CN104662010B - 芳香族胺衍生物以及使用其的有机电致发光元件 - Google Patents
芳香族胺衍生物以及使用其的有机电致发光元件 Download PDFInfo
- Publication number
- CN104662010B CN104662010B CN201380045222.9A CN201380045222A CN104662010B CN 104662010 B CN104662010 B CN 104662010B CN 201380045222 A CN201380045222 A CN 201380045222A CN 104662010 B CN104662010 B CN 104662010B
- Authority
- CN
- China
- Prior art keywords
- aromatic amine
- layer
- amine derivative
- formula
- group
- 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.)
- Active
Links
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 57
- -1 dibenzofuranyl Chemical group 0.000 claims abstract description 57
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 8
- 230000005540 biological transmission Effects 0.000 claims description 28
- 239000007924 injection Substances 0.000 claims description 27
- 238000002347 injection Methods 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000010408 film Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052738 indium Inorganic materials 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 22
- 125000000217 alkyl group Chemical group 0.000 abstract description 17
- 239000000470 constituent Substances 0.000 abstract 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 117
- 229910052799 carbon Inorganic materials 0.000 description 81
- 239000000463 material Substances 0.000 description 72
- 239000000543 intermediate Substances 0.000 description 58
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 44
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 29
- 150000001721 carbon Chemical class 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 238000000434 field desorption mass spectrometry Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 230000004888 barrier function Effects 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 150000004826 dibenzofurans Chemical group 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000004411 aluminium Substances 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 239000004327 boric acid Substances 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 238000002386 leaching Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 230000005684 electric field Effects 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- 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 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 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 4
- 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 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical group C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical group C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- 241000720974 Protium Species 0.000 description 2
- 239000005864 Sulphur Chemical group 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003613 toluenes Chemical class 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- YGLVWOUNCXBPJF-UHFFFAOYSA-N (2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene Chemical compound C1=CC=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YGLVWOUNCXBPJF-UHFFFAOYSA-N 0.000 description 1
- JCXLYAWYOTYWKM-UHFFFAOYSA-N (2,3,4-triphenylcyclopenta-1,3-dien-1-yl)benzene Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCXLYAWYOTYWKM-UHFFFAOYSA-N 0.000 description 1
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical class OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- 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 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- RLIPQCDHACHPJW-UHFFFAOYSA-N 2,3,4-trimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1C RLIPQCDHACHPJW-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical class O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- ZNGOZTGLIVGMQC-UHFFFAOYSA-N 9-methyl-9-phenylfluorene Chemical class C12=CC=CC=C2C2=CC=CC=C2C1(C)C1=CC=CC=C1 ZNGOZTGLIVGMQC-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910017083 AlN Inorganic materials 0.000 description 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101000679365 Homo sapiens Putative tyrosine-protein phosphatase TPTE Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 102100022578 Putative tyrosine-protein phosphatase TPTE Human genes 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 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
