WO2005043962A1 - 1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 - Google Patents
1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 Download PDFInfo
- Publication number
- WO2005043962A1 WO2005043962A1 PCT/JP2004/016095 JP2004016095W WO2005043962A1 WO 2005043962 A1 WO2005043962 A1 WO 2005043962A1 JP 2004016095 W JP2004016095 W JP 2004016095W WO 2005043962 A1 WO2005043962 A1 WO 2005043962A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- metal
- charge
- represented
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical group S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000011368 organic material Substances 0.000 title claims abstract description 19
- 239000002966 varnish Substances 0.000 claims abstract description 49
- 239000010409 thin film Substances 0.000 claims abstract description 29
- -1 phenylenevinylene Chemical group 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 61
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 39
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 26
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 26
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 239000002019 doping agent Substances 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 21
- 150000002430 hydrocarbons Chemical group 0.000 claims description 19
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229930192474 thiophene Natural products 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 16
- 150000007970 thio esters Chemical class 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- VIGMAPZYSWAUDT-UHFFFAOYSA-N N[SiH2]O Chemical compound N[SiH2]O VIGMAPZYSWAUDT-UHFFFAOYSA-N 0.000 claims description 14
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 13
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 13
- 239000010452 phosphate Substances 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005259 triarylamine group Chemical group 0.000 claims description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
- 150000003855 acyl compounds Chemical class 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 11
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 11
- 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 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical group S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001174 sulfone group Chemical group 0.000 claims description 8
- 239000003377 acid catalyst Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000000611 organothio group Chemical group 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 150000004032 porphyrins Chemical class 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims description 5
- 229910052755 nonmetal Inorganic materials 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 241000255925 Diptera Species 0.000 claims description 2
- 230000002195 synergetic effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 150000003573 thiols Chemical class 0.000 claims 7
- MOYNGINHGVIELF-UHFFFAOYSA-L hexadecylaluminum(2+);dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCCCCC[Al+2] MOYNGINHGVIELF-UHFFFAOYSA-L 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 17
- 229920000642 polymer Polymers 0.000 abstract description 7
- 239000000446 fuel Substances 0.000 abstract description 2
- 239000003990 capacitor Substances 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 150000003384 small molecules Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 38
- 239000000463 material Substances 0.000 description 25
- 239000000758 substrate Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000010304 firing Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- 229920000123 polythiophene Polymers 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000005486 sulfidation Methods 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- 238000001771 vacuum deposition Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 3
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 2
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000006872 improvement Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 2
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 1
- UAULZKIRDNZQHF-UHFFFAOYSA-N 2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol;$l^{1}-sulfane Chemical compound [SH].OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O UAULZKIRDNZQHF-UHFFFAOYSA-N 0.000 description 1
- RVYKTPRETIBSPK-UHFFFAOYSA-N 2-(2-Thienyl)furan Chemical compound C1=COC(C=2SC=CC=2)=C1 RVYKTPRETIBSPK-UHFFFAOYSA-N 0.000 description 1
- UDHZFLBMZZVHRA-UHFFFAOYSA-N 2-(furan-2-yl)furan Chemical compound C1=COC(C=2OC=CC=2)=C1 UDHZFLBMZZVHRA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- AMVKSLDIFMJFIG-AATRIKPKSA-N 2-[(e)-2-(furan-2-yl)ethenyl]furan Chemical group C=1C=COC=1/C=C/C1=CC=CO1 AMVKSLDIFMJFIG-AATRIKPKSA-N 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- LKRZCUQFUCYWLZ-UHFFFAOYSA-N 2-chloroacetyl bromide Chemical compound ClCC(Br)=O LKRZCUQFUCYWLZ-UHFFFAOYSA-N 0.000 description 1
- GKUAOYZMFRWOOC-UHFFFAOYSA-N 2-chloroacetyl fluoride Chemical compound FC(=O)CCl GKUAOYZMFRWOOC-UHFFFAOYSA-N 0.000 description 1
- CTVCBOZMKFQEAP-UHFFFAOYSA-N 2-ethynylfuran Chemical group C#CC1=CC=CO1 CTVCBOZMKFQEAP-UHFFFAOYSA-N 0.000 description 1
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 1
- PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical compound C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- UXKQNCDDHDBAPD-UHFFFAOYSA-N 4-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UXKQNCDDHDBAPD-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- MRUWJENAYHTDQG-UHFFFAOYSA-N 4H-pyran Chemical compound C1C=COC=C1 MRUWJENAYHTDQG-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000012905 Brassica oleracea var viridis Nutrition 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- KAUNVUOTZPSFER-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C1(C(=CC=CC1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C1(C(=CC=CC1)C1=CC=CC=C1)C1=CC=CC=C1 KAUNVUOTZPSFER-UHFFFAOYSA-N 0.000 description 1
- BBRAFLRAHCYZDL-UHFFFAOYSA-L CC[Al+2].[Cl-].[Cl-].Cl.Cl Chemical compound CC[Al+2].[Cl-].[Cl-].Cl.Cl BBRAFLRAHCYZDL-UHFFFAOYSA-L 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 241000577218 Phenes Species 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- NPRDEIDCAUHOJU-UHFFFAOYSA-N [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical class [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NPRDEIDCAUHOJU-UHFFFAOYSA-N 0.000 description 1
- IQPMXAAZNRKZCN-UHFFFAOYSA-N [Ti+4].[Ti+4] Chemical compound [Ti+4].[Ti+4] IQPMXAAZNRKZCN-UHFFFAOYSA-N 0.000 description 1
- ZPDLWVONTPDGQY-UHFFFAOYSA-N acetyl acetate;lithium Chemical compound [Li].CC(=O)OC(C)=O ZPDLWVONTPDGQY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- YZBHXERKJHIPKI-UHFFFAOYSA-K aluminum chloroethane trichloride Chemical compound C(C)Cl.[Cl-].[Al+3].[Cl-].[Cl-] YZBHXERKJHIPKI-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- MVIOINXPSFUJEN-UHFFFAOYSA-N benzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=CC=C1 MVIOINXPSFUJEN-UHFFFAOYSA-N 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- QTNDMWXOEPGHBT-UHFFFAOYSA-N dicesium;sulfide Chemical compound [S-2].[Cs+].[Cs+] QTNDMWXOEPGHBT-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical compound [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- ZBHDTYQJAQDBIH-UHFFFAOYSA-N fluoroacetyl chloride Chemical compound FCC(Cl)=O ZBHDTYQJAQDBIH-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- CUPFNGOKRMWUOO-UHFFFAOYSA-N hydron;difluoride Chemical compound F.F CUPFNGOKRMWUOO-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- GLNWILHOFOBOFD-UHFFFAOYSA-N lithium sulfide Chemical compound [Li+].[Li+].[S-2] GLNWILHOFOBOFD-UHFFFAOYSA-N 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- BGTFRFFRQKBWLS-UHFFFAOYSA-M lithium;quinolin-2-olate Chemical compound [Li+].C1=CC=CC2=NC([O-])=CC=C21 BGTFRFFRQKBWLS-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- GZORJAFFPJJJQU-UHFFFAOYSA-N n,n-dimethylacetamide;1-methylpyrrolidin-2-one Chemical compound CN(C)C(C)=O.CN1CCCC1=O GZORJAFFPJJJQU-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- GVGCUCJTUSOZKP-UHFFFAOYSA-N nitrogen trifluoride Chemical compound FN(F)F GVGCUCJTUSOZKP-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
- 150000007524 organic acids Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000000956 solid--liquid extraction Methods 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 238000005936 thiocarbonylation reaction Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- 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
-
- 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
- H10K50/155—Hole transporting layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- 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
- H10K85/311—Phthalocyanine
-
- 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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the present invention relates to a charge transporting organic material containing a compound having a 1,4-dithiin ring, a charge transporting thin film and an organic electroluminescent (hereinafter abbreviated as EL) device using the same.
