KR102654248B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents
Organic compound and organic electroluminescent device comprising the same Download PDFInfo
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- KR102654248B1 KR102654248B1 KR1020220003789A KR20220003789A KR102654248B1 KR 102654248 B1 KR102654248 B1 KR 102654248B1 KR 1020220003789 A KR1020220003789 A KR 1020220003789A KR 20220003789 A KR20220003789 A KR 20220003789A KR 102654248 B1 KR102654248 B1 KR 102654248B1
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 161
- 150000001875 compounds Chemical class 0.000 claims description 94
- 239000010410 layer Substances 0.000 claims description 91
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000001721 carbon Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 description 93
- 238000003786 synthesis reaction Methods 0.000 description 92
- 238000000034 method Methods 0.000 description 54
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 50
- 238000002360 preparation method Methods 0.000 description 50
- 239000007858 starting material Substances 0.000 description 50
- 239000000463 material Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 239000002019 doping agent Substances 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 13
- 229910052796 boron Inorganic materials 0.000 description 13
- -1 phenoxathienyl Chemical group 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 229940126214 compound 3 Drugs 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000002207 thermal evaporation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 3
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 3
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 3
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 3
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 3
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 3
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 3
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 3
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 3
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 3
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Abstract
본 발명은 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자에 관한 것으로, 보다 상세하게는 낮은 구동 전압 및 높은 효율을 나타내며, 수명이 향상된 신규 유기화합물 및 이를 포함하는 유기전계발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic light-emitting device containing the same, and more specifically, to a novel organic compound that exhibits low driving voltage and high efficiency and has improved lifespan, and to an organic electroluminescent device containing the same.
Description
본 발명은 유기 화합물 및 이를 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to organic compounds and organic electroluminescent devices containing the same.
유기전계발광 소자(OLED)는 기존 액정 표시 장치(LCD), 플라즈마 디스플레이 패널(PDP) 및 전계 방출 디스플레이(FED) 등의 타 평판 표시 소자에 비해 구조가 간단하고, 제조 공정상의 다양한 장점이 있으며, 높은 휘도 및 시야각 특성이 우수하고, 응답속도가 빠르며, 구동전압이 낮아 벽걸이 TV등의 평판 디스플레이 또는 디스플레이의 배면광, 조명, 광고판 등의 광원으로서 사용되도록 활발하게 개발 및 제품화되고 있다.Organic electroluminescent devices (OLEDs) have a simpler structure and various advantages in the manufacturing process compared to other flat panel display devices such as existing liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs). It has excellent high brightness and viewing angle characteristics, fast response speed, and low driving voltage, and is being actively developed and commercialized to be used as a light source for flat displays such as wall-mounted TVs, backlight of displays, lighting, and billboards.
유기전계발광 소자는 이스트만 코닥사의 탕(C. W. Tang) 등에 의해 최초의 유기 EL 소자가 보고(C. W. Tang, S. A. Vanslyke, Applied Physics Letters, 51권 913페이지, 1987년)되었으며, 이의 발광 원리는 일반적으로, 전압을 인가하였을 때, 양극으로부터 주입된 정공과 음극으로부터 주입된 전자가 재결합하여 전자-정공 쌍인 엑시톤을 형성하며, 이 엑시톤의 에너지를 발광 재료에 전달함에 의해 빛으로 변환되는 것을 기초로 한다.The first organic EL device was reported by C. W. Tang of Eastman Kodak and others (C. W. Tang, S. A. Vanslyke, Applied Physics Letters, Volume 51, Page 913, 1987), and its light-emitting principle is generally: When a voltage is applied, the holes injected from the anode and the electrons injected from the cathode recombine to form an exciton, an electron-hole pair, and the energy of this exciton is converted into light by transferring it to the light-emitting material.
더욱 구체적으로, 유기전계발광 소자는 음극(전자주입전극)과 양극(정공주입전극), 및 상기 두 전극 사이에 하나 이상의 유기층을 포함하는 구조를 갖는다. 이때, 유기전계발광 소자는 양극으로부터 정공주입층(HIL, hole injection layer), 정공수송층(HTL, hole transport layer), 발광층(EML, light emitting layer), 전자수송층 (ETL, electron transport layer) 또는 전자주입층(EIL, electron injection layer)의 순서로 적층되며, 발광 층의 효율을 높이기 위하여 정공수송보조층 또는 정공차단층(HBL, hole blocking layer)을 각각 발광층의 앞뒤에 추가로 포함할 수 있다.More specifically, the organic electroluminescent device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers between the two electrodes. At this time, the organic electroluminescent device consists of a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), or an electron transport layer (ETL) from the anode. It is laminated in the order of the electron injection layer (EIL), and to increase the efficiency of the light emitting layer, a hole transport auxiliary layer or a hole blocking layer (HBL) may be additionally included on the front and back of the light emitting layer, respectively.
상기 발광층은 호스트(host)와 도펀트(dopant)의 두 물질로 구성되며 도펀트는 양자 효율이 높아야 하며, 호스트 물질은 도펀트 물질보다 에너지 갭이 커서 도펀트로의 에너지 전이가 용이하게 일어나게 하는 것이 바람직하다.The light-emitting layer is composed of two materials, a host and a dopant. The dopant must have high quantum efficiency, and the host material preferably has a larger energy gap than the dopant material to facilitate energy transfer to the dopant.
기존의 청색 도펀트로 사용되는 물질은 페릴렌(Perylene), 쿠마린(Coumarine), 안트라센(Anthracene), 파이렌(Pyrene) 등의 형광 분자의 활용이 많은 비중을 차지했지만, 도펀트의 발광 스펙트럼 반치폭(Full width half the maximum)이 ~40nm 수준으로 넓어 진청색(Deep Blue)을 구현하기 어려우며, 전면발광 소자에서 광학적인 공진을 통해 일정 파장 구간을 증폭시킬 때에도 광학적인 손실이 발생한다.The materials used as existing blue dopants are mostly fluorescent molecules such as perylene, coumarine, anthracene, and pyrene, but the dopant's emission spectrum half width (full width) The width half the maximum is wide at ~40nm, making it difficult to implement deep blue, and optical loss occurs even when a certain wavelength range is amplified through optical resonance in a front-emitting device.
이를 해결하고자, 최근 소자의 발광 스텍트럼이 좁고 소자 효율이 높은 보론계 도펀트가 대두되고 있으나, 높은 효율과 우수한 색구현에도 불구하고, 낮은 수명으로 인해 더 높은 수명 성능이 요구된다. To solve this problem, boron-based dopants that have a narrow device emission spectrum and high device efficiency have recently emerged. However, despite high efficiency and excellent color implementation, higher lifetime performance is required due to low lifetime.
본 발명의 목적은 신규한 유기화합물과 이를 포함하는 유기전계발광 소자를 제공하고자 한다.The purpose of the present invention is to provide a novel organic compound and an organic electroluminescent device containing the same.
본 발명의 다른 목적은 기존 보론계 도펀트 대비 저 전압 및 높은 효율을 유지하면서, 수명을 향상시킬 수 있는 유기화합물로서 발광층 재료로 사용될 수 있는 신규 화합물을 제공하고자 한다.Another object of the present invention is to provide a new compound that can be used as a light-emitting layer material as an organic compound that can improve lifespan while maintaining low voltage and high efficiency compared to existing boron-based dopants.
본 발명의 다른 목적은 상기 유기화합물을 이용하여 보론 도펀트의 우수한 특성을 유지하며, AM-OLED에 적합한 청색 계열의 호스트/도펀트 조합으로, 수명 감소 문제를 해결할 수 있는 유기전계발광소자를 제공하고자 한다.Another object of the present invention is to provide an organic electroluminescent device that maintains the excellent properties of the boron dopant using the organic compound and can solve the problem of reduced lifespan by using a blue-based host/dopant combination suitable for AM-OLED. .
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
여기서,here,
n 및 m은 서로 동일하거나 상이하며, 각각 독립적으로 0 내지 3의 정수이며,n and m are the same or different from each other and are each independently an integer from 0 to 3,
X1은 N 또는 CR3이며,X 1 is N or CR 3 ,
X2는 NR4, O 및 S로 이루어진 군으로부터 선택되고,X 2 is selected from the group consisting of NR 4 , O and S,
Y은 B이고,Y is B,
Z1 및 Z2는 서로 동일하거나 상이하며, 각각 독립적으로 CR5R6, NR7, O 및 S로 이루어진 군으로부터 선택되며, Z 1 and Z 2 are the same or different from each other and are each independently selected from the group consisting of CR 5 R 6 , NR 7 , O and S,
A환은 치환 또는 비치환의 탄소수 6 내지 30의 아릴기 또는 치환 또는 비치환의 탄소수 3 내지 30의 헤테로아릴기이며, Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R1 내지 R7는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 시아노기, 트리플루오로메틸기, 니트로기, 할로겐기, 히드록시기, 치환 또는 비치환된 탄소수 1 내지 4의 알킬티오기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환된 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 헤테로아릴알킬기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기로 이루어진 군으로부터 선택되고, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R 1 to R 7 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group with 1 to 30 carbon atoms, substituted or unsubstituted arylamino group with 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group of 30 to 30 carbon atoms, substituted or unsubstituted heteroarylamino group of 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group of 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms and substituted or an unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be combined with adjacent groups to form a substituted or unsubstituted ring.
또한, 본 발명은 제1전극; 상기 제1전극에 대향된 제2전극; 상기 제1전극과 상기 제2전극 사이에 개재된 하나 이상의 유기물층을 포함하며, 상기 하나 이상의 유기물층은 상기 화학식 1에 따른 화합물을 하나 이상 포함하는 유기 전계발광 소자에 관한 것이다. In addition, the present invention includes a first electrode; a second electrode opposite the first electrode; It relates to an organic electroluminescent device comprising at least one organic material layer interposed between the first electrode and the second electrode, wherein the at least one organic material layer includes at least one compound according to Formula 1 above.
