisting of dicarboxylic, nitro and hydroxy may be equal to or greater than.
이하, 상기 화학식 1의 도판트 화합물과 상기 화학식 2의 호스트 화합물의 조합물을 포함하는 유기 전계 발광 소자에 대해 구체적으로 설명한다. Hereinafter, an organic electroluminescent device including a combination of the dopant compound of Formula 1 and the host compound of Formula 2 will be described in detail.
본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 가진다. 상기 제1전극과 제2전극 중 하나는 애노드이고 다른 하나는 캐소드일 수 있다. An organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And one or more organic layers sandwiched between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode and the other may be a cathode.
상기 유기물층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 1종 이상의 호스트 화합물 및 상기 화학식 2로 표시되는 1종 이상의 도판트 화합물의 조합물을 포함할 수 있다. 상기 발광층은 단일층일 수 있으며, 또는 2개 이상의 층이 적층된 복수의 층일 수 있다. 상기 발광층 중에서 도판트와 호스트의 조합비는 도판트와 호스트의 전체에 대하여 도판트가 20 중량% 미만인 것, 바람직하게는 17 중량% 미만인 것이 색순도, 발광 효율, 전력 효율, 구동 전압에 있어서 바람직하다. 상기 발광층은 화학식 1의 화합물 및 화학식 2의 화합물의 조합물 이외에, 1종 이상의 다른 물질, 예를 들어 추가의 제2 호스트 물질 등을 더 포함할 수도 있다. 상기 유기물층은 정공 주입층, 정공 전달층, 전자 전달층, 전자 주입층, 계면층(interlayer) 및 정공 차단층에서 선택되는 1층 이상을 더 포함할 수 있다.The organic layer may include a light emitting layer, and the light emitting layer may include a combination of at least one host compound represented by Formula 1 and at least one dopant compound represented by Formula 2. The light emitting layer may be a single layer, or may be a plurality of layers in which two or more layers are stacked. The combination ratio of the dopant and the host in the light emitting layer is preferably in the range of less than 20% by weight, preferably less than 17% by weight, in terms of color purity, luminous efficiency, power efficiency and driving voltage for the dopant and the host. The light emitting layer may further comprise at least one other substance such as an additional second host material and the like in addition to the combination of the compound of the formula (1) and the compound of the formula (2). The organic material layer may further include at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer and a hole blocking layer.
본 발명의 다른 양태에 의하면, 본 발명은 상기 화학식 1로 표시되는 도판트 화합물 하나 이상과 상기 화학식 2로 표시되는 호스트 화합물 하나 이상의 조합물을 제공한다. 또한, 본 발명은 상기 도판트 화합물과 상기 호스트 화합물의 조합물을 포함하는 유기 전계 발광 소자를 제공한다.According to another aspect of the present invention, there is provided a combination of at least one dopant compound represented by Formula 1 and at least one host compound represented by Formula 2. The present invention also provides an organic electroluminescent device comprising a combination of the dopant compound and the host compound.
본 발명은 추가의 양태로, 상기 화학식 1로 표시되는 도판트 화합물 하나 이상과 상기 화학식 2로 표시되는 호스트 화합물 하나 이상을 포함하는 유기물층을 제공한다. 상기 유기물층은 복수의 층을 포함하며, 상기 도판트 화합물과 상기 호스트 화합물은 동일한 층에 포함될 수도 있고, 각각 서로 다른 층에 포함될 수도 있다. 또한, 본 발명은 상기 유기물층을 포함하는 유기 전계 발광 소자를 제공한다.According to a further aspect of the present invention, there is provided an organic material layer comprising at least one dopant compound represented by the formula (1) and at least one host compound represented by the formula (2). The organic material layer includes a plurality of layers, and the dopant compound and the host compound may be included in the same layer or may be included in different layers, respectively. The present invention also provides an organic electroluminescent device including the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 더 포함할 수 있다. 또한, 본 발명의 유기 전계 발광 소자는, 유기물층에 1족, 2족, 4주기, 5주기 전이금속, 란탄 계열 금속 및 d-전이 원소의 유기 금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체 화합물을 더 포함할 수도 있다.The organic electroluminescent device of the present invention may further include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound in the organic material layer. The organic electroluminescent device of the present invention may further comprise at least one metal or complex compound selected from the group consisting of organic metals of group 1, group 2, group 4, group 5 transition metal, lanthanide series and d- As shown in FIG.
또한, 본 발명의 상기 유기 전계 발광 소자는 본 발명의 화합물 이외에 당업계에 알려진 청색, 적색 또는 녹색 발광 화합물을 포함하는 발광층 하나 이상을 더 포함함으로써 백색 발광을 할 수 있다. 또한, 필요에 따라, 황색 또는 오렌지색 발광층을 더 포함할 수도 있다.In addition, the organic electroluminescent device of the present invention may emit white light by further including at least one light emitting layer containing a blue, red or green light emitting compound known in the art, in addition to the compound of the present invention. Further, if necessary, it may further include a yellow or orange light emitting layer.
