TWI627169B - Thiophene derivative and utilization thereof and method for producing thiophene derivative - Google Patents
Thiophene derivative and utilization thereof and method for producing thiophene derivative Download PDFInfo
- Publication number
- TWI627169B TWI627169B TW103121013A TW103121013A TWI627169B TW I627169 B TWI627169 B TW I627169B TW 103121013 A TW103121013 A TW 103121013A TW 103121013 A TW103121013 A TW 103121013A TW I627169 B TWI627169 B TW I627169B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- carbon atoms
- substituted
- bis
- phenyl
- Prior art date
Links
- 150000003577 thiophenes Chemical class 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 27
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 199
- -1 ethylidene dioxy group Chemical group 0.000 claims description 164
- 229910052799 carbon Inorganic materials 0.000 claims description 64
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 abstract description 56
- 125000003342 alkenyl group Chemical group 0.000 abstract description 47
- 125000000304 alkynyl group Chemical group 0.000 abstract description 42
- 125000003118 aryl group Chemical group 0.000 abstract description 24
- 125000005110 aryl thio group Chemical group 0.000 abstract description 15
- 125000004104 aryloxy group Chemical group 0.000 abstract description 15
- 125000005368 heteroarylthio group Chemical group 0.000 abstract description 15
- 125000005109 alkynylthio group Chemical group 0.000 abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 13
- 125000005133 alkynyloxy group Chemical group 0.000 abstract description 12
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract description 12
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 55
- 239000010408 film Substances 0.000 description 43
- 238000000034 method Methods 0.000 description 41
- 239000003973 paint Substances 0.000 description 35
- 239000002253 acid Substances 0.000 description 34
- 125000005843 halogen group Chemical group 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 27
- 239000002019 doping agent Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 26
- 229930192474 thiophene Natural products 0.000 description 25
- 239000002904 solvent Substances 0.000 description 23
- 238000002347 injection Methods 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 20
- 239000000758 substrate Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 241000208340 Araliaceae Species 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 16
- 235000003140 Panax quinquefolius Nutrition 0.000 description 16
- 238000000576 coating method Methods 0.000 description 16
- 235000008434 ginseng Nutrition 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 229940123208 Biguanide Drugs 0.000 description 15
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 15
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000001153 fluoro group Chemical group F* 0.000 description 14
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 229910052707 ruthenium Inorganic materials 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000005108 alkenylthio group Chemical group 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 10
- 125000004149 thio group Chemical group *S* 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 6
- 229910052684 Cerium Inorganic materials 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 229910052746 lanthanum Inorganic materials 0.000 description 6
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 5
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZMMVETGEVDCFOB-UHFFFAOYSA-N tributyl-(3-methoxythiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=1SC=CC=1OC ZMMVETGEVDCFOB-UHFFFAOYSA-N 0.000 description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- RFSKGCVUDQRZSD-UHFFFAOYSA-N 3-methoxythiophene Chemical compound COC=1C=CSC=1 RFSKGCVUDQRZSD-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010304 firing Methods 0.000 description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 229910052715 tantalum Inorganic materials 0.000 description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XDPNCTNYEDMQEN-UHFFFAOYSA-N (1,1,1-triethoxy-2,3,3,4,4-pentafluorodecan-2-yl)benzene Chemical compound FC(C(C(C(OCC)(OCC)OCC)(C1=CC=CC=C1)F)(F)F)(CCCCCC)F XDPNCTNYEDMQEN-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- AVPWUAFYDNQGNZ-UHFFFAOYSA-N 2,3,4,5-tetrabromothiophene Chemical compound BrC=1SC(Br)=C(Br)C=1Br AVPWUAFYDNQGNZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 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 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000004715 keto acids Chemical class 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 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 3