본 발명에서 “수소”는 특별히 한정하지 않는 한, 수소, 경수소, 중수소 또는 삼중수소이다.In the present invention, “hydrogen” refers to hydrogen, light hydrogen, deuterium, or tritium, unless otherwise specified.
본 발명에서 “할로겐기”는 불소, 염소, 브롬 또는 요오드이다.In the present invention, the “halogen group” is fluorine, chlorine, bromine, or iodine.
본 발명에서 “알킬”은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, tert-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkyl” refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., but are not limited thereto.
본 발명에서 “알케닐(alkenyl)”은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.
본 발명에서 “알키닐(alkynyl)”은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2-propynyl, etc., but are not limited thereto.
본 발명에서 "알킬티오"는 황 연결(-S-)을 통해 결합된 상기 기재된 알킬기를 의미한다.In the present invention, “alkylthio” refers to the alkyl group described above bonded through a sulfur linkage (-S-).
본 발명에서 “아릴”은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있으며, 구체적으로 나프틸기, 안트라세닐기, 페난트릴기, 트리페닐기, 파이레닐기, 페날레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 플루오레닐기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, forms in which two or more rings are simply pendant or condensed with each other may also be included, specifically naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, phenalenyl group, perylenyl group, cryo group. It may be a cenyl group, a fluorenyl group, etc., but is not limited thereto. The fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
본 발명에서 “헤테로아릴”은 탄소수 6 내지 30개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a condensed form with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.
본 발명에서 “아릴옥시”는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R refers to aryl having 6 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.
본 발명에서 “알킬옥시”는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkyloxy” is a monovalent substituent represented by R'O-, where R' refers to alkyl having 1 to 40 carbon atoms and has a linear, branched, or cyclic structure. may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
본 발명에서 “알콕시”는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, “alkoxy” may be straight chain, branched chain, or ring chain. The number of carbon atoms of alkoxy is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be possible, but it is not limited to this.
본 발명에서 "아르알킬"은, 아릴 및 알킬이 상기한 바와 같은 아릴-알킬 그룹을 의미한다. 바람직한 아르알킬은 저급 알킬 그룹을 포함한다. 적합한 아르알킬 그룹의 비제한적인 예는 벤질, 2-펜에틸 및 나프탈레닐메틸을 포함한다. 모 잔기에 대한 결합은 알킬을 통해 이루어진다.As used herein, “aralkyl” refers to an aryl-alkyl group where aryl and alkyl are defined above. Preferred aralkyl contains lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl, and naphthalenylmethyl. Bonding to the parent moiety is via the alkyl.
본 발명에서 “아릴아미노기”는 탄소수 6 내지 30의 아릴기로 치환된 아민을 의미한다.In the present invention, “arylamino group” refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.
본 발명에서 “알킬아미노기”는 탄소수 1 내지 30의 알킬기로 치환된 아민을 의미한다.In the present invention, “alkylamino group” means an amine substituted with an alkyl group having 1 to 30 carbon atoms.
본 발명에서 “아르알킬아미노기”는 탄소수 6 내지 30의 아릴-알킬기로 치환된 아민을 의미한다.In the present invention, “aralkyl amino group” refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.
본 발명에서 “헤테로아릴아미노기”는 탄소수 6 내지 30의 아릴기 및 헤테로고리기로 치환된 아민기를 의미한다.In the present invention, “heteroarylamino group” refers to an amine group substituted with an aryl group or heterocyclic group having 6 to 30 carbon atoms.
본 발명에서 “헤테로아르알킬기”는 헤테로고리기로 치환된 아릴-알킬 그룹을 의미한다. In the present invention, “heteroaralkyl group” refers to an aryl-alkyl group substituted with a heterocyclic group.
본 발명에서 “시클로알킬”은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
본 발명에서 “헤테로시클로알킬”은 탄소수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se. It is substituted with a hetero atom such as Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.
본 발명에서 “알킬실릴”은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, “아릴실릴”은 탄소수 6 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 “축합고리”는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
본 발명에서 "인접하는 기와 서로 결합하여 고리를 형성한다"는 것은 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 지방족 헤테로고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 이들의 축합고리를 형성하는 것을 의미한다.In the present invention, "forming a ring by combining with adjacent groups" means a substituted or unsubstituted aliphatic hydrocarbon ring by combining with adjacent groups; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming a condensation ring thereof.
본 발명에서 “방향족 탄화수소고리”의 예로는 페닐기, 나프틸기, 안트라세닐기 등이 있으나 이들에만 한정되는 것은 아니다.In the present invention, examples of “aromatic hydrocarbon rings” include phenyl groups, naphthyl groups, and anthracenyl groups, but are not limited to these.
본 발명에서 “지방족 헤테로고리”란 헤테로원자 중 1개 이상을 포함하는 지방족고리를 의미한다.In the present invention, “aliphatic heterocycle” refers to an aliphatic ring containing one or more heteroatoms.
본 발명에서 “방향족 헤테로고리”란 헤테로원자 중 1개 이상을 포함하는 방향족고리를 의미한다.In the present invention, “aromatic heterocycle” refers to an aromatic ring containing one or more heteroatoms.
본 발명에서 “보론계 원소”, “보론계 화합물”, “보론계 도펀트”라 함은 원자번호 5인 보론(B) 원소, 보론을 포함하는 화합물 또는 도펀트를 의미한다.In the present invention, “boron-based element,” “boron-based compound,” and “boron-based dopant” mean boron (B) element with atomic number 5, a compound containing boron, or a dopant.
본 발명에서 "치환"은 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다. 상기 치환기는 시아노기, 니트로기, 할로겐기, 히드록시기, 탄소수 1 내지 30의 알킬기, 탄소수 2 내지 30의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 2 내지 30의 헤테로알킬기, 탄소수 6 내지 30의 아르알킬기, 탄소수 5 내지 30의 아릴기, 탄소수 2 내지 30의 헤테로아릴기, 탄소수 3 내지 30의 헤테로아릴알킬기, 탄소수 1 내지 30의 알콕시기, 탄소수 1 내지 30의 알킬아미노기, 탄소수 6 내지 30의 아릴아미노기, 탄소수 6 내지 30의 아르알킬아미노기 및 탄소수 2 내지 24의 헤테로 아릴아미노기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환될 수 있으나, 상기 예시에 국한되지 않는다.In the present invention, “substitution” means changing a hydrogen atom bonded to a carbon atom of a compound to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other. The substituents include cyano group, nitro group, halogen group, hydroxy group, alkyl group with 1 to 30 carbon atoms, alkenyl group with 2 to 30 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 2 to 30 carbon atoms, and 6 to 30 carbon atoms. Aralkyl group, aryl group with 5 to 30 carbon atoms, heteroaryl group with 2 to 30 carbon atoms, heteroarylalkyl group with 3 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, alkylamino group with 1 to 30 carbon atoms, 6 to 30 carbon atoms It may be substituted with one or more substituents selected from the group consisting of an arylamino group, an aralkylamino group with 6 to 30 carbon atoms, and a heteroarylamino group with 2 to 24 carbon atoms, but is not limited to the above examples.
본 발명은 기존 보론계 도펀트 대비 낮은 구동 전압 및 높은 효율을 유지하면서, 수명을 향상시킬 수 있는 유기화합물로서 발광층 재료로 사용될 수 있다. The present invention is an organic compound that can improve lifespan while maintaining low driving voltage and high efficiency compared to existing boron-based dopants, and can be used as a light-emitting layer material.
또한, 상기 유기화합물을 이용하여 보론 도펀트의 우수한 특성을 유지하며, AM-OLED에 적합한 청색 계열의 호스트/도펀트 조합으로, 유기전계발광소자의 수명 감소 문제를 해결할 수 있다.In addition, the excellent properties of the boron dopant can be maintained by using the organic compound, and the problem of reduced lifespan of organic electroluminescent devices can be solved by using a blue-based host/dopant combination suitable for AM-OLED.
이하, 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자가 용이하게 실시할 수 있도록 본 발명의 실시예에 대하여 상세히 설명한다. 그러나 본 발명은 여러 가지 상이한 형태로 구현될 수 있으며 여기에서 설명하는 실시예에 한정되지 않는다.Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement it. However, the present invention may be implemented in many different forms and is not limited to the embodiments described herein.
본 발명에 따른 유기 화합물은 분자 내에 비방향족 6각 고리를 포함하여, 평면 구조가 아닌 뒤틀린 구조를 가지며, 특히, 치환기로 시클로알킬기를 포함하여, 기존 보론계 도펀트 대비 낮은 구동 전압 및 높은 효율을 유지하면서, 수명을 향상시킬 수 있는 유기화합물로서 발광층 재료로 사용될 수 있다. The organic compound according to the present invention contains a non-aromatic hexagonal ring in the molecule and has a twisted structure rather than a planar structure. In particular, it contains a cycloalkyl group as a substituent, and maintains a low driving voltage and high efficiency compared to existing boron-based dopants. As an organic compound that can improve lifespan, it can be used as a light-emitting layer material.