- EL organic electroluminescent
- Organic EL elements are broadly classified into low-molecular-weight organic EL (hereinafter abbreviated as OLED) elements and high-molecular-weight organic EL (hereinafter abbreviated as PLED) elements.
- OLED low-molecular-weight organic EL
- PLED high-molecular-weight organic EL
- Non-Patent Document 1 In OLED devices, it has been found that by providing a copper phthalocyanine (CuPC) layer as a hole injection layer, it is possible to improve initial characteristics such as lowering of driving voltage and improvement of luminous efficiency, and also to improve life characteristics.
- CuPC copper phthalocyanine
- a polyaniline-based material for example, see Non-Patent Documents 2 and 3
- a polythiophene-based material for example, see Non-Patent Document 4
- a hole transport layer buffer layer
- a metal oxide for example, see Non-Patent Document 6
- a metal halide for example, see Non-Patent Document 6
- a metal complex for example, see Non-Patent Document 7
- a vapor deposition material As a hole injection material for an OLED element, a vapor deposition material is widely used.
- the problems with the vapor-deposited materials are that they require various properties, such as being amorphous solids, sublimability, high heat resistance, and having an appropriate ionization potential (hereinafter abbreviated as I).
- conjugated oligomers or polymers are materials having high charge transport properties. Many of them have low solubility and are difficult to make into varnishes. Many. In particular, in the case of an unsubstituted thiophene oligomer, a pentamer or more is almost insoluble in any solvent.
- Hole transport materials for PLED elements have required properties such as high charge transport properties, insolubility in luminescent polymer solvents such as toluene, and appropriate I. Polyary widely used today
- Non-Patent Documents 8-10 the synthesis of compounds having a 1,4-dithiin ring has been reported in literatures (for example, see Non-Patent Documents 8-10).
- the method for producing a compound having a 1,4-dithiine ring shown in Non-Patent Documents 9 and 10 has many steps and is difficult to mass-produce. Was needed.
- Non-Patent Document 1 Applied Physics Letters, USA, 1996, Vol. 69, p.2160-2162
- Non-Patent Document 2 Nature, UK, 1992, 357, p.477-479
- Non-Patent Document 3 Applied Physics Letters, USA, 19
- Non-Patent Document 4 Applied Physics Letters, U.S.A., 1998, Vol. 72, p.2660-2662
- Non-Patent Document 5 II. Transactions on Electron Devices, USA, 1997, 44, p. 1245—1248
- Non-Patent Document 6 Applied 'Physics' Letters (Applied Physics Letters), U.S.A., 1997, Volume 70, pp. 152-154
- Non-Patent Document 7 Japanese ⁇ Journal ⁇ Job ⁇ Applied ⁇ Physics (Japanese Journal of Applied Physics), 1999, Vol. 38, p ⁇ 1348—1350
- Non-Patent Document 8 Journal of American Chemical Society, 1953, Vol. 75, p. 1647—1651
- Non-Patent Document 9 Heterocycles, 1984, Vol. 22, p. 1527
- Non-Patent Document 10 Heterocycles, 1987, Vol. 26, p. 939-942
- Patent Document 1 JP 2002-151272 A
- the present invention has been made in view of the above circumstances, and particularly when used in an OLED element and a PLED element, enables excellent EL element characteristics, that is, low driving voltage and high luminous efficiency.
- An object of the present invention is to provide a charge transporting organic material and a charge transporting varnish containing a compound having a 1,4-dithiin ring, and a charge transporting thin film and an organic electroluminescent device using the same.
- the present inventor has conducted intensive studies to achieve the above object, and as a result, it has been found that compounds having a 1,4-dithiin ring can be used in organic solvents such as N, N-dimethylformamide (hereinafter abbreviated as DMF). In addition to finding that it is a soluble material, it exhibits charge transportability when combined with an electron-accepting dopant substance or a hole-accepting dopant, and is used as a charge-transporting thin film such as a hole injection layer in OLED devices. The inventors have found that voltage driving and luminous efficiency can be improved, and have completed the present invention.
- organic solvents such as N, N-dimethylformamide (hereinafter abbreviated as DMF).
- DMF N, N-dimethylformamide
- the present invention provides the following [1]-[11] inventions.
- R 4 are each independently hydrogen, hydroxyl, halogen, amino, Group, silanol group, thiol group, carboxyl group, sulfonic acid group, phosphate group, phosphate group, ester group, thioester group, amide group, nitro group, monovalent hydrocarbon group, organooxy group, organoamino group , An organosilyl group, an organothio group, an acyl group, or a sulfone group, and X and Y each independently represent a substituted or unsubstituted divalent co-functional unit, such as a-line, thiophene, furan, or pyrrole.
- At least one selected from the two sulfur atoms contained in the dithiin ring may be each independently an SO group or an SO group.
- R 1 is hydrogen, hydroxyl, halogen, amino, silanol, thiol, carboxyl, sulfonic, phosphoric, phosphate, ester, ester, thioester, amide
- X represents a nitro group, a monovalent hydrocarbon group, or an organooxy group
- X represents a substituted or unsubstituted divalent conjugated unit such as aline, thiophene, furan, pyrrole, ethylenylene, vinylene, Phenylene, naphthalene, anthracene, imidazole, oxazole, At least one selected from the group consisting of oxadiazole, quinoline, quinoxaline, pyridine, pyrimidine, pyrazine, phenylenevinylene, fluorene, carbazole, triarylamine, metal or metal-free phthalocyanine, and metal or metal-free porphyrinka Indicates
- R 2 is hydrogen, hydroxyl, halogen, amino, silanol, thiol, carboxyl, sulfonic, phosphoric, phosphate, ester, ester, thioester, amide
- Y represents a nitro group, a monovalent hydrocarbon group, or an organooxy group
- Y represents a substituted or unsubstituted divalent conjugated unit such as arin, thiophene, furan, pyrrole, ethylenylene, vinylene, Phenylene, naphthalene, anthracene, imidazole, oxazole, oxaziazole, quinoline, quinoxalin, pyridine, pyrimidine, pyrazine, phenylenevinylene, fluorene, carbazole, triarylamine, metal or metal-free phthalocyanine, and Represents at least one selected from metal or nonmetal porphyrinka, and r is
- Hal represents a halogen atom.
- a second step of producing a sulfide represented by the formula (7) followed by a third step of allowing a thiocarbonylating reagent to act on the sulfurated product represented by the formula (7) and closing the ring.
- a method for producing a compound having a 1,4-dithiin ring represented by the formula (1)
- R 1 R 2 , X, Y, ⁇ and r are the same as above.
- R 3 and R 4 are each independently hydrogen, hydroxyl, halogen, amino, silanol, thiol, carboxyl) , Sulfonate, phosphate, phosphate, ester, thioester, amide, nitro, monovalent hydrocarbon, organooxy, organoamino, organosilyl, organothiol, and acyl groups Or a sulfone group, and the two sulfur atoms contained in the dithiin ring may be each independently an SO group or an SO group, q is 0 or an integer of 1 or more,
- R 1 is hydrogen, hydroxyl, halogen, amino, silanol, thiol, A boxyl group, a sulfonic acid group, a phosphoric acid group, a phosphoric acid ester group, an ester group, a thioester group, an amide group, a nitro group, a monovalent hydrocarbon group, or an organooxy group;
- X is substituted or unsubstituted; and , Divalent conjugated units a-line, thiophene, furan, pyrrole, ethynylene, vinylene, phenylene, naphthalene, anthracene, imidazole, oxazole, oxaziazole, quinoline, quinoxaline, pyridine, pyrimidine, pyrazine, phene Nirene Virene, fluorene, carbazole, triarylamine, metal or metal-free phthalocyanine, and at least one
- R 2 is hydrogen, hydroxyl, halogen, amino, silanol, thiol, carboxyl, sulfonic, phosphoric, phosphate, ester, ester, thioester, amide
- Y represents a nitro group, a monovalent hydrocarbon group, or an organooxy group
- Y represents a substituted or unsubstituted divalent conjugated unit such as arin, thiophene, furan, pyrrole, ethylenylene, vinylene, Phenylene, naphthalene, anthracene, imidazole, oxazole, oxaziazole, quinoline, quinoxalin, pyridine, pyrimidine, pyrazine, phenylenevinylene, fluorene, carbazole, triarylamine, metal or metal-free phthalocyanine, and Represents at least one selected from metal or nonmetal porphyrinka, and r is
- Hal represents a halogen atom.