- 238000010422 painting Methods 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000002577 pseudohalo group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- ZYZZTJTXWRMMRA-UHFFFAOYSA-N (2,3,3,4,4-pentafluoro-1,1,1-trimethoxydecan-2-yl)benzene Chemical compound FC(C(C(C(OC)(OC)OC)(C1=CC=CC=C1)F)(F)F)(CCCCCC)F ZYZZTJTXWRMMRA-UHFFFAOYSA-N 0.000 description 2
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 2
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 2
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- SSDWEGUXNCFQOR-UHFFFAOYSA-N 1-(10,10,10-triethoxydecyl)-4-(trifluoromethyl)benzene Chemical compound C(C)OC(CCCCCCCCCC1=CC=C(C=C1)C(F)(F)F)(OCC)OCC SSDWEGUXNCFQOR-UHFFFAOYSA-N 0.000 description 2
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 2
- MOGTVLAYAVGOJK-UHFFFAOYSA-N 2-[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]pyridine Chemical compound FC(F)(F)C1=NNC(C=2N=CC=CC=2)=N1 MOGTVLAYAVGOJK-UHFFFAOYSA-N 0.000 description 2
- PKURFTDCIWJBDF-UHFFFAOYSA-N 2-hexylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCC)=CC=C21 PKURFTDCIWJBDF-UHFFFAOYSA-N 0.000 description 2
- OTYBVBDWIKXFDO-UHFFFAOYSA-N 3-(methylthio)thiophene Chemical compound CSC=1C=CSC=1 OTYBVBDWIKXFDO-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- RDEGOEYUQCUBPE-UHFFFAOYSA-N 3-ethoxythiophene Chemical compound CCOC=1C=CSC=1 RDEGOEYUQCUBPE-UHFFFAOYSA-N 0.000 description 2
- VKJKULUJHYKCGT-UHFFFAOYSA-N 3-propoxythiophene Chemical compound CCCOC=1C=CSC=1 VKJKULUJHYKCGT-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- VEQDVXUGVMZXKQ-UHFFFAOYSA-N 4-(1,1-dimethoxyethyl)-1,1,1-trifluorododecane Chemical compound FC(CCC(C(OC)(OC)C)CCCCCCCC)(F)F VEQDVXUGVMZXKQ-UHFFFAOYSA-N 0.000 description 2
- IYVKASORLNOINI-UHFFFAOYSA-N 9-(3-pyridin-2-ylphenyl)carbazole Chemical compound N1=CC=CC=C1C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 IYVKASORLNOINI-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- WZLJLVZOOISPPX-UHFFFAOYSA-N FC(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(C(F)(F)F)(F)F)C(OC(C(F)(F)F)(F)F)(OC(C(F)(F)F)(F)F)OC(C(F)(F)F)(F)F)(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)F Chemical compound FC(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(C(F)(F)F)(F)F)C(OC(C(F)(F)F)(F)F)(OC(C(F)(F)F)(F)F)OC(C(F)(F)F)(F)F)(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)F WZLJLVZOOISPPX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229930008407 benzylideneacetone Natural products 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-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
- 239000012535 impurity Substances 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- YVDLTFWKYPHOJN-UHFFFAOYSA-N isocyanatosulfanylurea Chemical group N(C(=O)N)SN=C=O YVDLTFWKYPHOJN-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
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000006138 lithiation reaction Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 2
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 2
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- RVFWUIFCUQFLFQ-UHFFFAOYSA-N (8-diphenylphosphanyldibenzothiophen-2-yl)-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=C2C3=CC(=CC=C3SC2=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 RVFWUIFCUQFLFQ-UHFFFAOYSA-N 0.000 description 1
- 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
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- OMFOGPIVPGTWNN-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluorobutane Chemical group F[C](F)C(F)(F)C(F)(F)C(F)(F)F OMFOGPIVPGTWNN-UHFFFAOYSA-N 0.000 description 1
- PCTZLSCYMRXUGW-UHFFFAOYSA-N 1,1,1,2,2-pentafluorobutane Chemical group [CH2]CC(F)(F)C(F)(F)F PCTZLSCYMRXUGW-UHFFFAOYSA-N 0.000 description 1
- AGGJWJFEEKIYOF-UHFFFAOYSA-N 1,1,1-triethoxydecane Chemical compound CCCCCCCCCC(OCC)(OCC)OCC AGGJWJFEEKIYOF-UHFFFAOYSA-N 0.000 description 1
- DQGPWNBGAYGUPK-UHFFFAOYSA-N 1,1,1-trifluoro-4-(trimethoxymethyl)dodecane Chemical compound FC(CCC(C(OC)(OC)OC)CCCCCCCC)(F)F DQGPWNBGAYGUPK-UHFFFAOYSA-N 0.000 description 1