구체적으로 본 발명의 화합물은 하기 화학식 1로 표시될 수 있다:Specifically, the compound of the present invention may be represented by the following formula (1):
[화학식 1][Formula 1]
여기서,here,
n 및 m은 서로 동일하거나 상이하며, 각각 독립적으로 0 내지 3의 정수이며,n and m are the same or different from each other and are each independently an integer from 0 to 3,
X1은 N 또는 CR3이며,X 1 is N or CR 3 ,
X2는 NR4, O 및 S로 이루어진 군으로부터 선택되고,X 2 is selected from the group consisting of NR 4 , O and S,
Y은 B이고,Y is B,
Z1 및 Z2는 서로 동일하거나 상이하며, 각각 독립적으로 CR5R6, NR7, O 및 S로 이루어진 군으로부터 선택되며, Z 1 and Z 2 are the same or different from each other and are each independently selected from the group consisting of CR 5 R 6 , NR 7 , O and S,
A환은 치환 또는 비치환의 탄소수 6 내지 30의 아릴기 또는 치환 또는 비치환의 탄소수 3 내지 30의 헤테로아릴기이며, Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R1 내지 R7는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 시아노기, 트리플루오로메틸기, 니트로기, 할로겐기, 히드록시기, 치환 또는 비치환된 탄소수 1 내지 4의 알킬티오기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환된 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 헤테로아릴알킬기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기로 이루어진 군으로부터 선택되고, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R 1 to R 7 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group with 1 to 30 carbon atoms, substituted or unsubstituted arylamino group with 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group of 30 to 30 carbon atoms, substituted or unsubstituted heteroarylamino group of 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group of 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms and substituted or an unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be combined with adjacent groups to form a substituted or unsubstituted ring.
상기 화학식 1로 표시되는 화합물은 하기 화학식 2로 표시되는 화합물일 수 있다:The compound represented by Formula 1 may be a compound represented by Formula 2 below:
[화학식 2][Formula 2]
여기서,here,
n, m, Y, X1, X2, R1, R2, Z2 및 A환은 상기 화학식 1과 같고, n , m , Y ,
o는 1 내지 10의 정수이다.o is an integer from 1 to 10.
상기 화학식 1로 표시되는 화합물은 구체적으로 하기 화학식 5로 표시되는 화합물일 수 있다:The compound represented by Formula 1 may be specifically a compound represented by Formula 5 below:
[화학식 5][Formula 5]
여기서,here,
n, m, Y, X1, X2, R1, R2, Z2 및 A환은 상기 화학식 1과 같고, n , m , Y ,
o는 1 내지 5의 정수이다.o is an integer from 1 to 5.
상기 화학식 1로 표시되는 화합물은 구체적으로 하기 화학식 6으로 표시되는 화합물일 수 있다:The compound represented by Formula 1 may be specifically a compound represented by Formula 6 below:
[화학식 6][Formula 6]
여기서,here,
n, m, Y, X1, X2, R1, R2 및 A환은 상기 화학식 1과 같다. n , m , Y ,
상기 A환은 하기 화학식 3 또는 화학식 4로 표시되는 화합물에서부터 선택될 수 있다:The A ring may be selected from compounds represented by Formula 3 or Formula 4 below:
[화학식 3][Formula 3]
[화학식 4][Formula 4]
여기서, here,
*는 결합되는 부분이며,* is the part that is combined,
p는 0 내지 4의 정수이며, p is an integer from 0 to 4,
Z3는 NR-11, O 및 S로 이루어진 군으로부터 선택되고,Z 3 is selected from the group consisting of NR- 11 , O and S,
R8 내지 R11은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소,시아노기, 니트로기, 할로겐기, 히드록시기, 치환 또는 비치환된 탄소수 1 내지 4의 알킬티오기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환된 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 헤테로아릴알킬기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기로 이루어진 군으로부터 선택되고, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R 8 to R 11 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted carbon number Alkyl group of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group of 2 to 24 carbon atoms, substituted or unsubstituted Aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 2 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl group with 6 to 30 carbon atoms, substituted or an unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl having 6 to 30 carbon atoms. Amino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and substituted or unsubstituted carbon atoms. It is selected from the group consisting of 6 to 30 aryloxy groups, and may be combined with adjacent groups to form a substituted or unsubstituted ring.
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나, 이에 한정되는 것은 아니다:The compound represented by Formula 1 according to the present invention may be represented by the following compounds, but is not limited thereto:
본 발명의 유기화합물은 발광층 형성용 재료로 유용하게 사용될 수 있다. 상기에서 발광층 형성용 재료는 상기 유기화합물을 발광층을 형성하는데 사용하기 위하여 필요한 형태로 제조할 때 통상적으로 첨가되는 물질, 예컨대, 호스트 물질 등을 더 포함할 수 있다.The organic compound of the present invention can be usefully used as a material for forming a light-emitting layer. In the above, the material for forming the light-emitting layer may further include materials typically added when manufacturing the organic compound into the form required for use in forming the light-emitting layer, such as a host material.
상기 발광층 형성용 재료는 도펀트(Dopant)용 재료일 수 있다.The material for forming the light emitting layer may be a dopant material.
또한, 본 발명은 상기 유기화합물을 포함하는 발광층 형성용 재료에 관한 것이다.Additionally, the present invention relates to a material for forming a light-emitting layer containing the above organic compound.
상기에서 발광층 형성용 재료는 상기 유기화합물을 발광층을 형성하는데 사용하기 위하여 필요한 형태로 제조할 때 통상적으로 첨가되는 물질, 예컨대, 호스트 물질 등을 더 포함할 수 있다. In the above, the material for forming the light-emitting layer may further include materials typically added when manufacturing the organic compound into the form required for use in forming the light-emitting layer, such as a host material.
또한, 본 발명은 음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 적층되어 있는 유기전계발광소자에 있어서,In addition, the present invention relates to an organic electroluminescent device in which an organic thin film layer consisting of one or multiple layers including at least a light-emitting layer is laminated between a cathode and an anode,
상기 발광층이 하기 화학식 1로 표시되는 화합물로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자에 관한 것이다:It relates to an organic electroluminescent device, wherein the light-emitting layer includes a compound represented by the following formula (1):
[화학식 1][Formula 1]
여기서,here,
n 및 m은 서로 동일하거나 상이하며, 각각 독립적으로 0 내지 3의 정수이며,n and m are the same or different from each other and are each independently an integer from 0 to 3,
X1은 N 또는 CR3이며,X 1 is N or CR 3 ,
X2는 NR4, O 및 S로 이루어진 군으로부터 선택되고,X 2 is selected from the group consisting of NR 4 , O and S,
Y은 B이고,Y is B,
Z1 및 Z2는 서로 동일하거나 상이하며, 각각 독립적으로 CR5R6, NR7, O 및 S로 이루어진 군으로부터 선택되며, Z 1 and Z 2 are the same or different from each other and are each independently selected from the group consisting of CR 5 R 6 , NR 7 , O and S,
A환은 치환 또는 비치환의 탄소수 6 내지 30의 아릴기 또는 치환 또는 비치환의 탄소수 3 내지 30의 헤테로아릴기이며, Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R1 내지 R7는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 시아노기, 트리플루오로메틸기, 니트로기, 할로겐기, 히드록시기, 치환 또는 비치환된 탄소수 1 내지 4의 알킬티오기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환된 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 헤테로아릴알킬기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기로 이루어진 군으로부터 선택되고, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R 1 to R 7 are the same or different from each other, and each independently represents hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted. Ringed alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or Unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 2 to 60 carbon atoms, substituted or unsubstituted heteroaryl with 6 to 30 carbon atoms Alkyl group, substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group with 1 to 30 carbon atoms, substituted or unsubstituted arylamino group with 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms aralkylamino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted It is selected from the group consisting of ringed aryloxy groups having 6 to 30 carbon atoms, and may be combined with adjacent groups to form a substituted or unsubstituted ring.
상기 유기전계발광소자는 양극, 정공주입층, 정공수송층, 발광층, 전자 수송층, 전자 주입층 및 음극이 적층된 구조를 가질 수 있으며, 필요에 따라 전자 차단층, 정공 차단층 등이 추가로 더 적층될 수 있다.The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and if necessary, an electron blocking layer, a hole blocking layer, etc. are further stacked. It can be.
이하에서, 본 발명의 유기전계발광소자에 대하여 예를 들어 설명한다. 그러나, 하기에 예시된 내용이 본 발명의 유기전계발광소자를 한정하는 것은 아니다.Below, the organic electroluminescent device of the present invention will be described as an example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.
본 발명의 유기전계발광소자는 양극(정공주입전극), 정공주입층(HIL), 정공수송층(HTL), 발광층(EML) 및 음극(전자주입전극)이 순차적으로 적층된 구조를 가질 수 있으며, 바람직하게는, 양극과 발광층 사이에 전자 차단층(EBL)을, 그리고 음극과 발광층 사이에 전자수송층(ETL), 전자주입층(EIL)을 추가로 포함할 수 있다. 또한 음극과 발광층 사이에 정공차단층(HBL)을 더 포함할 수도 있다.The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), and a cathode (electron injection electrode) are sequentially stacked, Preferably, an electron blocking layer (EBL) may be further included between the anode and the light emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) may be further included between the cathode and the light emitting layer. Additionally, a hole blocking layer (HBL) may be further included between the cathode and the light emitting layer.
본 발명에 따른 유기전계발광소자의 제조방법으로는, 먼저 기판 표면에 양극용 물질을 통상적인 방법으로 코팅하여 양극을 형성한다. 이때, 사용되는 기판은 투명성, 표면 평활성, 취급 용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 바람직하다. 또한, 양극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등이 사용될 수 있다.In the method of manufacturing an organic electroluminescent device according to the present invention, an anode is first formed by coating the surface of the substrate with an anode material in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and waterproofness. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, can be used as materials for the anode.
