WO2017069443A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents
Composé organique et élément électroluminescent organique le comprenant Download PDFInfo
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- WO2017069443A1 WO2017069443A1 PCT/KR2016/011335 KR2016011335W WO2017069443A1 WO 2017069443 A1 WO2017069443 A1 WO 2017069443A1 KR 2016011335 W KR2016011335 W KR 2016011335W WO 2017069443 A1 WO2017069443 A1 WO 2017069443A1
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- Prior art keywords
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- aryl
- compound
- alkyl
- organic
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 7
- 239000012044 organic layer Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 88
- 239000010410 layer Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000004429 atom Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 239000011368 organic material Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- -1 alkyl boron Chemical compound 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 11
- 125000005104 aryl silyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 82
- 238000003786 synthesis reaction Methods 0.000 description 82
- 238000002360 preparation method Methods 0.000 description 44
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 37
- 239000000463 material Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- MMAIMCOMSPMTKJ-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=CC=CC(C=2C=C(C=CC=2)C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MMAIMCOMSPMTKJ-UHFFFAOYSA-N 0.000 description 4
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 4
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
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- CTAHMZVXASKGMT-UHFFFAOYSA-N 18-chloro-21,21-dimethylpentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound ClC1=CC=2C(C3=C(C4=CC=CC=C4C=4C=CC=CC3=4)C=2C=C1)(C)C CTAHMZVXASKGMT-UHFFFAOYSA-N 0.000 description 3
- CRJXXAZXBFZRRV-UHFFFAOYSA-N 2-(5-chloro-2-phenanthren-9-ylphenyl)propan-2-ol Chemical compound ClC=1C=CC(=C(C=1)C(C)(C)O)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1 CRJXXAZXBFZRRV-UHFFFAOYSA-N 0.000 description 3
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- PZALSSAZMCAIIY-UHFFFAOYSA-N 21,21-dimethyl-18-(2-nitrophenyl)pentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound CC1(C=2C=C(C=CC=2C=2C3=CC=CC=C3C=3C=CC=CC=3C=21)C1=C(C=CC=C1)[N+](=O)[O-])C PZALSSAZMCAIIY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 238000000605 extraction Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
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- 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 2
- 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 2
- BAPXNJHZBPEAMA-UHFFFAOYSA-N (5-chloro-2-phenanthren-9-ylphenyl)-diphenylmethanol Chemical compound ClC=1C=CC(=C(C=1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1 BAPXNJHZBPEAMA-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- 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 2
- CZRMKGYSAXYEDF-UHFFFAOYSA-N 18-chloro-21,21-diphenylpentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound ClC1=CC=2C(C3=C(C4=CC=CC=C4C=4C=CC=CC3=4)C=2C=C1)(C1=CC=CC=C1)C1=CC=CC=C1 CZRMKGYSAXYEDF-UHFFFAOYSA-N 0.000 description 2
- OJTHNYLBXCFYAM-UHFFFAOYSA-N 2-(21,21-dimethyl-18-pentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C2C(C=3C(=CC=CC=3)C=3C4=CC=CC=3)=C4C(C)(C)C2=C1 OJTHNYLBXCFYAM-UHFFFAOYSA-N 0.000 description 2
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- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
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- 229940127007 Compound 39 Drugs 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
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- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 2
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
Abstract
La présente invention concerne un composé organique et un élément électroluminescent organique le comprenant. Le composé organique selon l'invention peut accroître le rendement lumineux, la tension de commande, la durée de vie, et autres d'un élément électroluminescent organique, quand il est utilisé dans une couche organique de l'élément électroluminescent organique.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020150146101A KR102487494B1 (ko) | 2015-10-20 | 2015-10-20 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| KR10-2015-0146101 | 2015-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2017069443A1 true WO2017069443A1 (fr) | 2017-04-27 |
Family
ID=58557622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2016/011335 WO2017069443A1 (fr) | 2015-10-20 | 2016-10-11 | Composé organique et élément électroluminescent organique le comprenant |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102487494B1 (fr) |
| WO (1) | WO2017069443A1 (fr) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080109000A (ko) * | 2006-07-11 | 2008-12-16 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 신규 물질 |
| KR20110050588A (ko) * | 2008-07-29 | 2011-05-16 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자 |
| KR20120065214A (ko) * | 2010-12-10 | 2012-06-20 | (주)씨에스엘쏠라 | 치환된 카발졸계 유기 광화합물 및 이를 이용한 유기 광소자 |
| KR20120081539A (ko) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
| KR20150048883A (ko) * | 2012-09-04 | 2015-05-07 | 메르크 파텐트 게엠베하 | 전자 소자용 접속부 |
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| KR100841417B1 (ko) | 2006-10-31 | 2008-06-25 | 주식회사 대림화학 | 2,6-치환기를 갖는 9,10-디페닐안트라센 발광 화합물 및이를 발광재료로서 채용하고 있는 발광소자 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080109000A (ko) * | 2006-07-11 | 2008-12-16 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 신규 물질 |
| KR20110050588A (ko) * | 2008-07-29 | 2011-05-16 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자 |
| KR20120065214A (ko) * | 2010-12-10 | 2012-06-20 | (주)씨에스엘쏠라 | 치환된 카발졸계 유기 광화합물 및 이를 이용한 유기 광소자 |
| KR20120081539A (ko) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
| KR20150048883A (ko) * | 2012-09-04 | 2015-05-07 | 메르크 파텐트 게엠베하 | 전자 소자용 접속부 |
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| KR102487494B1 (ko) | 2023-01-12 |
| KR20170045952A (ko) | 2017-04-28 |
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