- ANBBCZAIOXDZPV-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methyldecane Chemical compound CC(C(OC)(OC)OC)CCCCCCCC ANBBCZAIOXDZPV-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- WAZUPKBMTSPHDS-UHFFFAOYSA-N 1-(1,1,1,2,3,3,3-heptafluoropropan-2-yloxy)-4-(triethoxymethyl)dodecane Chemical compound FC(C(C(F)(F)F)(OCCCC(C(OCC)(OCC)OCC)CCCCCCCC)F)(F)F WAZUPKBMTSPHDS-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group 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 1
- BUTXVZBLXLIJNJ-UHFFFAOYSA-N 1-(3-indol-1-ylphenyl)indole Chemical compound C1=CC2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C=C2)=CC=C1 BUTXVZBLXLIJNJ-UHFFFAOYSA-N 0.000 description 1
- YTJGGHUSUKMXAO-UHFFFAOYSA-N 1-(4-indol-1-ylphenyl)indole Chemical compound C1=CC2=CC=CC=C2N1C(C=C1)=CC=C1N1C2=CC=CC=C2C=C1 YTJGGHUSUKMXAO-UHFFFAOYSA-N 0.000 description 1
- WHVJWWHIECLMNO-UHFFFAOYSA-N 1-(5-indol-1-ylpyridin-3-yl)indole Chemical compound N1(C=CC2=CC=CC=C12)C=1C=NC=C(C=1)N1C=CC2=CC=CC=C12 WHVJWWHIECLMNO-UHFFFAOYSA-N 0.000 description 1
- PDQMIWKASJWFEM-UHFFFAOYSA-N 1-[5-(trifluoromethyl)-1h-pyrazol-3-yl]isoquinoline Chemical compound N1N=C(C(F)(F)F)C=C1C1=NC=CC2=CC=CC=C12 PDQMIWKASJWFEM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- VLEUQKONNIFBCB-UHFFFAOYSA-N 1-methyl-2-(4-naphthalen-2-ylphenyl)imidazole Chemical compound CN1C=CN=C1C1=CC=C(C=2C=C3C=CC=CC3=CC=2)C=C1 VLEUQKONNIFBCB-UHFFFAOYSA-N 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- ZOSMPLGIBBPIGW-UHFFFAOYSA-N 1-methylpyrrole 1H-pyridin-2-one Chemical compound N1C(C=CC=C1)=O.CN1C=CC=C1 ZOSMPLGIBBPIGW-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- MSMBJGOHHPYVEN-UHFFFAOYSA-N 2,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC3=CC(C4=CC5=CC=CC=C5C=C4)=CC=C3C(C=3C=C4C=CC=CC4=CC=3)=C21 MSMBJGOHHPYVEN-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- GCZWJRLXIPVNLU-UHFFFAOYSA-N 2,2-dimethoxy-3-methylundecane Chemical compound CC(C(OC)(OC)C)CCCCCCCC GCZWJRLXIPVNLU-UHFFFAOYSA-N 0.000 description 1
- WZXXZHONLFRKGG-UHFFFAOYSA-N 2,3,4,5-tetrachlorothiophene Chemical compound ClC=1SC(Cl)=C(Cl)C=1Cl WZXXZHONLFRKGG-UHFFFAOYSA-N 0.000 description 1
- VWDOXSASHQWCRB-UHFFFAOYSA-N 2,3,4,5-tetraiodothiophene Chemical compound IC=1SC(I)=C(I)C=1I VWDOXSASHQWCRB-UHFFFAOYSA-N 0.000 description 1
- ORILGKWRXJSJRO-UHFFFAOYSA-N 2,4-diphenyl-6-(2-phenylphenyl)-1,3,5-triazine Chemical group C1(=CC=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C1=CC=CC=C1 ORILGKWRXJSJRO-UHFFFAOYSA-N 0.000 description 1
- NDDQPTQQWHEHJC-UHFFFAOYSA-N 2,9-dinaphthalen-2-ylanthracene Chemical compound C1=C(C=CC2=CC=CC=C12)C=1C2=CC=CC=C2C=C2C=CC(=CC=12)C1=CC2=CC=CC=C2C=C1 NDDQPTQQWHEHJC-UHFFFAOYSA-N 0.000 description 1
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 description 1
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 1
- SSABEFIRGJISFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC=CC=N1 SSABEFIRGJISFH-UHFFFAOYSA-N 0.000 description 1
- WGGFTVFWKATEEM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine ruthenium 2-[5-(trifluoromethyl)-1H-pyrazol-3-yl]pyridine Chemical compound [Ru].FC1=CC=C(C(=C1)F)C1=NC=CC=C1.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F WGGFTVFWKATEEM-UHFFFAOYSA-N 0.000 description 1
- FSBYOEHUNSUUTD-UHFFFAOYSA-N 2-(2,5-dioxabicyclo[2.1.0]pentan-3-yloxy)ethanol Chemical compound C1(C2C(O2)O1)OCCO FSBYOEHUNSUUTD-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- JMTCQDNRTSGBGC-UHFFFAOYSA-N 2-(3-methylphenyl)pyridine Chemical compound CC1=CC=CC(C=2N=CC=CC=2)=C1 JMTCQDNRTSGBGC-UHFFFAOYSA-N 0.000 description 1
- CRGSMSNUTNRNQM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=CO1 CRGSMSNUTNRNQM-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- WHKKNVAGWPTSRS-UHFFFAOYSA-N 2-dodecylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCCCCCCCC)=CC=C21 WHKKNVAGWPTSRS-UHFFFAOYSA-N 0.000 description 1
- HVOAFLJLVONUSZ-UHFFFAOYSA-N 2-ethylperoxythiophene Chemical compound CCOOC1=CC=CS1 HVOAFLJLVONUSZ-UHFFFAOYSA-N 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- TZYPEOJJHBWOKE-UHFFFAOYSA-N 2-methyl-4-[3-methyl-4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]-n,n-bis(3-methylphenyl)aniline Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C(=CC(=CC=2)C=2C=C(C)C(N(C=3C=C(C)C=CC=3)C=3C=C(C)C=CC=3)=CC=2)C)=C1 TZYPEOJJHBWOKE-UHFFFAOYSA-N 0.000 description 1
- HNWFFTUWRIGBNM-UHFFFAOYSA-N 2-methyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C)=CC=C21 HNWFFTUWRIGBNM-UHFFFAOYSA-N 0.000 description 1