- R 3 and R 4 are each independently hydrogen, hydroxyl, halogen, amino, silanol, thiol, carboxyl, sulfonate, Group, phosphoric acid group, phosphoric ester group, ester group, thioester group, amide group, nitro group, valent hydrocarbon group, organooxy group, organoamino group, organosilyl group, or It represents a ganotio group, an acyl group or a sulfone group, and the two sulfur atoms contained in the dithiin ring may be each independently an SO group or an SO group.
- q is 0 or an integer of 1 or more
- the electrode and the organic layer can be separated. As a result, the charge injection barrier is lowered, and the driving voltage driving is reduced and the luminous efficiency is improved.
- This charge-transporting varnish differs from the conventionally used aqueous solution-type charge-transporting varnish, and can be used only with an organic solvent, and is a wet process that can prevent the incorporation of moisture that causes device deterioration as much as possible. Since a coating film can be easily formed by using the method, it is not necessary to form the film by a vacuum deposition method. Therefore, a group of conjugated oligomers having poor sublimability and heat resistance can be applied to the organic EL device.
- the compound having a dithiine ring contained in the charge-transporting organic material of the present invention can be easily doped using a charge-accepting dopant substance.
- the charge-transporting varnish of the present invention has good processability, and a thin film obtained from the varnish has high charge-transporting properties. It is also effective for application to batteries and fuel cells.
- FIG. 1 is a view showing a photograph of a light emitting surface of the OLED element obtained in Example 7.
- FIG. 2 is a view showing a photograph of a light emitting surface of the OLED element obtained in Comparative Example 4.
- the charge-transporting organic material (charge-transporting varnish) according to the present invention contains a charge-transporting substance that is the main body of the charge-transporting mechanism.
- the charge-transporting organic material may be a combination of a charge-transporting substance and a charge-accepting dopant that improves the charge-transporting property of the charge-transporting substance.
- the charge transporting varnish contains two combinations of a charge transporting substance and a solvent. Or a combination of a charge-transporting substance, a charge-accepting dopant substance, and a solvent, which are completely dissolved by the solvent and are uniformly dispersed.
- the charge transporting property is synonymous with the conductivity, and means any of a hole transporting property, an electron transporting property, and a charge transporting property of both holes and electrons.
- the charge-transporting varnish may have a charge-transporting property itself, or may have a charge-transporting property in a solid film capable of obtaining a varnish force.
- the charge transporting substance contained in the charge transporting organic material (charge transporting varnish) of the present invention is a compound having a 1,4-dithiin ring represented by the following formula (1).
- R 4 are each independently hydrogen, hydroxyl, halogen, amino, silanol, thiol, carboxyl, sulfonic, phosphoric, phosphoric, ester, ester, thioester, or amide.
- a nitro group, a monovalent hydrocarbon group, an organooxy group, an organoamino group, an organosilyl group, an organothio group, an acyl group or a sulfone group, X and Y are each independently substituted or unsubstituted, and
- the bivalent synergistic units a-line, thiophene, furan, pyrrole, ethylene, bi-len, phenylene, naphthalene, anthracene, imidazole, oxazole, oxaziazole, quinoline, quinoxalin, pyridine, pyrimidine , Pyrazine, phenylenevinylene, phenolic, phenol, triarylamine, metal- Metal free - phthalocyanine, and metal - young properly is at least one selected metal-free porphyrin mosquitoes, two sulfur atoms contained in the dithiin ring may be SO group or an SO group independently.
- p, q, and r are more preferably p + q + r ⁇ 20, and more preferably p + q + r ⁇ 10, from the viewpoint of enhancing the solubility of the compound. Furthermore, from the viewpoint of exhibiting high charge transportability, 3 ⁇ p + q + r is preferable, and 5 ⁇ p + q + r is particularly preferable.
- the conjugate units represented by X and Y in the formula are an atom capable of transporting charge, an aromatic ring, and a conjugate group.
- it is not particularly limited as long as it is preferable, it is preferably substituted or unsubstituted divalent a-line, thiophene, furan, pyro-monole, ethylene, bilen, phenylene, Naphthalene, anthracene, imidazole, oxazole, oxaziazole, quinoline, quinoxalin, pyridine, pyrimidine, pyrazine, phenylenevinylene, funolelene, phenolic phenol, triphenylamine, metal or metal-free phthalocyanine, and metal or metal-free porphyrin Can be mentioned.
- thiophene, furan, pyrrole, phenylene, triarylamine and the like are mentioned.
- substituents include, independently of each other, a hydroxyl group, a halogen group, an amino group, a silanol group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, a phosphoric acid ester group, an ester group.
- the monovalent hydrocarbon group examples include an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a t-butyl group, a hexyl group, an octyl group and a decyl group, a cyclopentyl group, and a cyclohexyl group.
- an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a t-butyl group, a hexyl group, an octyl group and a decyl group, a cyclopentyl group, and a cyclohexyl group.
- Groups such as cycloalkyl group, bicycloalkyl group such as bicyclohexyl group, butyl group, 1-propyl group, 2-propyl group, isopropyl group, 1-methyl-2-probe group Alkenyl groups such as 1-, 2- or 3-butyryl groups and hexyl groups, phenyl groups such as phenyl groups, xylyl groups, tolyl groups, biphenyl groups and naphthyl groups, benzyl groups and phenyl groups Aralkyl groups such as -ruethyl group and phenylcyclohexyl group;
- Examples thereof include those obtained by substituting a part or all of the hydrogen atoms of these monovalent hydrocarbon groups with a halogen atom, a hydroxyl group, an alkoxy group, or the like.
- organooxy group examples include an alkoxy group, an alkoxy group, an aryloxy group, and the like.
- examples of the alkyl group, the alkoxy group, and the aryl group include the same as those exemplified above. .
- organoamino group examples include a methylamino group, an ethylamino group, a propylamino group, a butylamino group, a pentylamino group, a hexylamino group, a heptylamino group, an octylamino group, an alkylamino group such as a noramino group, a decylamino group, and a laurylamino group; Dimethyla Dialkylamino groups such as mino group, getylamino group, dipropylamino group, dibutylamino group, dipentylamino group, dihexylamino group, diheptylamino group, dioctylamino group, dino-amino group and didecylamino group, cyclohexylamino group and morpholino group And so on.
- Dimethyla Dialkylamino groups such as mino
- organosilyl group examples include a trimethylsilyl group, a triethylsilyl group, a tripropylsilyl group, a tributylsilyl group, a tripentylsilyl group, a trihexylsilyl group, a pentyldimethylsilyl group, a hexyldimethylsilyl group, and an octyldimethylsilyl group. And a decyldimethylsilyl group.
- organothio group examples include an alkylthio group such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, and a laurylthio group.
- alkylthio group such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, and a laurylthio group.
- Examples of the acryl group include a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, and a benzoyl group.
- the number of carbon atoms in a monovalent hydrocarbon group, an organooxy group, an organoamino group, an organosilyl group, an organothio group, an acyl group, etc. is not particularly limited, but is generally 1120, preferably 118. is there.
- Preferred substituents include fluorine, a sulfonic acid group, a substituted or unsubstituted organooxy group, an alkyl group and an organosilyl group.
