CN106543172A - 有机电子传输材料 - Google Patents
有机电子传输材料 Download PDFInfo
- Publication number
- CN106543172A CN106543172A CN201610937123.7A CN201610937123A CN106543172A CN 106543172 A CN106543172 A CN 106543172A CN 201610937123 A CN201610937123 A CN 201610937123A CN 106543172 A CN106543172 A CN 106543172A
- Authority
- CN
- China
- Prior art keywords
- electron transport
- transport material
- expressed
- organic electron
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000463 material Substances 0.000 title claims abstract description 31
- 239000004065 semiconductor Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 238000006579 Tsuji-Trost allylation reaction Methods 0.000 claims abstract description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- -1 Phenyl Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 230000027756 respiratory electron transport chain Effects 0.000 abstract description 11
- 230000005540 biological transmission Effects 0.000 abstract description 9
- 238000005401 electroluminescence Methods 0.000 abstract description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 30
- 230000005684 electric field Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 0 *c1nc(c2nccc(-c3ccccc3)c2cc2)c2c(-c2ccccc2)c1 Chemical compound *c1nc(c2nccc(-c3ccccc3)c2cc2)c2c(-c2ccccc2)c1 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- JFCUOQFGWGJTER-UHFFFAOYSA-N CC(C1)=Nc2c3nccc(-c(cc4)cc5c4-c4ccccc4C54c5ccccc5C5C=CC=CC45)c3ccc2C1c1ccccc1 Chemical compound CC(C1)=Nc2c3nccc(-c(cc4)cc5c4-c4ccccc4C54c5ccccc5C5C=CC=CC45)c3ccc2C1c1ccccc1 JFCUOQFGWGJTER-UHFFFAOYSA-N 0.000 description 1
- XTXUKZQPYPRYJF-UHFFFAOYSA-N Cc1nc(c2nccc(-c(cccc3)c3-c3ccccc3)c2cc2)c2c(-c2ccccc2-c2ccccc2)c1 Chemical compound Cc1nc(c2nccc(-c(cccc3)c3-c3ccccc3)c2cc2)c2c(-c2ccccc2-c2ccccc2)c1 XTXUKZQPYPRYJF-UHFFFAOYSA-N 0.000 description 1
- MVHMIZMPZCZTNY-UHFFFAOYSA-N Cc1nc(c2nccc(-c3cc(-c4ccccc4)ccc3)c2cc2)c2c(-c2cccc(-c3ccccc3)c2)c1 Chemical compound Cc1nc(c2nccc(-c3cc(-c4ccccc4)ccc3)c2cc2)c2c(-c2cccc(-c3ccccc3)c2)c1 MVHMIZMPZCZTNY-UHFFFAOYSA-N 0.000 description 1
- YNHYUHOHUXYYLR-UHFFFAOYSA-N Cc1nc(c2nccc(-c3cccc4c3cccc4)c2cc2)c2c(-c2ccccc2)c1 Chemical compound Cc1nc(c2nccc(-c3cccc4c3cccc4)c2cc2)c2c(-c2ccccc2)c1 YNHYUHOHUXYYLR-UHFFFAOYSA-N 0.000 description 1
- RQRFVMNYUJWARB-UHFFFAOYSA-N Cc1nc(c2nccc(-c3ccccc3)c2cc2)c2c(-c2cccc3c2cccc3)c1 Chemical compound Cc1nc(c2nccc(-c3ccccc3)c2cc2)c2c(-c2cccc3c2cccc3)c1 RQRFVMNYUJWARB-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001894 space-charge-limited current method Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- 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
-
- 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
- H10K50/16—Electron transporting layers
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
- H10K2102/302—Details of OLEDs of OLED structures
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
峰号 | 保留时间 | 面积 | 高度 | 面积% | 高度% |
1 | 4.042 | 253 | 35 | 0.003 | 0.005 |
2 | 5.310 | 3801 | 408 | 0.047 | 0.062 |
3 | 7.509 | 591 | 80 | 0.007 | 0.012 |
4 | 7.983 | 8109838 | 659953 | 99.533 | 99.575 |
5 | 8.703 | 3336 | 355 | 0.041 | 0.054 |
6 | 9.412 | 1054 | 82 | 0.013 | 0.012 |
7 | 10.481 | 25386 | 1632 | 0.312 | 0.246 |
8 | 11.604 | 3644 | 224 | 0.045 | 0.034 |
总计 | 8147904 | 662769 | 100.000 | 100.000 |
Claims (8)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2015107604045 | 2015-11-10 | ||
CN201510760404 | 2015-11-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106543172A true CN106543172A (zh) | 2017-03-29 |
CN106543172B CN106543172B (zh) | 2019-02-26 |
Family
ID=58392877
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610937123.7A Active CN106543172B (zh) | 2015-11-10 | 2016-10-25 | 有机电子传输材料 |
Country Status (3)
Country | Link |
---|---|
CN (1) | CN106543172B (zh) |
TW (1) | TWI612047B (zh) |
WO (1) | WO2017080445A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018006679A1 (zh) * | 2016-07-08 | 2018-01-11 | 广东阿格蕾雅光电材料有限公司 | 高Tg有机电子传输器件 |
KR20200107855A (ko) * | 2019-03-08 | 2020-09-16 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1097981A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Organic electroluminescent device |
CN1546477A (zh) * | 2003-12-04 | 2004-11-17 | 复旦大学 | 电子传输/空穴阻挡材料及其电致红光器件的制备方法 |
JP2006131782A (ja) * | 2004-11-08 | 2006-05-25 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP2006156635A (ja) * | 2004-11-29 | 2006-06-15 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
CN101076904A (zh) * | 2004-11-24 | 2007-11-21 | 普林斯顿大学理事会 | 具有菲咯啉激子阻挡层的有机光敏光电器件 |
-
2016
- 2016-10-25 CN CN201610937123.7A patent/CN106543172B/zh active Active
- 2016-11-01 TW TW105135394A patent/TWI612047B/zh active
- 2016-11-09 WO PCT/CN2016/105147 patent/WO2017080445A1/zh active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1097981A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Organic electroluminescent device |
CN1546477A (zh) * | 2003-12-04 | 2004-11-17 | 复旦大学 | 电子传输/空穴阻挡材料及其电致红光器件的制备方法 |
JP2006131782A (ja) * | 2004-11-08 | 2006-05-25 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
CN101076904A (zh) * | 2004-11-24 | 2007-11-21 | 普林斯顿大学理事会 | 具有菲咯啉激子阻挡层的有机光敏光电器件 |
JP2006156635A (ja) * | 2004-11-29 | 2006-06-15 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018006679A1 (zh) * | 2016-07-08 | 2018-01-11 | 广东阿格蕾雅光电材料有限公司 | 高Tg有机电子传输器件 |
KR20200107855A (ko) * | 2019-03-08 | 2020-09-16 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102430678B1 (ko) | 2019-03-08 | 2022-08-09 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Also Published As
Publication number | Publication date |
---|---|
TWI612047B (zh) | 2018-01-21 |
CN106543172B (zh) | 2019-02-26 |
WO2017080445A1 (zh) | 2017-05-18 |
TW201716407A (zh) | 2017-05-16 |
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