- LEXCBRKPOZULQO-UHFFFAOYSA-N 2-n,2-n,6-n,6-n-tetraphenylnaphthalene-2,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC(=CC2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LEXCBRKPOZULQO-UHFFFAOYSA-N 0.000 description 1
- PQCAURRJHOJJNQ-UHFFFAOYSA-N 2-n,7-n-dinaphthalen-1-yl-2-n,7-n,9,9-tetraphenylfluorene-2,7-diamine 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)C2(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 PQCAURRJHOJJNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- MEFNVSITOPKYCS-UHFFFAOYSA-N 2-octylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCCCC)=CC=C21 MEFNVSITOPKYCS-UHFFFAOYSA-N 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 1
- MFRXQRCKOQUENC-UHFFFAOYSA-N 3,4-diethoxythiophene Chemical compound CCOC1=CSC=C1OCC MFRXQRCKOQUENC-UHFFFAOYSA-N 0.000 description 1
- ZUDCKLVMBAXBIF-UHFFFAOYSA-N 3,4-dimethoxythiophene Chemical compound COC1=CSC=C1OC ZUDCKLVMBAXBIF-UHFFFAOYSA-N 0.000 description 1
- GWHSOUPRKHXZPK-UHFFFAOYSA-N 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=C3C4=CC(=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=2C=C(C=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GWHSOUPRKHXZPK-UHFFFAOYSA-N 0.000 description 1
- MGDRPFQPEQPOTL-UHFFFAOYSA-N 3,6-bis(sulfanyl)naphthalene-1-sulfonic acid Chemical compound SC1=CC2=CC(=CC=C2C(=C1)S(=O)(=O)O)S MGDRPFQPEQPOTL-UHFFFAOYSA-N 0.000 description 1
- QQEAKKMJHBCNRT-UHFFFAOYSA-N 3,6-di(carbazol-9-yl)-9-(2-ethylhexyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C2N(CC(CC)CCCC)C3=CC=C(N4C5=CC=CC=C5C5=CC=CC=C54)C=C3C2=C1 QQEAKKMJHBCNRT-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- LBIHNTAFJVHBLJ-UHFFFAOYSA-N 3-(triethoxymethyl)undec-1-ene Chemical compound C(=C)C(C(OCC)(OCC)OCC)CCCCCCCC LBIHNTAFJVHBLJ-UHFFFAOYSA-N 0.000 description 1
- IIEWMRPKJCXTAD-UHFFFAOYSA-N 3-(trimethoxymethyl)undecane Chemical compound C(C)C(C(OC)(OC)OC)CCCCCCCC IIEWMRPKJCXTAD-UHFFFAOYSA-N 0.000 description 1
- GFMFFNAOXIHABA-UHFFFAOYSA-N 3-[2-[2-[3-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]phenyl]-n,n-bis(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1N(C=1C=C(C=CC=1)C=1C(=CC=CC=1)C=1C(=CC=CC=1)C=1C=C(C=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GFMFFNAOXIHABA-UHFFFAOYSA-N 0.000 description 1
- WCXKTQVEKDHQIY-UHFFFAOYSA-N 3-[3-[3-(3,5-dipyridin-3-ylphenyl)phenyl]-5-pyridin-3-ylphenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=NC=CC=2)=C1 WCXKTQVEKDHQIY-UHFFFAOYSA-N 0.000 description 1
- KPOCSQCZXMATFR-UHFFFAOYSA-N 3-butylthiophene Chemical compound CCCCC=1C=CSC=1 KPOCSQCZXMATFR-UHFFFAOYSA-N 0.000 description 1
- GIEZWIDCIFCQPS-UHFFFAOYSA-N 3-ethyl-3-methylpentane Chemical compound CCC(C)(CC)CC GIEZWIDCIFCQPS-UHFFFAOYSA-N 0.000 description 1
- SLDBAXYJAIRQMX-UHFFFAOYSA-N 3-ethylthiophene Chemical compound CCC=1C=CSC=1 SLDBAXYJAIRQMX-UHFFFAOYSA-N 0.000 description 1
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- PIQKSZYJGUXAQF-UHFFFAOYSA-N 3-pentylthiophene Chemical compound CCCCCC=1C=CSC=1 PIQKSZYJGUXAQF-UHFFFAOYSA-N 0.000 description 1
- QZNFRMXKQCIPQY-UHFFFAOYSA-N 3-propylthiophene Chemical compound CCCC=1C=CSC=1 QZNFRMXKQCIPQY-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- AUJBNJFBJPKHPY-UHFFFAOYSA-N 4,4-diethoxy-5-methyltridecane Chemical compound CC(C(OCC)(OCC)CCC)CCCCCCCC AUJBNJFBJPKHPY-UHFFFAOYSA-N 0.000 description 1
- UAPJIXSMWIFQEH-UHFFFAOYSA-N 4,4-dimethoxy-5-methyltridecane Chemical compound CC(C(OC)(OC)CCC)CCCCCCCC UAPJIXSMWIFQEH-UHFFFAOYSA-N 0.000 description 1
- FXPCFGZWQHOKJF-UHFFFAOYSA-N 4-(1,1-diethoxyethyl)dodecan-1-amine Chemical compound NCCCC(C(OCC)(OCC)C)CCCCCCCC FXPCFGZWQHOKJF-UHFFFAOYSA-N 0.000 description 1
- RUERFVDCGFKEJD-UHFFFAOYSA-N 4-(4-aminophenyl)-1-N',4-N-dinaphthalen-2-yl-1-N',4-N-diphenylcyclohexa-2,5-diene-1,1,4-triamine Chemical compound C1=C(C=CC2=CC=CC=C12)N(C1(C=CC(N)(C=C1)N(C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C1)C1=CC=C(N)C=C1)C1=CC=CC=C1 RUERFVDCGFKEJD-UHFFFAOYSA-N 0.000 description 1
- SXPGQGNWEWPWQZ-UHFFFAOYSA-N 4-(triethoxymethyl)dodecan-1-amine Chemical compound NCCCC(C(OCC)(OCC)OCC)CCCCCCCC SXPGQGNWEWPWQZ-UHFFFAOYSA-N 0.000 description 1
- GNPSQUCXOBDIDY-UHFFFAOYSA-N 4-(trimethoxymethyl)dodecane Chemical compound C(CCCCCCC)C(C(OC)(OC)OC)CCC GNPSQUCXOBDIDY-UHFFFAOYSA-N 0.000 description 1
- GYPAGHMQEIUKAO-UHFFFAOYSA-N 4-butyl-n-[4-[4-(n-(4-butylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound C1=CC(CCCC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(CCCC)=CC=1)C1=CC=CC=C1 GYPAGHMQEIUKAO-UHFFFAOYSA-N 0.000 description 1
