CN107698570A - 化合物及其有机电子装置 - Google Patents
化合物及其有机电子装置 Download PDFInfo
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- CN107698570A CN107698570A CN201710674244.1A CN201710674244A CN107698570A CN 107698570 A CN107698570 A CN 107698570A CN 201710674244 A CN201710674244 A CN 201710674244A CN 107698570 A CN107698570 A CN 107698570A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000002541 furyl group Chemical group 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 154
- 229910052799 carbon Inorganic materials 0.000 claims description 154
- 239000010410 layer Substances 0.000 claims description 100
- -1 D-atom Chemical group 0.000 claims description 31
- 125000000524 functional group Chemical group 0.000 claims description 29
- 239000012044 organic layer Substances 0.000 claims description 21
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- 230000027756 respiratory electron transport chain Effects 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000000707 boryl group Chemical group B* 0.000 claims description 15
- 230000004888 barrier function Effects 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
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- HQUYYJLLBHWCML-UHFFFAOYSA-N N#CC#N.[C] Chemical compound N#CC#N.[C] HQUYYJLLBHWCML-UHFFFAOYSA-N 0.000 claims 2
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- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
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- 239000003446 ligand Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical class BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
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- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
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- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
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- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
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- SKKKJNPBIGQNEJ-UHFFFAOYSA-N 9h-fluorene-1,9-diamine Chemical group C1=CC(N)=C2C(N)C3=CC=CC=C3C2=C1 SKKKJNPBIGQNEJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
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- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
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- FHFJGNMPGCZWCW-UHFFFAOYSA-N 5,14-dibromotricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-one Chemical compound Brc1ccc2ccc3ccc(Br)cc3c(=O)c2c1 FHFJGNMPGCZWCW-UHFFFAOYSA-N 0.000 description 1
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- RUQICFLRSLDXDP-UHFFFAOYSA-N 9-naphthalen-2-yl-10-(4-naphthalen-1-ylphenyl)anthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=2C3=CC=CC=C3C=CC=2)C=C1 RUQICFLRSLDXDP-UHFFFAOYSA-N 0.000 description 1
- NVFINOHFZXRPAD-UHFFFAOYSA-N 9h-fluorene-1,2-diamine Chemical class C1=CC=C2CC3=C(N)C(N)=CC=C3C2=C1 NVFINOHFZXRPAD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
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- C07C255/00—Carboxylic acid nitriles