다음으로, 상기 양극 표면에 정공주입층(HIL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 정공주입층을 형성한다. 이러한 정공주입층 물질로는 구리프탈로시아닌(CuPc), 4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민(m-MTDATA), 4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠(m-MTDAPB), 스타버스트(starburst)형 아민류인 4,4',4"-트리(N-카바졸릴)트리페닐아민(TCTA), 4,4',4"-트리스(N-(2-나프틸)-N-페닐아미노)-트리페닐아민(2-TNATA) 또는 이데미츠사(Idemitsu)에서 구입가능한 IDE406을 예로 들 수 있다.Next, a hole injection layer (HIL) material is formed on the anode surface by vacuum thermal evaporation or spin coating using a conventional method. Such hole injection layer materials include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenyl) Amino)phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris Examples include (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.
상기 정공주입층 표면에 정공수송층(HTL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 정공수송층을 형성한다. 이때, 정공수송층 물질로는 비스(N-(1-나프틸-n-페닐))벤지딘(α-NPD), N,N'-다이(나프탈렌-1-일)-N,N'-바이페닐-벤지딘(NPB) 또는 N,N'-바이페닐-N,N'-비스(3-메틸페닐)-1,1'-바이페닐-4,4'-다이아민(TPD)을 예로 들 수 있다.A hole transport layer (HTL) material is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, the hole transport layer materials include bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N,N'-biphenyl Examples include -benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD).
상기 정공수송층 표면에 발광층(EML) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 발광층을 형성한다. 발광층 물질 중 발광 호스트와 함께 사용될 수 있는 도펀트(Dopant)의 경우, 본 발명의 상기 화학식 1로 표시되는 화합물이 바람직하게 사용될 수 있다.An emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal evaporation or spin coating using a conventional method. In the case of a dopant that can be used together with a light-emitting host among the light-emitting layer materials, the compound represented by Formula 1 of the present invention can be preferably used.
선택적으로는, 정공수송층과 발광층 사이에 전자차단층(EBL)을 추가로 형성할 수 있다. Optionally, an electron blocking layer (EBL) may be additionally formed between the hole transport layer and the light emitting layer.
상기 발광층 표면에 전자수송층(ETL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 전자수송층을 형성한다. 이때, 사용되는 전자수송층 물질의 경우 특별히 제한되지 않으며, 바람직하게는 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)을 사용할 수 있다.An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, the electron transport layer material used is not particularly limited, and tris(8-hydroxyquinolinolato)aluminum (Alq 3 ) can be preferably used.
선택적으로는, 발광층과 전자수송층 사이에 정공차단층(HBL)을 추가로 형성하고 발광층에 인광 도펀트(Dopant)를 함께 사용함으로써, 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지할 수 있다. Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer, diffusion of triplet excitons or holes into the electron transport layer can be prevented. .
정공차단층의 형성은 정공차단층 물질을 통상적인 방법으로 진공 열증착 및 스핀 코팅하여 실시할 수 있으며, 정공차단층 물질의 경우 특별히 제한되지는 않으나, 바람직하게는 (8-하이드록시퀴놀리놀라토)리튬(Liq), 비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄비페녹사이드(BAlq), 바쏘쿠프로인 (bathocuproine, BCP) 및 LiF 등을 사용할 수 있다.The formation of the hole blocking layer can be performed by vacuum thermal evaporation and spin coating of the hole blocking layer material by conventional methods. The hole blocking layer material is not particularly limited, but is preferably (8-hydroxyquinolinola) To) Lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), and LiF can be used.
상기 전자수송층 표면에 전자주입층(EIL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 전자주입층을 형성한다. 이때, 사용되는 전자주입층 물질로는 LiF, Liq, Li2O, BaO, NaCl, CsF 등의 물질이 사용될 수 있다.An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, materials such as LiF, Liq, Li 2 O, BaO, NaCl, and CsF may be used as the electron injection layer material.
상기 전자주입층 표면에 음극용 물질을 통상적인 방법으로 진공 열증착하여 음극을 형성한다.A cathode material is vacuum thermally deposited on the surface of the electron injection layer using a conventional method to form a cathode.
이때, 사용되는 음극용 물질로는 리튬(Li), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘(Mg), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 사용될 수 있다. 또한, 전면 발광 유기전계발광소자의 경우 산화인듐주석(ITO) 또는 산화인듐아연(IZO)를 사용하여 빛이 투과할 수 있는 투명한 음극을 형성할 수도 있다.At this time, the cathode materials used include lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver. (Mg-Ag) etc. may be used. Additionally, in the case of a top-emitting organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) can be used to form a transparent cathode through which light can transmit.
상기 음극의 표면에는 캡핑층 형성용 조성물에 의해 캡핑층(CPL)이 형성될 수 있다.A capping layer (CPL) may be formed on the surface of the cathode using a capping layer forming composition.
이하에서, 상기 화합물들의 합성 방법을 대표적인 예를 들어 하기에 설명한다. 그러나, 본 발명의 화합물들의 합성 방법이 하기 예시된 방법으로 한정되는 것은 아니며, 본 발명의 화합물들은 하기에 예시된 방법과 이 분야의 공지의 방법에 의해 제조될 수 있다.Hereinafter, methods for synthesizing the above compounds will be described with representative examples. However, the method of synthesizing the compounds of the present invention is not limited to the methods exemplified below, and the compounds of the present invention can be prepared by the methods exemplified below and methods known in the art.
[합성예 1: 화합물 3의 제조][Synthesis Example 1: Preparation of Compound 3]
출발물질 1.30 g (2.00 mmol)을 o-Dichlorobenzene (15 ml)에 녹인 후 질소 분위기 하에서 삼요오드화 붕소(Boron triiodide) 1.48 g (4.00 mmol)를 첨가한 후 상온에서 160 ℃로 온도를 올려 12시간 교반하였다. 반응액을 실온까지 냉각시키고 Ethyl acetate와 Water를 이용하여 유기층을 추출하였다. 추출한 유기층의 용매를 제거한 후 실리카겔 컬럼 크로마토그래피 (DCM/Hexane) 방법을 이용하여 정제하였다. 이후 DCM/Acetone 혼합 용매로 재결정 정제하 상기 화합물 3 0.24 g을 18.5 % 수율로 얻었다.Dissolve 1.30 g (2.00 mmol) of the starting material in o-Dichlorobenzene (15 ml), add 1.48 g (4.00 mmol) of boron triiodide under a nitrogen atmosphere, raise the temperature from room temperature to 160°C, and stir for 12 hours. did. The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. After removing the solvent of the extracted organic layer, it was purified using silica gel column chromatography (DCM/Hexane). After recrystallization and purification using a DCM/Acetone mixed solvent, 0.24 g of Compound 3 was obtained with a yield of 18.5%.
MS (MALDI-TOF) m/z: 648 [M]+MS (MALDI-TOF) m/z: 648 [M]+
[합성예 2: 화합물 4의 제조][Synthesis Example 2: Preparation of Compound 4]
출발물질 1.52 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 4 0.24 g을 15.6 % 수율로 얻었다.0.24 g of Compound 4 was obtained in 15.6% yield through the same method as Synthesis Example 1, except that 1.52 g of starting material was used.
MS (MALDI-TOF) m/z: 768 [M]+MS (MALDI-TOF) m/z: 768 [M]+
[합성예 3: 화합물 9의 제조][Synthesis Example 3: Preparation of Compound 9]
출발물질 1.45 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 9 0.25 g을 17.1 % 수율로 얻었다.0.25 g of Compound 9 was obtained in a 17.1% yield through the same method as Synthesis Example 1, except that 1.45 g of starting material was used.
MS (MALDI-TOF) m/z: 730 [M]+MS (MALDI-TOF) m/z: 730 [M]+
[합성예 4: 화합물 15의 제조][Synthesis Example 4: Preparation of Compound 15]
출발물질 1.49 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 15 0.20 g을 12.9 % 수율로 얻었다.0.20 g of Compound 15 was obtained in a 12.9% yield through the same method as Synthesis Example 1, except that 1.49 g of starting material was used.
MS (MALDI-TOF) m/z: 750 [M]+MS (MALDI-TOF) m/z: 750 [M]+
[합성예 5: 화합물 24의 제조][Synthesis Example 5: Preparation of Compound 24]
출발물질 1.51 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 24 0.28 g을 18.4 % 수율로 얻었다.0.28 g of Compound 24 was obtained in 18.4% yield through the same method as Synthesis Example 1, except that 1.51 g of starting material was used.
MS (MALDI-TOF) m/z: 762 [M]+MS (MALDI-TOF) m/z: 762 [M]+
[합성예 6: 화합물 35의 제조][Synthesis Example 6: Preparation of Compound 35]
출발물질 1.04 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 35 0.22 g을 20.8 % 수율로 얻었다.0.22 g of Compound 35 was obtained in a 20.8% yield through the same method as Synthesis Example 1, except that 1.04 g of starting material was used.
MS (MALDI-TOF) m/z: 526 [M]+MS (MALDI-TOF) m/z: 526 [M]+
[합성예 7: 화합물 39의 제조][Synthesis Example 7: Preparation of Compound 39]
출발물질 1.52 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 39 0.28 g을 18.2 % 수율로 얻었다.0.28 g of Compound 39 was obtained in 18.2% yield through the same method as Synthesis Example 1, except that 1.52 g of starting material was used.
MS (MALDI-TOF) m/z: 746 [M]+MS (MALDI-TOF) m/z: 746 [M]+
[합성예 8: 화합물 59의 제조][Synthesis Example 8: Preparation of Compound 59]
출발물질 1.12 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 59 0.20 g을 17.6 % 수율로 얻었다.0.20 g of the compound 59 was obtained in a 17.6% yield through the same method as Synthesis Example 1, except that 1.12 g of the starting material was used.