본 발명의 유기 전계 발광 소자는 한 쌍의 전극의 적어도 한쪽의 내측 표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 1층(이하, 이들을 "표면층"이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1=X=2), AlOX(1=X=1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO 등이 있다.The organic electroluminescent device of the present invention is characterized in that one or more layers selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer " . Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO X (1 = X = 2), AlO x (1 = X = 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
또한, 본 발명의 유기 전계 발광 소자는, 이렇게 제조된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광 소자를 제조할 수 있다.Further, in the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of the electron transfer compound and the reducing dopant, or a mixed region of the hole transfer compound and the oxidative dopant, on at least one surface of the thus- Do. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.
본 발명의 유기 전계 발광 소자의 각 층의 형성은 진공증착, 스퍼터링, 플라즈마, 이온플레이팅 등의 건식 성막법이나 스핀 코팅, 침지 코팅(dip coating), 플로우 코팅 등의 습식 성막법 중의 어느 하나의 방법을 적용할 수 있다. 본 발명의 상기 화학식 1의 화합물과 화학식 2의 화합물은 예를 들어, 공증착에 의해 하나의 층으로 될 수 있다.The formation of each layer of the organic electroluminescent device of the present invention can be performed by any one of dry film formation methods such as vacuum deposition, sputtering, plasma, and ion plating, wet film formation methods such as spin coating, dip coating and flow coating Method can be applied. The compound of Formula 1 and the compound of Formula 2 of the present invention may be a single layer, for example, by co-deposition.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 화합물, 이의 제조방법 및 소자의 발광특성을 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.
Hereinafter, for a detailed understanding of the present invention, the compounds according to the present invention, the preparation method thereof and the luminescent characteristics of the device are described for the representative compounds of the present invention, but the present invention is not limited thereto. It is not intended to limit the scope.
[[ 합성예Synthetic example 1] 화합물 D-2의 제조 1] Preparation of compound D-2
화합물 1-1의 제조Preparation of Compound 1-1
2-페닐피리딘(10g, 32mmol)과 이리듐(III) 클로라이드 하이드레이트(IrCl3·xH2O)(8.1g, 29mmol), 2-에톡시 에탄올(220mL) 및 H2O(74mL)를 140℃에서 24시간 동안 교반하였다. 반응 종료 후 실온으로 식히고, 물 및 메탄올(MeOH)로 세척한 후 건조시켜 화합물 1-1(11g, 71%)을 얻었다(8.1 g, 29 mmol), 2-ethoxyethanol (220 mL) and H 2 O (74 mL) were added to a solution of 2-phenylpyridine (10 g, 32 mmol) and iridium (III) chloride hydrate (IrCl 3 .xH 2 O) Stir for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, washed with water and methanol (MeOH), and dried to obtain Compound 1-1 (11 g, 71%
화합물 1-2의 제조Preparation of Compound 1-2
화합물 1-1(10g, 9 mmol)을 메틸렌 클로라이드(MC) 4L에 녹이고 여기에 은 트리플루오로메탄설페이트(AgOTf)(5g, 19mmol)를 MeOH(400 mL)에 녹인 것을천천히 가한후 12시간 동안 실온에서 교반하였다. 반응 종료 후 반응 혼합물을여과한 후 여액을 건조시켜 화합물 1-2(12g, 94%)를 얻었다.Compound 1 (10 g, 9 mmol) was dissolved in 4 L of methylene chloride (MC), and silver trifluoromethane sulphate (AgOTf) (5 g, 19 mmol) was dissolved in MeOH (400 mL) Stir at room temperature. After completion of the reaction, the reaction mixture was filtered, and the filtrate was dried to obtain Compound 1-2 (12 g, 94%).
화합물 1-3의 제조Preparation of compounds 1-3
2-브로모피리딘(10g, 63mmol), 다이벤조[b,d]푸란-4-일 보론산(16g, 76mmol), 테트라키스(트리페닐포스핀)팔라듐(O)[Pd(PPh3)4](2.2g, 2mmol), Na2CO3(20g, 19mmol), 톨루엔(300mL), 에탄올(EtOH)(150 mL) 및 H2O(10mL)를 넣고, 100℃에서 2시간 동안 교반하였다. 반응 종료 후 실온에서 식히고, 에틸 아세테이트(EA)로 추출한 다음 MgSO4로 수분을 제거한 후, 감압증류하였다. MC/헥산(Hx) = 1/3으로 컬럼 크로마토그래피하여 백색 고체의 화합물 1-3(10g, 63%)을 얻었다.2-bromopyridine (10g, 63mmol), dibenzo [b, d] furan-4-yl boronic acid (16g, 76mmol), tetrakis (triphenylphosphine) palladium (O) [Pd (PPh 3 ) 4 (2.2 g, 2 mmol), Na 2 CO 3 (20 g, 19 mmol), toluene (300 mL), ethanol (EtOH) (150 mL) and H 2 O (10 mL) were placed and stirred at 100 ° C for 2 hours. After completion of the reaction, the reaction mixture was cooled at room temperature, extracted with ethyl acetate (EA), and then dehydrated with MgSO 4 , followed by distillation under reduced pressure. Column chromatography of MC / hexane (Hx) = 1/3 yielded compound 1-3 (10 g, 63%) as a white solid.
