TW201345877A - 新穎之聯三伸苯衍生物及使用該衍生物的有機電致發光元件 - Google Patents

新穎之聯三伸苯衍生物及使用該衍生物的有機電致發光元件 Download PDF

Info

Publication number: TW201345877A
Authority: TW; Taiwan
Prior art keywords: group; layer; organic; triazine derivative; compound
Prior art date: 2012-04-18

Application number

TW102112352A

Other languages

English (en)

Chinese (zh)

Inventor

Norimasa Yokoyama

Hiroshi Ookuma

Makoto Nagaoka

Daizou Kanda

Shuichi Hayashi

Original Assignee

Hodogaya Chemical Co Ltd

Priority date (The priority date 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 date listed.)

2012-04-18

Filing date

2013-04-08

Publication date

2013-11-16

2013-04-08 Application filed by Hodogaya Chemical Co Ltd filed Critical Hodogaya Chemical Co Ltd

2013-11-16 Publication of TW201345877A publication Critical patent/TW201345877A/zh

Links

125000005580 triphenylene group Chemical group 0.000 title abstract description 12
238000002347 injection Methods 0.000 claims abstract description 29
239000007924 injection Substances 0.000 claims abstract description 29
230000000903 blocking effect Effects 0.000 claims abstract description 26
239000010410 layer Substances 0.000 claims description 125
150000003918 triazines Chemical class 0.000 claims description 40
239000012044 organic layer Substances 0.000 claims description 25
230000005525 hole transport Effects 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 17
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 14
238000005401 electroluminescence Methods 0.000 claims description 9
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 6
125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 57
239000000463 material Substances 0.000 abstract description 46
-1 aromatic tertiary amine Chemical class 0.000 abstract description 32
125000003118 aryl group Chemical group 0.000 abstract description 10
230000002349 favourable effect Effects 0.000 abstract 1
239000010409 thin film Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
239000011799 hole material Substances 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000005160 1H NMR spectroscopy Methods 0.000 description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000000843 powder Substances 0.000 description 12
239000000758 substrate Substances 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
150000001412 amines Chemical class 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 10
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 9
238000005259 measurement Methods 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
238000007740 vapor deposition Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000011521 glass Substances 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
230000001678 irradiating effect Effects 0.000 description 6
125000001302 tertiary amino group Chemical group 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
229910001873 dinitrogen Chemical group 0.000 description 5
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000012046 mixed solvent Substances 0.000 description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000001648 tannin Substances 0.000 description 5
229920001864 tannin Polymers 0.000 description 5
235000018553 tannin Nutrition 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
150000004982 aromatic amines Chemical class 0.000 description 4
150000001716 carbazoles Chemical class 0.000 description 4
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
150000004696 coordination complex Chemical class 0.000 description 4
239000007772 electrode material Substances 0.000 description 4
230000009477 glass transition Effects 0.000 description 4
230000006872 improvement Effects 0.000 description 4
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
238000000034 method Methods 0.000 description 4
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
GEDOYYDMCZUHNW-UHFFFAOYSA-N 2-bromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=CC=C3C2=C1 GEDOYYDMCZUHNW-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
241000208340 Araliaceae Species 0.000 description 3
ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 3
229940126639 Compound 33 Drugs 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 3
235000003140 Panax quinquefolius Nutrition 0.000 description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229940126543 compound 14 Drugs 0.000 description 3
238000006880 cross-coupling reaction Methods 0.000 description 3
239000002019 doping agent Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
235000008434 ginseng Nutrition 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229960005181 morphine Drugs 0.000 description 3
239000002861 polymer material Substances 0.000 description 3
125000001725 pyrenyl group Chemical group 0.000 description 3
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
229910052707 ruthenium Inorganic materials 0.000 description 3
239000002356 single layer Substances 0.000 description 3
ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000005259 triarylamine group Chemical group 0.000 description 3
PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 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 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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 2
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 2
ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000001454 anthracenes Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
238000000576 coating method Methods 0.000 description 2
125000006612 decyloxy group Chemical group 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical group C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
