KR102157997B1 - 중합체, 유기 전계 발광 소자용 조성물, 유기 전계 발광 소자, 유기 el 표시 장치 및 유기 el 조명 - Google Patents
중합체, 유기 전계 발광 소자용 조성물, 유기 전계 발광 소자, 유기 el 표시 장치 및 유기 el 조명 Download PDFInfo
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- KR102157997B1 KR102157997B1 KR1020167008575A KR20167008575A KR102157997B1 KR 102157997 B1 KR102157997 B1 KR 102157997B1 KR 1020167008575 A KR1020167008575 A KR 1020167008575A KR 20167008575 A KR20167008575 A KR 20167008575A KR 102157997 B1 KR102157997 B1 KR 102157997B1
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- 229920000642 polymer Polymers 0.000 title claims abstract description 142
- 239000000203 mixture Substances 0.000 title claims description 66
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 56
- 125000001424 substituent group Chemical group 0.000 claims abstract description 55
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 52
- 125000005647 linker group Chemical group 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 316
- 238000002347 injection Methods 0.000 claims description 114
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- 238000000034 method Methods 0.000 claims description 99
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- 230000015572 biosynthetic process Effects 0.000 claims description 67
- 239000000758 substrate Substances 0.000 claims description 24
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- 238000004519 manufacturing process Methods 0.000 claims description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000005286 illumination Methods 0.000 claims description 5
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
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- 125000003118 aryl group Chemical group 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 7
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- YZERDTREOUSUHF-UHFFFAOYSA-N pentafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1F YZERDTREOUSUHF-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229920002545 silicone oil Polymers 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
-
- H01L51/0003—
-
- H01L51/0035—
-
- H01L51/0043—
-
- H01L51/5056—
-
- H01L51/5088—
-
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- 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
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- 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
- H10K85/151—Copolymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
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PCT/JP2014/076459 WO2015050232A1 (ja) | 2013-10-04 | 2014-10-02 | 重合体、有機電界発光素子用組成物、有機電界発光素子、有機el表示装置及び有機el照明 |
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JP6996240B2 (ja) * | 2017-11-10 | 2022-01-17 | 東ソー株式会社 | アリールアミンポリマー、および電荷輸送材料 |
WO2019177175A1 (ja) * | 2018-03-16 | 2019-09-19 | 三菱ケミカル株式会社 | 重合体、有機電界発光素子用組成物、有機電界発光素子、有機el表示装置、有機el照明及び有機電界発光素子の製造方法 |
KR102561759B1 (ko) * | 2018-09-28 | 2023-07-28 | 주식회사 엘지화학 | 신규한 고분자 및 이를 포함하는 유기 발광 소자 |
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KR20210100250A (ko) | 2020-02-05 | 2021-08-17 | 삼성디스플레이 주식회사 | 폴리머를 포함하는 조성물, 이로부터 제조된 중간층 및 이를 포함하는 장치 |
CN112679471B (zh) * | 2020-12-25 | 2022-03-29 | 华南理工大学 | 一种分离有机发光材料中卤代杂质的方法 |
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JP2011506626A (ja) | 2007-11-19 | 2011-03-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電気活性材料 |
WO2012087977A1 (en) | 2010-12-20 | 2012-06-28 | E. I. Du Pont De Nemours And Company | Process and materials for making contained layers and devices made with same |
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US5352906A (en) * | 1993-01-29 | 1994-10-04 | Iowa State University Research Foundation, Inc. | Poly (p-phenyleneneacetylene) light-emitting diodes |
JP2009043896A (ja) * | 2007-08-08 | 2009-02-26 | Canon Inc | 有機発光素子及びディスプレイ |
JP5564801B2 (ja) * | 2008-02-15 | 2014-08-06 | 三菱化学株式会社 | 共役ポリマー、有機電界発光素子材料、有機電界発光素子用組成物、ポリマーの製造方法、有機電界発光素子、有機elディスプレイ、及び有機el照明 |
US8692234B2 (en) * | 2008-04-02 | 2014-04-08 | Mitsubishi Chemical Corporation | Polymer compound, net-like polymer compound produced by crosslinking the polymer compound, composition for organic electroluminescence element, organic electroluminescence element, organic EL display, and organic EL lighting |
JP5491796B2 (ja) * | 2008-08-11 | 2014-05-14 | 三菱化学株式会社 | 電荷輸送性ポリマー、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
WO2010065700A2 (en) * | 2008-12-04 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Electroactive materials |
CN102725350B (zh) | 2009-12-25 | 2014-08-27 | 住友化学株式会社 | 组合物及使用该组合物制造的发光元件 |
JP5710994B2 (ja) | 2010-01-28 | 2015-04-30 | 住友化学株式会社 | 高分子化合物及びそれを用いてなる発光素子 |
TW201204687A (en) * | 2010-06-17 | 2012-02-01 | Du Pont | Electroactive materials |
TW201200975A (en) * | 2010-06-17 | 2012-01-01 | Du Pont | Process and materials for making contained layers and devices made with same |
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JP6565678B2 (ja) | 2019-08-28 |
JPWO2015050232A1 (ja) | 2017-03-09 |
KR20160067847A (ko) | 2016-06-14 |
CN105683255B (zh) | 2018-05-29 |
TW201518340A (zh) | 2015-05-16 |
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