화합물 D-2의 제조Preparation of Compound D-2
화합물 1-3(7g, 28mmol)과 화합물 1-2(10g, 14mmol)에 MeOH(200mL)을 가하고 12시간 동안 환류 교반하였다. 반응 종료 후 실온으로 냉각시킨 후 여과하고 클로로포름(CHCl3)으로 컬럼 크로마토그래피하여 화합물 D-2(2g, 17%)를 얻었다.MeOH (200 mL) was added to compound 1-3 (7 g, 28 mmol) and compound 1-2 (10 g, 14 mmol) and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered and then subjected to column chromatography using chloroform (CHCl 3 ) to obtain a compound D-2 (2 g, 17%).
mp 400℃ 이상, UV 292nm, PL 525nm, LC 99.06%
mp 400 DEG C or higher, UV 292 nm, PL 525 nm, LC 99.06%
[[ 합성예Synthetic example 2] 화합물 D-3의 제조 2] Preparation of compound D-3
화합물 2-1의 제조Preparation of Compound 2-1
2-브로모-5-메틸피리딘(15g, 87mmol), 페닐보론산(14g, 114mmol), Pd(PPh3)4(3g, 2.6mmol), Na2CO3(36g, 260mmol), 톨루엔(300mL), EtOH(150mL) 및 H2O(130mL)를 넣고, 100℃에서 3시간 동안 교반하였다. 반응 종료 후 EA로추출하고 MgSO4로 수분을 제거한 후, 감압증류하였다. 그리고 MC/Hx = 1/2로 컬럼 크로마토그래피하여 백색 고체의 화합물 2-1(10g, 68%)을 얻었다.2-bromo-5-methylpyridine (15g, 87mmol), phenylboronic acid (14g, 114mmol), Pd ( PPh 3) 4 (3g, 2.6mmol), Na 2 CO 3 (36g, 260mmol), toluene (300mL ), EtOH (150 mL) and H 2 O (130 mL) were added, and the mixture was stirred at 100 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with EA, and water was removed with MgSO 4 , followed by distillation under reduced pressure. And subjected to column chromatography with MC / Hx = 1/2 to obtain Compound 2-1 (10 g, 68%) as a white solid.
화합물 2-2의 제조Preparation of Compound 2-2
화합물 2-1(10g, 30mmol)과 IrCl3·xH2O(8g, 27mmol), 2-에톡시 에탄올(200mL) 및 H2O(70mL)를 140℃에서 24시간 동안 교반하였다. 반응 종료 후 실온으로 식히고 H2O 및 MeOH로 세척한 후 건조시켜 화합물 2-2(11g, 75%)를 얻었다.Compound 2-1 (10 g, 30 mmol), IrCl 3 .xH 2 O (8 g, 27 mmol), 2-ethoxyethanol (200 mL) and H 2 O (70 mL) were stirred at 140 ° C for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, washed with H 2 O and MeOH, and dried to obtain Compound 2-2 (11 g, 75%).
화합물 2-3의 제조Preparation of Compound 2-3
화합물 2-2(11g, 10mmol)를 MC 4L에 녹이고 여기에 AgOTf(5g, 20mmol)를 MeOH(400mL)에 녹인 것을 천천히 가한 후 12시간 동안 실온에서 교반하였다. 반응 종료 후 혼합물을 여과한 후 여액을 건조시켜 화합물 2-3(13g, 89%)을 얻었다.Compound 2-2 (11 g, 10 mmol) was dissolved in 4 L of MC, and AgOTf (5 g, 20 mmol) was dissolved in MeOH (400 mL), followed by slow addition and stirring at room temperature for 12 hours. After completion of the reaction, the mixture was filtered, and the filtrate was dried to obtain Compound 2-3 (13 g, 89%).