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- WOIHABYNKOEWFG-UHFFFAOYSA-N [Sr].[Ba] Chemical compound [Sr].[Ba] WOIHABYNKOEWFG-UHFFFAOYSA-N 0.000 description 1
- LBGCRGLFTKVXDZ-UHFFFAOYSA-M ac1mc2aw Chemical compound [Al+3].[Cl-].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LBGCRGLFTKVXDZ-UHFFFAOYSA-M 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 229920002892 amber Polymers 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N caesium oxide Chemical compound [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 229910001942 caesium oxide Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- CUIWZLHUNCCYBL-UHFFFAOYSA-N decacyclene Chemical compound C12=C([C]34)C=CC=C4C=CC=C3C2=C2C(=C34)C=C[CH]C4=CC=CC3=C2C2=C1C1=CC=CC3=CC=CC2=C31 CUIWZLHUNCCYBL-UHFFFAOYSA-N 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
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 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
- 239000000395 magnesium oxide Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- JACPFCQFVIAGDN-UHFFFAOYSA-M sipc iv Chemical compound [OH-].[Si+4].CN(C)CCC[Si](C)(C)[O-].C=1C=CC=C(C(N=C2[N-]C(C3=CC=CC=C32)=N2)=N3)C=1C3=CC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 JACPFCQFVIAGDN-UHFFFAOYSA-M 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 230000008093 supporting effect Effects 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—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
-
- 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
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
-
- 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
- H10K85/649—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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
-
- 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
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
- H10K50/15—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
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- 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
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/81—Anodes
-
- 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
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/82—Cathodes
-
- 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
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/82—Cathodes
- H10K50/826—Multilayers, e.g. opaque multilayers
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
下式(1)表示的芳香族胺衍生物作为有机EL元件的构成成分是有用的,实现即使低电压驱动效率也高,且寿命长的有机EL元件。(式中,HAr1为二苯并呋喃基或二苯并噻吩基,Ar2是烷基、芳基或杂环基等,L1~L3分别独立地是单键或亚苯基)。
Description
技术领域
本发明涉及芳香族胺衍生物以及使用其的有机电致发光元件。例如,涉及具有三亚苯骨架以及二苯并呋喃骨架和二苯并噻吩骨架的一者或两者的芳香族胺衍生物以及使用其的有机电致发光元件。
背景技术
一般有机电致发光(EL)元件由阳极、阴极和夹在阳极和阴极之间的1层以上有机薄膜层构成。如果在两电极间施加电压,则电子由阴极侧、空穴由阳极侧注入发光区域,所注入的电子和空穴在发光区域再结合,形成激发状态,激发状态返回基态时发光。因此,将电子或空穴高效地传输至发光区域,使电子和空穴的再结合变得容易的化合物的开发对于得到高效率有机EL元件是重要的。
通常,如果将有机EL元件在高温环境下驱动或保管,则产生发光色的变化、发光效率的降低、驱动电压的上升、发光寿命的缩短等问题。为了防止这样的问题,作为空穴传输材料,专利文献1公开了具有N-咔唑基直接键合于9,9-二苯基芴骨架的结构的芳香族胺衍生物,专利文献2公开了具有3-咔唑基直接键合于9,9-二甲基芴骨架的结构的芳香族胺衍生物,专利文献3公开了具有N-咔唑基苯基通过氮原子键合于9,9-二苯基芴骨架的结构的芳香族胺衍生物,专利文献4公开了具有3-咔唑基通过氮原子键合于9,9-二苯基芴骨架的结构的芳香族胺衍生物。专利文献5记载了具有选自芴骨架、咔唑骨架、二苯并呋喃骨架、二苯并噻吩骨架中的骨架的芳香族胺衍生物。
但是,专利文献1~5中公开的芳香族胺衍生物对于驱动电压的降低、低电压驱动时的效率和长寿命化的改善不能说是充分的,要求进一步改善。
专利文献6记载了具有三亚苯骨架和二苯并呋喃骨架(或二苯并噻吩骨架)的芳香族胺化合物。这样的芳香族胺化合物的例示化合物的大半必须具有咔唑骨架或末端二芳基氨基。专利文献6还记载了下述化合物。
[化1]
上述化合物具有1-二苯并噻吩基或1-二苯并呋喃基。这些基团的效率、寿命改善效果低,因此具有1-二苯并噻吩基或1-二苯并呋喃基的上述胺化合物的效率和寿命不充分。
因此,要求开发可以实现即使低电压驱动效率也高、且寿命长的有机EL元件的有机EL元件用材料,特别是空穴传输材料。
现有技术文献
专利文献
专利文献1:国际公开第07/148660号小册子
专利文献2:国际公开第08/062636号小册子
专利文献3:美国专利公开2007-0215889号公报
专利文献4:日本特开2005-290000号公报
专利文献5:国际公开第2011/021520号小册子
专利文献6:国际公开第2012/039534号小册子。
发明内容
发明要解决的课题
本发明是为了解决上述课题而进行的,目的在于提供能够实现可低电压驱动、长寿命且高效率的有机EL元件的有机EL元件用材料,例如空穴传输材料。
解决课题的手段
本发明人为了达到上述目的进行了深入研究,结果发现,具有三亚苯骨架、具有2-或4-二苯并呋喃基和2-或4-二苯并噻吩基的一者或二者直接或通过连接基键合于氮原子的结构的化合物的空穴注入性和空穴传输性良好,可实现能够低电压驱动、寿命长且高效率的有机EL元件。
即,本发明提供下式(1)表示的芳香族胺衍生物,
[化2]
(式中,HAr1表示选自下式(2)~(5)中的基团,
[化3]
式(2)~(5)中,n为0~4的整数,R分别独立地表示取代或未取代的碳数1~20的烷基、取代或未取代的环碳数6~50的芳基、取代或未取代的环原子数3~50的杂环基、卤素原子、取代或未取代的碳数1~20的氟烷基、取代或未取代的碳数1~20的烷氧基、取代或未取代的碳数1~20的氟烷氧基、取代或未取代的环碳数6~50的芳氧基或氰基,R存在多个时,该多个R可以相同也可以不同,
L1~L3可以相同也可以不同,分别独立地表示单键、下式(6)表示的基团或式(7)表示的基团,
[化4]
Ar2表示取代或未取代的碳数1~20的烷基、取代或未取代的环碳数6~50的芳基、取代或未取代的环原子数3~50的杂环基、取代或未取代的碳数1~20的氟烷基、取代或未取代的碳数1~20的烷氧基、取代或未取代的碳数1~20的氟烷氧基、取代或未取代的碳数6~50的芳氧基或选自下式(8)~(11)中的基团,其中,Ar2不包括咔唑骨架和取代或未取代的氨基,