150000002429 hydrazines Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
239000011368 organic material Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
150000004032 porphyrins Chemical group 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
230000006798 recombination Effects 0.000 description 2
238000005215 recombination Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000005504 styryl group Chemical group 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
125000006617 triphenylamine group Chemical group 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
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 1
GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
IIQNQNSTGCPKQM-UHFFFAOYSA-N 2-bromo-1H-triazine Chemical compound BrN1NC=CC=N1 IIQNQNSTGCPKQM-UHFFFAOYSA-N 0.000 description 1
AVWYETCDUMCCNK-UHFFFAOYSA-N 2-dibenzofuran-4-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC2=C1OC1=CC=CC=C12 AVWYETCDUMCCNK-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QKWORTBZGYIMOM-UHFFFAOYSA-N 9-(2-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 QKWORTBZGYIMOM-UHFFFAOYSA-N 0.000 description 1
FOUNKDBOYUMWNP-UHFFFAOYSA-N 9-[4-[2-(4-carbazol-9-ylphenyl)-2-adamantyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C(C2)CC3CC1CC2C3 FOUNKDBOYUMWNP-UHFFFAOYSA-N 0.000 description 1
JTCLSJGCRPXRKY-UHFFFAOYSA-N 9-[4-[9-(4-carbazol-9-ylphenyl)-10H-anthracen-9-yl]phenyl]carbazole Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C1=CC=C(C=C1)C1(C2=CC=CC=C2CC=2C=CC=CC1=2)C1=CC=C(C=C1)N1C2=CC=CC=C2C=2C=CC=CC1=2 JTCLSJGCRPXRKY-UHFFFAOYSA-N 0.000 description 1
229910001316 Ag alloy Inorganic materials 0.000 description 1
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
238000007125 Buchwald synthesis reaction Methods 0.000 description 1
LGNMSIIZODGYIR-UHFFFAOYSA-N C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Yb] Chemical compound C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Yb] LGNMSIIZODGYIR-UHFFFAOYSA-N 0.000 description 1
ZISFUHGNPJDQSJ-UHFFFAOYSA-N CC(C)(C)C1=CC=C(C=C1)C1=CC=C(NC2=CC=C(C=C2)C2=CC=CC=C2)C=C1 Chemical compound CC(C)(C)C1=CC=C(C=C1)C1=CC=C(NC2=CC=C(C=C2)C2=CC=CC=C2)C=C1 ZISFUHGNPJDQSJ-UHFFFAOYSA-N 0.000 description 1
241000284156 Clerodendrum quadriloculare Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
229910000846 In alloy Inorganic materials 0.000 description 1
229910000861 Mg alloy Inorganic materials 0.000 description 1
229920000265 Polyparaphenylene Polymers 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000006069 Suzuki reaction reaction Methods 0.000 description 1
SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
MSWAMBBAEMLQPW-UHFFFAOYSA-N [Al+3].C1(=CC=CC=C1)C1=C(C=CC=C1)O Chemical compound [Al+3].C1(=CC=CC=C1)C1=C(C=CC=C1)O MSWAMBBAEMLQPW-UHFFFAOYSA-N 0.000 description 1
JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
125000005427 anthranyl group Chemical group 0.000 description 1
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 description 1
125000002102 aryl alkyloxo group Chemical group 0.000 description 1
125000003609 aryl vinyl group Chemical group 0.000 description 1
150000007980 azole derivatives Chemical class 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
150000001562 benzopyrans Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
229910052614 beryl Inorganic materials 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000010549 co-Evaporation Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
238000010030 laminating Methods 0.000 description 1
239000004973 liquid crystal related substance Substances 0.000 description 1
ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
229910001635 magnesium fluoride Inorganic materials 0.000 description 1
SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
SGDMQXAOPGGMAH-UHFFFAOYSA-N phenol;thiophene Chemical compound C=1C=CSC=1.OC1=CC=CC=C1 SGDMQXAOPGGMAH-UHFFFAOYSA-N 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
239000000047 product Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000012827 research and development Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
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
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
VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000003967 siloles Chemical class 0.000 description 1
SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000004528 spin coating Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
150000007979 thiazole derivatives Chemical class 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000013638 trimer Substances 0.000 description 1
DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- 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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- 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
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—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
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
- C07D333/76—Dibenzothiophenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
- 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
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
- 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)
Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Electroluminescent Light Sources (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW102112352A 2012-04-18 2013-04-08 新穎之聯三伸苯衍生物及使用該衍生物的有機電致發光元件 TW201345877A (zh)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2012094329A JP2015155378A (ja)	2012-04-18	2012-04-18	トリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子