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- ICTSJDQTIQLGSE-UHFFFAOYSA-N 4-hexylnaphthalene-1-sulfonic acid Chemical compound CCCCCCc1ccc(c2ccccc12)S(O)(=O)=O ICTSJDQTIQLGSE-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- SKRQCHDXFSWTHN-UHFFFAOYSA-N 4-methyl-n-[4-[2-[4-[1-(4-methyl-n-(4-methylphenyl)anilino)-2-phenylethenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C(C=1C=CC(C=CC=2C=CC(=CC=2)N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=CC=1)=CC1=CC=CC=C1 SKRQCHDXFSWTHN-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
- CRHRWHRNQKPUPO-UHFFFAOYSA-N 4-n-naphthalen-1-yl-1-n,1-n-bis[4-(n-naphthalen-1-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 CRHRWHRNQKPUPO-UHFFFAOYSA-N 0.000 description 1
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 description 1
- PDVGPRKWYIVXGR-UHFFFAOYSA-N 4-phenylcyclohexa-2,4-diene-1,1-diamine Chemical compound C1=CC(N)(N)CC=C1C1=CC=CC=C1 PDVGPRKWYIVXGR-UHFFFAOYSA-N 0.000 description 1
- UEXKIEYHNLJFQH-UHFFFAOYSA-N 4-phenylthieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1C1=CC=CC=C1 UEXKIEYHNLJFQH-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UYTVVNSQPNBRAV-UHFFFAOYSA-N 4-quinolin-8-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=CC2=CC=CN=C12 UYTVVNSQPNBRAV-UHFFFAOYSA-N 0.000 description 1
- VRJFPWVYVHZDHH-UHFFFAOYSA-N 4-tert-butyl-2-[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]pyridine Chemical compound CC(C)(C)C1=CC=NC(C=2N=C(NN=2)C(F)(F)F)=C1 VRJFPWVYVHZDHH-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- YPKBCLZFIYBSHK-UHFFFAOYSA-N 5-methylindole Chemical compound CC1=CC=C2NC=CC2=C1 YPKBCLZFIYBSHK-UHFFFAOYSA-N 0.000 description 1
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- UBFXCBRNQSHADT-UHFFFAOYSA-N 6-methyl-2-[4-[10-[4-(6-methyl-1,3-benzothiazol-2-yl)phenyl]anthracen-9-yl]phenyl]-1,3-benzothiazole Chemical group C12=CC=CC=C2C(C2=CC=C(C=C2)C2=NC3=CC=C(C=C3S2)C)=C(C=CC=C2)C2=C1C1=CC=C(C=2SC3=CC(C)=CC=C3N=2)C=C1 UBFXCBRNQSHADT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- NUPJNQVNIZSKPF-UHFFFAOYSA-N 9-(triethoxymethyl)henicosane Chemical compound C(CCCCCCCCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC NUPJNQVNIZSKPF-UHFFFAOYSA-N 0.000 description 1
- SWUBEMMFTUPINB-UHFFFAOYSA-N 9-[3-carbazol-9-yl-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=C(C=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)=N1 SWUBEMMFTUPINB-UHFFFAOYSA-N 0.000 description 1
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 description 1
- ZWHCLDHSEXFKIK-MBALSZOMSA-N 9-[4-[(e)-2-[4-[(e)-2-(4-carbazol-9-ylphenyl)ethenyl]phenyl]ethenyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1/C=C/C(C=C1)=CC=C1/C=C/C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 ZWHCLDHSEXFKIK-MBALSZOMSA-N 0.000 description 1
- UXJDSNKBYFJNDO-UHFFFAOYSA-N 9-[4-[2-[2-(4-carbazol-9-ylphenyl)phenyl]phenyl]phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UXJDSNKBYFJNDO-UHFFFAOYSA-N 0.000 description 1
- JOPSDMLWJFJSGS-UHFFFAOYSA-N 9-[7-carbazol-9-yl-9,9-bis(4-methylphenyl)-10H-anthracen-2-yl]carbazole Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C1=CC=2C(C3=CC(=CC=C3CC=2C=C1)N1C2=CC=CC=C2C=2C=CC=CC1=2)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C JOPSDMLWJFJSGS-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- JZHKIUBMQMDQRG-UHFFFAOYSA-N C(=C)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)OC)CCCCCCCC JZHKIUBMQMDQRG-UHFFFAOYSA-N 0.000 description 1
- AYWXDPHRLSGVBS-UHFFFAOYSA-N C(=C)CC(CCCCCCCCC)(OC)OC Chemical compound C(=C)CC(CCCCCCCCC)(OC)OC AYWXDPHRLSGVBS-UHFFFAOYSA-N 0.000 description 1
- IBMOXDVZVHBZTK-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C)(C)(C)C1=CC=C(C=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 IBMOXDVZVHBZTK-UHFFFAOYSA-N 0.000 description 1
- BNIOOHXVEYTDJT-UHFFFAOYSA-N C(C)(C)C(C(OC)(OC)C(C)C)CCCCCCCC Chemical compound C(C)(C)C(C(OC)(OC)C(C)C)CCCCCCCC BNIOOHXVEYTDJT-UHFFFAOYSA-N 0.000 description 1
- BQKVVWQPYDKCQO-UHFFFAOYSA-N C(C)(C)N(CCCCCCCCCC)C(C)C.[Li] Chemical compound C(C)(C)N(CCCCCCCCCC)C(C)C.[Li] BQKVVWQPYDKCQO-UHFFFAOYSA-N 0.000 description 1
- QNGUFVBAHBNZGW-UHFFFAOYSA-N C(C)C(C(OC)(OC)CC)CCCCCCCC Chemical compound C(C)C(C(OC)(OC)CC)CCCCCCCC QNGUFVBAHBNZGW-UHFFFAOYSA-N 0.000 description 1
- XEPAKJGFUVCJOW-UHFFFAOYSA-N C(C)C(C(OCC)(OCC)CC)CCCCCCCC Chemical compound C(C)C(C(OCC)(OCC)CC)CCCCCCCC XEPAKJGFUVCJOW-UHFFFAOYSA-N 0.000 description 1
