KR20080071969A - 신규한 디아민 유도체, 이의 제조방법 및 이를 이용한유기전자소자 - Google Patents
신규한 디아민 유도체, 이의 제조방법 및 이를 이용한유기전자소자 Download PDFInfo
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- KR20080071969A KR20080071969A KR1020080072695A KR20080072695A KR20080071969A KR 20080071969 A KR20080071969 A KR 20080071969A KR 1020080072695 A KR1020080072695 A KR 1020080072695A KR 20080072695 A KR20080072695 A KR 20080072695A KR 20080071969 A KR20080071969 A KR 20080071969A
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- 150000004985 diamines Chemical class 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title description 86
- 238000000034 method Methods 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000001624 naphthyl group Chemical class 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 7
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims abstract description 5
- 125000001725 pyrenyl group Chemical group 0.000 claims abstract description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims abstract description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 178
- 239000011368 organic material Substances 0.000 claims description 27
- 238000002347 injection Methods 0.000 claims description 25
- 239000007924 injection Substances 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 17
- -1 peryllenyl Chemical group 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000005264 aryl amine group Chemical group 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 125000006835 (C6-C20) arylene group Chemical group 0.000 abstract 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract 1
- 125000004431 deuterium atom Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 description 52
- 239000010410 layer Substances 0.000 description 46
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 10
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- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 9
- IPLAQSRFBRURHW-UHFFFAOYSA-N 3,9-dibromoperylene Chemical group C=12C3=CC=CC2=C(Br)C=CC=1C1=CC=CC2=C1C3=CC=C2Br IPLAQSRFBRURHW-UHFFFAOYSA-N 0.000 description 8
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- WYEKIIDIPHGLRP-UHFFFAOYSA-N 3,4-dibromochrysene Chemical compound C1=CC=CC2=CC=C(C=3C(=CC=C(C=3Br)Br)C=C3)C3=C21 WYEKIIDIPHGLRP-UHFFFAOYSA-N 0.000 description 7
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 7
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 239000012153 distilled water Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- 238000010992 reflux Methods 0.000 description 4
- PAYRUJLWNCNPSJ-RALIUCGRSA-N 2,3,4,5,6-pentadeuterioaniline Chemical compound [2H]C1=C([2H])C([2H])=C(N)C([2H])=C1[2H] PAYRUJLWNCNPSJ-RALIUCGRSA-N 0.000 description 3
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- 238000005406 washing Methods 0.000 description 3
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-RALIUCGRSA-N 1-bromo-2,3,4,5,6-pentadeuteriobenzene Chemical compound [2H]C1=C([2H])C([2H])=C(Br)C([2H])=C1[2H] QARVLSVVCXYDNA-RALIUCGRSA-N 0.000 description 2
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
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- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 2
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- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 229940126086 compound 21 Drugs 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
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- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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Abstract
Description
Claims (10)
- 하기 화학식 1로 표시되는 디아민 유도체.<화학식 1>상기 화학식 1에서,여기서, n은 1 ~ 5의 정수이고,상기 X는 적어도 하나가 -GeRR'R", -SiRR'R" 및 중수소 중에서 선택되며, 나머지는 수소, CN, NO2, C6~C20의 아릴 아민기, C6~C20의 아릴 티오펜기, C3~C20의 시클로알킬기, -OR, -SR, -SeR, -TeR, -BRR', -AlRR', -SnRR'R", C6~C20의 아릴기, C8~C20의 아릴알케닐기, 및 C4~C20의 알킬렌기가 상기 페닐기 또는 나프틸기에 접합(fused)되어 축합고리를 형성한 기 중에서 선택된 하나이며,Y1 및 Y2는 서로 독립적으로 동일하거나 상이하며, C6~C20의 아릴렌기 또는 2가의 C5~C20의 헤테로고리기이며,Z1 및 Z2는 서로 독립적으로 같거나 다를 수 있으며, 수소, 할로겐, 중수소, CN, NO2, C1~C20의 알킬기, C1~C20의 알콕시기, C6~C20의 아릴기, C6~C20의 아릴 아민기, C6~C20의 아릴 티오펜기, C3~C20의 시클로알킬기, -OR, -SR, -SeR, -TeR, -BRR', -AlRR', -SiRR'R", -GeRR'R", -SnRR'R", C6~C20의 아릴기, C8~C20의 아릴알케닐기, 및 C4~C20의 알킬렌기가 상기 페닐기 또는 나프틸기에 접합(fused)되어 축합고리를 형성한 기 중에서 선택된 하나이고,상기 R, R' 및 R"는 서로 독립적으로 동일하거나 상이하며, 수소, C1~C20의 알킬기, C3~C20의 시클로알킬기, C6~C20의 아릴기 또는 C5~C20의 헤테로고리기이다.