Publications (1)

Publication Number	Publication Date
TW201345877A true TW201345877A (zh)	2013-11-16

Family

ID=49383332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW102112352A TW201345877A (zh)	2012-04-18	2013-04-08	新穎之聯三伸苯衍生物及使用該衍生物的有機電致發光元件

Country Status (3)

Country	Link
JP (1)	JP2015155378A (fr)
TW (1)	TW201345877A (fr)
WO (1)	WO2013157367A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN107922402A (zh) *	2015-08-14	2018-04-17	默克专利有限公司	用于有机电致发光器件的吩噁嗪衍生物

Families Citing this family (85)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102012011335A1 (de)	2012-06-06	2013-12-12	Merck Patent Gmbh	Verbindungen für Organische Elekronische Vorrichtungen
US9929361B2 (en)	2015-02-16	2018-03-27	Universal Display Corporation	Organic electroluminescent materials and devices
US9812649B2 (en) *	2015-02-17	2017-11-07	Luminescence Technology Corp.	Indenotriphenylene-based amine derivative for organic electroluminescent device
US11056657B2 (en)	2015-02-27	2021-07-06	University Display Corporation	Organic electroluminescent materials and devices
US9859510B2 (en)	2015-05-15	2018-01-02	Universal Display Corporation	Organic electroluminescent materials and devices
US10418568B2 (en)	2015-06-01	2019-09-17	Universal Display Corporation	Organic electroluminescent materials and devices
US11127905B2 (en)	2015-07-29	2021-09-21	Universal Display Corporation	Organic electroluminescent materials and devices
US10672996B2 (en)	2015-09-03	2020-06-02	Universal Display Corporation	Organic electroluminescent materials and devices
EP3336077B1 (fr) *	2015-09-25	2019-09-11	LG Chem, Ltd.	Composé à base d'amine et élément électroluminescent organique comprenant celui-ci
US20170229663A1 (en)	2016-02-09	2017-08-10	Universal Display Corporation	Organic electroluminescent materials and devices
US10236456B2 (en)	2016-04-11	2019-03-19	Universal Display Corporation	Organic electroluminescent materials and devices
US10862054B2 (en)	2016-06-20	2020-12-08	Universal Display Corporation	Organic electroluminescent materials and devices
US10672997B2 (en)	2016-06-20	2020-06-02	Universal Display Corporation	Organic electroluminescent materials and devices
US11482683B2 (en)	2016-06-20	2022-10-25	Universal Display Corporation	Organic electroluminescent materials and devices
US10608186B2 (en)	2016-09-14	2020-03-31	Universal Display Corporation	Organic electroluminescent materials and devices
US10680187B2 (en)	2016-09-23	2020-06-09	Universal Display Corporation	Organic electroluminescent materials and devices
US11196010B2 (en)	2016-10-03	2021-12-07	Universal Display Corporation	Organic electroluminescent materials and devices
US11011709B2 (en)	2016-10-07	2021-05-18	Universal Display Corporation	Organic electroluminescent materials and devices
US12317745B2 (en)	2016-11-09	2025-05-27	Universal Display Corporation	Organic electroluminescent materials and devices
KR102111149B1 (ko) *	2016-11-11	2020-05-14	주식회사 엘지화학	유기 발광 소자
US10680188B2 (en)	2016-11-11	2020-06-09	Universal Display Corporation	Organic electroluminescent materials and devices
US11780865B2 (en)	2017-01-09	2023-10-10	Universal Display Corporation	Organic electroluminescent materials and devices
US10844085B2 (en)	2017-03-29	2020-11-24	Universal Display Corporation	Organic electroluminescent materials and devices
US10944060B2 (en)	2017-05-11	2021-03-09	Universal Display Corporation	Organic electroluminescent materials and devices
US12098157B2 (en)	2017-06-23	2024-09-24	Universal Display Corporation	Organic electroluminescent materials and devices