[化5]
式(8)~(11)中,n为0~4的整数,R分别独立地表示取代或未取代的碳数1~20的烷基、取代或未取代的环碳数6~50的芳基、取代或未取代的环原子数3~50的杂环基、卤素原子、取代或未取代的碳数1~20的氟烷基、取代或未取代的碳数1~20的烷氧基、取代或未取代的碳数1~20的氟烷氧基、取代或未取代的环碳数6~50的芳氧基或氰基,R存在多个时,该多个R可以相同也可以不同。
进一步地,本发明提供有机电致发光元件,其具有阳极、阴极和阳极与阴极之间的1层以上的有机薄膜层,该1层以上的有机薄膜层含有发光层,其特征在于,该有机薄膜层的至少1层含有上式(1)表示的芳香族胺衍生物。
发明效果
通过使用本发明的芳香族胺衍生物,可以得到能够低电压驱动的长寿命、高效率有机EL元件。
具体实施方式
本说明书中,“取代或未取代的碳数a~b的X基”这一表述中的“碳数a~b”表示的是X基未取代的情况下的碳数,不包括X基被取代时的取代基的碳数。
另外“氢原子”包括中子数不同的同位素,即氕(protium)、氘(deuterium)、氚(tritium)。
进一步地,“取代或未取代”时的任意取代基选自碳数1~50(优选1~10、更优选1~5)的烷基;环碳数3~50(优选3~6、更优选5或6)的环烷基;环碳数6~50(优选6~24、更优选6~12)的芳基;具有环碳数6~50(优选6~24、更优选6~12)的芳基的碳数1~50(优选1~10、更优选1~5)的芳烷基;氨基;具有碳数1~50(优选1~10、更优选1~5)的烷基的单或二烷基氨基;具有环碳数6~50(优选6~24、更优选6~12)的芳基的单或二芳基氨基;具有碳数1~50(优选1~10、更优选1~5)的烷基的烷氧基;具有环碳数6~50(优选6~24、更优选6~12)的芳基的芳氧基;具有选自碳数1~50(优选1~10、更优选1~5)的烷基和环碳数6~50(优选6~24、更优选6~12)的芳基中的基团的单、二或三取代甲硅烷基;环原子数5~50(优选5~24、更优选5~12)、含有1~5个(优选1~3个、更优选1~2个)杂原子(氮原子、氧原子、硫原子)的杂芳基;卤素原子(氟原子、氯原子、溴原子、碘原子);氰基;硝基。
本发明的芳香族胺衍生物具有三亚苯骨架,用下式(1)表示。
[化6]
三亚苯骨架的平面性优异,因此本发明的芳香族胺衍生物在薄膜中分子之间密合地排列,薄膜的取向性好。结果可以使驱动电压降低。另外,三亚苯骨架由于玻璃化转变温度(Tg)高,因此本发明的芳香族胺衍生物的Tg高,稳定,有机EL元件的寿命变长。
式(1)中,HAr1表示选自下式(2)~(5)中的基团。
[化7]
HAr1如果是式(2)或(3)表示的基团则可以期待长寿命化,如果为式(4)或(5)表示的基团,则可以期待高效率化。
式(2)~(5)中,n为0~4的整数,优选为0~2的整数,特别优选为0。n=0表示不存在取代基R。
R分别独立地表示取代或未取代的碳数1~20、优选1~5、更优选1~4的烷基、取代或未取代的环碳数6~50、优选6~24、更优选6~18的芳基、取代或未取代的环原子数3~50、优选3~24、更优选3~18的杂环基、卤素原子、取代或未取代的碳数1~20、优选1~5、更优选1~4的氟烷基、取代或未取代的碳数1~20、优选1~5、更优选1~4的烷氧基、取代或未取代的碳数1~20、优选1~5、更优选1~4的氟烷氧基、取代或未取代的环碳数6~50、优选6~24、更优选6~18的芳氧基或氰基。R存在多个时,该多个R可以相同也可以不同。
作为上述碳数1~20的烷基,可列举例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基(包括异构体)、己基(包括异构体)、庚基(包括异构体)、辛基(包括异构体)、壬基(包括异构体)、癸基(包括异构体)、十一烷基(包括异构体)、和十二烷基(包括异构体)等,优选甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基和戊基(包括异构体),更优选甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基,特别优选甲基和叔丁基。
作为上述环碳数为6~50的芳基,可列举例如苯基、萘基苯基、联苯基、三联苯基、亚联苯基、萘基、苯基萘基、苊基、蒽基、苯并蒽基、苯并苊基、菲基、苯并菲基、phenalenyl、芴基、9,9-二甲基芴基、7-苯基-9,9-二甲基芴基、并五苯基、基、五苯基、芘基、䓛基、苯并䓛基、s-苯并二茚基、as-苯并二茚基、荧蒽基和苝基等,优选苯基、萘基苯基、联苯基、三联苯基、萘基、9,9-二甲基芴基,更优选苯基、联苯基、萘基、9,9-二甲基芴基,特别优选苯基。
上述环原子数为3~50的杂环基含有至少1个、优选1~2个杂环子、例如氮原子、硫原子或氧原子。作为该杂环基,可列举例如吡咯基、呋喃基、噻吩基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、咪唑基、噁唑基、噻唑基、吡唑基、异噁唑基、异噻唑基、噁二唑基、噻二唑基、三唑基、吲哚基、异吲哚基、苯并呋喃基、异苯并呋喃基、苯并噻吩基、吲嗪基、喹嗪基、喹啉基、异喹啉基、噌啉基、酞嗪基、喹唑啉基、喹喔啉基、苯并咪唑基、苯并噁唑基、苯并噻唑基、吲唑基、苯并异噁唑基、苯并异噻唑基、二苯并呋喃基、二苯并噻吩基、菲啶基、吖啶基、菲咯啉基、吩嗪基、吩噻嗪基、吩噁嗪基和呫吨基等,优选呋喃基、噻吩基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、二苯并噻吩基,更优选苯并呋喃基、苯并噻吩基、二苯并呋喃基、二苯并噻吩基。
上述卤素原子为氟原子、氯原子、溴原子和碘原子,特别优选氟原子。
作为上述碳数为1~20的氟烷基,可列举例如上述碳数1~20的烷基的至少1个氢原子、优选1~7个氢原子被氟原子取代得到的基团,优选七氟丙基、五氟乙基、2,2,2-三氟乙基、三氟甲基,更优选五氟乙基、2,2,2-三氟乙基、三氟甲基,特别优选三氟甲基。
上述碳数1~20的烷氧基用-OR10表示,R10表示上述碳数为1~20的烷基。作为该烷氧基,优选叔丁氧基、丙氧基、乙氧基、甲氧基,更优选乙氧基、甲氧基,特别优选甲氧基。
上述碳数为1~20的氟烷氧基用-OR11表示,R11表示上述碳数为1~20的氟烷基。作为该氟烷氧基,优选七氟丙氧基、五氟乙氧基、2,2,2-三氟乙氧基、三氟甲氧基,更优选五氟乙氧基、2,2,2-三氟乙氧基、三氟甲氧基,特别优选三氟甲氧基。
环碳数为6~50的芳氧基用-OR12表示,R12表示上述环碳数6~50的芳基。作为该芳氧基,优选R12为三联苯基、联苯基、苯基,更优选联苯基、苯基,特别优选苯基。
在本发明的优选方式中,式(2)~(5)中的R为取代或未取代的碳数1~20、优选1~5、更优选1~4的烷基、特别优选甲基和叔丁基;取代或未取代的环碳数6~50、优选6~24、更优选6~18的芳基、特别优选苯基;卤素原子、更优选氟原子;或氰基。另外,R优选键合于2-或4-二苯并呋喃基、2-或4-二苯并噻吩基的6位和/或8位。
[化8]
式(1)中,L1~L3可以相同也可以不同,分别独立地表示单键、下式(6)表示的基团、或式(7)表示的基团。
[化9]
式(6)表示的基团包括邻亚苯基、间亚苯基和对亚苯基,式(7)表示的基团包括邻亚联苯基、间亚联苯基和对亚联苯基。
L1~L3分别优选为单键、对亚苯基或对亚联苯基,L1特别优选为对亚苯基,L3特别优选为单键、对亚苯基或对亚联苯基。
式(1)中,Ar2表示取代或未取代的碳数1~20、优选1~5、更优选1~4的烷基,取代或未取代的环碳数6~50、优选6~24、更优选6~18的芳基,取代或未取代的环原子数3~50、优选3~24、更优选3~18的杂环基,取代或未取代的碳数1~20、优选1~5、更优选1~4的氟烷基,取代或未取代的碳数1~20、优选1~5、更优选1~4的烷氧基,取代或未取代的碳数1~20、优选1~5、更优选1~4的氟烷氧基,取代或未取代的环碳数6~50、优选6~24、更优选6~18的芳氧基或选自下式(8)~(11)中的基团。
[化10]
Ar2所表示的烷基、芳基、杂环基、氟烷基、烷氧基、氟烷氧基和芳氧基与对于式(2)~(5)的R所记载的各基团的定义相同(优选方式也相同)。但是,Ar2不包括咔唑骨架和取代或未取代的氨基。另外,HAr1也优选不包括咔唑骨架和取代或未取代的氨基。
式(8)~(11)中的R和n与对于式(2)~(5)记载的R和n的定义相同(优选方式也相同),R优选键合于2-或4-二苯并呋喃基、2-或4-二苯并噻吩基的6位和/或8位。
Ar2优选为取代或未取代的环碳数6~50、优选6~24、更优选6~18的芳基或选自式(8)~(11)的基团。特别是,芳基优选为苯基、联苯-2-基、联苯-3-基、联苯-4-基、1,1’:4’,1’’-三联苯-4-基、1,1’:3’,1’’-三联苯-4-基、1,1’:2’,1’’-三联苯-4-基、1,1’:4’,1’’-三联苯-3-基、1,1’:3’,1’’-三联苯-3-基、1,1’:2’,1’’-三联苯-3-基、1,1’:4’,1’’-三联苯-2-基、1,1’:3’,1’’-三联苯-2-基、1,1’:3’,1’’-三联苯-2’-基、1,1’:3’,1’’-三联苯-4’-基、1-萘基、2-萘基、9,9-二甲基芴-2-基、9-甲基-9-苯基芴-2-基、9,9-二苯基芴-2-基、三亚苯-2-基、和选自式(8)~(11)中的基团。
Ar2所表示的各基团可以被选自碳数1~20、优选1~5、更优选1~4的烷基、例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基;环碳数6~50、优选6~24、更优选6~18的芳基、例如苯基;卤素原子,例如氟原子;碳数1~20、优选1~5、更优选1~4的氟烷基,例如三氟甲基;碳数1~20、优选1~5、更优选1~4的烷氧基,例如甲氧基;碳数1~20、优选1~5、更优选1~4的氟烷氧基,例如三氟甲氧基;和氰基中的至少一个基团取代,更优选未取代。
本发明的芳香族胺衍生物优选用下式(12)表示,
[化11]