화합물 D-3의 제조Preparation of compound D-3
화합물 1-3(7g, 28mmol)과 화합물 2-3(10g, 14mmol)에 MeOH(200mL)을 가하고 12시간 동안 환류 교반하였다. 반응 종료 후 실온으로 냉각시킨 후 여과하고 CHCl3으로 컬럼 크로마토그래피하여 화합물 D-3(3.5g, 33%)을 얻었다.MeOH (200 mL) was added to compound 1-3 (7 g, 28 mmol) and compound 2-3 (10 g, 14 mmol) and the mixture was refluxed with stirring for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, and then subjected to column chromatography using CHCl 3 to obtain 3.5 g (33%) of compound D-3.
mp 400℃ 이상, UV 292nm, PL 527nm, LC 99.19%
mp 400 DEG C or higher, UV 292 nm, PL 527 nm, LC 99.19%
[[ 합성예Synthetic example 3] 화합물 D-95의 제조 3] Preparation of compound D-95
화합물 3-1의 제조Preparation of Compound 3-1
2-브로모-4-메틸피리딘(10g, 63mmol), 다이벤조[b,d]푸란-4-일 보론산(15g, 76mmol), 테트라키스(트리페닐포스핀)팔라듐(O)[Pd(PPh3)4](2.2g, 2mmol), Na2CO3(20g, 19mmol), 톨루엔(300mL), 에탄올(EtOH)(150mL) 및 H2O(10mL)를 넣고, 100℃에서 2시간 동안 교반하였다. 반응 종료 후 실온에서 식히고, 에틸 아세테이트(EA)로 추출한 다음 MgSO4로 수분을 제거한 후, 감압증류하였다. MC/헥산(Hx) = 1/3으로 컬럼 크로마토그래피하여 백색 고체의 화합물 3-1(11g, 67%)을 얻었다.(10 g, 63 mmol), dibenzo [b, d] furan-4-ylboronic acid (15 g, 76 mmol), tetrakis (triphenylphosphine) palladium (0) [Pd PPh 3) 4] (2.2g, 2mmol), Na 2 CO 3 (20g, 19mmol), put the toluene (300mL), ethanol (EtOH) (150mL) and H 2 O (10mL), for 2 hours at 100 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was cooled at room temperature, extracted with ethyl acetate (EA), and then dehydrated with MgSO 4 , followed by distillation under reduced pressure. Column chromatography was performed with MC / hexane (Hx) = 1/3 to obtain Compound 3-1 (11 g, 67%) as a white solid.
화합물 D-95의 제조Preparation of compound D-95
화합물 3-1(7g, 28mmol)과 화합물 2-3(10g, 14mmol)에 MeOH(200mL)을 가하고 12시간 동안 환류 교반하였다. 반응 종료 후 실온으로 냉각시킨 후 여과하고 클로로포름(CHCl3)으로 컬럼 크로마토그래피하여 화합물 D-95(1.5g, 15%)를 얻었다.MeOH (200 mL) was added to compound 3-1 (7 g, 28 mmol) and compound 2-3 (10 g, 14 mmol) and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered and then subjected to column chromatography using chloroform (CHCl 3 ) to obtain Compound D-95 (1.5 g, 15%).
mp 400℃ 이상, UV 292nm, PL 519nm, LC 99.12%
mp 400 DEG C or higher, UV 292 nm, PL 519 nm, LC 99.12%
[[ 합성예Synthetic example 4] 화합물 D-96의 제조 4] Preparation of Compound D-96
화합물 4-1의 제조Preparation of Compound 4-1
2-브로모-5-메틸피리딘(10g, 63mmol), 다이벤조[b,d]푸란-4-일 보론산(15g, 76mmol), 테트라키스(트리페닐포스핀)팔라듐(O)[Pd(PPh3)4](2.2g, 2mmol), Na2CO3(20g, 19mmol), 톨루엔(300mL), 에탄올(EtOH)(150mL) 및 H2O(10mL)를 넣고, 100℃에서 2시간 동안 교반하였다. 반응 종료 후 실온에서 식히고, 에틸 아세테이트(EA)로 추출한 다음 MgSO4로 수분을 제거한 후, 감압증류하였다. MC/헥산(Hx) = 1/3으로 컬럼 크로마토그래피하여 백색 고체의 화합물 4-1(13g, 80%)을 얻었다.Dibenzo [b, d] furan-4-ylboronic acid (15 g, 76 mmol), tetrakis (triphenylphosphine) palladium (O) [Pd PPh 3) 4] (2.2g, 2mmol), Na 2 CO 3 (20g, 19mmol), put the toluene (300mL), ethanol (EtOH) (150mL) and H 2 O (10mL), for 2 hours at 100 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was cooled at room temperature, extracted with ethyl acetate (EA), and then dehydrated with MgSO 4 , followed by distillation under reduced pressure. Column chromatography was performed with MC / hexane (Hx) = 1/3 to obtain Compound 4-1 (13 g, 80%) as a white solid.