US11228010B2 (en)	2017-07-26	2022-01-18	Universal Display Corporation	Organic electroluminescent materials and devices
US11744142B2 (en)	2017-08-10	2023-08-29	Universal Display Corporation	Organic electroluminescent materials and devices
JP7234532B2 (ja) *	2017-08-18	2023-03-08	東ソー株式会社	ジベンゾ［ｇ，ｐ］クリセン化合物
US12180230B2 (en)	2017-11-28	2024-12-31	University Of Southern California	Carbene compounds and organic electroluminescent devices
EP3492480B1 (fr)	2017-11-29	2021-10-20	Universal Display Corporation	Matériaux et dispositifs électroluminescents organiques
US11937503B2 (en)	2017-11-30	2024-03-19	Universal Display Corporation	Organic electroluminescent materials and devices
US11542289B2 (en)	2018-01-26	2023-01-03	Universal Display Corporation	Organic electroluminescent materials and devices
US11165028B2 (en)	2018-03-12	2021-11-02	Universal Display Corporation	Organic electroluminescent materials and devices
KR102227046B1 (ko) *	2018-06-14	2021-03-12	주식회사 엘지화학	화합물 및 이를 포함하는 유기 발광 소자
JP7143670B2 (ja) *	2018-08-03	2022-09-29	東ソー株式会社	トリフェニレン化合物及びその用途
US12453279B2 (en)	2018-08-22	2025-10-21	Universal Display Corporation	Organic electroluminescent materials and devices
CN109293516B (zh) *	2018-11-03	2022-01-14	长春海谱润斯科技股份有限公司	一种三芳胺类化合物及其有机发光器件
US11737349B2 (en)	2018-12-12	2023-08-22	Universal Display Corporation	Organic electroluminescent materials and devices
US11780829B2 (en)	2019-01-30	2023-10-10	The University Of Southern California	Organic electroluminescent materials and devices
US12477890B2 (en)	2019-02-01	2025-11-18	Universal Display Corporation	Organic electroluminescent materials and devices
JP2020158491A (ja)	2019-03-26	2020-10-01	ユニバーサルディスプレイコーポレイション	有機エレクトロルミネセンス材料及びデバイス
US12281128B2 (en)	2019-07-30	2025-04-22	Universal Display Corporation	Organic electroluminescent materials and devices
US12139501B2 (en)	2019-08-16	2024-11-12	Universal Display Corporation	Organic electroluminescent materials and devices
US20210135130A1 (en)	2019-11-04	2021-05-06	Universal Display Corporation	Organic electroluminescent materials and devices
US12538698B2 (en)	2020-01-06	2026-01-27	Universal Display Corporation	Organic electroluminescent materials and devices
US12426495B2 (en)	2020-01-28	2025-09-23	Universal Display Corporation	Organic electroluminescent materials and devices
JP7721110B2 (ja) *	2020-04-27	2025-08-12	国立大学法人電気通信大学	固体蓄光材料
EP3937268B1 (fr)	2020-07-10	2025-05-07	Universal Display Corporation	Delo plasmoniques et émetteurs à dipôle vertical
US12187748B2 (en)	2020-11-02	2025-01-07	Universal Display Corporation	Organic electroluminescent materials and devices
US20220158096A1 (en)	2020-11-16	2022-05-19	Universal Display Corporation	Organic electroluminescent materials and devices
US20220165967A1 (en)	2020-11-24	2022-05-26	Universal Display Corporation	Organic electroluminescent materials and devices
US12325717B2 (en)	2020-11-24	2025-06-10	Universal Display Corporation	Organic electroluminescent materials and devices
US12575316B2 (en)	2021-02-03	2026-03-10	Universal Display Corporation	Organic electroluminescent materials and devices
EP4060758A3 (fr)	2021-02-26	2023-03-29	Universal Display Corporation	Matériaux et dispositifs électroluminescents organiques
EP4723858A2 (fr)	2021-02-26	2026-04-08	Universal Display Corporation	Matériaux électroluminescents organiques et dispositifs
US12606582B2 (en)	2021-03-05	2026-04-21	Universal Display Corporation	Organic electroluminescent materials and devices