- the conjugated chain formed by connecting the conjugated units may include a cyclic portion. However, it is desirable that this cyclic portion does not have any substituent in order to exhibit high charge transportability.
- This are specific examples of the compound represented by the above formula (1).
- the method for synthesizing a compound containing a 1,4-dithiin ring is not particularly limited, and examples thereof include literature, Heterocycles, 1987, Vol. 26, p. 939-942, and Heterocycles. Heterocycles, 1987, Vol. 26, p.1793-1796, can be mentioned. In the present invention, in particular, a manufacturing method having the following three steps is used. Preferred,. [0030] [Formula 24]
- the first step is a step of acylating the starting compound represented by the formula (2) or (3) using an acid catalyst.
- thiophene 2,2′-bithiophene (hereinafter abbreviated as BT), 2, 2 ′: 5 ′, 2, terthiophene, diphen- Lumin, N, N-diphenyl-1,4-phenylenediamine, furan, 2, 2'-bifuran, 2, 2 ': 5', 2 "terflan, pyrrole, 2,2, -bipyrrole, 2, 2 ,: 5,, 2 "tervirol, 1,2-di (2-cell) ethylene, 1,2-di (2-cell) acetylene, 1,2-di (2-furyl) ethylene, 1,, 2-di (2-furyl) acetylene, 2-furylthiophene, 5-furyl 2,2,1-bithiophene, 2-phenylthiophene, 2-biphenylthiophene, 5-phenyl-2,2, -bithiophene ,
- the acylating reagent is represented by the formula (4), specifically, 2-chloroacetyl chloride, 2-chloroacetyl fluoride, 2-chloroacetyl bromide, 2-chloroacetyl chloride. And chloroacetyl chloride, 2-fluoroacetyl chloride, 2-bromoacetyl chloride, 2-chloroacetyl chloride, and 2-chloroacetyl chloride is particularly preferred.
- the amount of the acylating reagent to be used is preferably 0.8 to 1.5 times the mol of the starting material represented by the formula (2) or (3), but is 1.0 to 1.2 times the mol. Is particularly preferred.
- dichloride ethyl aluminum chloride which is preferably used by a Lewis acid, and ethyl chloride aluminum chloride are particularly preferable.
- the amount of the acid catalyst used is preferably 0.1 to 5.0 times the mol of the starting material represented by the formula (2) or (3), but 1.0 to 1.2 times the mol. Particularly preferred.
- the reaction solvent is preferably an aprotic solvent such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, nitromethane, acetonitrile, diisopropyl ether, cyclohexane and the like.
- Dichloromethane and dichloroethane are particularly preferred.
- the amount of the reaction solvent to be used is preferably 1 to 200 times by weight relative to the starting material represented by the formula (2) or (3), but is more preferably 5 to 30 times. ,.
- the reaction temperature is particularly preferably 20-30 ° C, which is usually about 80-50 ° C.
- the progress of the reaction can be detected by thin-layer chromatography (hereinafter abbreviated as TLC) or liquid chromatography (hereinafter abbreviated as LC).
- liquid-liquid extraction operation After the reaction is completed, liquid-liquid extraction operation, water-washing operation, solid-liquid extraction operation, hot filtration operation, concentration operation, and drying operation can be used for purification. Further recrystallization or silica gel column chromatography It is also possible to improve purity.
- the second step is a step of producing a sulfur ridden product represented by the formula (7) from the acylid ligated product represented by the formulas (5) and (6) obtained in the first process. is there.
- the ratio of the acylyl compound represented by the formula (5) to the acyl compound represented by the formula (6) is not particularly limited. However, it is preferable that the power is 1: 1 and each is the same compound.
- sulfidation reagent examples include lithium sulfide, sodium sulfidation, potassium sulfidation, and cesium sulfide. Among them, sodium sulfidation is particularly preferred.
- the amount of the sulfurizing reaction reagent used is 0.2 to 1.2 times the mole of the sum of the number of moles of the acyl compound represented by (5) and the number of moles of the acyl compound represented by formula (6) used in the reaction. Is preferred 0.45-0.55 times monole power especially preferred! / ⁇ .
- the reaction solvent is not particularly limited as long as it dissolves a part or all of the starting material and the alkali metal sulfide.
- a mixed solvent of water and a water-soluble organic solvent such as methoxyethanol, 1,2-propylene glycol, diethylene glycol getyl ether and the like is preferred.
- the mixing ratio of the organic solvent and water is not particularly limited, but the amount of water in the mixed solvent is preferably set to 10 to 50 wt%.
- the amount of the reaction solvent used is preferably 11 to 200 times by weight based on the total amount of the acyl compound represented by the formula (5) and the acyl conjugate represented by the formula (6) used in the reaction. , 5 to 30 times the amount is particularly preferred.
- the reaction temperature is particularly preferably a force of 0 to 60 ° C, which is usually about 20 to 100 ° C.
- the progress of the reaction can be detected by TLC or LC.
- the sulfide represented by the formula (7) obtained in the second step is reacted with a thiocarbonitrile reagent to cyclize the sulfide and represented by the formula (1)
- This is a process for producing a compound having a 1,4-dithiin ring.
- a Lawson reagent such as a Lawson reagent, sodium sulfide and hydrogen sulfide is particularly preferable.
- the amount of the thiocarbonylating reagent to be used is preferably from 0.3 to 5.0 times the molar amount of the sulfide represented by the formula (7) to the starting material, and particularly preferably from 0.8 to 1.5 times the molar amount of the starting material. .
- the reaction solvent is not particularly limited, but includes dichloromethane, dichloroethane, chloroform, carbon tetrachloride, nitromethane, acetonitrile, diisopropyl ether, tetrahydrofuran, dioxane, toluene, xylene, N, N-dimethylformamide, N, N— Dichloroethane, dioxane, and toluene are particularly preferred, with dimethylacetamide, N-methylpyrrolidone, N, N, 1-dimethylimidazolidinone, and dimethylsulfoxide being preferred.
- the amount of the reaction solvent used is preferably 11 to 200 times the weight of the sulfide represented by the formula (7), but is more preferably 5 to 50 times.
- the reaction temperature of the thiocarbylation reaction is particularly preferably a power of 10 to 80 ° C, which is usually about 0 to 120 ° C.
- the progress of the thiocarbonitrile reaction can be detected by TLC or LC.
- the cyclization reaction proceeds sequentially to form a 1,4-dithiin ring, but the reaction temperature may be changed to a suitable temperature for the progress of the cyclization reaction.
- the reaction temperature of this cyclization reaction is preferably from 0 to 120 ° C, particularly preferably from 10 to 80 ° C.
- the progress of the cyclization reaction can also be detected by TLC or LC.
- a compound having a 1,4-dithiin ring represented by the formula (1) is obtained.
- the compound having a 1,4-dithiin ring represented by the formula (1) is dissolved in a solvent. Dissolve or evenly disperse, or use in combination with charge-accepting dopant material Transportable varnishes can be produced.
- the charge-accepting dopant substance is not particularly limited as long as it has a high charge-accepting property and is soluble in at least one solvent.
- the electron-accepting dopant substance include inorganic strong acids such as hydrogen chloride, sulfuric acid, nitric acid, and phosphoric acid; aluminum chloride (III) (A1C1), titanium titanium (IV) (TiCl), Chemical ho
- Phosphorus chloride PF
- tris (4-bromophenyl) amido-hexaclo mouth antimonate TCP
- AH AH
- benzenesulfonic acid tosylic acid, camphorsulfonic acid, hydroxybenzenesulfonic acid, 5-sulfosalicylic acid, dodecylbenzenesulfonic acid, polystyrenesulfonic acid, described in Japanese Patent Application No. 2003-181025.
- 1,4-Benzodioxane disulfonic acid derivative which is described in Japanese Patent Application No. 2004-251774 !