MS (MALDI-TOF) m/z: 568 [M]+MS (MALDI-TOF) m/z: 568 [M]+
[합성예 9: 화합물 65의 제조][Synthesis Example 9: Preparation of Compound 65]
출발물질 1.48 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 65 0.28 g을 18.6 % 수율로 얻었다.0.28 g of Compound 65 was obtained in 18.6% yield through the same method as Synthesis Example 1, except that 1.48 g of starting material was used.
MS (MALDI-TOF) m/z: 750 [M]+MS (MALDI-TOF) m/z: 750 [M]+
[합성예 10: 화합물 72의 제조][Synthesis Example 10: Preparation of Compound 72]
출발물질 1.49 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 72 0.25 g을 16.6 % 수율로 얻었다.0.25 g of the compound 72 was obtained in a 16.6% yield through the same method as Synthesis Example 1, except that 1.49 g of the starting material was used.
MS (MALDI-TOF) m/z: 750 [M]+MS (MALDI-TOF) m/z: 750 [M]+
[합성예 11: 화합물 75의 제조][Synthesis Example 11: Preparation of Compound 75]
출발물질 1.57 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 75 0.26 g을 16.4 % 수율로 얻었다.0.26 g of the compound 75 was obtained in a 16.4% yield through the same method as Synthesis Example 1, except that 1.57 g of the starting material was used.
MS (MALDI-TOF) m/z: 793 [M]+MS (MALDI-TOF) m/z: 793 [M]+
[합성예 12: 화합물 92의 제조][Synthesis Example 12: Preparation of Compound 92]
출발물질 1.49 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 92 0.27 g을 17.9 % 수율로 얻었다.0.27 g of Compound 92 was obtained in a 17.9% yield through the same method as Synthesis Example 1, except that 1.49 g of starting material was used.
MS (MALDI-TOF) m/z: 750 [M]+MS (MALDI-TOF) m/z: 750 [M]+
[합성예 13: 화합물 101의 제조][Synthesis Example 13: Preparation of Compound 101]
출발물질 1.49 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 101 0.28 g을 18.6 % 수율로 얻었다.0.28 g of the compound 101 was obtained with a yield of 18.6% through the same method as in Synthesis Example 1, except that 1.49 g of the starting material was used.
MS (MALDI-TOF) m/z: 752 [M]+MS (MALDI-TOF) m/z: 752 [M]+
[합성예 14: 화합물 108의 제조][Synthesis Example 14: Preparation of Compound 108]
출발물질 1.48 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 108 0.28 g을 18.7 % 수율로 얻었다.0.28 g of the compound 108 was obtained with a yield of 18.7% through the same method as Synthesis Example 1, except that 1.48 g of the starting material was used.
MS (MALDI-TOF) m/z: 748 [M]+MS (MALDI-TOF) m/z: 748 [M]+
[합성예 15: 화합물 125의 제조][Synthesis Example 15: Preparation of Compound 125]
출발물질 1.45 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 125 0.26 g을 17.7 % 수율로 얻었다.0.26 g of the compound 125 was obtained in a 17.7% yield through the same method as Synthesis Example 1, except that 1.45 g of the starting material was used.
MS (MALDI-TOF) m/z: 730 [M]+MS (MALDI-TOF) m/z: 730 [M]+
[합성예 16: 화합물 127의 제조][Synthesis Example 16: Preparation of Compound 127]
출발물질 1.76 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 127 0.34 g을 19.1 % 수율로 얻었다.0.34 g of the compound 127 was obtained in a 19.1% yield through the same method as Synthesis Example 1, except that 1.76 g of the starting material was used.
MS (MALDI-TOF) m/z: 888 [M]+MS (MALDI-TOF) m/z: 888 [M]+
[합성예 17: 화합물 150의 제조][Synthesis Example 17: Preparation of Compound 150]
출발물질 1.62 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 150 0.29 g을 17.7 % 수율로 얻었다.0.29 g of the compound 150 was obtained with a yield of 17.7% through the same method as Synthesis Example 1, except that 1.62 g of the starting material was used.
MS (MALDI-TOF) m/z: 815 [M]+MS (MALDI-TOF) m/z: 815 [M]+
[합성예 18: 화합물 161의 제조][Synthesis Example 18: Preparation of Compound 161]
출발물질 1.35 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 161 0.24 g을 17.6 % 수율로 얻었다.0.24 g of the compound 161 was obtained in a 17.6% yield through the same method as Synthesis Example 1, except that 1.35 g of the starting material was used.
MS (MALDI-TOF) m/z: 684 [M]+MS (MALDI-TOF) m/z: 684 [M]+
[합성예 19: 화합물 7의 제조][Synthesis Example 19: Preparation of Compound 7]
출발물질 1.45 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 7 0.27 g을 18.4 % 수율로 얻었다.0.27 g of Compound 7 was obtained in 18.4% yield through the same method as Synthesis Example 1, except that 1.45 g of starting material was used.
MS (MALDI-TOF) m/z: 730 [M]+MS (MALDI-TOF) m/z: 730 [M]+
[합성예 20: 화합물 66의 제조][Synthesis Example 20: Preparation of Compound 66]
출발물질 1.52 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 66 0.28 g을 18.2 % 수율로 얻었다.0.28 g of Compound 66 was obtained in 18.2% yield through the same method as Synthesis Example 1, except that 1.52 g of starting material was used.
MS (MALDI-TOF) m/z: 766 [M]+MS (MALDI-TOF) m/z: 766 [M]+
[합성예 21: 화합물 19의 제조][Synthesis Example 21: Preparation of Compound 19]
출발물질 1.68 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 19 0.21 g을 12.4 % 수율로 얻었다.0.21 g of Compound 19 was obtained in a 12.4% yield through the same method as Synthesis Example 1, except that 1.68 g of starting material was used.
MS (MALDI-TOF) m/z: 844 [M]+MS (MALDI-TOF) m/z: 844 [M]+
[합성예 22: 화합물 69의 제조][Synthesis Example 22: Preparation of Compound 69]
출발물질 1.28 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 69 0.24 g을 18.5 % 수율로 얻었다.0.24 g of Compound 69 was obtained in 18.5% yield through the same method as Synthesis Example 1, except that 1.28 g of starting material was used.
MS (MALDI-TOF) m/z: 648 [M]+MS (MALDI-TOF) m/z: 648 [M]+
[합성예 23: 화합물 30의 제조][Synthesis Example 23: Preparation of Compound 30]
출발물질 1.78 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 30 0.23 g을 12.8 % 수율로 얻었다.0.23 g of Compound 30 was obtained in a 12.8% yield through the same method as Synthesis Example 1, except that 1.78 g of starting material was used.
MS (MALDI-TOF) m/z: 899 [M]+MS (MALDI-TOF) m/z: 899 [M]+
[합성예 24: 화합물 90의 제조][Synthesis Example 24: Preparation of Compound 90]
출발물질 1.68 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 90 0.24 g을 14.2 % 수율로 얻었다.0.24 g of the compound 90 was obtained in a 14.2% yield through the same method as Synthesis Example 1, except that 1.68 g of the starting material was used.
MS (MALDI-TOF) m/z: 848 [M]+MS (MALDI-TOF) m/z: 848 [M]+
[합성예 25: 화합물 37의 제조][Synthesis Example 25: Preparation of Compound 37]
출발물질 1.50 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 37 0.26 g을 17.2 % 수율로 얻었다.0.26 g of Compound 37 was obtained in a 17.2% yield through the same method as Synthesis Example 1, except that 1.50 g of starting material was used.
MS (MALDI-TOF) m/z: 758 [M]+MS (MALDI-TOF) m/z: 758 [M]+
[합성예 26: 화합물 99의 제조][Synthesis Example 26: Preparation of Compound 99]
출발물질 1.36 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 99 0.21 g을 15.3 % 수율로 얻었다.0.21 g of Compound 99 was obtained in a 15.3% yield through the same method as Synthesis Example 1, except that 1.36 g of starting material was used.
MS (MALDI-TOF) m/z: 688 [M]+MS (MALDI-TOF) m/z: 688 [M]+
[합성예 27: 화합물 57의 제조][Synthesis Example 27: Preparation of Compound 57]
출발물질 1.58 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 57 0.30 g을 18.8 % 수율로 얻었다.0.30 g of Compound 57 was obtained in 18.8% yield through the same method as Synthesis Example 1, except that 1.58 g of starting material was used.
MS (MALDI-TOF) m/z: 796 [M]+MS (MALDI-TOF) m/z: 796 [M]+
[합성예 28: 화합물 103의 제조][Synthesis Example 28: Preparation of Compound 103]
출발물질 1.34 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 103 0.18 g을 13.3 % 수율로 얻었다.0.18 g of the compound 103 was obtained in a 13.3% yield through the same method as Synthesis Example 1, except that 1.34 g of the starting material was used.
MS (MALDI-TOF) m/z: 678 [M]+MS (MALDI-TOF) m/z: 678 [M]+
[합성예 29: 화합물 140의 제조][Synthesis Example 29: Preparation of Compound 140]
출발물질 1.25 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 140 0.16 g을 12.6 % 수율로 얻었다.0.16 g of the compound 140 was obtained in a 12.6% yield through the same method as Synthesis Example 1, except that 1.25 g of the starting material was used.
MS (MALDI-TOF) m/z: 633 [M]+MS (MALDI-TOF) m/z: 633 [M]+
[합성예 30: 화합물 163의 제조][Synthesis Example 30: Preparation of Compound 163]
출발물질 1.64 g을 사용한 것을 제외하고 합성예 1과 동일한 방법을 통해 상기 화합물 163 0.24 g을 14.5 % 수율로 얻었다.0.24 g of the compound 163 was obtained in a 14.5% yield through the same method as Synthesis Example 1, except that 1.64 g of the starting material was used.