- 제 1항에 있어서, 상기 Y1 및 Y2는 서로 독립적으로 같거나 다를 수 있으며, 페닐, 바이페닐, 나프탈레닐, 테트랄리닐, 안트라세닐, 스틸베닐, 페난트레닐, 파이레닐, 페릴레닐, 크라이세닐 및 카바졸릴 중에서 선택된 하나인 디아민 유도체.
- 디브로모 아릴 화합물과 아릴아민 화합물을 팔라듐 촉매 하에 반응시켜 제조하는 것을 특징으로 하는 제 1항의 디아민 유도체의 제조방법.
- 제 4항에 있어서, 상기 아릴아민 화합물은 게르마늄기, 실릴기 및 중수소 중에서 선택된 하나 이상을 포함하는 것을 특징으로 하는 제 1항의 디아민 유도체의 제조방법.
- 제 1 전극, 제 2 전극, 및 상기 제 1 전극과 제 2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기전자소자로서, 상기 유기물층 중 1 층 이상은 제 1항 내지 제 3항 중 어느 한 항의 화합물을 포함하는 것을 특징으로 하는 유기전자소자.
- 제 6항에 있어서, 상기 유기물층은 정공주입층, 정공수송층 및 정공주입 및 정공수송으로 이루어진 층들로부터 선택된 1층 이상의 층을 포함하고, 상기 층들 중에서 하나의 층이 상기 화학식 1로 표시되는 디아민 유도체를 포함하는 것을 특징으로 하는 유기전자소자.
- 제 6항에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층이 상기 화학식 1로 표시되는 디아민 유도체를 포함하는 것을 특징으로 하는 유기전자소자.
- 제 6항에 있어서, 상기 유기물층은 전자수송층을 포함하고, 상기 전자수송층이 상기 화학식 1로 표시되는 디아민 유도체를 포함하는 것을 특징으로 하는 유기전자소자.
- 제 6항에 있어서, 상기 유기전자소자는 유기발광소자, 유기태양전지, 유기감광체(OPC) 및 유기트랜지스터로 이루어진 군으로부터 선택되는 것을 특징으로 하는 유기전자소자.
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US (1) | US8173272B2 (ko) |
EP (1) | EP1996540B1 (ko) |
JP (1) | JP5165671B2 (ko) |
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US9425416B2 (en) | 2013-06-07 | 2016-08-23 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
US9876176B2 (en) | 2013-06-04 | 2018-01-23 | Samsung Display Co., Ltd. | Aryl amine condensed cyclic compound comprising pyrene moieties and organic light-emitting diode (OLED) including the same |
WO2019156397A1 (ko) * | 2018-02-08 | 2019-08-15 | 주식회사 엘지화학 | 화합물, 이를 포함하는 코팅 조성물, 이를 이용한 유기 발광 소자 및 이의 제조방법 |
US11864460B2 (en) | 2018-09-20 | 2024-01-02 | Lg Chem, Ltd. | Organic light emitting device |
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US8115378B2 (en) | 2006-12-28 | 2012-02-14 | E. I. Du Pont De Nemours And Company | Tetra-substituted chrysenes for luminescent applications |
US8257836B2 (en) | 2006-12-29 | 2012-09-04 | E I Du Pont De Nemours And Company | Di-substituted pyrenes for luminescent applications |
US8465848B2 (en) | 2006-12-29 | 2013-06-18 | E I Du Pont De Nemours And Company | Benzofluorenes for luminescent applications |
KR100874472B1 (ko) * | 2007-02-28 | 2008-12-18 | 에스에프씨 주식회사 | 청색발광화합물 및 이를 이용한 유기전계발광소자 |
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Also Published As
Publication number | Publication date |
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CN101405255A (zh) | 2009-04-08 |
EP1996540B1 (en) | 2015-07-08 |
EP1996540A4 (en) | 2011-12-28 |
JP5165671B2 (ja) | 2013-03-21 |
JP2009530371A (ja) | 2009-08-27 |
EP1996540A1 (en) | 2008-12-03 |
US8173272B2 (en) | 2012-05-08 |
US20090134781A1 (en) | 2009-05-28 |
CN101405255B (zh) | 2013-01-30 |
KR20070096917A (ko) | 2007-10-02 |
WO2007108666A1 (en) | 2007-09-27 |
KR100867526B1 (ko) | 2008-11-06 |
KR100877876B1 (ko) | 2009-01-13 |
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