(式中,HAr1、Ar2、L2和L3分别如上式(1)所定义)。
另外也优选式(1)和(12)中L3为单键、或下式(13)或(14)表示的基团的化合物。
[化12]
。
另外,上式(12)和由上式(2)~(5)作为HAr1选择的基团部分地含有对联苯基结构。直接键合于中心氮原子的苯环的对位为电子密度高、电化学上脆弱的位置,由于对联苯基结构,成为不是未取代而是被苯基保护的形式,因而化合物的稳定性提高,材料的劣化被抑制,结果有机EL元件寿命变长。
以下示出式(1)表示的本发明的芳香族胺衍生物的具体例子,但是不限于下述化合物。
[化13]
[化14]
[化15]
[化16]
[化17]
[化18]
[化19]
[化20]
[化21]
[化22]
[化23]
[化24]
[化25]
。
本发明的式(1)表示的芳香族胺衍生物作为有机EL元件用材料,特别是空穴注入层材料或空穴传输层材料是有用的。对本发明的芳香族胺衍生物的制造方法没有特别限制,如果是本领域技术人员,可以参照本说明书的实施例对公知的合成反应进行利用和变更而容易地制造。
以下对本发明的有机EL元件结构进行说明。
本发明的有机EL元件的代表性元件结构可列举以下的(1)~(13),但不特别限定于这些。要说明的是,优选使用(8)的元件结构。
(1)阳极/发光层/阴极
(2)阳极/空穴注入层/发光层/阴极
(3)阳极/发光层/电子注入层/阴极
(4)阳极/空穴注入层/发光层/电子注入层/阴极
(5)阳极/有机半导体层/发光层/阴极
(6)阳极/有机半导体层/电子阻挡层/发光层/阴极
(7)阳极/有机半导体层/发光层/附着改善层/阴极
(8)阳极/空穴注入层/空穴传输层/发光层/(电子传输层/)电子注入层/阴极
(9)阳极/绝缘层/发光层/绝缘层/阴极
(10)阳极/无机半导体层/绝缘层/发光层/绝缘层/阴极
(11)阳极/有机半导体层/绝缘层/发光层/绝缘层/阴极
(12)阳极/绝缘层/空穴注入层/空穴传输层/发光层/绝缘层/阴极
(13)阳极/绝缘层/空穴注入层/空穴传输层/发光层/(电子传输层/)电子注入层/阴极。
另外,在本发明的有机EL元件中,本发明的芳香族胺衍生物难以结晶,可以用于上述任意一个有机薄膜层中,但从以更低的电压驱动的角度考虑,优选包含在空穴注入层或空穴传输层中,更优选包含在空穴传输层中。使用本发明的芳香族胺衍生物的有机EL元件不仅可以低电压驱动,而且发光效率高,寿命长。
本发明的芳香族胺衍生物在有机薄膜层、优选在空穴注入层或空穴传输层中的含量相对于有机薄膜层的所有成分优选为30~100摩尔%,更优选为50~100摩尔%,进一步优选为80~100摩尔%,特别优选实质为100摩尔%。
以下作为优选的方式,对空穴传输层中含有本发明的上述芳香族胺衍生物的结构的有机EL元件的各层进行说明。
基板
有机EL元件通常在透光性基板上制作。该透光性基板是支撑有机EL元件的基板,优选波长400~700nm的可见光区域的光的透射率为50%以上的基板,进一步优选使用平滑的基板。
作为这样的透光性基板,可列举例如玻璃板、合成树脂板等。作为玻璃板,可列举由钠钙玻璃、含有钡·锶的玻璃、铅玻璃、铝硅酸玻璃、硼硅酸玻璃、钡硼硅酸玻璃、石英等成型的板。另外,作为合成树脂板,可列举聚碳酸酯树脂、丙烯酸树脂、聚对苯二甲酸乙二醇树脂、聚醚硫化物树脂、聚砜树脂等的板。
阳极
阳极起到将空穴注入空穴传输层或发光层中的作用,具有4eV以上(优选4.5eV以上)的功函数是有效的。作为阳极材料的具体例子,可列举碳、铝、钒、铁、钴、镍、钨、银、金、铂、钯等以及它们的合金、ITO基板、NESA基板中使用的氧化锡、氧化铟等金属氧化物、聚噻吩、聚吡咯等有机导电性树脂。
阳极通过将这些阳极材料用蒸镀法、溅射法等方法形成薄膜而得到。
由阳极取出由发光层发出的光时,阳极对发光的透射率优选大于10%。另外,阳极的薄层电阻(シート抵抗)优选为几百Ω/□以下。阳极的膜厚因材料而有所不同,通常为10nm~1µm,优选为10nm~200nm。
阴极
作为阴极,使用将功函数小(小于4eV)的金属、合金、导电性化合物以及它们的混合物作为电极物质的阴极。作为这样的电极物质的具体例子,可使用镁、钙、锡、铅、钛、钇、锂、钌、锰、铝、氟化锂等以及它们的合金,但不特别限定于这些。作为该合金,可列举镁/银、镁/铟、锂/铝等作为代表例,但是不特别限定于这些。合金的比率通过蒸镀源的温度、气氛、真空度等控制,选择适当的比率。阳极和阴极如有必要可以通过两层以上的层结构形成。
该阴极可以通过将这些电极物质用蒸镀、溅射等方法形成薄膜而得到。
在此,由阴极取出由发光层发出的光时,阴极对发光的透射率优选大于10%。另外,作为阴极的薄层电阻优选为几百Ω/□以下。进一步地,阴极的膜厚通常为10nm~1µm,优选为50nm~200nm。
绝缘层
有机EL元件由于对超薄膜施加电场,容易产生泄露(リーク)、短路(ショート)导致的像素缺陷。为了防止其,优选在一对电极间插入包含绝缘性的薄膜层的绝缘层。
作为绝缘层中使用的材料,可列举例如氧化铝、氟化锂、氧化锂、氟化铯、氧化铯、氧化镁、氟化镁、氧化钙、氟化钙、氮化铝、氧化钛、氧化硅、氧化锗、氮化硅、氮化硼、氧化钼、氧化钌、氧化钒等。可以使用它们的混合物、叠层物。
发光层
有机EL元件的发光层同时具有下述(1)~(3)的功能。
(1)注入功能:施加电场时可以通过阳极或空穴注入层注入空穴,可以通过阴极或电子注入层注入电子的功能。
(2)传输功能:使得所注入的电荷(电子和空穴)通过电场力移动的功能。
(3)发光功能:提供电子和空穴再结合的场所,使其发光的功能。
向发光层注入空穴的容易度和注入电子的容易度可以不同,另外用空穴迁移率和电子迁移率表示的发光层的空穴传输能力和电子传输能力可以不同,优选使得任何一方的电荷移动。
对发光层中可以使用的基质材料或掺杂材料没有特别限制。选自例如萘、菲、红荧烯、蒽、并四苯、芘、苝、䓛、十环烯、晕苯、四苯基环戊二烯、五苯基环戊二烯、芴、螺芴、9,10-二苯基蒽、9,10-双(苯基乙炔基)蒽、1,4-双(9'-乙炔基蒽基)苯等稠合多聚芳香族化合物和它们的衍生物、三(8-羟基喹啉)铝、双-(2-甲基-8-羟基喹啉)-4-(苯基苯酚)铝等有机金属配合物、芳基胺衍生物、苯乙烯胺衍生物、茋衍生物、香豆素衍生物、吡喃衍生物、噁嗪酮衍生物、苯并噻唑衍生物、苯并噁唑衍生物、苯并咪唑衍生物、吡嗪衍生物、肉桂酸酯衍生物、二酮吡咯并吡咯衍生物、吖啶酮衍生物、喹吖啶酮衍生物等。在这些中,优选芳基胺衍生物、苯乙烯胺衍生物,更优选苯乙烯胺衍生物。
空穴注入层/空穴传输层
空穴注入层/空穴传输层是帮助向发光层注入空穴,将空穴传输至发光区域的层,空穴迁移率大,电离能小,通常为5.7eV以下。作为这样的空穴注入层/空穴传输层,优选以更低的电场强度将空穴传输至发光层的材料,进一步地空穴的迁移率优选施加例如104~106V/cm的电场时,为10-4cm2/V·秒以上。
如上所述,本发明的芳香族胺衍生物优选作为空穴注入层材料、特别是空穴传输层材料使用。空穴传输层可以由本发明的芳香族胺衍生物单独形成,也可以由与其他材料的混合物形成。作为与本发明的芳香族胺衍生物混合形成空穴传输层的其他材料,只要是具有上述优选性质的材料则没有特别限制,可以由以往在光传导材料中作为空穴传输材料惯用的材料、有机EL元件的空穴传输层中使用的公知的材料中选择任意的材料使用。本发明中具有空穴传输能力、可以用于空穴传输带域的材料叫做空穴传输材料。
本发明的芳香族胺衍生物以外的空穴传输层用的其他材料的具体例子,可列举酞菁衍生物、萘酞菁衍生物、卟啉衍生物、噁唑、噁二唑、三唑、咪唑、咪唑酮、咪唑硫酮(イミダゾールチオン)、吡唑啉、吡唑啉酮、四氢咪唑、噁唑、噁二唑、腙、酰腙、多芳基烷烃、茋、丁二烯、联苯胺型三苯基胺、苯乙烯胺型三苯基胺、二胺型三苯基胺等、上述化合物的衍生物和聚乙烯基咔唑、聚硅烷、导电性高分子等高分子材料,但不特别限定于这些。
作为空穴注入层用的材料,只要是具有上述优选性质的材料则没有特别限制,可以由以往在光传导材料中作为空穴注入材料惯用的材料、有机EL元件的空穴传输层中使用的公知的材料中选择任意的材料使用。本发明中具有空穴注入能力、可以用于空穴注入带域的材料叫做空穴注入材料。可以通过在空穴注入材料中添加受电子物质来增感。
本发明的有机EL元件中,作为空穴注入材料,优选使用下式(A)表示的六氮杂三亚苯化合物。
[化26]
上式(A)中,R111~R116分别独立地表示氰基、-CONH2、羧基、或-COOR117(R117是碳数为1~20的烷基),或者、R111和R112、R113和R114、或者R115和R116一起表示-CO-O-CO-所示的基团。
要说明的是,优选R111~R116相同,表示氰基、-CONH2、羧基、或者-COOR117。另外,优选R111和R112、R113和R114、以及R115和R116都一起表示-CO-O-CO-所示的基团。
本发明的有机EL元件中可以使用的其他空穴注入材料可列举例如芳香族叔胺衍生物和酞菁衍生物。
作为芳香族叔胺衍生物,例如为三苯基胺、三甲苯基胺、甲苯基二苯基胺、N,N’-二苯基-N,N’-(3-甲基苯基)-1,1’-联苯基-4,4’-二胺、N,N,N’,N’-(4-甲基苯基)-1,1’-苯基-4,4’-二胺、N,N,N’,N’-(4-甲基苯基)-1,1’-联苯基-4,4’-二胺、N,N’-二苯基-N,N’-二萘基-1,1’-联苯基-4,4’-二胺、N,N’-( 甲基苯基)-N,N’-(4-正丁基苯基)-菲-9,10-二胺、N,N-双(4-二-4-甲苯基氨基苯基)-4-苯基-环己烷等或具有来自这些芳香族叔胺的结构单元的低聚物或聚合物,但不特别限定于这些。
作为酞菁(Pc)衍生物,有例如H2Pc、CuPc、CoPc、NiPc、ZnPc、PdPc、FePc、MnPc、ClAlPc、ClGaPc、ClInPc、ClSnPc、Cl2SiPc、(HO)AlPc、(HO)GaPc、VOPc、TiOPc、MoOPc、GaPc-O-GaPc等酞菁衍生物和萘酞菁衍生物,但不限定于这些。另外,本发明的有机EL元件优选在发光层和阳极之间具有含有这些芳香族叔胺衍生物和/或酞菁衍生物的层,例如上述空穴传输层或空穴注入层。