- arylarylsulfonic acid derivative which is described in Japanese Patent Application No.
- hole-accepting dopant substance examples include alkali metals (Li, Na, K, Cs), lithium quinolinolate (Liq), and lithium acetyl acetate (Li (acac)). Forces exemplified by metal complexes are not limited to these.
- Particularly preferred charge-accepting dopant substances include 5_sulfosalicylic acid, dodecylbenzenesulfonic acid, polystyrenesulfonic acid, and 1,4-benzodioxanedisulfonic acid derivatives described in Japanese Patent Application No. 2003-181025. And an electron-accepting dopant substance that is a strong organic acid such as a dino-l-naphthalenesulfonic acid derivative described in Japanese Patent Application No. 2003-320072.
- Solvents used for preparing the charge transporting varnish include water; methanol, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, N, N, 1-dimethyl.
- organic solvents such as imidazolidinone, dimethylsulfoxide, chloroform, toluene, etc.
- organic solvents are preferred, especially N, N-dimethyl Preferred are ruformamide, N, N-dimethylacetamide N-methylpyrrolidone and N, N, -dimethylimidazolidinone.
- a solvent that imparts the flatness of the film at the time of firing to the varnish for the purpose of improving the wettability to the substrate, adjusting the surface tension of the solvent, adjusting the polarity, adjusting the boiling point, etc. may be mixed at a rate of 1 to 90% by mass, preferably at a rate of 1 to 50% by mass, based on the whole solvent used.
- Such a solvent include butyl cetyl sorb, diethylene glycol ethyl enoate ether, dipropylene glycol monomethyl ether, ethynolecanolebitone, diacetone alcohol, ⁇ -butyrolatatone, ethyl lactate, acetonitrile, ethanol, ⁇ - Forces include lopanol, i-propanol, n-butanol, i-butanol, t-butanol, acetone, 2-butanone, carbon disulfide, nitromethane, etc., but are not limited to these.
- the charge transporting varnish is applied on a substrate, and the solvent is evaporated to form a charge transporting coating on the substrate.
- Examples of the coating method include, but are not particularly limited to, a dip method, a spin coating method, a transfer printing method, a roll coating method, a brush coating, an ink jet method, and a spray method.
- the method for evaporating the solvent is not particularly limited.For example, using a hot plate oven, vaporization is performed in an appropriate atmosphere, that is, in the atmosphere, an inert gas such as nitrogen, in a vacuum, or the like. It is possible to obtain a suitable film formation surface.
- the firing temperature is not particularly limited as long as the solvent can be evaporated, but it is preferable that the firing be performed at 40 to 250 ° C. In this case, two or more steps of temperature change may be applied for the purpose of developing a higher uniform film forming property or promoting the reaction on the substrate.
- the thickness of the charge transporting thin film obtained by the coating and evaporating operation is desirably 5 to 200 nm when used as a charge injection layer in a particularly limited organic EL device.
- a method of changing the film thickness there are a method of changing a solid content concentration in a varnish, a method of changing a solution amount on a substrate at the time of application, and the like.
- Examples of the method for producing an OLED device using the charge-transporting varnish of the present invention and the materials to be used include the following, but are not limited thereto. It is preferable that the electrode substrate to be used is previously cleaned by liquid cleaning with a detergent, alcohol, pure water, or the like.For example, for the anode substrate, surface treatment such as ozone treatment or oxygen plasma treatment is performed immediately before use. It is preferred ⁇ . However, when the anode material is mainly composed of an organic substance, the surface treatment may not be performed.
- a hole transporting varnish is used for an OLED element
- the following method can be used.
- the hole-transporting varnish is applied on the anode substrate, and a hole-transporting thin film is formed on the electrode by the above method.
- This is introduced into a vacuum evaporation apparatus, and a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode metal are sequentially deposited to form an OLED element.
- a carrier block layer may be provided between any layers to control the light emitting region.
- anode material examples include transparent electrodes typified by indium tin oxide (ITO) and indium zinc oxide (IZO), and those subjected to a flattening treatment are preferable.
- ITO indium tin oxide
- IZO indium zinc oxide
- Polythiophene derivatives and polyalines having high charge transportability can also be used.
- Materials for forming the hole transporting layer include (triphenylamine) dimer derivative (TPD),
- a-Naphthyldiphenylamine) dimer ⁇ NPD
- [(triphenylamine) dimer] Triarylamines such as spirodimer (Spiro-TAD), 4, 4 ', 4 "-tris [3-methylphenyl Starburst amines such as (Fer) amino] triphenylamine (m-MTDATA), 4, 4 ', 4 "-Tris [1-naphthyl (phenyl) amino] triphenylamine (1 TNATA), And 5,5 "bis- ⁇ 4 [bis (4-methylphenyl) amino] phenyl ⁇ -2, 2 ': 5', 2" -oligothiophenes such as tarthiophene (BMA-3T) it can.
- Materials for forming the light emitting layer include tris (8-quinolinolate) aluminum ( ⁇ ) (Alq3), bis (8-quinolinolate) zinc ( ⁇ ) (Znq), bis (2-methyl-8-quinolinolate) (p -
- Ruphenolate) aluminum (III) (BAlq) and 4,4'bis (2,2-diphenyl-biphenyl) biphenyl (DPVBi), etc., and include an electron transporting material or a hole transporting material and a luminescent dopant. May be co-evaporated to form a light emitting layer.
- electron transport materials include Alq, BAlq, DPVBi, (2— (4-biphenyl) —5— (4 t
- PBD As a material for forming the carrier block layer, PBD, TAZ, BCP and the like can be mentioned.
- Materials for forming the electron injection layer include lithium oxide (Li 0) and magnesium oxide (Mg).
- cathode material examples include aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, and cesium.
- the method for producing an OLED device using the charge-transporting varnish of the present invention is not particularly limited, and the following methods can be mentioned.
- the electron-transporting varnish is coated on the cathode substrate to form an electron-transporting thin film, introduced into a vacuum deposition apparatus, and made of the same materials as described above for the electron-transporting layer, the light-emitting layer, and the hole-transporting layer.
- the anode material is formed into a film by a method such as sputtering to form an OLED element.
- the method for producing a PLED device using the charge-transporting varnish of the present invention is not particularly limited.
- the charge of the present invention is formed by forming a luminescent charge transport polymer layer.
- a PLED device including a charge transporting thin film formed by a transporting varnish can be manufactured.
- the hole-transporting varnish is applied on an anode substrate to form a hole-transporting thin film by the above method, and a light-emitting charge-transporting polymer layer is formed thereon. Then, a cathode electrode is deposited to form a PLED element.
- the electron-transporting varnish is applied on a cathode substrate to form an electron-transporting thin film by the above-described method, a luminescent charge-transporting polymer layer is formed thereon, and an anode electrode is sputtered and deposited. It is manufactured by a method such as spin coating to obtain a PLED element.
- the cathode and anode materials to be used the same substances as those used in the production of the OLED element can be used, and the same cleaning treatment and surface treatment can be performed.
- a solvent is added to a luminescent charge transporting polymer material or a material to which a luminescent dopant is added to dissolve or uniformly disperse, and the hole is formed.
- PDA poly (9,9-dialkylfluorene)
- polyfluorene derivatives poly (2-methoxy-5- (2, -ethylhexoxy) -1,4 phen-lenvylene) (MEH-PPV); Polythiophene derivatives such as alkylthiophene) (PAT); polyvinylcarbazole (PVCz); and the like.
- Examples of the solvent include toluene, xylene, and chloroform.
- Examples of the dissolution or uniform dispersion method include a method of dissolving or uniformly dispersing by a method such as stirring, heating, stirring, or ultrasonic dispersion.
- Examples of the coating method include, but are not particularly limited to, an ink jet method, a spray method, a dive method, a spin coating method, a transfer printing method, a roll coating method, and brush coating.