MS (MALDI-TOF) m/z: 825 [M]+MS (MALDI-TOF) m/z: 825 [M]+
[합성예 31: 화합물 78의 제조][Synthesis Example 31: Preparation of Compound 78]
출발물질 19.33 g (20.0 mmol)과 삼브롬화 붕소(Boron tribromide) 3.80 mL (40.0 mmol)를 ortho-디클로로벤젠(ortho-Dichlorobenzene, 400 ml)이 들어있는 1,000 mL 플라스크에 N2 조건에서 투입하였다. 이 후 온도를 80 ℃로 올려 3시간 교반하고 다시 온도를 180 ℃로 올려 12시간 교반하였다. 얇은 막 크로마토그래피 방법을 이용해 반응이 완결되는 것을 확인하였다. 반응액을 실온까지 냉각 후 물(Water)을 투입하고 유기층을 에틸 아세테이트(Ethyl acetate)를 이용하여 추출하였다. 추출한 유기층의 용매를 MgSO4로 건조하고 여과, 농축한 후 실리카겔 컬럼 크로마토그래피 (Dichloromethane/Hexane) 방법을 이용하여 정제하였다. 이후 Dichloromethane/Acetone 혼합 용매로 재결정 정제하여, 상기 화합물 78 4.18 g을 21.4 % 수율로 얻었다.19.33 g (20.0 mmol) of starting material and 3.80 mL (40.0 mmol) of boron tribromide were added to a 1,000 mL flask containing ortho-Dichlorobenzene (400 ml) under N 2 conditions. Afterwards, the temperature was raised to 80°C and stirred for 3 hours, and then the temperature was raised to 180°C and stirred for 12 hours. The completion of the reaction was confirmed using thin layer chromatography. After cooling the reaction solution to room temperature, water was added, and the organic layer was extracted using ethyl acetate. The solvent of the extracted organic layer was dried with MgSO 4 , filtered, concentrated, and purified using silica gel column chromatography (Dichloromethane/Hexane). After recrystallization and purification using a Dichloromethane/Acetone mixed solvent, 4.18 g of the above compound 78 was obtained with a yield of 21.4%.
MS (MALDI-TOF) m/z: 974 [M]+MS (MALDI-TOF) m/z: 974 [M]+
[합성예 32: 화합물 13의 제조][Synthesis Example 32: Preparation of Compound 13]
출발물질 18.65 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 13 4.85 g을 25.8 % 수율로 얻었다.4.85 g of Compound 13 was obtained in 25.8% yield through the same method as Synthesis Example 31, except that 18.65 g of starting material was used.
MS (MALDI-TOF) m/z: 939 [M]+MS (MALDI-TOF) m/z: 939 [M]+
[합성예 33: 화합물 32의 제조][Synthesis Example 33: Preparation of Compound 32]
출발물질 18.73 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 32 3.52 g을 18.6 % 수율로 얻었다.3.52 g of Compound 32 was obtained in 18.6% yield through the same method as Synthesis Example 31, except that 18.73 g of starting material was used.
MS (MALDI-TOF) m/z: 943 [M]+MS (MALDI-TOF) m/z: 943 [M]+
[합성예 34: 화합물 51의 제조][Synthesis Example 34: Preparation of Compound 51]
출발물질 19.29 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 51 4.88 g을 25.1 % 수율로 얻었다.4.88 g of Compound 51 was obtained in a 25.1% yield through the same method as Synthesis Example 31, except that 19.29 g of starting material was used.
MS (MALDI-TOF) m/z: 971 [M]+MS (MALDI-TOF) m/z: 971 [M]+
[합성예 35: 화합물 138의 제조][Synthesis Example 35: Preparation of Compound 138]
출발물질 14.44 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 138 2.91 g을 19.9 % 수율로 얻었다.2.91 g of the compound 138 was obtained in a 19.9% yield through the same method as Synthesis Example 31, except that 14.44 g of the starting material was used.
MS (MALDI-TOF) m/z: 729 [M]+MS (MALDI-TOF) m/z: 729 [M]+
[합성예 36: 화합물 165의 제조][Synthesis Example 36: Preparation of Compound 165]
출발물질 13.72 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 165 2.62 g을 18.9 % 수율로 얻었다.2.62 g of Compound 165 was obtained in 18.9% yield through the same method as Synthesis Example 31, except that 13.72 g of starting material was used.
MS (MALDI-TOF) m/z: 693 [M]+MS (MALDI-TOF) m/z: 693 [M]+
[합성예 37: 화합물 45의 제조][Synthesis Example 37: Preparation of Compound 45]
출발물질 20.49 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 45 3.55 g을 17.2 % 수율로 얻었다.3.55 g of Compound 45 was obtained in a 17.2% yield through the same method as Synthesis Example 31, except that 20.49 g of starting material was used.
MS (MALDI-TOF) m/z: 1031 [M]+MS (MALDI-TOF) m/z: 1031 [M]+
[합성예 38: 화합물 112의 제조][Synthesis Example 38: Preparation of Compound 112]
출발물질 16.64 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 112 3.12 g을 18.6 % 수율로 얻었다.3.12 g of Compound 112 was obtained in 18.6% yield through the same method as Synthesis Example 31, except that 16.64 g of starting material was used.
MS (MALDI-TOF) m/z: 839 [M]+MS (MALDI-TOF) m/z: 839 [M]+
[합성예 39: 화합물 115의 제조][Synthesis Example 39: Preparation of Compound 115]
출발물질 16.96 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 115 3.22 g을 18.8 % 수율로 얻었다.3.22 g of Compound 115 was obtained in 18.8% yield through the same method as Synthesis Example 31, except that 16.96 g of starting material was used.
MS (MALDI-TOF) m/z: 855 [M]+MS (MALDI-TOF) m/z: 855 [M]+
[합성예 40: 화합물 134의 제조][Synthesis Example 40: Preparation of Compound 134]
출발물질 16.96 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 134 2.88 g을 16.8 % 수율로 얻었다.2.88 g of the compound 134 was obtained in a 16.8% yield through the same method as Synthesis Example 31, except that 16.96 g of the starting material was used.
MS (MALDI-TOF) m/z: 855 [M]+MS (MALDI-TOF) m/z: 855 [M]+
[합성예 41: 화합물 148의 제조][Synthesis Example 41: Preparation of Compound 148]
출발물질 16.08 g을 사용한 것을 제외하고 합성예 31과 동일한 방법을 통해 상기 화합물 148 1.95 g을 12.0 % 수율로 얻었다.1.95 g of the compound 148 was obtained in a 12.0% yield through the same method as Synthesis Example 31, except that 16.08 g of the starting material was used.
MS (MALDI-TOF) m/z: 811 [M]+MS (MALDI-TOF) m/z: 811 [M]+
[합성예 42: 화합물 81의 제조][Synthesis Example 42: Preparation of Compound 81]
출발물질 1.32 g (2.00 mmol)과 비스(4-(터트-부틸)페닐)아민(bis(4-(tert-butyl)phenyl)amine) 0.56 g (2.00 mmol), 소듐 터트-부톡사이드(Sodium tert-butoxide) 0.38g (4.00 mmol), 트리스(디벤질리덴아세톤)디팔라듐(0)( Tris(dibenzylideneacetone)dipalladium(0)) 0.03 g (0.04 mmol), 2-디사이클로헥실포스피노-2', 6'-디메톡시바이페닐(2-Dicyclohexylphosphino-2', 6'-dimethoxybiphenyl) 0.03 g (0.08 mmol)을 N2 조건에서 톨루엔 50ml에 투입하였다. 이후 온도를 100 ℃로 올려 4시간 교반하였다. 얇은 막 크로마토그래피 방법을 이용해 반응이 완결되는 것을 확인하였다. 반응액을 실온까지 냉각 후 물(Water)을 투입하고 유기층을 디클로로 메탄(Dichloromethane)를 이용하여 추출하였다. 추출한 유기층의 용매를 MgSO4로 건조하고 여과, 농축한 후 실리카겔 컬럼 크로마토그래피(Dichloromethane/Hexane) 방법을 이용하여 정제하였다. 이후 Dichloromethane/Acetone 혼합 용매로 재결정 정제하여, 상기 화합물 81 1.24 g을 68.5 % 수율로 얻었다.Starting material 1.32 g (2.00 mmol) and bis(4-(tert-butyl)phenyl)amine (bis(4-(tert-butyl)phenyl)amine) 0.56 g (2.00 mmol), sodium tert-butoxide (Sodium tert) -butoxide) 0.38g (4.00 mmol), Tris(dibenzylideneacetone)dipalladium(0)(Tris(dibenzylideneacetone)dipalladium(0)) 0.03 g (0.04 mmol), 2-dicyclohexylphosphino-2', 0.03 g (0.08 mmol) of 6'-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl was added to 50 ml of toluene under N 2 conditions. Afterwards, the temperature was raised to 100°C and stirred for 4 hours. The completion of the reaction was confirmed using thin layer chromatography. After cooling the reaction solution to room temperature, water was added, and the organic layer was extracted using dichloromethane. The solvent of the extracted organic layer was dried with MgSO 4 , filtered, concentrated, and purified using silica gel column chromatography (Dichloromethane/Hexane). After recrystallization and purification using a mixed solvent of Dichloromethane/Acetone, 1.24 g of Compound 81 was obtained with a yield of 68.5%.