也可以通过在空穴注入材料中添加受电子物质来增感。
电子注入层/电子传输层
电子注入层/电子传输层是帮助向发光层注入电子、将电子传输至发光区域的层,电子迁移率大。附着改善层是包含与阴极的附着特别好的材料的电子注入层。
已知所发出的光被电极(此时为阴极)反射,因此直接由阳极取出的发光与经过电极的反射由阳极取出的发光干涉。为了有效利用该干涉效果,电子传输层的膜厚适当选择为几nm~几μm,特别是膜厚厚时,为了避免电压上升,优选在施加104~106V /cm的电场时电子迁移率至少为10-5cm2/Vs以上。
作为电子注入层中使用的材料,具体地可列举芴酮、蒽醌二甲烷、diphenoquinone、噻喃二氧化物、噁唑、噁二唑、三唑、咪唑、苝四甲酸、亚芴基甲烷、蒽醌二甲烷、蒽酮等与它们的衍生物,但是不特别限定于这些。另外也可以通过在电子注入材料中添加供电子性物质来增感。
其它有效的电子注入材料为金属配位化合物和含氮五元环衍生物。
作为上述金属配位化合物,可列举例如8-羟基喹啉锂、三(8-羟基喹啉)铝、双(2-甲基-8-喹啉)(1-萘酚)铝等,但是不特别限定于这些。
作为上述含氮五元衍生物,例如优选噁唑、噻唑、噁二唑、噻二唑、三唑衍生物。
特别是在本发明中,作为上述含氮五元衍生物,优选下式(1)~(3)的任意一个表示的苯并咪唑衍生物。
[化27]
上式(1)~(3)中,Z1、Z2和Z3各自独立地为氮原子或碳原子。
R11和R12分别独立地为取代或未取代的环碳数为6~60的芳基、取代或未取代的环碳数为3~60的杂芳基、碳数为1~20的烷基、碳数为1~20的卤代烷基或碳数为1~20的烷氧基。
m为0~5的整数,m为2以上的整数时,多个R11可以相同也可以不同。另外,相邻的2个R11可以相互键合形成取代或未取代的芳香族烃环。作为该取代或未取代的芳香族烃环,可列举例如苯环、萘环、蒽环等。
Ar1为取代或未取代的环碳数为6~60的芳基或取代或未取代的环碳数为3~60的杂芳基。
Ar2为氢原子、碳数为1~20的烷基、碳数为1~20的卤代烷基、碳数为1~20的烷氧基、取代或未取代的环碳数为6~60的芳基或取代或未取代的环碳数为3~60的杂芳基。
Ar3为取代或未取代的环碳数为6~60的亚芳基或取代或未取代的环碳数为3~60的亚杂芳基。
L1、L2和L3各自独立地为单键、取代或未取代的环碳数为6~60的亚芳基、取代或未取代的环原子数为9~60的杂稠环基或取代或未取代的亚芴基。
在本发明的有机EL元件中,含有本发明的芳香族胺衍生物的层中可以含有发光材料、掺杂材料、空穴注入材料或电子注入材料。
含有发明的芳香族胺衍生物的层中根据需要可以使用公知的发光材料、掺杂材料、空穴注入材料、电子注入材料,也可将本发明的芳香族胺衍生物用作掺杂材料。
有机EL元件通过形成多个有机薄膜层,可以防止猝灭导致的亮度、寿命的降低。根据需要可以将发光材料、掺杂材料、空穴注入材料、电子注入材料组合使用。另外,掺杂材料可以使发光亮度、发光效率提高,使发光色变化。
本发明的有机EL元件的空穴传输层可以制成第1空穴传输层(阳极侧)和第2空穴传输层(阴极侧)的2层结构。此时,本发明的芳香族胺衍生物可以包含在第1空穴传输层和第2空穴传输层的任意一个中。
另外从通过本发明得到的有机EL元件对温度、湿度、气氛等的稳定性提高的角度考虑,可以在元件表面设置保护层、或通过硅油、树脂等保护元件整体。
本发明的有机EL元件的各层的形成可以采用真空蒸镀、溅射、等离子体、离子镀等干式成膜法,旋涂、蘸涂、流涂等湿式成膜法的任意一种方法。
湿式成膜法的情况下,将形成各层的材料溶解或分散在乙醇、氯仿、四氢呋喃、二噁烷等适当的溶剂中,使用所得到的溶液或分散液形成薄膜。另外,为了提高成膜性,防止膜的针孔(pinhole)等,该溶液或分散液可以含有树脂、添加剂。作为该树脂,可列举聚苯乙烯、聚碳酸酯、聚芳酯、聚酯、聚酰胺、聚氨酯、聚砜、聚甲基丙烯酸甲酯、聚丙烯酸甲酯、纤维素等绝缘性树脂和它们的共聚物、聚-N-乙烯基咔唑、聚硅烷等光导电性树脂、聚噻吩、聚吡咯等导电性树脂。另外,作为添加剂,可列举抗氧化剂、紫外线吸收剂、增塑剂等。
对各层的膜厚没有特别限定,为可以得到良好的元件性能的膜厚即可。膜厚如果过厚,则为了得到一定的光功率,需要大的施加电压,效率变差。如果膜厚过薄,则产生针孔等,即使施加电场也得不到充分的发光亮度。通常的膜厚适合为5nm~10μm的范围,更优选为10nm~0.2μm的范围。
实施例
以下通过实施例具体说明本发明,但是本发明不受这些实施例的任何限定。
中间体合成例1-1(中间体1-1的合成)
在氩气氛下在2-溴三亚苯50.8g(150.0mmol)、二苯基胺25.4g(150.0mmol)、叔丁氧基钠28.8g(300.0mmol)中加入脱水甲苯750ml,并搅拌。加入乙酸钯674mg(3.0mmol)、三叔丁基膦607mg(3.0mmol),在80℃反应8小时。
冷却后,使反应混合物通过celite/硅胶进行过滤,将滤液在减压下浓缩。将得到的残渣用甲苯进行重结晶,将其滤取后进行干燥,得到48.3g的白色固体。通过FD-MS(场解析质谱分析)鉴定为下述中间体1-1。(收率82%)
[化28]
。
中间体合成例1-2(中间体1-2的合成)
在氩气氛下,在中间体1-1 20.0g(50.6mmol)中加入甲苯500ml、乙酸乙酯300ml并搅拌。加入N-溴代琥珀酰亚胺18.0g(101.2mmol),在室温反应24小时。进一步加入N-溴代琥珀酰亚胺1.0g(5.6mmol),在室温反应3小时。
加入水300ml,用甲苯萃取。用饱和食盐水洗涤有机层后,用MgSO4干燥,过滤、浓缩。将得到的残渣用甲苯重结晶,将其滤取后进行干燥,得到24.4g白色固体。通过FD-MS分析,鉴定为下述中间体1-2。(收率87%)
[化29]
。
中间体合成例1-3(中间体1-3的合成)
在氩气氛下在2-溴三亚苯49.1g(160.0mmol)、4-氯苯硼酸25.0g(160.0mmol)、Pd[PPh3]43.7g(3.20mmol)中加入甲苯500ml、二甲氧基乙烷300ml、2M Na2CO3水溶液160ml(320.0mmol),加热回流搅拌30小时。
反应结束后冷却至室温,将样品移至分液漏斗,用二氯甲烷萃取。有机层用MgSO4干燥后,过滤、浓缩。将得到的残渣用甲苯重结晶,将其滤取后进行干燥,得到49.0g的白色固体。通过FD-MS分析,鉴定为下述中间体1-3。(收率90%)
[化30]
。
中间体合成例1-4(中间体1-4的合成)
在中间体合成例1-1中,除了使用30.0g中间体1-3代替2-溴三亚苯以外同样地进行反应,结果得到30.0g白色固体。通过FD-MS分析,鉴定为下述中间体1-4。(收率71%)
[化31]
。
中间体合成例1-5(中间体1-5的合成)
在中间体合成例1-2中,除了使用30.0g中间体1-4代替中间体1-1以外同样地进行反应,结果得到25.4g白色固体。通过FD-MS分析,鉴定为下述中间体1-5。(收率63%)
[化32]
。
中间体合成例2-1(中间体2-1的合成)
在氩气氛下在4-碘溴苯28.3g(100.0mmol)、二苯并呋喃-4-硼酸22.3g(105.0mmol)、Pd[PPh3]4 2.31g(2.00mmol)中加入甲苯150ml、二甲氧基乙烷150ml、2MNa2CO3水溶液150ml(300.0mmol),加热回流搅拌10小时。
反应结束后冷却至室温,将样品移至分液漏斗,用二氯甲烷萃取。有机层用MgSO4干燥后,过滤、浓缩。将浓缩残渣通过硅胶柱色谱纯化,得到26.2g的白色固体。通过FD-MS分析,鉴定为下述中间体2-1。(收率81%)
[化33]
。
中间体合成例2-2(中间体2-2的合成)
在氩气氛下在4'-溴乙酰苯胺24.0g(112.0mmol)、二苯并呋喃-4-硼酸28.6g(135.0mmol)、Pd[PPh3]4 2.6g(2.24mmol)中加入甲苯450ml、二甲氧基乙烷100ml、2M Na2CO3水溶液110ml(220.0mmol),加热回流搅拌10小时。
反应结束后冷却至室温,过滤析出的结晶。将得到的结晶溶解于四氢呋喃,通过celite/硅胶过滤,将滤液在减压下浓缩。将得到的残渣用甲醇/己烷洗涤、干燥,得到18.0g白色固体。通过FD-MS分析,鉴定为下述中间体2-2。(收率53%)
[化34]
。
中间体合成例2-3(中间体2-3的合成)
在中间体2-2 18.0g(59.7mmol)中加入二甲苯120ml、水1200ml、乙醇60ml,并进行搅拌。加入氢氧化钾20.0g(360.0mmol),加热回流搅拌10小时。
反应结束后冷却至室温,将样品移至分液漏斗,用二甲苯萃取。将有机层用MgSO4干燥后,过滤、浓缩。将得到的残渣用二甲苯重结晶,将其滤取后进行干燥,得到14.7g的白色固体。通过FD-MS分析,鉴定为下述中间体2-3。(收率95%)
[化35]
。
中间体合成例2-4(中间体2-4的合成)
在氮气氛下向二苯并呋喃150g(0.89mol)中加入乙酸1000ml,加热溶解。进一步地滴加溴188g(1.18mol)后,在室温下搅拌20小时。滤取析出的结晶,依次用乙酸、水洗涤。将粗产物用甲醇重复几次重结晶,得到66.8g的白色结晶。通过FD-MS分析,鉴定为下述中间体2-4。(收率30%)
[化36]
。
中间体合成例2-5(中间体2-5的合成)
在氩气氛下,在中间体2-4 24.7g(100.0mmol)中加入脱水四氢呋喃400毫升,并冷却至-40℃。进一步地慢慢加入1.6M浓度的正丁基锂-己烷溶液63ml(100.0mmol)。将反应溶液加热至0℃的同时搅拌1小时后,将反应溶液再次冷却至-78℃,滴加硼酸三甲酯26.0g(250.0mmol)的脱水四氢呋喃的50ml溶液。滴加后,将反应溶液在室温下搅拌5小时。加入1N盐酸200ml,搅拌1小时后,除去水层。将有机层用MgSO4干燥,减压蒸馏除去溶剂。将得到的固体用甲苯洗涤,得到15.2g的白色结晶。(收率72%)
[化37]
。
中间体合成例2-6(中间体2-6的合成)