- the coating is desirably performed under an inert gas such as nitrogen or argon.
- Examples of the method for evaporating the solvent include a method of heating with an oven or a hot plate under an inert gas or in a vacuum.
- BBD 2,6-bis (2,2′-bitophyl) -1,4-dithiin
- the first step is described below. Under a nitrogen atmosphere, 240 ml of dehydrated dichloromethane (Kanto Iridakuna) was added to 12.00 g (72.18 mmol) of 2,2'-bithione (BT, abbreviation, manufactured by Tokyo Chemical Industry Co., Ltd.) as a starting material. Was dissolved and cooled to 0 ° C, and 82.70 ml (79.39 mmol) of a 0.96 M n-hexane solution of ethyl aluminum dichloride was added dropwise by vigorous stirring for 13 minutes. .
- BT 2,2'-bithione
- the second step is described below.
- 106 ml of acetone manufactured by Junsei Chemical Co., Ltd.
- sodium sulfide 9-hydrate was added to the resulting solution.
- a solution obtained by calming 53 ml of pure water to 2.632 g (10.96 mmol) of the product was added dropwise over 15 minutes.
- the reaction system was stirred at 20 ° C. for 3 hours and then at 50 ° C. for 30 minutes, allowed to cool to room temperature, and concentrated under reduced pressure to distill off acetone.
- the varnish obtained above was applied by spin coating on an ITO glass substrate that had been subjected to ozone cleaning for 40 minutes, and baked on a hot plate in the air to obtain a thin film.
- Table 1 shows the ionization potential (hereinafter abbreviated as I) of the thin film with respect to the firing conditions.
- a hole transporting thin film was formed on an ITO glass substrate using the varnish, introduced into a vacuum deposition apparatus, and ⁇ -NPD, Alq, LiF, and A1 were sequentially deposited.
- the film thickness is
- the deposition rate was 0.3-0.4 nmZs except for LiF, and 0.01-0.03 nmZs for LiF.
- the moving operation during the vapor deposition operation was performed in a vacuum. Table 2 shows the characteristics of the obtained OLED device.
- Example 6 Using a varnish obtained by the method described in Example 2, coating was performed by a spin coating method on an ITO glass substrate which had been washed with ozone for 40 minutes, and baked on a hot plate in the atmosphere to obtain a thin film.
- Table 1 shows the ionization potential (hereinafter abbreviated as I) of the thin film against the firing conditions.
- a hole transporting thin film was formed on an ITO glass substrate using the present varnish, introduced into a vacuum evaporation apparatus, and ⁇ -NPD, Alq, LiF, and A1 were sequentially evaporated.
- the film thickness is
- Each 40 nm, 60 nm, 0. 5 nm, and LOOnm, from each 8 X 10- 4 Pa or less the pressure and a connexion perform deposition operation, the deposition rate and except for LiF 0. 35-0. 40nmZs, the Li F Is 0.01-10.03 nmZs.
- the moving operation during the vapor deposition operation was performed in a vacuum. When a voltage was applied to the obtained OLED element, the entire light emitting surface emitted light uniformly, and no defects were seen. Table 2 shows the characteristics of the obtained OLED device.
- a film forming operation was performed on an ITO glass substrate by the method described in Example 6 to produce an OLED element.
- voltage was applied to the obtained OLED element, the entire light emitting surface emitted light uniformly, and no defects were observed.
- Fig. 1 shows a photograph of the light emitting surface of the obtained OLED device. The I and OLED characteristics of the obtained thin film
- Example 6 An ITO glass substrate under the same conditions as in Example 6 was introduced into a vacuum evaporation apparatus, and ⁇ -NPD, Alq, LiF, and A1 were formed under the same conditions as in Example 1 without forming a hole injection layer. Sequential deposition
- Table 1 shows the I of the ITO glass substrate used, and Table 2 shows the characteristics of the obtained OLED device.
- Example 6 An aqueous solution of polyethylene dioxythiophene polystyrene sulfonic acid was applied on an ITO glass substrate under the same conditions as in Example 6 by spin coating, and then baked to form a uniform thin film.
- Table 1 shows the firing conditions and I of the obtained thin film.
- a hole transporting thin film was formed on an ITO glass substrate by the same method, and an OLED element was manufactured under the same conditions as the method described in Example 1.
- Table 2 shows the characteristics of the obtained OLED device. At each of 5V and 7V, the OLED element characteristics of luminance and current efficiency are inferior to those of Examples 6-1-8! /.
- Figure 2 shows a photograph of the light emitting surface of the OLED device.
- the viscosity was measured using an E-type viscometer ELD-50 manufactured by Tokyo Keiki.
- the film thickness was measured using a surface shape measuring device DEKTAK3ST manufactured by Japan Vacuum Technology.
- the ammeter was a digital multimeter 7555 manufactured by Yokogawa Electric Corporation, the voltage generator was a DC voltage current source R6145 manufactured by Advantest, and the luminance meter was a luminance meter BM-8 manufactured by Topcon.
- Ion-dani potential is a photoelectron manufactured by Riken Keiki Measured using spectrometer AC-2
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200480035466XA CN1887033B (zh) | 2003-10-31 | 2004-10-29 | 含带有1,4-二噻因环的化合物的电荷传输性有机材料 |
KR1020067007845A KR101150743B1 (ko) | 2003-10-31 | 2004-10-29 | 1,4-디티인 환을 갖는 화합물을 포함하는 전하수송성유기재료 |
EP04793203.3A EP1691586B1 (en) | 2003-10-31 | 2004-10-29 | Charge-transporting organic material containing compound having 1,4-dithiin ring |
JP2005515167A JP4811573B2 (ja) | 2003-10-31 | 2004-10-29 | 1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 |
US10/577,438 US7795452B2 (en) | 2003-10-31 | 2004-10-29 | Charge-transporting organic material containing compound having 1,4-dithiin ring |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003-371782 | 2003-10-31 | ||
JP2003371782 | 2003-10-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005043962A1 true WO2005043962A1 (ja) | 2005-05-12 |