US12428599B2 (en)	2021-03-09	2025-09-30	Universal Display Corporation	Organic electroluminescent materials and devices
US20220298190A1 (en)	2021-03-12	2022-09-22	Universal Display Corporation	Organic electroluminescent materials and devices
US12421262B2 (en)	2021-03-15	2025-09-23	Universal Display Corporation	Organic electroluminescent materials and devices
US20220340607A1 (en)	2021-04-05	2022-10-27	Universal Display Corporation	Organic electroluminescent materials and devices
US12480042B2 (en)	2021-04-09	2025-11-25	Universal Display Corporation	Organic electroluminescent materials and devices
EP4075531A1 (fr)	2021-04-13	2022-10-19	Universal Display Corporation	Delo plasmoniques et émetteurs à dipôle vertical
US20220352478A1 (en)	2021-04-14	2022-11-03	Universal Display Corporation	Organic eletroluminescent materials and devices
US20220407020A1 (en)	2021-04-23	2022-12-22	Universal Display Corporation	Organic electroluminescent materials and devices
US20230006149A1 (en)	2021-04-23	2023-01-05	Universal Display Corporation	Organic electroluminescent materials and devices
US20230133787A1 (en)	2021-06-08	2023-05-04	University Of Southern California	Molecular Alignment of Homoleptic Iridium Phosphors
US12550611B2 (en)	2021-08-03	2026-02-10	Universal Display Corporation	Organic electroluminescent materials and devices
EP4151699A1 (fr)	2021-09-17	2023-03-22	Universal Display Corporation	Matériaux et dispositifs électroluminescents organiques
US12473318B2 (en)	2021-10-08	2025-11-18	Universal Display Corporation	Organic electroluminescent materials and devices
US12509628B2 (en)	2021-12-16	2025-12-30	Universal Display Corporation	Organic electroluminescent materials and devices
EP4231804A3 (fr)	2022-02-16	2023-09-20	Universal Display Corporation	Matériaux et dispositifs électroluminescents organiques
US20230292592A1 (en)	2022-03-09	2023-09-14	Universal Display Corporation	Organic electroluminescent materials and devices
US20230337516A1 (en)	2022-04-18	2023-10-19	Universal Display Corporation	Organic electroluminescent materials and devices
US20230389421A1 (en)	2022-05-24	2023-11-30	Universal Display Corporation	Organic electroluminescent materials and devices
EP4293001A1 (fr)	2022-06-08	2023-12-20	Universal Display Corporation	Matériaux électroluminescents organiques et dispositifs
US20240016051A1 (en)	2022-06-28	2024-01-11	Universal Display Corporation	Organic electroluminescent materials and devices
US20240107880A1 (en)	2022-08-17	2024-03-28	Universal Display Corporation	Organic electroluminescent materials and devices
US20240188316A1 (en)	2022-10-27	2024-06-06	Universal Display Corporation	Organic electroluminescent materials and devices
US20240196730A1 (en)	2022-10-27	2024-06-13	Universal Display Corporation	Organic electroluminescent materials and devices
US20240188419A1 (en)	2022-10-27	2024-06-06	Universal Display Corporation	Organic electroluminescent materials and devices
US20240188319A1 (en)	2022-10-27	2024-06-06	Universal Display Corporation	Organic electroluminescent materials and devices
US20240180025A1 (en)	2022-10-27	2024-05-30	Universal Display Corporation	Organic electroluminescent materials and devices
US20240247017A1 (en)	2022-12-14	2024-07-25	Universal Display Corporation	Organic electroluminescent materials and devices
US20250204238A1 (en)	2023-12-15	2025-06-19	Universal Display Corporation	Organic electroluminscent materials and devices
US20250204239A1 (en)	2023-12-15	2025-06-19	Universal Display Corporation	Organic electroluminescent materials and devices