在氩气氛下在4-碘溴苯28.3g(100.0mmol)、中间体2-5 22.3g(105.0mmol)、Pd[PPh3]4 2.31g(2.00mmol)中加入甲苯150ml、二甲氧基乙烷150ml、2M Na2CO3水溶液150ml(300.0mmol),加热回流搅拌10小时。
反应结束后,将样品移至分液漏斗,用二氯甲烷萃取。有机层用MgSO4干燥后,过滤、浓缩。将浓缩残渣通过硅胶柱色谱纯化,得到24.2g的白色固体。通过FD-MS分析,鉴定为下述中间体2-6。(收率75%)
[化38]
。
中间体合成例2-7(中间体2-7的合成)
在合成例2-5中除了使用2-溴二苯并噻吩26.3g代替中间体2-4以外同样地进行反应,得到14.8g白色固体。通过FD-MS分析,鉴定为下述中间体2-7。(收率65%)
[化39]
。
中间体合成例2-8(中间体2-8的合成)
在氩气氛下在2-溴三亚苯16.9g(50.0mmol)、中间体2-3 13.0g(50.0mmol)、叔丁氧基钠9.6g(100.0mmol)中加入脱水甲苯250ml,并搅拌。加入乙酸钯225mg(1.0mmol)、三叔丁基膦202mg(1.0mmol),在80℃反应8小时。
冷却后,使反应混合物通过celite/硅胶进行过滤,将滤液在减压下浓缩。将得到的残渣用甲苯进行重结晶,将其滤取后进行干燥,得到19.9g的白色固体。通过FD-MS分析,鉴定为下述中间体2-8。(收率82%)
[化40]
。
合成实施例1(芳香族胺衍生物(H1)的制造)
在氩气氛下在中间体1-2 8.3g(15.0mmol)、二苯并呋喃-4-硼酸7.0g(33.0mmol)、Pd[PPh3]4 0.87g(0.75mmol)中加入甲苯50ml、二甲氧基乙烷25ml、2M Na2CO3水溶液23ml(46.0mmol),加热回流搅拌10小时。
反应结束后,将样品移至分液漏斗,用甲苯萃取。将有机层用MgSO4干燥后,过滤、浓缩。将浓缩残渣通过硅胶柱色谱纯化。将得到的粗产物用甲苯重结晶,滤取后,进行干燥,得到7.9g的白色固体。通过FD-MS分析,鉴定为下述芳香族胺衍生物(H1)。(收率72%)
[化41]
。
合成实施例2(芳香族杂环衍生物(H2)的制造)
在合成实施例1中,除了使用7.0g中间体2-5 代替二苯并呋喃-4-硼酸以外同样地进行反应,得到6.9g白色结晶。通过FD-MS分析,鉴定为下述芳香族胺衍生物(H2)。(收率63%)
[化42]
。
合成实施例3(芳香族杂环衍生物(H3)的制造)
在合成实施例1中,除了使用 6.8g中间体2-7代替二苯并呋喃-4-硼酸以外同样地进行反应,得到3.4g白色结晶。通过FD-MS分析,鉴定为下述芳香族胺衍生物(H3)。(收率33%)
[化43]
。
合成实施例4(芳香族杂环衍生物(H4)的制造)
在氩气氛下,在3.2g(10.0mmol)中间体2-6、4.9g(10.0mmol)中间体2-8、Pd 2 (dba) 3 0.14g(0.15mmol)、P(tBU) 3 HBF 4 0.087g(0.3mmol)、叔丁氧基钠1.9g(20.0mmol)中加入无水二甲苯50ml,加热回流8小时。
反应结束后,将反应液冷却至50℃,通过celite和硅胶进行过滤,浓缩滤液。将得到的浓缩残渣通过硅胶柱色谱纯化,得到白色固体。将粗产物用甲苯重结晶,得到3.6g的白色结晶。通过FD-MS分析,鉴定为下述芳香族杂环衍生物(H4)。(收率50%)
[化44]
。
合成实施例5(芳香族杂环衍生物(H5)的制造)
在合成实施例4中,除了使用3.1g 4-溴三联苯代替中间体2-6以外同样地进行反应,得到3.9g白色结晶。通过FD-MS分析,鉴定为下述芳香族胺衍生物(H5)。(收率55%)
[化45]
。
合成实施例6(芳香族杂环衍生物(H6)的制造)
在合成实施例4中,除了使用2.7g 2-溴-9,9-二甲基芴代替中间体2-6以外同样地进行反应,得到3.5g白色结晶。通过FD-MS分析,鉴定为下述芳香族胺衍生物(H6)。(收率52%)
[化46]
。
合成实施例7(芳香族杂环衍生物(H7)的制造)
在合成实施例1中,除了使用9.4g中间体1-5代替中间体1-2以外同样地进行反应,得到4.1g白色结晶。通过FD-MS分析,鉴定为下述芳香族胺衍生物(H7)。(收率32%)
[化47]
。
合成实施例8(芳香族杂环衍生物(H8)的制造)
在合成实施例1中,除了使用6.8g二苯并噻吩-4-硼酸代替二苯并呋喃-4-硼酸以外同样地进行反应,得到3.0g白色结晶。通过FD-MS分析,鉴定为下述芳香族胺衍生物(H8)。(收率26%)
[化48]
。
实施例1
有机EL元件的制作
对附有25mm×75mm×1.1mm的ITO透明电极线的玻璃基板(ジオマティック社制)在异丙醇中实施5分钟的超声波洗涤,进一步实施30分钟的UV(Ultraviolet)臭氧洗涤。
将洗涤后的附有透明电极线的玻璃基板装配在真空蒸镀装置的基板支架上,首先在形成有透明电极线的面上以覆盖上述透明电极的方式蒸镀下述受电子性化合物(A),得到膜厚为5nm的膜A。
在该膜A上作为第1空穴传输材料蒸镀下述芳香族胺衍生物(TPTE),形成膜厚为65nm的第1空穴传输层。
接着第1空穴传输层的成膜,作为第2空穴传输材料蒸镀上述芳香族胺衍生物(H1),得到膜厚为10nm的第2空穴传输层。
在该空穴传输层上共蒸镀作为第一基质材料的化合物(host1-X)、作为第二基质材料的化合物(host2-X)和磷光发光性掺杂材料Ir(bzq)3。由此形成发绿光的厚度为25nm的发光层。磷光发光性掺杂材料的浓度为10质量%,第一基质材料的浓度为45质量%,第二基质材料的浓度为45质量%。
接着,在该磷光发光层上依次层叠厚度为35nm的化合物(C)膜、厚度为1nm的LiF膜、厚度为80nm的金属Al膜,形成阴极。而且,作为电子注入性电极的LiF以1Å/min的成膜速度形成。
[化49]
。
实施例2~8
有机EL元件的制作
除了作为第2空穴传输材料使用表1记载的上述芳香族胺衍生物以外,与实施例1同样地制作实施例2~8的各有机EL元件。
比较例1、2
有机EL元件的制作
除了作为第2空穴传输材料使用表1记载的下述比较化合物1或2以外,与实施例1同样地制作比较例1、2的各有机EL元件。比较化合物1为专利文献6记载的化合物(104段)。
[化50]
。
(有机EL元件的发光性能评价)
通过直流电流驱动使如上制作的有机EL元件发光,测定亮度(L)、电流密度,由测定结果求出电流密度10mA/cm2下的电流效率(L/J)、驱动电压(V)。进一步地求出电流密度50mA/cm2下的元件寿命。80%寿命是指在一定电流驱动时亮度衰减为初期亮度的80%时的时间。结果如表1所示。
[表1]
由表1的结果可知,通过使用本发明的芳香族胺衍生物,可得到即使以低电压驱动效率也高、且寿命长的有机EL元件。
Claims (12)
1.下式(1)表示的芳香族胺衍生物,
[化1]
式中,HAr1表示选自下式(2)~(5)中的基团,
[化2]
式(2)~(5)中,n为0~2的整数,R分别独立地表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、苯基、氟原子或氰基,R存在多个时,该多个R可以相同也可以不同,
L1~L3可以相同也可以不同,分别独立地表示单键或下式(6)表示的基团,
[化3]
Ar2表示选自下式(8)~(11)中的基团,
[化4]
式(8)~(11)中,n为0~2的整数,R分别独立地表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、苯基、氟原子或氰基,R存在多个时,该多个R可以相同也可以不同。
2.根据权利要求1所述的芳香族胺衍生物,其中,式(6)表示的基团为邻亚苯基、间亚苯基或对亚苯基。
3.根据权利要求1所述的芳香族胺衍生物,其中,L1~L3分别为单键或对亚苯基。
4.根据权利要求1所述的芳香族胺衍生物,其用下式(12)表示,
[化5]
式中,HAr1、Ar2、L2和L3分别如上式(1)中所定义。
5.根据权利要求1所述的芳香族胺衍生物,其中,L3为单键或下式(13)表示的基团,
[化6]
。
6.根据权利要求1所述的芳香族胺衍生物,其中,L3为单键。
7.根据权利要求1所述的芳香族胺衍生物,其中,式(2)~(5)中,R键合于2-或4-二苯并呋喃基、或者、2-或4-二苯并噻吩基的6位和/或8位。
8.根据权利要求1所述的芳香族胺衍生物,其中,式(2)~(5)的n为0。
9.根据权利要求1所述的芳香族胺衍生物,其中,式(8)~(11)中,R键合于2-或4-二苯并呋喃基、或者、2-或4-二苯并噻吩基的6位和/或8位。
10.根据权利要求1所述的芳香族胺衍生物,其中,式(8)~(11)的n为0。
11.有机电致发光元件,其具有阳极、阴极和该阳极与阴极之间的1层以上的有机薄膜层,该1层以上的有机薄膜层含有发光层,其特征在于,该有机薄膜层的至少1层含有权利要求1~10中任一项所述的芳香族胺衍生物。
12.根据权利要求11所述的有机电致发光元件,其中,上述有机薄膜层具有空穴注入层或空穴传输层,该空穴注入层或空穴传输层含有上述芳香族胺衍生物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710648042.XA CN107266399A (zh) | 2012-08-30 | 2013-08-29 | 芳香族胺衍生物以及使用其的有机电致发光元件 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012-190598 | 2012-08-30 | ||
JP2012190598 | 2012-08-30 | ||
PCT/JP2013/073183 WO2014034793A1 (ja) | 2012-08-30 | 2013-08-29 | 芳香族アミン誘導体およびこれを用いた有機エレクトロルミネッセンス素子 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201710648042.XA Division CN107266399A (zh) | 2012-08-30 | 2013-08-29 | 芳香族胺衍生物以及使用其的有机电致发光元件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104662010A CN104662010A (zh) | 2015-05-27 |