화합물 D-96의 제조Preparation of Compound D-96
화합물 4-1(7g, 28mmol)과 화합물 2-3(10g, 14mmol)에 MeOH(200mL)을 가하고 12시간 동안 환류 교반하였다. 반응 종료 후 실온으로 냉각시킨 후 여과하고 클로로포름(CHCl3)으로 컬럼 크로마토그래피하여 화합물 D-96(3.0g, 30%)를 얻었다.MeOH (200 mL) was added to compound 4-1 (7 g, 28 mmol) and compound 2-3 (10 g, 14 mmol), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, and subjected to column chromatography using chloroform (CHCl 3 ) to obtain Compound D-96 (3.0 g, 30%).
mp 390℃, UV 290nm, PL 521nm, LC 96.31%
mp 390 C, UV 290 nm, PL 521 nm, LC 96.31%
[[ 합성예Synthetic example 5] 화합물 H-1의 제조 5] Preparation of Compound H-1
플라스크에서 9-페닐-9H,9'H-3,3'-비카바졸 10g(22.4mmol)을 넣고, 디메틸포름아미드(DMF) 150ml에 녹이고 NaH 1.3g(33.6mmol)을 넣었다. 30분 후 2-클로로-4,6-디페닐-1,3,5-트리아진 5g(18.6mmol)을 넣었다. 4시간 동안 상온에서 교반하고 메탄올을 넣었다. 생성된 고체를 감압 여과하고 컬럼 분리하여 화합물 H-1 6.5g(54 %)를 얻었다.10 g (22.4 mmol) of 9-phenyl-9H, 9'H-3,3'-bicarbazole was placed in a flask and dissolved in 150 ml of dimethylformamide (DMF), and 1.3 g (33.6 mmol) of NaH was added thereto. After 30 minutes, 5 g (18.6 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was added. Stir at room temperature for 4 hours and add methanol. The resulting solid was filtered under reduced pressure and subjected to column separation to obtain 6.5 g (54%) of the compound H-1.
[[ 합성예Synthetic example 6] 화합물 H-19의 제조 6] Preparation of compound H-19
플라스크에 9-페닐-9H,9'H-3,3'-비카바졸 36.2g(93.2mmol), 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 40g(97.9mmol), Pd(OAc)2 (1.25g, 5.59mmol), 2-디사이클로헥실포스피노-2'-6'-디메톡시비페닐(S-Phos) (4.6g, 11.18mmol), NaO(t-부틸) (26.8g, 279.7mmol) 및 o-자일렌 (450ml) 를 넣고 환류 교반하였다. 6시간 후 상온으로 냉각하고 생성 고체를 감압 여과하였다. 컬럼 분리하여 화합물 H-19 (34.8g, 52.1%)을 얻었다. The flask was charged with 36.2 g (93.2 mmol) of 9-phenyl-9H, 9'H-3,3'-bicarbazole, 2- (3-bromophenyl) Pd (OAc) 2 (1.25 g, 5.59 mmol) and 2-dicyclohexylphosphino-2'-6'-dimethoxybiphenyl (S-Phos) (4.6 g, 11.18 mmol ), NaO (t-butyl) (26.8 g, 279.7 mmol) and o-xylene (450 ml) were added and stirred under reflux. After 6 hours, the mixture was cooled to room temperature and the resulting solid was filtered under reduced pressure. The column was separated to obtain a compound H-19 (34.8 g, 52.1%).
[[ 합성예Synthetic example 7] 화합물 H-25의 제조 7] Preparation of compound H-25
플라스크에서 9'-페닐-9H,9'H-2,3'-비카바졸 (7g, 17.14mmol) 및 2-클로로-4,6-디페닐-1,3,5-트리아진 (5.1g, 18.85mmol)을 사용하여 화합물 H-1와 동일한 방법으로 합성하여 화합물 H-25 (9.5g, 86%)을 얻었다. In a flask, 9'-phenyl-9H, 9'H-2,3'-bicarbazole (7g, 17.14mmol) and 2-chloro-4,6-diphenyl-1,3,5- , 18.85 mmol) was used to synthesize the compound H-25 (9.5 g, 86%).
상기 합성예 5 내지 7에서 제조된 호스트 화합물 및 이로부터 용이하게 제조할 수 있는 다른 호스트 화합물에 대한 데이터를 하기 표 1에 나타내었다.Data for the host compounds prepared in Synthesis Examples 5 to 7 and other host compounds easily prepared therefrom are shown in Table 1 below.