MS (MALDI-TOF) m/z: 905 [M]+MS (MALDI-TOF) m/z: 905 [M]+
[합성예 43: 화합물 83의 제조][Synthesis Example 43: Preparation of Compound 83]
출발물질 1.45 g을 사용한 것을 제외하고 합성예 42와 동일한 방법을 통해 상기 화합물 83 1.16 g을 59.5 % 수율로 얻었다.1.16 g of Compound 83 was obtained in 59.5% yield through the same method as Synthesis Example 42, except that 1.45 g of starting material was used.
MS (MALDI-TOF) m/z: 973 [M]+MS (MALDI-TOF) m/z: 973 [M]+
[합성예 44: 화합물 84의 제조][Synthesis Example 44: Preparation of Compound 84]
출발물질 1.49 g을 사용한 것을 제외하고 합성예 42와 동일한 방법을 통해 상기 화합물 84 1.31 g을 66.2 % 수율로 얻었다.1.31 g of the compound 84 was obtained with a yield of 66.2% through the same method as Synthesis Example 42, except that 1.49 g of the starting material was used.
MS (MALDI-TOF) m/z: 989 [M]+MS (MALDI-TOF) m/z: 989 [M]+
[합성예 45: 화합물 87의 제조][Synthesis Example 45: Preparation of Compound 87]
출발물질 1.45 g을 사용한 것을 제외하고 합성예 42와 동일한 방법을 통해 상기 화합물 87 1.32 g을 68.0 % 수율로 얻었다.1.32 g of Compound 87 was obtained in 68.0% yield through the same method as Synthesis Example 42, except that 1.45 g of starting material was used.
MS (MALDI-TOF) m/z: 969 [M]+MS (MALDI-TOF) m/z: 969 [M]+
[합성예 46: 화합물 26의 제조][Synthesis Example 46: Preparation of Compound 26]
출발물질 1.41 g을 사용한 것과 비스(4-(터트-부틸)페닐)아민(bis(4-(tert-butyl)phenyl)amine) 0.56 g (2.00 mmol) 대신 다이페닐아민(diphenylamine) 0.34 g (2.00 mmol)을 사용한 것을 제외하고 합성예 42와 동일한 방법을 통해 상기 화합물 26 1.01 g을 60.2 % 수율로 얻었다.1.41 g of starting material was used and 0.34 g (2.00 mmol) of diphenylamine was used instead of 0.56 g (2.00 mmol) of bis(4-(tert-butyl)phenyl)amine. 1.01 g of Compound 26 was obtained with a yield of 60.2% through the same method as Synthesis Example 42 except that mmol) was used.
MS (MALDI-TOF) m/z: 835 [M]+MS (MALDI-TOF) m/z: 835 [M]+
[비교예 1: 화합물 A의 제조][Comparative Example 1: Preparation of Compound A]
출발물질 4.91 g (10.0mmol)과 터트-부틸벤젠(tert-Buthylbenzene) (50 ml)에 녹인 후 0 ℃까지 냉각하였다. 질소 분위기 하에서 2.5 M n-부틸리튬(n-BuLi) 용액(in hexane) 7.9 mL (20.0 mmol)을 첨가하고 실온에서 5시간 교반한다. 이후 다시 반응물을 0 ℃까지 냉각하고 삼브롬화 붕소(Boron tribromide) 5.00 g (20.0 mmol)를 첨가한 후 상온에서 6시간 교반하였다. 다시 반응물을 0 ℃까지 냉각하고 N,N-디이소프로필에틸아민(N,N-Diisopropylethylamine) 3.48 mL (20 mmol)를 첨가한 후 60~70 ℃ 에서 2시간 교반하였다. 반응액을 실온까지 냉각시키고 디클로로메탄(Dichloromethane)과 물(Water)를 이용하여 유기층을 추출하였다. 추출한 유기층의 용매를 MgSO4로 건조한 후, 여과하였다. 여액을 감압 농축시킨 후, 실리카겔 컬럼 크로마토그래피 (DCM/Hexane) 방법을 이용하여 정제하였다. 이 후 DCM/Acetone 혼합 용매로 재결정 정제하여, 상기 비교화합물 1 0.95 g을 22.6 % 수율로 얻었다.4.91 g (10.0 mmol) of the starting material was dissolved in tert-Butylbenzene (50 ml) and cooled to 0°C. Add 7.9 mL (20.0 mmol) of 2.5 M n -butyllithium (n-BuLi) solution (in hexane) under a nitrogen atmosphere and stir at room temperature for 5 hours. Afterwards, the reaction was cooled to 0°C again, 5.00 g (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 6 hours. The reaction was cooled to 0°C again, 3.48 mL (20 mmol) of N , N -Diisopropylethylamine was added, and the mixture was stirred at 60-70°C for 2 hours. The reaction solution was cooled to room temperature, and the organic layer was extracted using dichloromethane and water. The solvent of the extracted organic layer was dried with MgSO 4 and then filtered. The filtrate was concentrated under reduced pressure and purified using silica gel column chromatography (DCM/Hexane). Afterwards, the mixture was recrystallized and purified using a DCM/Acetone mixed solvent to obtain 0.95 g of Comparative Compound 1 with a yield of 22.6%.
MS (MALDI-TOF) m/z: 420 [M]+MS (MALDI-TOF) m/z: 420 [M]+
[비교예 2: 화합물 B의 제조][Comparative Example 2: Preparation of Compound B]
출발물질 8.20 g을 사용한 것을 제외하고 비교예 1과 동일한 방법을 통해 상기 비교화합물 2 1.63 g을 21.7 % 수율로 얻었다.1.63 g of Comparative Compound 2 was obtained in a 21.7% yield through the same method as Comparative Example 1, except that 8.20 g of starting material was used.
MS (MALDI-TOF) m/z: 748 [M]+MS (MALDI-TOF) m/z: 748 [M]+
[비교예 3: 화합물 C의 제조][Comparative Example 3: Preparation of Compound C]
출발물질 11.60 g을 사용한 것을 제외하고 합성예 30과 동일한 방법을 통해 상기 비교화합물 3 2.78 g을 23.6 % 수율로 얻었다.2.78 g of Comparative Compound 3 was obtained in 23.6% yield through the same method as Synthesis Example 30, except that 11.60 g of starting material was used.
MS (MALDI-TOF) m/z: 587 [M]+MS (MALDI-TOF) m/z: 587 [M]+
[비교예 4: 화합물 D의 제조][Comparative Example 4: Preparation of Compound D]
출발물질 0.91 g을 사용한 것을 제외하고 합성예 44와 동일한 방법을 통해 상기 비교화합물 4 0.81 g을 68.8 % 수율로 얻었다.0.81 g of Comparative Compound 4 was obtained in 68.8% yield through the same method as Synthesis Example 44, except that 0.91 g of starting material was used.
MS (MALDI-TOF) m/z: 587 [M]+MS (MALDI-TOF) m/z: 587 [M]+
[실시예 1: 유기전계발광소자 제조][Example 1: Manufacturing organic electroluminescent device]
유기전계발광 소자의 양극인 ITO(100 nm)를 적층된 기판을 노광(Photo-Lithograph)공정을 통해 음극과 양극영역 그리고 절연층으로 구분하여 패터닝(Patterning)하였고, 이후 양극(ITO)의 일함수(work-function) 증대와 세정을 목적으로 UV Ozone 처리와 O2:N2 플라즈마로 표면처리 하였다. 그 위에 정공주입층(HIL)으로 HAT-CN을 10 nm 두께로 형성하였다. 이어 상기 정공주입층 상부에, 정공수송층으로서 N4,N4,N4',N4'-테트라([1,1'-비페닐]-4-일)-[1,1'-비페닐]-4,4'-디아민(N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine)을 진공 증착하여 90 nm 두께로 형성하고, 상기 정공수송층(HTL) 상부에 전자차단층(EBL)으로서 N-페닐-N-(4-(스피로[벤조[d,e]안트라센-7,9'-플루오렌]-2'-일)페닐)디벤조[b,d]푸란-4-아민(N-Phenyl-N-(4-(spiro[benzo[d, e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine)을 15 nm두께로 형성하였다. 상기 전자차단층(EBL) 상부에 발광층의 호스트로서 9-(1-나프틸)-10-(2-나프틸)안트라센 (9-(1-Naphtyl)-10-(2-Naphtyl)anthracene)을 증착시키면서 동시에 도펀트로 화합물 3을 2 % 도핑하여 25 nm 두께로 발광층(EML)을 형성하였다.The substrate on which ITO (100 nm), the anode of the organic electroluminescent device, was laminated was patterned by dividing it into a cathode, anode region, and insulating layer through an exposure (Photo-Lithograph) process, and then the work function of the anode (ITO) was patterned. For the purpose of increasing (work-function) and cleaning, the surface was treated with UV Ozone treatment and O 2 :N 2 plasma. On top of this, HAT-CN was formed to a thickness of 10 nm as a hole injection layer (HIL). Then, on top of the hole injection layer, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4, as a hole transport layer, Vacuum deposition of 4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) It is formed to a thickness of 90 nm, and N-phenyl-N-(4-(spiro[benzo[d,e]anthracene-7,9'-fluorene) is used as an electron blocking layer (EBL) on top of the hole transport layer (HTL). ]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine (N-Phenyl-N-(4-(spiro[benzo[d, e]anthracene-7,9'-fluorene]- 2'-yl)phenyl)dibenzo[b,d]furan-4-amine) was formed to a thickness of 15 nm. 9-(1-Naphtyl)-10-(2-naphthyl)anthracene (9-(1-Naphtyl)-10-(2-Naphtyl)anthracene) was placed on the electron blocking layer (EBL) as a host for the light emitting layer. While depositing, 2% of Compound 3 was doped as a dopant to form an emitting layer (EML) with a thickness of 25 nm.