CN104662010B true CN104662010B (zh) | 2017-08-25 |
Family
ID=50183598
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201380045222.9A Active CN104662010B (zh) | 2012-08-30 | 2013-08-29 | 芳香族胺衍生物以及使用其的有机电致发光元件 |
CN201710648042.XA Pending CN107266399A (zh) | 2012-08-30 | 2013-08-29 | 芳香族胺衍生物以及使用其的有机电致发光元件 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201710648042.XA Pending CN107266399A (zh) | 2012-08-30 | 2013-08-29 | 芳香族胺衍生物以及使用其的有机电致发光元件 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10985325B2 (zh) |
EP (2) | EP3312167A1 (zh) |
JP (2) | JP6367117B2 (zh) |
KR (1) | KR102196594B1 (zh) |
CN (2) | CN104662010B (zh) |
TW (2) | TWI646089B (zh) |
WO (1) | WO2014034793A1 (zh) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2013061805A1 (ja) * | 2011-10-24 | 2015-04-02 | 保土谷化学工業株式会社 | 新規なトリフェニレン誘導体及び該誘導体が使用されている有機エレクトロルミネッセンス素子 |
CN104662010B (zh) * | 2012-08-30 | 2017-08-25 | 出光兴产株式会社 | 芳香族胺衍生物以及使用其的有机电致发光元件 |
US9748492B2 (en) | 2012-11-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
CN105683174A (zh) * | 2014-02-28 | 2016-06-15 | 出光兴产株式会社 | 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
KR102065817B1 (ko) * | 2016-06-02 | 2020-01-13 | 주식회사 엘지화학 | 유기 발광 소자 |
KR102065816B1 (ko) * | 2016-06-02 | 2020-01-13 | 주식회사 엘지화학 | 유기 발광 소자 |
TWI804474B (zh) * | 2016-09-14 | 2023-06-11 | 日商半導體能源研究所股份有限公司 | 有機化合物、發光元件、發光裝置、電子裝置及照明設備 |
CN108063188B (zh) * | 2016-11-08 | 2020-08-11 | 株式会社Lg化学 | 有机发光元件 |
WO2018164239A1 (ja) * | 2017-03-08 | 2018-09-13 | 出光興産株式会社 | 化合物、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、及び電子機器 |
KR20190125937A (ko) * | 2018-04-30 | 2019-11-07 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
CN108658801A (zh) * | 2018-06-21 | 2018-10-16 | 中国林业科学研究院林产化学工业研究所 | 一类基于脱氢枞酸芳环的化合物及其制备方法 |
CN108658800A (zh) * | 2018-06-21 | 2018-10-16 | 中国林业科学研究院林产化学工业研究所 | 一类基于脱氢枞酸芳环二取代的化合物及其制备方法 |
KR102169567B1 (ko) * | 2018-12-21 | 2020-10-23 | 엘지디스플레이 주식회사 | 유기 발광 소자 |
KR102221900B1 (ko) | 2019-03-15 | 2021-03-02 | 이데미쓰 고산 가부시키가이샤 | 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기 |
TWI706943B (zh) * | 2019-10-31 | 2020-10-11 | 昱鐳光電科技股份有限公司 | 胺基氧芴化合物及其有機電激發光元件 |
WO2021093377A1 (zh) * | 2019-11-12 | 2021-05-20 | 广州华睿光电材料有限公司 | 含光取出层材料的有机电致发光器件 |
WO2021230715A1 (ko) * | 2020-05-14 | 2021-11-18 | 주식회사 엘지화학 | 유기 발광 소자 |
CN112687797B (zh) * | 2020-11-12 | 2023-03-24 | 烟台海森大数据有限公司 | 一种有机电致发光器件及包含该器件的显示装置 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101432272A (zh) * | 2006-04-26 | 2009-05-13 | 出光兴产株式会社 | 芳香族胺衍生物及使用了它们的有机电致发光元件 |
WO2012039534A1 (ko) * | 2010-09-20 | 2012-03-29 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
WO2012091428A2 (ko) * | 2010-12-29 | 2012-07-05 | 주식회사 엘지화학 | 새로운 화합물 및 이를 이용한 유기 발광 소자 |
WO2013061805A1 (ja) * | 2011-10-24 | 2013-05-02 | 保土谷化学工業株式会社 | 新規なトリフェニレン誘導体及び該誘導体が使用されている有機エレクトロルミネッセンス素子 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59157473A (ja) | 1983-02-23 | 1984-09-06 | 松下冷機株式会社 | 冷・温切換式の貯蔵庫 |
KR100669716B1 (ko) | 2004-07-14 | 2007-01-16 | 삼성에스디아이 주식회사 | 페닐카르바졸 화합물 및 이를 이용한 유기 전계 발광 소자 |
US8188315B2 (en) | 2004-04-02 | 2012-05-29 | Samsung Mobile Display Co., Ltd. | Organic light emitting device and flat panel display device comprising the same |
KR100573137B1 (ko) | 2004-04-02 | 2006-04-24 | 삼성에스디아이 주식회사 | 플루오렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR100787425B1 (ko) | 2004-11-29 | 2007-12-26 | 삼성에스디아이 주식회사 | 페닐카바졸계 화합물 및 이를 이용한 유기 전계 발광 소자 |
US8021765B2 (en) | 2004-11-29 | 2011-09-20 | Samsung Mobile Display Co., Ltd. | Phenylcarbazole-based compound and organic electroluminescent device employing the same |
US20070215889A1 (en) | 2006-03-20 | 2007-09-20 | Semiconductor Energy Laboratory Co., Ltd. | Aromatic amine compound, and light-emitting element, light-emitting device, and electronic appliance using the aromatic amine compound |
KR101422864B1 (ko) | 2006-06-22 | 2014-07-24 | 소니 주식회사 | 복소환 함유 아릴아민 유도체를 이용한 유기 전계발광 소자 |
CN101535256B (zh) | 2006-11-24 | 2013-05-22 | 出光兴产株式会社 | 芳香族胺衍生物及使用其的有机电致发光元件 |
JP5218131B2 (ja) * | 2009-02-17 | 2013-06-26 | 株式会社デンソー | 有機el素子 |
KR20100041043A (ko) | 2008-10-13 | 2010-04-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 |