[[ 실시예Example 1] 본 발명에 따른 유기 발광 화합물을 이용한 1] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-바이페닐]-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐 벤젠-1,4-디아민)을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-디(4-바이페닐)-N,N'-디(4-바이페닐)-4,4'-디아미노 바이페닐을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명의 화합물 H-19를 넣고, 또 다른 셀에는 도판트로서 화합물 D-2을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 15중량%으로 도핑함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 2-(4-(9,10-디(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸을 넣고, 또 다른 셀에는 리튬 퀴놀레이트 (Lithium quinolate)를 각각 넣은 후, 두 물질을 같은 속도로 증발시켜 50중량%으로 도핑 함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로 리튬 퀴놀레이트를 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, the ITO substrate was mounted on the substrate holder of the vacuum vapor deposition apparatus, and then N1, N1 '- ([1,1'-biphenyl] -4,4'-diyl) bis N4, N4-diphenylbenzene-1,4-diamine) was added to the chamber and the chamber was evacuated until the degree of vacuum reached 10 -6 torr. Then, current was applied to the cell to evaporate the ITO substrate Lt; RTI ID = 0.0 > 60nm < / RTI > Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl was added to another cell in the vacuum vapor- And evaporated to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. The compound H-19 of the present invention was added as a host to one cell in the vacuum vapor deposition apparatus and the other compound was doped with compound D-2 as a dopant. Then, the two materials were evaporated at different rates and doped to 15 wt% A light emitting layer with a thickness of 30 nm was deposited on the hole transporting layer. (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) - 1 as an electron transfer layer on one side of the light emitting layer, Benzo [d] imidazole, lithium quinolate was added to another cell, and the two materials were evaporated at the same rate and doped to 50 wt%, thereby forming a 30 nm electron transport layer Respectively. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition equipment to fabricate an OLED device. Each compound was purified by vacuum sublimation under 10 -6 torr.
그 결과, 3.4V의 전압에서 36.6lm/W의 전력효율을 보였으며, 2430 cd/m2의 녹색발광이 확인되었다. As a result, a power efficiency of 36.6 lm / W was obtained at a voltage of 3.4 V, and green light emission of 2430 cd / m 2 was confirmed.
[[ 실시예Example 2] 본 발명에 따른 유기 발광 화합물을 이용한 2] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 화합물 H-49, 도판트에는 화합물 D-3을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.0V의 전압에서 43.2lm/W의 전력효율을 보였으며, 3440 cd/m2의 녹색발광이 확인되었다. An OLED device was fabricated in the same manner as in Example 1 except that the compound H-49 was used as the host material and the compound D-3 was used as the dopant. As a result, a power efficiency of 43.2 lm / W was obtained at a voltage of 3.0 V, and a green emission of 3440 cd / m 2 was confirmed.
[[ 실시예Example 3] 본 발명에 따른 유기 발광 화합물을 이용한 3] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 화합물 H-93, 도판트에는 화합물 D-2을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.1V의 전압에서 25.7lm/W의 전력효율을 보였으며, 1210 cd/m2의 녹색발광이 확인되었다. An OLED device was fabricated in the same manner as in Example 1 except that Compound H-93 was used as a host material and Compound D-2 was used as a dopant. As a result, a power efficiency of 25.7 lm / W was obtained at a voltage of 3.1 V, and green emission of 1210 cd / m 2 was confirmed.
[[ 실시예Example 4] 본 발명에 따른 유기 발광 화합물을 이용한 4] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 화합물 H-19, 도판트에는 화합물 D-3을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 2.7 V의 전압에서 60.6lm/W의 전력효율을 보였으며, 3840 cd/m2의 녹색발광이 확인되었다. An OLED device was fabricated in the same manner as in Example 1 except that Compound H-19 was used as a host material and Compound D-3 was used as a dopant. As a result, a power efficiency of 60.6 lm / W was obtained at a voltage of 2.7 V, and green emission of 3840 cd / m 2 was confirmed.
[[ 실시예Example 5] 본 발명에 따른 유기 발광 화합물을 이용한 5] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 화합물 H-49, 도판트에는 화합물 D-2을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.2 V의 전압에서 42.3lm/W의 전력효율을 보였으며, 930 cd/m2의 녹색발광이 확인되었다. An OLED device was fabricated in the same manner as in Example 1, except that the compound H-49 was used as the host material and the compound D-2 was used as the dopant. As a result, the power efficiency was 42.3 lm / W at a voltage of 3.2 V, and green light emission of 930 cd / m 2 was confirmed.
[[ 실시예Example 6] 본 발명에 따른 유기 발광 화합물을 이용한 6] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 화합물 H-19, 도판트에는 화합물 D-96을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 2.6 V의 전압에서 55.5lm/W의 전력효을 보였으며, 1210 cd/m2의 녹색발광이 확인되었다. An OLED device was fabricated in the same manner as in Example 1 except that Compound H-19 was used as a host material and Compound D-96 was used as a dopant. As a result, a power efficiency of 55.5 lm / W was obtained at a voltage of 2.6 V, and a green emission of 1210 cd / m 2 was confirmed.