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- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
Description
Claims (18)
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CN110563662A (zh) * | 2018-06-05 | 2019-12-13 | 上海嵘彩光电材料有限公司 | 化合物及其有机电子装置 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103833507A (zh) * | 2013-12-25 | 2014-06-04 | 石家庄诚志永华显示材料有限公司 | 一系列有机电致发光材料及其制备方法与应用 |
CN103936720A (zh) * | 2013-12-12 | 2014-07-23 | 石家庄诚志永华显示材料有限公司 | 含有螺芴结构单元的化合物及其制备方法与应用 |
KR20150065225A (ko) * | 2013-12-04 | 2015-06-15 | 한국화학연구원 | 내재적 마이크로 기공성 폴리아릴렌에테르계 공중합체, 이의 제조방법 및 이를 이용한 기체 분리막 |
CN105646367A (zh) * | 2014-10-15 | 2016-06-08 | 彩丰精技股份有限公司 | 以顺式二苯乙烯/芴螺旋体衍生的双极型化合物 |
CN105778891A (zh) * | 2016-03-11 | 2016-07-20 | 中节能万润股份有限公司 | 有机光电材料、其制备方法以及包括该有机材料的有机电致发光器件 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6229012B1 (en) * | 1998-10-01 | 2001-05-08 | Xerox Corporation | Triazine compositions |
JP2010024149A (ja) | 2008-07-16 | 2010-02-04 | Toyo Ink Mfg Co Ltd | 7員環構造を有する化合物およびその用途 |
KR101161290B1 (ko) * | 2009-10-16 | 2012-07-02 | 에스에프씨 주식회사 | 축합방향족화합물 및 이를 이용한 유기전계발광소자 |
KR101531612B1 (ko) * | 2010-12-02 | 2015-06-25 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR101996651B1 (ko) | 2011-02-14 | 2019-07-04 | 에스에프씨 주식회사 | 플루오렌 유도체 및 이를 포함하는 유기전계발광소자 |
KR20120110347A (ko) * | 2011-03-29 | 2012-10-10 | 현대제철 주식회사 | 강판 제조방법 |
KR102004385B1 (ko) * | 2011-04-01 | 2019-07-26 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
KR101923936B1 (ko) | 2011-04-29 | 2018-11-30 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
US8735528B1 (en) * | 2011-09-20 | 2014-05-27 | The United States Of America As Represented By The Secretary Of The Air Force | Two-photon absorbing cross-linked polyurethanes containing diphenylamino-dialkylfluorene-1,3,5-triazine units |
US8318888B1 (en) * | 2011-09-20 | 2012-11-27 | The United States Of America As Represented By The Secretary Of The Air Force | Two-photon absorbing cross-linked polyurethanes containing delphenylamino-dialkyffluorene-1,3,5-triazine units |
KR101497134B1 (ko) * | 2011-12-29 | 2015-03-02 | 제일모직 주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
KR102013400B1 (ko) | 2012-03-29 | 2019-08-22 | 에스에프씨 주식회사 | 인데노페난트렌 유도체 및 이를 포함하는 유기전계발광소자 |
KR20120135501A (ko) | 2012-10-29 | 2012-12-14 | 에스에프씨 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102182270B1 (ko) * | 2013-02-21 | 2020-11-24 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
TWI466849B (zh) * | 2013-04-17 | 2015-01-01 | Nat Univ Tsing Hua | 用於有機發光二極體的光電材料及使用該光電材料的有機發光二極體元件 |
CN105829292A (zh) * | 2013-12-19 | 2016-08-03 | 默克专利有限公司 | 杂环螺环化合物 |
WO2015142036A1 (en) * | 2014-03-17 | 2015-09-24 | Rohm And Haas Electronic Materials Korea Ltd. | Electron buffering material and organic electroluminescent device comprising the same |
KR102240004B1 (ko) * | 2014-03-31 | 2021-04-14 | 에스에프씨주식회사 | 신규한 방향족 유기발광 화합물 및 이를 포함하는 유기 발광 소자 |
WO2015194839A1 (en) * | 2014-06-17 | 2015-12-23 | Rohm And Haas Electronic Materials Korea Ltd. | Electron buffering material and organic electroluminescent device |