KR101754432B1 (ko) | 2009-03-23 | 2017-07-05 | 바스프 에스이 | 유기 반도체 장치에 사용하기 위한 디케토피롤로피롤 중합체 |
JP2011098948A (ja) * | 2009-06-25 | 2011-05-19 | Yamagata Promotional Organization For Industrial Technology | ビピリジン誘導体及びそれを含む有機エレクトロルミネッセンス素子 |
DE202010018533U1 (de) | 2009-08-19 | 2017-06-08 | Idemitsu Kosan Co., Ltd. | Aromatische Amin-Derivate und diese verwendende organische Elektrolumineszenzelemente |
KR101097339B1 (ko) * | 2010-03-08 | 2011-12-23 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 및 이의 제조 방법 |
KR20110112098A (ko) * | 2010-04-06 | 2011-10-12 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
EP2626346B1 (en) * | 2010-10-08 | 2018-01-10 | Idemitsu Kosan Co., Ltd. | Benzo[k]fluoranthene derivative and organic electroluminescence element containing same |
WO2012049828A1 (ja) * | 2010-10-12 | 2012-04-19 | 出光興産株式会社 | 芳香族複素環誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
US9133173B2 (en) * | 2010-10-15 | 2015-09-15 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole compound, material for light-emitting element, organic semiconductor material, light-emitting element |
TWI545175B (zh) * | 2010-12-17 | 2016-08-11 | 半導體能源研究所股份有限公司 | 有機化合物,發光元件,發光裝置,電子裝置,以及照明裝置 |
KR101874657B1 (ko) * | 2011-02-07 | 2018-07-04 | 이데미쓰 고산 가부시키가이샤 | 비스카바졸 유도체 및 그것을 이용한 유기 전기발광 소자 |
KR101908384B1 (ko) * | 2011-06-17 | 2018-10-17 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 평판 표시 장치 |
KR102079019B1 (ko) * | 2011-10-13 | 2020-02-20 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN104662010B (zh) * | 2012-08-30 | 2017-08-25 | 出光兴产株式会社 | 芳香族胺衍生物以及使用其的有机电致发光元件 |
-
2013
- 2013-08-29 CN CN201380045222.9A patent/CN104662010B/zh active Active
- 2013-08-29 US US14/424,703 patent/US10985325B2/en active Active
- 2013-08-29 EP EP17198969.2A patent/EP3312167A1/en not_active Withdrawn
- 2013-08-29 KR KR1020157005239A patent/KR102196594B1/ko active IP Right Grant
- 2013-08-29 EP EP13832674.9A patent/EP2891653B1/en active Active
- 2013-08-29 WO PCT/JP2013/073183 patent/WO2014034793A1/ja active Application Filing
- 2013-08-29 JP JP2014533087A patent/JP6367117B2/ja active Active
- 2013-08-29 CN CN201710648042.XA patent/CN107266399A/zh active Pending
- 2013-08-30 TW TW102131416A patent/TWI646089B/zh active
- 2013-08-30 TW TW106136814A patent/TW201802077A/zh unknown
-
2017
- 2017-10-05 JP JP2017195220A patent/JP2018016638A/ja active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101432272A (zh) * | 2006-04-26 | 2009-05-13 | 出光兴产株式会社 | 芳香族胺衍生物及使用了它们的有机电致发光元件 |
WO2012039534A1 (ko) * | 2010-09-20 | 2012-03-29 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
WO2012091428A2 (ko) * | 2010-12-29 | 2012-07-05 | 주식회사 엘지화학 | 새로운 화합물 및 이를 이용한 유기 발광 소자 |
WO2013061805A1 (ja) * | 2011-10-24 | 2013-05-02 | 保土谷化学工業株式会社 | 新規なトリフェニレン誘導体及び該誘導体が使用されている有機エレクトロルミネッセンス素子 |
Also Published As
Publication number | Publication date |
---|---|
JP2018016638A (ja) | 2018-02-01 |
EP2891653A1 (en) | 2015-07-08 |
EP3312167A1 (en) | 2018-04-25 |
WO2014034793A1 (ja) | 2014-03-06 |
JPWO2014034793A1 (ja) | 2016-08-08 |
TW201408654A (zh) | 2014-03-01 |
EP2891653B1 (en) | 2018-01-17 |
US10985325B2 (en) | 2021-04-20 |
US20150263292A1 (en) | 2015-09-17 |
CN104662010A (zh) | 2015-05-27 |
JP6367117B2 (ja) | 2018-08-01 |
EP2891653A4 (en) | 2016-04-20 |
CN107266399A (zh) | 2017-10-20 |
TWI646089B (zh) | 2019-01-01 |
KR102196594B1 (ko) | 2020-12-30 |
TW201802077A (zh) | 2018-01-16 |
KR20150046069A (ko) | 2015-04-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104662010B (zh) | 芳香族胺衍生物以及使用其的有机电致发光元件 | |
CN104583176B (zh) | 芳香族胺衍生物和使用了其的有机电致发光元件 | |
WO2011059099A1 (ja) | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 | |
JPWO2012144176A1 (ja) | ピレン誘導体、有機発光媒体、及びこれらを含む有機エレクトロルミネッセンス素子 | |
JP5903271B2 (ja) | 芳香族アミン誘導体、及びそれを用いた有機エレクトロルミネッセンス素子。 | |
JPWO2010122799A1 (ja) | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 | |
TW201331160A (zh) | 芳香族胺衍生物及使用其之有機電致發光元件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
EXSB | Decision made by sipo to initiate substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20160304 Address after: Japan within Tokyo Chiyoda Ku pill 3 chome 1 No. 1 Applicant after: IDEMITSU KOSAN Co.,Ltd. Address before: Japan within Tokyo Chiyoda Ku pill 3 chome 1 No. 1 Applicant before: IDEMITSU KOSAN Co.,Ltd. Applicant before: MITSUI CHEMICALS, Inc. |
|
GR01 | Patent grant | ||
GR01 | Patent grant |