[[ 비교예1Comparative Example 1 ] 종래에 발광재료를 이용한 ] Conventionally, OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 비교화합물 1, 도판트로는 화합물 D-2을 사용하고, 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 4-(3-(트리페닐렌-2-일)페닐)디벤조[b,d]티오펜을 10nm 두께로 증착한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.그 결과, 6.9V의 전압에서 16.8lm/W의 전력효율을 보였으며, 3000 cd/m2의 녹색발광이 확인되었다. As a light emitting material, a comparative compound 1 was used as a host, a compound D-2 was used as a dopant, a light emitting layer with a thickness of 30 nm was deposited on the hole transport layer, and 4- (3- (triphenylene- Phenyl) dibenzo [b, d] thiophene was deposited to a thickness of 10 nm, an OLED device was fabricated in the same manner as in Example 1. As a result, a power efficiency of 16.8 lm / W was obtained at a voltage of 6.9 V , Green light emission of 3000 cd / m 2 was confirmed.
<compound 1><compound 1>
본 발명에서 개발한 유기 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 전자 재료용 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.It was confirmed that the luminescent characteristics of the organic luminescent compounds developed in the present invention are superior to those of the conventional materials. In addition, the device using the compound for organic electronic material according to the present invention as a host material for luminescence not only excels in luminescence characteristics but also can lower the driving voltage, thereby inducing an increase in power efficiency and improving power consumption.
Claims (10)
[화학식 1]
IrL1L2L3
상기 화학식 1에서,
L1 내지 L3은 각각 독립적으로 하기의 구조에서 선택되고,
단, L1 내지 L3 중 적어도 하나는 A-1, A-2 또는 A-3의 구조를 가져야 하며;
X는 O 또는 S이고;
R1 내지 R11은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-30)알킬, 치환 또는 비치환된 (C3-30)시클로알킬, 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며;
a 내지 h는 각각 독립적으로 0 내지 4의 정수이고, a 내지 h가 2이상인 정수의 경우, 각각의 R1 내지 R8는 서로 동일하거나 상이할 수 있고;
[화학식 2]
상기 화학식 2에서,
Y1은 O, S, -NR31 또는 -CR32R33이고,
L4 및 L5은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며,
R21 내지 R24은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-30)알킬, 치환 또는 비치환된 (C6-30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 실릴, 또는 치환 또는 비치환된 아미노이거나, 인접한 치환체와 서로 결합하여 (3-30원)의 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지방족 또는 방향족 환의 탄소원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
Ar1은 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원) 헤테로아릴이며;
R31 내지 R33은 각각 독립적으로 수소, 치환 또는 비치환된(C1-30)알킬, 치환 또는 비치환된 (C6-30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이거나, 인접한 치환체와 서로 결합하여 (3-30원) 단일환 또는 다환의 지방족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지방족 또는 방향족 환의 탄소원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
o 및 p은 각각 독립적으로 0 내지 4의 정수이며, o 또는 p가 2이상인 정수의 경우, 각각의 R21 또는 각각의 R22은 서로 동일하거나 상이할 수 있고,
q 및 r은 각각 독립적으로 0 내지 3의 정수이며, q 또는 r이 2 이상인 정수의 경우 각각의 R23 또는 각각의 R24은 서로 동일하거나 상이할 수 있고,
상기 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.An organic electroluminescent device comprising an organic layer between an anode and a cathode, wherein the organic layer comprises a light emitting layer containing at least one dopant compound represented by the following formula (1) and at least one host compound represented by the following formula An electroluminescent device.
[Chemical Formula 1]
IrL 1 L 2 L 3
In Formula 1,
L 1 to L 3 are each independently selected from the following structures,
Provided that at least one of L 1 to L 3 has a structure of A-1, A-2 or A-3;
X is O or S;
R 1 to R 11 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-30) alkyl, substituted or unsubstituted (C3-30) cycloalkyl, substituted or unsubstituted -30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;
each of a to h is independently an integer of 0 to 4, and when a to h are an integer of 2 or more, each of R 1 to R 8 may be the same or different from each other;
(2)
In Formula 2,
Y 1 is O, S, -NR 31 or -CR 32 R 33 ,
L 4 and L 5 are each independently a single bond, substituted or unsubstituted (C6-30) aryl, or substituted or unsubstituted (5-30 membered heteroaryl)
R 21 to R 24 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-30) alkyl, substituted or unsubstituted (C6-30) aryl, substituted or unsubstituted (5- Or a substituted or unsubstituted amino, or may combine with adjacent substituents to form a (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring, , The carbon atom of the aliphatic or aromatic ring formed may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
Ar 1 is substituted or unsubstituted (C6-30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;
R 31 to R 33 are each independently hydrogen, substituted or unsubstituted (C1-30) alkyl, substituted or unsubstituted (C6-30) aryl, or substituted or unsubstituted (5-30 membered) (3-30 members) to form a monocyclic or polycyclic aliphatic or aromatic ring, and the carbon atom of the aliphatic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be;
o and p are each independently an integer of 0 to 4, and when o or p is an integer of 2 or more, each R 21 or each R 22 may be the same or different from each other,
q and r are each independently an integer of 0 to 3, and when q or r is an integer of 2 or more, each R 23 or each R 24 may be the same or different from each other,
The heteroaryl comprises at least one heteroatom selected from B, N, O, S, P (= O), Si and P.