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2205499A (en) *	1997-12-31	1999-07-19	Incyte Pharmaceuticals, Inc.	Human regulatory proteins
JP4703139B2 (ja) *	2003-08-04	2011-06-15	富士フイルム株式会社	有機電界発光素子
JP2006143845A (ja) *	2004-11-18	2006-06-08	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
KR101311935B1 (ko) *	2010-04-23	2013-09-26	제일모직주식회사	유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20110122051A (ko) *	2010-05-03	2011-11-09	제일모직주식회사	유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR101815908B1 (ko) *	2010-07-19	2018-01-09	에스에프씨 주식회사	피리딘 유도체 및 이를 포함하는 유기전계발광소자
US20120199820A1 (en) *	2010-08-05	2012-08-09	Idemitsu Kosan Co., Ltd.	Monoamine derivative and organic electroluminescent element using same
DE112010005815B4 (de) *	2010-08-20	2020-12-10	Universal Display Corp.	Bicarbazolverbindungen für OLEDs
US8932734B2 (en) *	2010-10-08	2015-01-13	Universal Display Corporation	Organic electroluminescent materials and devices

2012
- 2012-04-18 JP JP2012094329A patent/JP2015155378A/ja active Pending
2013
- 2013-03-27 WO PCT/JP2013/058998 patent/WO2013157367A1/fr not_active Ceased
- 2013-04-08 TW TW102112352A patent/TW201345877A/zh unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN107922402A (zh) *	2015-08-14	2018-04-17	默克专利有限公司	用于有机电致发光器件的吩噁嗪衍生物
TWI721001B (zh) *	2015-08-14	2021-03-11	德商麥克專利有限公司	用於有機電致發光裝置之材料

Also Published As

Publication number	Publication date
WO2013157367A1 (fr)	2013-10-24
JP2015155378A (ja)	2015-08-27

Publication	Publication Date	Title
TWI551602B (zh)	2016-10-01	具有吲哚并咔唑環結構之化合物及有機電致發光元件
TW201345877A (zh)	2013-11-16	新穎之聯三伸苯衍生物及使用該衍生物的有機電致發光元件
TWI646097B (zh)	2019-01-01	具有氮雜茀環結構之螺化合物、發光材料及有機電致發光元件
TWI469966B (zh)	2015-01-21	具有咔唑環構造的化合物及有機電致發光元件
TWI699350B (zh)	2020-07-21	有機電致發光元件
TWI502048B (zh)	2015-10-01	具有９，１０－二氫吖啶環構造的化合物及有機電致發光元件
TWI620735B (zh)	2018-04-11	茚并吲哚衍生物及有機電致發光元件
TWI721990B (zh)	2021-03-21	芳胺化合物及有機電致發光元件
JP6814156B2 (ja)	2021-01-13	有機エレクトロルミネッセンス素子
TWI537253B (zh)	2016-06-11	具有吖啶滿環結構之化合物及有機電致發光元件
TW201323378A (zh)	2013-06-16	新穎之聯三伸苯衍生物及使用該衍生物之有機電致發光元件
TW201418260A (zh)	2014-05-16	新穎之苯并噻吩并吲哚衍生物及使用該衍生物之有機電致發光元件
TW201412719A (zh)	2014-04-01	具有吖啶滿環結構之化合物及有機電致發光元件
TWI627172B (zh)	2018-06-21	新穎之嘧啶衍生物及有機電致發光元件
TWI741047B (zh)	2021-10-01	有機電致發光元件
TWI637038B (zh)	2018-10-01	二咔唑衍生物及有機電致發光元件
TWI622590B (zh)	2018-05-01	苯并吡啶并吲哚衍生物及有機電致發光元件
TWI822914B (zh)	2023-11-21	唑環構造之化合物及有機電致發光元件
TW202140748A (zh)	2021-11-01	有機電致發光元件
CN103328475A (zh)	2013-09-25	具有被取代的联吡啶基和吡啶并吲哚环结构的化合物以及有机电致发光器件
TW201418259A (zh)	2014-05-16	新穎之噻吩并吲哚衍生物及使用該衍生物之有機電致發光元件
TW201434819A (zh)	2014-09-16	具有茚并吖啶滿環結構之化合物以及有機電致發光元件
TWI598340B (zh)	2017-09-11	具有吖啶滿環結構之化合物及有機電致發光元件
TW201538505A (zh)	2015-10-16	苯并呋喃并吲哚衍生物及有機電致發光元件
TW201429951A (zh)	2014-08-01	具有菲并吖啶滿環結構之化合物及有機電致發光元件