- UEYMLSDWUUKDND-UHFFFAOYSA-N C(C)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(C)C(C(OCC)(OCC)OCC)CCCCCCCC UEYMLSDWUUKDND-UHFFFAOYSA-N 0.000 description 1
- HUQVYDPAGWDJKZ-UHFFFAOYSA-N C(C)N(CCCCCCCCCC)CC.[Li] Chemical compound C(C)N(CCCCCCCCCC)CC.[Li] HUQVYDPAGWDJKZ-UHFFFAOYSA-N 0.000 description 1
- ZHSUITFUDTUGKT-UHFFFAOYSA-N C(C)OC(CCCCCCCCCC=1SC=CC1)(OCC)OCC Chemical compound C(C)OC(CCCCCCCCCC=1SC=CC1)(OCC)OCC ZHSUITFUDTUGKT-UHFFFAOYSA-N 0.000 description 1
- YCDHUYADNHUCJV-UHFFFAOYSA-N C(C)OC(CCCCCCCCCF)(OCC)OCC Chemical compound C(C)OC(CCCCCCCCCF)(OCC)OCC YCDHUYADNHUCJV-UHFFFAOYSA-N 0.000 description 1
- GHDHVFYKUQKSRV-UHFFFAOYSA-N C(C1=CC=CC=C1)C(CCCCCCCCC)(OC)OC Chemical compound C(C1=CC=CC=C1)C(CCCCCCCCC)(OC)OC GHDHVFYKUQKSRV-UHFFFAOYSA-N 0.000 description 1
- GKLXZYMUWOOVDQ-UHFFFAOYSA-N C(C1CO1)OCCCC(C(OC)(OC)C)CCCCCCCC Chemical compound C(C1CO1)OCCCC(C(OC)(OC)C)CCCCCCCC GKLXZYMUWOOVDQ-UHFFFAOYSA-N 0.000 description 1
- XYSNGNNDJGSUMY-UHFFFAOYSA-N C(C1CO1)OCCCC(C(OCC)(OCC)C)CCCCCCCC Chemical compound C(C1CO1)OCCCC(C(OCC)(OCC)C)CCCCCCCC XYSNGNNDJGSUMY-UHFFFAOYSA-N 0.000 description 1
- MTDLVDBRMBSPBJ-UHFFFAOYSA-N C(C1CO1)OCCCC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(C1CO1)OCCCC(C(OCC)(OCC)OCC)CCCCCCCC MTDLVDBRMBSPBJ-UHFFFAOYSA-N 0.000 description 1
- XRNDMACZMJPCRX-UHFFFAOYSA-N C(CC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CC)C(C(OCC)(OCC)OCC)CCCCCCCC XRNDMACZMJPCRX-UHFFFAOYSA-N 0.000 description 1
- GHTQBJZRHNNLIS-UHFFFAOYSA-N C(CCC)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(CCC)C(C(OC)(OC)OC)CCCCCCCC GHTQBJZRHNNLIS-UHFFFAOYSA-N 0.000 description 1
- FPYZFGNMCPBDBU-UHFFFAOYSA-N C(CCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CCC)C(C(OCC)(OCC)OCC)CCCCCCCC FPYZFGNMCPBDBU-UHFFFAOYSA-N 0.000 description 1
- BPDIDNOQBXCJJL-UHFFFAOYSA-N C(CCCC)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(CCCC)C(C(OC)(OC)OC)CCCCCCCC BPDIDNOQBXCJJL-UHFFFAOYSA-N 0.000 description 1
- RDAJSLMSQSSYML-UHFFFAOYSA-N C(CCCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CCCC)C(C(OCC)(OCC)OCC)CCCCCCCC RDAJSLMSQSSYML-UHFFFAOYSA-N 0.000 description 1
- OHEJQMYOWUSLBR-UHFFFAOYSA-N C(CCCCCC)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(CCCCCC)C(C(OC)(OC)OC)CCCCCCCC OHEJQMYOWUSLBR-UHFFFAOYSA-N 0.000 description 1
- LYNXWHHSWPJSRJ-UHFFFAOYSA-N C(CCCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CCCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC LYNXWHHSWPJSRJ-UHFFFAOYSA-N 0.000 description 1
- ZOVPDUNYPRDKJF-UHFFFAOYSA-N C(CCCCCCCC)C12C(C3=CC=CC=C3C3C1S3)(CCCCCCCCC)S2 Chemical compound C(CCCCCCCC)C12C(C3=CC=CC=C3C3C1S3)(CCCCCCCCC)S2 ZOVPDUNYPRDKJF-UHFFFAOYSA-N 0.000 description 1
- UMUVKMNHJFWLQT-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(CCCCCCCCCCCCCCCCC)C(C(OC)(OC)OC)CCCCCCCC UMUVKMNHJFWLQT-UHFFFAOYSA-N 0.000 description 1
- CJKMLHDKHGIHLL-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CCCCCCCCCCCCCCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC CJKMLHDKHGIHLL-UHFFFAOYSA-N 0.000 description 1
- PSAZQIAGASBTHT-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(C1=CC=C(C=C1)C=1C=NC=CC1)(C1=CC=C(C=C1)C=1C=NC=CC1)C1=CC=CC=C1)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(C1=CC=C(C=C1)C=1C=NC=CC1)(C1=CC=C(C=C1)C=1C=NC=CC1)C1=CC=CC=C1)CCCCCCCC PSAZQIAGASBTHT-UHFFFAOYSA-N 0.000 description 1
- JSGRIFNBTXDZQU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC JSGRIFNBTXDZQU-UHFFFAOYSA-N 0.000 description 1
- WMAZOIVUIWQRKU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC WMAZOIVUIWQRKU-UHFFFAOYSA-N 0.000 description 1
- XYDVYCSKHBUPIJ-UHFFFAOYSA-N C1(=CC=CC=C1)C(CCCCCCCCCC1=CC(=CC=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(CCCCCCCCCC1=CC(=CC=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 XYDVYCSKHBUPIJ-UHFFFAOYSA-N 0.000 description 1
- JVMYVPPVHDQZFM-UHFFFAOYSA-N C1(=CC=CC=C1)C(CCCCCCCCCC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(CCCCCCCCCC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 JVMYVPPVHDQZFM-UHFFFAOYSA-N 0.000 description 1
- BXWLKCUYXSVDPO-UHFFFAOYSA-N C1(=CC=CC=C1)C(CCCCCCCCCC1=CC=C(C=C1)C1=CC=C(C=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)C(CCCCCCCCCC1=CC=C(C=C1)C1=CC=C(C=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 BXWLKCUYXSVDPO-UHFFFAOYSA-N 0.000 description 1
- LCMUPYONTJKSTN-UHFFFAOYSA-N C1(=CC=CC=C1)C(CCCCCCCCCC1=CC=C(C=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(CCCCCCCCCC1=CC=C(C=C1)CCCCCCCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 LCMUPYONTJKSTN-UHFFFAOYSA-N 0.000 description 1