Family
ID=34543973
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/016095 WO2005043962A1 (ja) | 2003-10-31 | 2004-10-29 | 1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7795452B2 (ja) |
EP (1) | EP1691586B1 (ja) |
JP (1) | JP4811573B2 (ja) |
KR (1) | KR101150743B1 (ja) |
CN (2) | CN101817810A (ja) |
TW (1) | TW200519184A (ja) |
WO (1) | WO2005043962A1 (ja) |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008010474A1 (fr) | 2006-07-18 | 2008-01-24 | Nissan Chemical Industries, Ltd. | Vernis contenant des charges |
WO2008032617A1 (fr) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Composé d'oligoaniline et son utilisation |
WO2008129947A1 (ja) | 2007-04-12 | 2008-10-30 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物 |
CN100479228C (zh) * | 2006-08-08 | 2009-04-15 | 中国科学院化学研究所 | 基于电子受体材料的蓝光有机发光二极管的制备方法 |
WO2010041701A1 (ja) | 2008-10-09 | 2010-04-15 | 日産化学工業株式会社 | 電荷輸送性ワニス |
JP2010098306A (ja) * | 2008-09-18 | 2010-04-30 | Mitsubishi Chemicals Corp | 電荷輸送膜用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
WO2010058776A1 (ja) | 2008-11-19 | 2010-05-27 | 日産化学工業株式会社 | 電荷輸送性材料および電荷輸送性ワニス |
JP2011044605A (ja) * | 2009-08-21 | 2011-03-03 | Fuji Xerox Co Ltd | 有機電界発光素子及び表示媒体 |
JP2011202124A (ja) * | 2010-03-26 | 2011-10-13 | Mitsubishi Chemicals Corp | 電荷輸送膜用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
JP2013229370A (ja) * | 2012-04-24 | 2013-11-07 | Hitachi Chemical Co Ltd | 色変化防止剤、該色変化防止剤を含むインク組成物、該インク組成物を用いて形成した有機薄膜、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、及び表示装置 |
JP5401791B2 (ja) * | 2005-10-28 | 2014-01-29 | 日産化学工業株式会社 | スプレー又はインクジェット塗布用電荷輸送性ワニス |
WO2015050253A1 (ja) | 2013-10-04 | 2015-04-09 | 日産化学工業株式会社 | アニリン誘導体およびその利用 |
WO2015053320A1 (ja) | 2013-10-09 | 2015-04-16 | 日産化学工業株式会社 | アリールスルホン酸化合物及びその利用並びにアリールスルホン酸化合物の製造方法 |
WO2017135117A1 (ja) | 2016-02-03 | 2017-08-10 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2017150412A1 (ja) | 2016-03-03 | 2017-09-08 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2017164158A1 (ja) | 2016-03-24 | 2017-09-28 | 日産化学工業株式会社 | アリールアミン誘導体とその利用 |
JPWO2016148184A1 (ja) * | 2015-03-17 | 2017-12-28 | 日産化学工業株式会社 | 光センサ素子の正孔捕集層形成用組成物および光センサ素子 |
WO2018147204A1 (ja) | 2017-02-07 | 2018-08-16 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2018186340A1 (ja) | 2017-04-05 | 2018-10-11 | 日産化学株式会社 | 電荷輸送性ワニス |
WO2018216507A1 (ja) | 2017-05-25 | 2018-11-29 | 日産化学株式会社 | 電荷輸送性薄膜の製造方法 |
KR20190018499A (ko) | 2016-06-16 | 2019-02-22 | 닛산 가가쿠 가부시키가이샤 | 설폰산에스터 화합물 및 그 이용 |
KR20190018498A (ko) | 2016-06-16 | 2019-02-22 | 닛산 가가쿠 가부시키가이샤 | 설폰산에스터 화합물 및 그 이용 |
WO2019124413A1 (ja) | 2017-12-20 | 2019-06-27 | 日産化学株式会社 | 電荷輸送性ワニス及び電荷輸送性薄膜 |
WO2019124412A1 (ja) | 2017-12-20 | 2019-06-27 | 日産化学株式会社 | スルホン酸エステル化合物及びその利用 |
WO2020066979A1 (ja) | 2018-09-25 | 2020-04-02 | 日産化学株式会社 | 有機機能膜付き基板の製造方法 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101064529B1 (ko) * | 2002-11-07 | 2011-09-14 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 니스 |
WO2005107335A1 (ja) * | 2004-04-30 | 2005-11-10 | Nissan Chemical Industries, Ltd. | 良溶媒及び貧溶媒を含有するワニス |
KR20090082778A (ko) | 2008-01-28 | 2009-07-31 | 삼성모바일디스플레이주식회사 | 유기전계발광소자 및 그 제조방법 |
CN102686592B (zh) | 2010-01-30 | 2013-11-27 | 海洋王照明科技股份有限公司 | 含芴卟啉-蒽共聚物、其制备方法和应用 |
CN102712652B (zh) * | 2010-03-23 | 2014-03-19 | 海洋王照明科技股份有限公司 | 含芴卟啉-苯共聚物、其制备方法和应用 |
CN102295757B (zh) * | 2010-06-25 | 2013-04-17 | 海洋王照明科技股份有限公司 | 含咔唑卟啉-噻吩并吡嗪共聚物及其制备方法和应用 |
CN102329415B (zh) * | 2010-07-13 | 2013-04-17 | 海洋王照明科技股份有限公司 | 含咔唑卟啉-喹喔啉共聚物及其制备方法和应用 |
US9431621B2 (en) | 2012-03-13 | 2016-08-30 | The Regents Of The University Of Michigan | Metal oxide charge transport material doped with organic molecules |
CN104513513B (zh) * | 2013-10-04 | 2018-11-06 | 日产化学工业株式会社 | 电荷传输性清漆、电荷传输性薄膜和有机电致发光元件 |
EP3270433A4 (en) * | 2015-03-13 | 2019-02-20 | Nissan Chemical Corporation | COMPOSITION FOR FORMATION OF CHARGE TRANSPORT THIN FILM FOR ORGANIC ELECTROLUMINESCENT ELEMENTS, CHARGE TRANSPORT THIN FILM FOR ORGANIC ELECTROLUMINESCENT ELEMENTS, AND ORGANIC ELECTROLUMINESCENCE ELEMENT |
KR102153447B1 (ko) * | 2015-12-01 | 2020-09-08 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
CN111430553B (zh) * | 2020-04-07 | 2022-06-21 | 杭州纤纳光电科技有限公司 | 一种稳定的钙钛矿太阳能电池及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5649304A (en) * | 1979-09-29 | 1981-05-02 | Hodogaya Chem Co Ltd | Expellent against soil injurious organism |
JPS57140782A (en) * | 1980-12-02 | 1982-08-31 | Uniroyal Ltd | Manufacture of 2,3-dihydro-1,4-dithiin |
JPS61152677A (ja) * | 1984-12-26 | 1986-07-11 | Seitetsu Kagaku Co Ltd | 2−ハロアセチルチオフエン類の製造法 |
JP2002151272A (ja) * | 2000-11-09 | 2002-05-24 | Nissan Chem Ind Ltd | 電界発光素子 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2876718B2 (ja) * | 1990-06-11 | 1999-03-31 | 株式会社デンソー | 自動車用空調装置 |
KR101064529B1 (ko) * | 2002-11-07 | 2011-09-14 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 니스 |
-
2004
- 2004-10-29 CN CN201010168167A patent/CN101817810A/zh active Pending
- 2004-10-29 JP JP2005515167A patent/JP4811573B2/ja not_active Expired - Fee Related
- 2004-10-29 TW TW093132998A patent/TW200519184A/zh unknown
- 2004-10-29 KR KR1020067007845A patent/KR101150743B1/ko active IP Right Grant
- 2004-10-29 WO PCT/JP2004/016095 patent/WO2005043962A1/ja active Application Filing
- 2004-10-29 EP EP04793203.3A patent/EP1691586B1/en not_active Expired - Fee Related
- 2004-10-29 CN CN200480035466XA patent/CN1887033B/zh active Active
- 2004-10-29 US US10/577,438 patent/US7795452B2/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5649304A (en) * | 1979-09-29 | 1981-05-02 | Hodogaya Chem Co Ltd | Expellent against soil injurious organism |
JPS57140782A (en) * | 1980-12-02 | 1982-08-31 | Uniroyal Ltd | Manufacture of 2,3-dihydro-1,4-dithiin |
JPS61152677A (ja) * | 1984-12-26 | 1986-07-11 | Seitetsu Kagaku Co Ltd | 2−ハロアセチルチオフエン類の製造法 |
JP2002151272A (ja) * | 2000-11-09 | 2002-05-24 | Nissan Chem Ind Ltd | 電界発光素子 |
Non-Patent Citations (2)
Title |
---|
NAKAYAMA J. ET AL.: "Preparation of alpha-quinone- and alpha-septithiop henes and their positional isomeres", HETEROCYCLES, vol. 26, no. 4, 1987, pages 939, XP002986703 * |