JP6556764B2 (ja) * | 2014-06-25 | 2019-08-07 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
TWI558688B (zh) * | 2014-10-15 | 2016-11-21 | 彩豐精技股份有限公司 | 順式二苯乙烯/芴螺旋體衍生的光電材料 |
TWI572591B (zh) | 2014-10-15 | 2017-03-01 | 彩豐精技股份有限公司 | 有機發光二極體及其太陽能電池載子傳輸層 |
US10224492B2 (en) * | 2014-12-22 | 2019-03-05 | Merck Patent Gmbh | Materials for electronic devices |
US10217947B2 (en) * | 2015-08-04 | 2019-02-26 | Nichem Fine Technology Co., Ltd. | Organic compound and electronic device using same |
CN106432078B (zh) * | 2015-08-04 | 2019-05-24 | 彩丰精技股份有限公司 | 化合物及使用其的有机电子装置 |
US10211410B2 (en) * | 2015-08-04 | 2019-02-19 | Nichem Fine Technology Co., Ltd | Organic compound and electronic device using same |
CN105481811B (zh) * | 2015-12-18 | 2018-01-16 | 上海道亦化工科技有限公司 | 一种具有螺结构的化合物及其有机电致发光器件 |
US10312459B2 (en) * | 2016-01-27 | 2019-06-04 | Nichem Fine Technology Co., Ltd. | Compound and organic electronic device using the same |
CN106467740B (zh) | 2016-06-13 | 2019-05-14 | 江苏三月光电科技有限公司 | 一种有机电致荧光化合物及其在电致发光器件中的应用 |
TW201835014A (zh) * | 2017-03-24 | 2018-10-01 | 傑秀有限公司 | 順式二苯乙烯/芴螺旋體衍生物材料以及有機發光二極體元件 |
TW201837012A (zh) * | 2017-04-13 | 2018-10-16 | 傑秀有限公司 | 順式二苯乙烯/芴螺旋體衍生物材料以及有機發光二極體元件 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150065225A (ko) * | 2013-12-04 | 2015-06-15 | 한국화학연구원 | 내재적 마이크로 기공성 폴리아릴렌에테르계 공중합체, 이의 제조방법 및 이를 이용한 기체 분리막 |
CN103936720A (zh) * | 2013-12-12 | 2014-07-23 | 石家庄诚志永华显示材料有限公司 | 含有螺芴结构单元的化合物及其制备方法与应用 |
CN103833507A (zh) * | 2013-12-25 | 2014-06-04 | 石家庄诚志永华显示材料有限公司 | 一系列有机电致发光材料及其制备方法与应用 |
CN105646367A (zh) * | 2014-10-15 | 2016-06-08 | 彩丰精技股份有限公司 | 以顺式二苯乙烯/芴螺旋体衍生的双极型化合物 |
CN105778891A (zh) * | 2016-03-11 | 2016-07-20 | 中节能万润股份有限公司 | 有机光电材料、其制备方法以及包括该有机材料的有机电致发光器件 |
Non-Patent Citations (1)
Title |
---|
WEI Y,等: "Emission mechanism of doubly ortho-linked quinoxaline/diphenylfluorene or cis-stilbene/fluorene hybrid compounds based on the transient absorption and emission measurements during pulse radiolysis.", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110563662A (zh) * | 2018-06-05 | 2019-12-13 | 上海嵘彩光电材料有限公司 | 化合物及其有机电子装置 |
CN110571338A (zh) * | 2018-06-05 | 2019-12-13 | 上海嵘彩光电材料有限公司 | 用于有机电子装置的组合物及使用其的有机电子装置 |
CN110563707A (zh) * | 2018-06-05 | 2019-12-13 | 上海嵘彩光电材料有限公司 | 新颖化合物及使用其的有机电子装置 |
CN110571338B (zh) * | 2018-06-05 | 2022-03-04 | 上海嵘彩光电材料有限公司 | 用于有机电子装置的组合物及使用其的有机电子装置 |
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CN107698531A (zh) | 2018-02-16 |
US10693075B2 (en) | 2020-06-23 |
TWI644911B (zh) | 2018-12-21 |
KR101956660B1 (ko) | 2019-03-11 |
JP2018058823A (ja) | 2018-04-12 |
JP6498243B2 (ja) | 2019-04-10 |
US20180047918A1 (en) | 2018-02-15 |
US10454039B2 (en) | 2019-10-22 |
KR20180018380A (ko) | 2018-02-21 |
TW201811774A (zh) | 2018-04-01 |
CN107698531B (zh) | 2022-08-19 |
JP2018052919A (ja) | 2018-04-05 |
JP6475795B2 (ja) | 2019-02-27 |
KR101963675B1 (ko) | 2019-03-29 |
KR20180018381A (ko) | 2018-02-21 |
TWI644884B (zh) | 2018-12-21 |
TW201811719A (zh) | 2018-04-01 |
US20180047907A1 (en) | 2018-02-15 |
CN107698570B (zh) | 2021-02-23 |
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