그 위에 전자수송층(ETL)으로 2-(4-(9,10-디(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸(2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole)과 LiQ를 1:1의 중량비로 혼합하여 25 nm 증착하였으며, 상기 전자 수송층 상에 전자 주입층을 1 nm 증착하고, 음극으로 알루미늄을 100 nm 두께로 증착시켰다. 이후, UV 경화형 접착제로 흡착제(getter)를 포함한 씰 캡(seal cap)을 합착하여 대기 중의 산소나 수분으로부터 유기전계발광 소자를 보호할 수 있게 하여 유기전계발광소자를 제조하였다.On top of this, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole(2- (4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole) and LiQ were mixed at a weight ratio of 1:1 to form 25 nm An electron injection layer of 1 nm was deposited on the electron transport layer, and aluminum was deposited to a thickness of 100 nm as a cathode. Afterwards, an organic electroluminescent device was manufactured by bonding a seal cap containing an adsorbent (getter) with a UV curable adhesive to protect the organic electroluminescent device from oxygen or moisture in the atmosphere.
[실시예 2 내지 44: 유기전계발광소자의 제조][Examples 2 to 44: Manufacturing of organic electroluminescent devices]
도펀트로서 상기 화합물 3 대신 화합물 4, 9, 15, 24, 59, 72, 75, 65, 101, 108, 125, 127, 150, 161, 7, 66, 19, 30, 90, 57, 103, 140, 163, 35, 39, 37, 32, 78, 13, 51, 138, 165, 45, 112, 115, 134, 148, 83, 84, 87 및 26을 사용한 것을 제외하고는, 실시예 1과 동일한 방법을 이용하여 유기전계발광소자를 제조하였다. As a dopant, instead of compound 3, compound 4, 9, 15, 24, 59, 72, 75, 65, 101, 108, 125, 127, 150, 161, 7, 66, 19, 30, 90, 57, 103, 140 The same as Example 1, except that 163, 35, 39, 37, 32, 78, 13, 51, 138, 165, 45, 112, 115, 134, 148, 83, 84, 87 and 26 were used. An organic electroluminescent device was manufactured using the method.
[비교예 5 내지 8: 유기전계발광소자의 제조][Comparative Examples 5 to 8: Manufacturing of organic electroluminescent devices]
도펀트로서 상기 화합물 3 대신 화합물 A 내지 화합물 D(비교예 1 내지 4)를 사용한 것을 제외하고는 실시예 1과 동일한 방법을 이용하여 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured using the same method as Example 1, except that Compound A to Compound D (Comparative Examples 1 to 4) was used as a dopant instead of Compound 3.
[실험예: 유기전계발광소자의 특성 분석][Experimental example: Analysis of characteristics of organic electroluminescent devices]
실시예 1 내지 44 및 비교예 5 내지 8에서 제조한 유기전계발광소자를 10 mA/cm2 전류를 인가하여 전광특성을 측정하고 10 mA/cm2의 정전류 구동으로 수명을 측정한 결과를 하기 표 1에 비교하여 나타냈다.The electro-optical characteristics of the organic electroluminescent devices prepared in Examples 1 to 44 and Comparative Examples 5 to 8 were measured by applying a current of 10 mA/cm 2 and the lifespan was measured by driving a constant current of 10 mA/cm 2. The results are shown in the table below. It is compared to 1.
(V)Voltage
(V)
(%)external quantum efficiency
(%)
T95
(hr)life span
T95
(hr)
본 발명과 같은 특징을 공유하여 평면 구조가 아닌 뒤틀린 구조를 가지는 화합물이며, 본 발명의 실시예 1 내지 44는 동일한 구조적인 특징을 공유하며, 구체적으로 보론계 화합물의 N 및 페닐기 간에 치환기가 축합하여 고리화합물을 포함하고, 상기 고리화합물에 사이클로알킬기가 결합된 것을 특징으로 한다. 반면, 비교예 1 내지 4 화합물은 보론계 화합물의 N과 페닐기 간에 치환기가 축합하여 고리 화합물을 형성하지 않고, 사이클로알킬기를 페닐기의 치환기로 포함하는 것에서 구조적인 차이가 존재한다. It is a compound that shares the same characteristics as the present invention and has a twisted structure rather than a planar structure. Examples 1 to 44 of the present invention share the same structural characteristics, and specifically, the substituent is condensed between the N and phenyl groups of the boron-based compound. It contains a ring compound and is characterized in that a cycloalkyl group is bonded to the ring compound. On the other hand, the compounds of Comparative Examples 1 to 4 have a structural difference in that the substituents between N and the phenyl group of the boron-based compound do not condense to form a ring compound, and a cycloalkyl group is included as a substituent for the phenyl group.
상기 비교예 및 합성예의 화합물을 포함하는 유기전계발광소자를 제작한 후, 이의 구동전압, 외부양자효율 및 수명 특성을 비교한 결과는 상기 표 1과 같다. 상기 화합물 간의 구조적인 차이에 따라, 유지전계발광소자의 구동전압, 외부양자효율 및 수명 특성에서 큰 차이를 나타냄을 확인할 수 있다. After manufacturing organic electroluminescent devices containing the compounds of the comparative and synthetic examples, the results of comparing their driving voltage, external quantum efficiency, and lifespan characteristics are shown in Table 1 above. Depending on the structural differences between the compounds, it can be seen that there is a significant difference in the driving voltage, external quantum efficiency, and lifespan characteristics of the sustaining electroluminescent device.
이상에서 본 발명의 바람직한 실시예에 대하여 상세하게 설명하였지만 본 발명의 권리범위는 이에 한정되는 것은 아니고 다음의 청구범위에서 정의하고 있는 본 발명의 기본 개념을 이용한 당업자의 여러 변형 및 개량 형태 또한 본 발명의 권리범위에 속하는 것이다.Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims are also possible. falls within the scope of rights.
Claims (6)
[화학식 6]
여기서,
n 및 m은 서로 동일하거나 상이하며, 각각 독립적으로 0 내지 3의 정수이며,
X1은 N 또는 CR3이며,
X2는 NR4, O 및 S로 이루어진 군으로부터 선택되고,
Y은 B이고,
A환은 치환 또는 비치환의 탄소수 6 내지 30의 아릴기 또는 치환 또는 비치환의 탄소수 3 내지 30의 헤테로아릴기이며,
R1 및 R3은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 시아노기, 트리플루오로메틸기, 니트로기, 할로겐기, 히드록시기, 치환 또는 비치환된 탄소수 1 내지 4의 알킬티오기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환된 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 헤테로아릴알킬기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기로 이루어진 군으로부터 선택되고, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,
R2 및 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 시아노기, 트리플루오로메틸기, 니트로기, 할로겐기, 히드록시기, 치환 또는 비치환된 탄소수 1 내지 4의 알킬티오기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환된 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 헤테로아릴알킬기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기로 이루어진 군으로부터 선택된다.Compound represented by the following formula (6):
[Formula 6]
here,
n and m are the same or different from each other and are each independently an integer from 0 to 3,
X 1 is N or CR 3 ,
X 2 is selected from the group consisting of NR 4 , O and S,
Y is B,
Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R 1 and R 3 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group with 1 to 30 carbon atoms, substituted or unsubstituted arylamino group with 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group of 30 to 30 carbon atoms, substituted or unsubstituted heteroarylamino group of 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group of 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms and substituted or an unsubstituted aryloxy group having 6 to 30 carbon atoms, which may be combined with adjacent groups to form a substituted or unsubstituted ring,
R 2 and R 4 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group with 1 to 30 carbon atoms, substituted or unsubstituted arylamino group with 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group of 30 to 30 carbon atoms, substituted or unsubstituted heteroarylamino group of 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group of 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms and substituted or an unsubstituted aryloxy group having 6 to 30 carbon atoms.
상기 A환은 하기 화학식 3 또는 화학식 4로 표시되는 화합물로부터 선택되는 화합물:
[화학식 3]
[화학식 4]
여기서,
*는 결합되는 부분이며,
p는 0 내지 4의 정수이며,
Z3는 NR-11, O 및 S로 이루어진 군으로부터 선택되고,
R8 내지 R11은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 시아노기, 니트로기, 할로겐기, 히드록시기, 치환 또는 비치환된 탄소수 1 내지 4의 알킬티오기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환된 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 30의 헤테로아릴알킬기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기로 이루어진 군으로부터 선택되고, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.According to paragraph 1,
The A ring is a compound selected from compounds represented by the following Formula 3 or Formula 4:
[Formula 3]
[Formula 4]
here,
* is the part that is combined,
p is an integer from 0 to 4,
Z 3 is selected from the group consisting of NR- 11 , O and S,
R 8 to R 11 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted carbon number Alkyl group of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group of 2 to 24 carbon atoms, substituted or unsubstituted Aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 2 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl group with 6 to 30 carbon atoms, substituted or an unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl having 6 to 30 carbon atoms. Amino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and substituted or unsubstituted carbon atoms. It is selected from the group consisting of 6 to 30 aryloxy groups, and may be combined with adjacent groups to form a substituted or unsubstituted ring.
상기 하나 이상의 유기물층은 제1항에 따른 화합물을 하나 이상 포함하는 유기 전계발광 소자.first electrode; a second electrode opposite the first electrode; It includes one or more organic layers interposed between the first electrode and the second electrode,
The at least one organic material layer is an organic electroluminescent device comprising at least one compound according to claim 1.
상기 유기물층은 정공주입층, 정공수송층, 발광층, 정공차단층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택되는 유기 전계 발광 소자.According to clause 4,
The organic material layer is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
상기 유기물층은 발광층인 유기 전계 발광 소자.According to clause 4,
An organic electroluminescent device in which the organic material layer is a light-emitting layer.
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