[화학식 3]
[화학식 4]
[화학식 5]
상기 화학식 3 내지 5에서,
R1 내지 R6, a 내지 f, X, L2, 및 L3은 제1항에서의 정의와 동일하다.The organic electroluminescent device according to claim 1, wherein at least one dopant compound represented by the formula (1) is at least one of compounds represented by the following formulas (3) to (5).
(3)
[Chemical Formula 4]
[Chemical Formula 5]
In the above formulas 3 to 5,
R 1 to R 6 , a to f, X, L 2 , and L 3 are the same as defined in claim 1.
[화학식 6]
[화학식 7]
[화학식 8]
[화학식 9]
[화학식 10]
[화학식 11]
[화학식 12]
상기 화학식 6 내지 12에서,
R21 내지 R24, Y1, L1, L2, Ar1, o, p, q 및 r은 제1항에서의 정의와 동일하다.The organic electroluminescent device according to claim 1, wherein at least one of the host compounds represented by Formula 2 is at least one of compounds represented by Formulas 6 to 12 below.
[Chemical Formula 6]
(7)
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
In the above formulas (6) to (12)
R 21 to R 24 , Y 1 , L 1 , L 2 , Ar 1 , o, p, q and r are as defined in claim 1.
상기 R21 내지 R24는 각각 독립적으로, 수소, 치환 또는 비치환된 (C1-C10)알킬, 치환 또는 비치환된 (C6-C20)아릴, 치환 또는 비치환된 (5-20원)헤테로아릴이거나, 인접한 치환체와 서로 결합하여 (3-30원) 단일환 또는 다환의 지방족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지방족 또는 방향족 환의 탄소원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
상기 Y1은 O, S 또는 -NR31이며, 상기 R31은 치환 또는 비치환된 (C1-C10)알킬, 또는 치환 또는 비치환된 (C6-20)아릴이며;
상기 Ar1은 치환 또는 비치환된 (C6-20)아릴, 또는 헤테로원자로서 1 내지 3개의 질소를 포함하는 치환 또는 비치환된 (5-20원)헤테로아릴이고, 여기서, 상기 Ar1의 치환 (C6-18)아릴 및 치환 (5-20원)헤테로아릴의 치환체는, 각각 독립적으로, 할로겐 또는 (C1-10)알킬로 치환되거나 비치환된 (C6-20)아릴, (C1-10)알킬로 치환되거나 비치환된 (5-20원)헤테로아릴, 트리(C6-20)아릴실릴, 디(C1-10)알킬(C6-20)아릴실릴, (C1-10)알킬디(C6-20)아릴실릴, 모노 또는 디(C6-20)아릴아미노, 및 (C1-10)알킬(C6-20)아릴아미노로 이루어진 군에서 선택되는 1종 이상인 유기 전계 발광 소자.The compound according to claim 1, wherein L 4 and L 5 are each independently a single bond, a substituted or unsubstituted (C 6-20) aryl, or a substituted or unsubstituted (5-20 membered) heteroaryl ;
Each of R 21 to R 24 is independently selected from the group consisting of hydrogen, substituted or unsubstituted (C 1 -C 10) alkyl, substituted or unsubstituted (C 6 -C 20) aryl, substituted or unsubstituted (5-20 membered) Or may form a monocyclic or polycyclic aliphatic or aromatic ring by bonding with adjacent substituents (3-30 members), and the carbon atom of the aliphatic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >
Y < 1 > is O, S or -NR < 31 & Substituted or unsubstituted (C1-C10) alkyl, or substituted or unsubstituted (C6-20) aryl;
Wherein Ar 1 is substituted or unsubstituted (C6-20) aryl or substituted or unsubstituted (5-20 membered) heteroaryl containing 1 to 3 nitrogen as a heteroatom, wherein substitution of Ar 1 (C6-20) aryl and substituted (5-20 membered) heteroaryl are each independently selected from the group consisting of (C6-20) aryl optionally substituted by halogen or (C1-10) alkyl, (C6-20) arylsilyl, di (C1-10) alkyl (C6-20) arylsilyl, (C1-10) alkyldi (C6-20) (C6-20) arylamino, and (C1-10) alkyl (C6-20) arylamino. The organic electroluminescent device according to claim 1,
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| PCT/KR2014/009734 WO2015056993A1 (en) | 2013-10-18 | 2014-10-16 | Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same |
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| CN105636971A (en) | 2016-06-01 |
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