- GEKPKSZCBAHCSO-UHFFFAOYSA-N C1(=CC=CC=C1)P(C1=CC=2C(C3=CC(=CC=C3C2C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C=1C=CC=2N(C3=CC=CC=C3C2C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)P(C1=CC=2C(C3=CC(=CC=C3C2C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C=1C=CC=2N(C3=CC=CC=C3C2C1)C1=CC=CC=C1)C1=CC=CC=C1 GEKPKSZCBAHCSO-UHFFFAOYSA-N 0.000 description 1
- LTVDBAPRHUUKJQ-UHFFFAOYSA-N C1(CC2C(CC1)O2)CCC(CC(OC)(OC)C)CCCCCCC Chemical compound C1(CC2C(CC1)O2)CCC(CC(OC)(OC)C)CCCCCCC LTVDBAPRHUUKJQ-UHFFFAOYSA-N 0.000 description 1
- UZQBVFNKOUKLCP-UHFFFAOYSA-N C1(CCCCC1)N(CCCCCCCCCC)C1CCCCC1.[Li] Chemical compound C1(CCCCC1)N(CCCCCCCCCC)C1CCCCC1.[Li] UZQBVFNKOUKLCP-UHFFFAOYSA-N 0.000 description 1
- ZSRSSJJZGVIMHT-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3N(C12)C=1C=C(C=C(C1)N1C2=CC=CC=C2C=2C=CC=CC12)C(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)N1C2=CC=CC=C2C=2C=CC=CC12)N1C2=CC=CC=C2C=2C=CC=CC12 Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C12)C=1C=C(C=C(C1)N1C2=CC=CC=C2C=2C=CC=CC12)C(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)N1C2=CC=CC=C2C=2C=CC=CC12)N1C2=CC=CC=C2C=2C=CC=CC12 ZSRSSJJZGVIMHT-UHFFFAOYSA-N 0.000 description 1
- NLGRYYOCCPULGM-UHFFFAOYSA-N CC(C(CC)(C)N(CCCCCCCCCC)C(C(CCCCCCCC)C)(C)CC)CCCCCCCC Chemical compound CC(C(CC)(C)N(CCCCCCCCCC)C(C(CCCCCCCC)C)(C)CC)CCCCCCCC NLGRYYOCCPULGM-UHFFFAOYSA-N 0.000 description 1
- GGGZEAQPQFUYCJ-UHFFFAOYSA-N CC(C(OC)(OC)CC)CCCCCCCC Chemical compound CC(C(OC)(OC)CC)CCCCCCCC GGGZEAQPQFUYCJ-UHFFFAOYSA-N 0.000 description 1
- LNEJJQMNHUGXDW-UHFFFAOYSA-N CC(C(OCC)(OCC)C)CCCCCCCC Chemical compound CC(C(OCC)(OCC)C)CCCCCCCC LNEJJQMNHUGXDW-UHFFFAOYSA-N 0.000 description 1
- PZKBIVOXIFYDRI-UHFFFAOYSA-N CC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound CC(C(OCC)(OCC)OCC)CCCCCCCC PZKBIVOXIFYDRI-UHFFFAOYSA-N 0.000 description 1
- IZOWAAYDURJWLW-UHFFFAOYSA-N CC1=C(C(=CC(=C1C=1C=NC=CC=1)C)C)B Chemical compound CC1=C(C(=CC(=C1C=1C=NC=CC=1)C)C)B IZOWAAYDURJWLW-UHFFFAOYSA-N 0.000 description 1
- MQWJTOVSYKACHO-UHFFFAOYSA-N CC1=C(C=CC=C1)C(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)C1=C(C=CC=C1)C Chemical compound CC1=C(C=CC=C1)C(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)C1=C(C=CC=C1)C MQWJTOVSYKACHO-UHFFFAOYSA-N 0.000 description 1
- UIVXCPGVSFNWLY-UHFFFAOYSA-N CCC=COCCCC(C(OC)(OC)C)CCCCCCCC Chemical compound CCC=COCCCC(C(OC)(OC)C)CCCCCCCC UIVXCPGVSFNWLY-UHFFFAOYSA-N 0.000 description 1
- KOIGTNYADMQQMS-UHFFFAOYSA-N CCC=COCCCC(C(OCC)(OCC)C)CCCCCCCC Chemical compound CCC=COCCCC(C(OCC)(OCC)C)CCCCCCCC KOIGTNYADMQQMS-UHFFFAOYSA-N 0.000 description 1
- UDYCQCSHSJLKFG-UHFFFAOYSA-N CCCCCCCCCCCCc1cc2ccccc2cc1S(O)(=O)=O Chemical compound CCCCCCCCCCCCc1cc2ccccc2cc1S(O)(=O)=O UDYCQCSHSJLKFG-UHFFFAOYSA-N 0.000 description 1
- XPQOEOAEOZRAIS-UHFFFAOYSA-N CCCCCCc1ccc(CCCCCC)c(c1)S(O)(=O)=O Chemical compound CCCCCCc1ccc(CCCCCC)c(c1)S(O)(=O)=O XPQOEOAEOZRAIS-UHFFFAOYSA-N 0.000 description 1
- ZINICSCDQVBRJU-UHFFFAOYSA-N CCCCCCc1ccc2cc(ccc2c1)S(O)(=O)=O Chemical compound CCCCCCc1ccc2cc(ccc2c1)S(O)(=O)=O ZINICSCDQVBRJU-UHFFFAOYSA-N 0.000 description 1
- MYKHUARBDBEWFH-UHFFFAOYSA-N CCCCCCc1ccc2cccc(c2c1)S(O)(=O)=O Chemical compound CCCCCCc1ccc2cccc(c2c1)S(O)(=O)=O MYKHUARBDBEWFH-UHFFFAOYSA-N 0.000 description 1
- GGXWDWNWNOINTP-UHFFFAOYSA-N CCCCOCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound CCCCOCCCC(C(OC)(OC)OC)CCCCCCCC GGXWDWNWNOINTP-UHFFFAOYSA-N 0.000 description 1
- JYAVIPNDJHQFON-UHFFFAOYSA-N CCCCc1cc2ccc(cc2cc1CCCC)S(O)(=O)=O Chemical compound CCCCc1cc2ccc(cc2cc1CCCC)S(O)(=O)=O JYAVIPNDJHQFON-UHFFFAOYSA-N 0.000 description 1
- BAPGKQHLISBEMH-UHFFFAOYSA-N CCOC(CCCCCCCCCC1CCCCC1)(OCC)OCC Chemical compound CCOC(CCCCCCCCCC1CCCCC1)(OCC)OCC BAPGKQHLISBEMH-UHFFFAOYSA-N 0.000 description 1
- LOZYPXZJZSTREJ-UHFFFAOYSA-N CN(CCCCCCCCCC)C.[Li] Chemical compound CN(CCCCCCCCCC)C.[Li] LOZYPXZJZSTREJ-UHFFFAOYSA-N 0.000 description 1
- BVNQVVUFBYXAHN-UHFFFAOYSA-N CSC1=C(SC=C1)[Sn](CCCC)(CCCC)CCCC Chemical compound CSC1=C(SC=C1)[Sn](CCCC)(CCCC)CCCC BVNQVVUFBYXAHN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GSABLVFEPODNGG-UHFFFAOYSA-N FC=1C(=C(C=C(C=1)F)C1=C(C(=NC=C1)C(=O)O)[Ru]C=1C(=NC=CC=1C1=C(C(=CC(=C1)F)F)C1=NC=CC=C1)C(=O)O)C1=NC=CC=C1 Chemical compound FC=1C(=C(C=C(C=1)F)C1=C(C(=NC=C1)C(=O)O)[Ru]C=1C(=NC=CC=1C1=C(C(=CC(=C1)F)F)C1=NC=CC=C1)C(=O)O)C1=NC=CC=C1 GSABLVFEPODNGG-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- XJDCHDFUMGSEHD-UHFFFAOYSA-N NCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound NCCCC(C(OC)(OC)OC)CCCCCCCC XJDCHDFUMGSEHD-UHFFFAOYSA-N 0.000 description 1