See also references of EP1691586A4 * |
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5401791B2 (ja) * | 2005-10-28 | 2014-01-29 | 日産化学工業株式会社 | スプレー又はインクジェット塗布用電荷輸送性ワニス |
US8575392B2 (en) | 2006-07-18 | 2013-11-05 | Nissan Chemical Industries, Ltd. | Charge-transporting varnish |
WO2008010474A1 (fr) | 2006-07-18 | 2008-01-24 | Nissan Chemical Industries, Ltd. | Vernis contenant des charges |
JP5196175B2 (ja) * | 2006-07-18 | 2013-05-15 | 日産化学工業株式会社 | 電荷輸送性ワニス |
CN100479228C (zh) * | 2006-08-08 | 2009-04-15 | 中国科学院化学研究所 | 基于电子受体材料的蓝光有机发光二极管的制备方法 |
WO2008032617A1 (fr) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Composé d'oligoaniline et son utilisation |
US8357770B2 (en) | 2006-09-13 | 2013-01-22 | Nissan Chemical Industries, Ltd. | Oligoaniline compound and use thereof |
WO2008129947A1 (ja) | 2007-04-12 | 2008-10-30 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物 |
US8298444B2 (en) | 2007-04-12 | 2012-10-30 | Nissan Chemical Industries, Ltd. | Oligoaniline compound |
JP2010098306A (ja) * | 2008-09-18 | 2010-04-30 | Mitsubishi Chemicals Corp | 電荷輸送膜用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
WO2010041701A1 (ja) | 2008-10-09 | 2010-04-15 | 日産化学工業株式会社 | 電荷輸送性ワニス |
US8747700B2 (en) | 2008-10-09 | 2014-06-10 | Nissan Chemical Industries, Ltd. | Charge-transporting varnishes |
WO2010058776A1 (ja) | 2008-11-19 | 2010-05-27 | 日産化学工業株式会社 | 電荷輸送性材料および電荷輸送性ワニス |
US9049771B2 (en) | 2008-11-19 | 2015-06-02 | Nissan Chemical Industries, Ltd. | Charge-transporting material and charge-transporting varnish |
KR20160088440A (ko) | 2008-11-19 | 2016-07-25 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 재료 및 전하수송성 바니시 |
JP2011044605A (ja) * | 2009-08-21 | 2011-03-03 | Fuji Xerox Co Ltd | 有機電界発光素子及び表示媒体 |
JP2011202124A (ja) * | 2010-03-26 | 2011-10-13 | Mitsubishi Chemicals Corp | 電荷輸送膜用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
JP2013229370A (ja) * | 2012-04-24 | 2013-11-07 | Hitachi Chemical Co Ltd | 色変化防止剤、該色変化防止剤を含むインク組成物、該インク組成物を用いて形成した有機薄膜、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、及び表示装置 |
WO2015050253A1 (ja) | 2013-10-04 | 2015-04-09 | 日産化学工業株式会社 | アニリン誘導体およびその利用 |
WO2015053320A1 (ja) | 2013-10-09 | 2015-04-16 | 日産化学工業株式会社 | アリールスルホン酸化合物及びその利用並びにアリールスルホン酸化合物の製造方法 |
JP7141826B2 (ja) | 2015-03-17 | 2022-09-26 | 日産化学株式会社 | 光センサ素子の正孔捕集層形成用組成物および光センサ素子 |
EP4109573A1 (en) | 2015-03-17 | 2022-12-28 | Nissan Chemical Corporation | Photosensor element |
JP2022153435A (ja) * | 2015-03-17 | 2022-10-12 | 日産化学株式会社 | 光センサ素子 |
JPWO2016148184A1 (ja) * | 2015-03-17 | 2017-12-28 | 日産化学工業株式会社 | 光センサ素子の正孔捕集層形成用組成物および光センサ素子 |
WO2017135117A1 (ja) | 2016-02-03 | 2017-08-10 | 日産化学工業株式会社 | 電荷輸送性ワニス |
JPWO2017135117A1 (ja) * | 2016-02-03 | 2018-12-06 | 日産化学株式会社 | 電荷輸送性ワニス |
WO2017150412A1 (ja) | 2016-03-03 | 2017-09-08 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2017164158A1 (ja) | 2016-03-24 | 2017-09-28 | 日産化学工業株式会社 | アリールアミン誘導体とその利用 |
US10847725B2 (en) | 2016-06-16 | 2020-11-24 | Nissan Chemical Corporation | Sulfonic acid ester compound and use therefor |
US10513491B2 (en) | 2016-06-16 | 2019-12-24 | Nissan Chemical Corporation | Sulfonic acid ester compound and use therefor |
KR20190018499A (ko) | 2016-06-16 | 2019-02-22 | 닛산 가가쿠 가부시키가이샤 | 설폰산에스터 화합물 및 그 이용 |
KR20190018498A (ko) | 2016-06-16 | 2019-02-22 | 닛산 가가쿠 가부시키가이샤 | 설폰산에스터 화합물 및 그 이용 |
WO2018147204A1 (ja) | 2017-02-07 | 2018-08-16 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2018186340A1 (ja) | 2017-04-05 | 2018-10-11 | 日産化学株式会社 | 電荷輸送性ワニス |
WO2018216507A1 (ja) | 2017-05-25 | 2018-11-29 | 日産化学株式会社 | 電荷輸送性薄膜の製造方法 |
CN111492497A (zh) * | 2017-12-20 | 2020-08-04 | 日产化学株式会社 | 电荷传输性清漆和电荷传输性薄膜 |
KR20200098630A (ko) | 2017-12-20 | 2020-08-20 | 닛산 가가쿠 가부시키가이샤 | 전하 수송성 바니시 및 전하 수송성 박막 |
KR20200100767A (ko) | 2017-12-20 | 2020-08-26 | 닛산 가가쿠 가부시키가이샤 | 술폰산에스테르 화합물 및 그 이용 |
WO2019124412A1 (ja) | 2017-12-20 | 2019-06-27 | 日産化学株式会社 | スルホン酸エステル化合物及びその利用 |
WO2019124413A1 (ja) | 2017-12-20 | 2019-06-27 | 日産化学株式会社 | 電荷輸送性ワニス及び電荷輸送性薄膜 |
CN111492497B (zh) * | 2017-12-20 | 2023-05-26 | 日产化学株式会社 | 电荷传输性清漆和电荷传输性薄膜 |
WO2020066979A1 (ja) | 2018-09-25 | 2020-04-02 | 日産化学株式会社 | 有機機能膜付き基板の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
CN1887033A (zh) | 2006-12-27 |
JPWO2005043962A1 (ja) | 2007-05-17 |
EP1691586A4 (en) | 2009-07-01 |
EP1691586A1 (en) | 2006-08-16 |
CN101817810A (zh) | 2010-09-01 |
JP4811573B2 (ja) | 2011-11-09 |
US20070043222A1 (en) | 2007-02-22 |
TW200519184A (en) | 2005-06-16 |
KR20060096057A (ko) | 2006-09-05 |
KR101150743B1 (ko) | 2012-06-08 |
US7795452B2 (en) | 2010-09-14 |
EP1691586B1 (en) | 2015-10-14 |
TWI355411B (ja) | 2012-01-01 |
CN1887033B (zh) | 2010-12-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4811573B2 (ja) | 1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 | |
KR101473294B1 (ko) | 올리고아닐린 화합물 및 그 이용 | |
KR101484740B1 (ko) | 아릴술폰산 화합물 및 전자수용성 물질로서의 이용 | |
JP4591681B2 (ja) | 電荷輸送性ワニス | |
JP4596165B2 (ja) | 1,4−ベンゾジオキサンスルホン酸化合物及び電子受容性物質としての利用 | |
JP5196175B2 (ja) | 電荷輸送性ワニス | |
JP5024498B2 (ja) | 電荷輸送性ワニス、電荷輸送性薄膜および有機エレクトロルミネッセンス素子 | |
JP5136795B2 (ja) | スルホン酸エステル化合物からなる電子受容性物質前駆体およびその利用 | |
Pu et al. | Solution-processable organic fluorescent dyes for multicolor emission in organic light emitting diodes | |
US9074043B2 (en) | Compound for carrier transport, element and electronic device using the same | |
JP5217231B2 (ja) | オリゴアニリン化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200480035466.X Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DPEN | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1020067007845 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2005515167 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2007043222 Country of ref document: US Ref document number: 10577438 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004793203 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 2004793203 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1020067007845 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: 10577438 Country of ref document: US |