- KTGXWDZUZLWXOF-UHFFFAOYSA-N NCCNCCCC(C(OC)(OC)C)CCCCCCCC Chemical compound NCCNCCCC(C(OC)(OC)C)CCCCCCCC KTGXWDZUZLWXOF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- KJNMFTZWJLGHIS-UHFFFAOYSA-N SCCCC(C(OC)(OC)C)CCCCCCCC Chemical compound SCCCC(C(OC)(OC)C)CCCCCCCC KJNMFTZWJLGHIS-UHFFFAOYSA-N 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- QSQTUTCZMKBSBW-UHFFFAOYSA-N [4-(3-diphenylphosphanylcarbazol-9-yl)phenyl]-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC(=CC=1)N1C2=CC=C(C=C2C2=CC=CC=C21)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 QSQTUTCZMKBSBW-UHFFFAOYSA-N 0.000 description 1
- KODFMTITTUYYKL-UHFFFAOYSA-N [Al+3].OC=1C=CC=C2C=CC=NC12.[Ar] Chemical compound [Al+3].OC=1C=CC=C2C=CC=NC12.[Ar] KODFMTITTUYYKL-UHFFFAOYSA-N 0.000 description 1
- OBTZHKFZVSDGIF-UHFFFAOYSA-N [Bi].C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Bi].C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 OBTZHKFZVSDGIF-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- WXZIKFXSSPSWSR-UHFFFAOYSA-N [Li]CCCCC Chemical compound [Li]CCCCC WXZIKFXSSPSWSR-UHFFFAOYSA-N 0.000 description 1
- MKBRSCCBNYBMBB-UHFFFAOYSA-K [Ru+3].C(C)(=O)CC(C(=O)[O-])=O.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O Chemical compound [Ru+3].C(C)(=O)CC(C(=O)[O-])=O.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O MKBRSCCBNYBMBB-UHFFFAOYSA-K 0.000 description 1
- SJWRNNIRDDFVBW-UHFFFAOYSA-K [Ru+3].C(C)(=O)CC(C(=O)[O-])=O.CC1=NC2=C3C(=C4C(=C2N=C1)C=CC=C4)C=CC=C3.CC3=NC4=C1C(=C2C(=C4N=C3)C=CC=C2)C=CC=C1.C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O Chemical compound [Ru+3].C(C)(=O)CC(C(=O)[O-])=O.CC1=NC2=C3C(=C4C(=C2N=C1)C=CC=C4)C=CC=C3.CC3=NC4=C1C(=C2C(=C4N=C3)C=CC=C2)C=CC=C1.C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O SJWRNNIRDDFVBW-UHFFFAOYSA-K 0.000 description 1
- WQJXHRDMMJAQTK-UHFFFAOYSA-N [Ru+3].C(CCCCC)C1=CC=C(C=C1)C1=NC2=CC=CC=C2C=C1 Chemical compound [Ru+3].C(CCCCC)C1=CC=C(C=C1)C1=NC2=CC=CC=C2C=C1 WQJXHRDMMJAQTK-UHFFFAOYSA-N 0.000 description 1
- YHWUQFSBYMUZJQ-UHFFFAOYSA-N [Ru+3].C1(=CC=CC=C1)C1=NC=CC=C1 Chemical compound [Ru+3].C1(=CC=CC=C1)C1=NC=CC=C1 YHWUQFSBYMUZJQ-UHFFFAOYSA-N 0.000 description 1
- ZXQORACUFNFTJH-UHFFFAOYSA-N [Ru+3].CC1=CC=C(C=C1)C1=NC=CC=C1 Chemical compound [Ru+3].CC1=CC=C(C=C1)C1=NC=CC=C1 ZXQORACUFNFTJH-UHFFFAOYSA-N 0.000 description 1
- DENPHGHUHDADMV-UHFFFAOYSA-N [Ru].C(C1=CC=CC=C1)P(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F Chemical compound [Ru].C(C1=CC=CC=C1)P(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F DENPHGHUHDADMV-UHFFFAOYSA-N 0.000 description 1
- RBAGNDGANLXYFZ-UHFFFAOYSA-N [Ru].C(CCCCC)C1=CC=C(C=C1)C1=NC2=CC=CC=C2C=C1 Chemical compound [Ru].C(CCCCC)C1=CC=C(C=C1)C1=NC2=CC=CC=C2C=C1 RBAGNDGANLXYFZ-UHFFFAOYSA-N 0.000 description 1
- UNBFUOSPMYMDFT-UHFFFAOYSA-N [Ru].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C=C1 Chemical compound [Ru].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C=C1 UNBFUOSPMYMDFT-UHFFFAOYSA-N 0.000 description 1
- UASYZJMPYJVOLA-UHFFFAOYSA-N [Ru].C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 Chemical compound [Ru].C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 UASYZJMPYJVOLA-UHFFFAOYSA-N 0.000 description 1
- MNPONRBKPKFXKK-UHFFFAOYSA-N [Ru].FC(C1=NNC(=N1)C1=NC=CC=C1)(F)F.FC1=CC=C(C(=C1)F)C1=NC=CC=C1.FC1=CC=C(C(=C1)F)C1=NC=CC=C1 Chemical compound [Ru].FC(C1=NNC(=N1)C1=NC=CC=C1)(F)F.FC1=CC=C(C(=C1)F)C1=NC=CC=C1.FC1=CC=C(C(=C1)F)C1=NC=CC=C1 MNPONRBKPKFXKK-UHFFFAOYSA-N 0.000 description 1
- MSDUBHNRIXBCDH-UHFFFAOYSA-N [Ru].FC1=C(CP(OC2=CC=CC=C2)(OC2=CC=CC=C2)=O)C=CC(=C1)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F Chemical compound [Ru].FC1=C(CP(OC2=CC=CC=C2)(OC2=CC=CC=C2)=O)C=CC(=C1)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F MSDUBHNRIXBCDH-UHFFFAOYSA-N 0.000 description 1
- VXBQIRSIXXFJLM-UHFFFAOYSA-N [Ru].N1=C(C=CC=C1)C1=NN=NN1.FC1=C(C=CC(=C1)F)C1=NC=CC=C1.FC1=C(C=CC(=C1)F)C1=NC=CC=C1 Chemical compound [Ru].N1=C(C=CC=C1)C1=NN=NN1.FC1=C(C=CC(=C1)F)C1=NC=CC=C1.FC1=C(C=CC(=C1)F)C1=NC=CC=C1 VXBQIRSIXXFJLM-UHFFFAOYSA-N 0.000 description 1
- DBVIZWMZENPHBU-UHFFFAOYSA-N [Ru].O1CCOCC1 Chemical compound [Ru].O1CCOCC1 DBVIZWMZENPHBU-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- VZSNNUDOANMGNX-UHFFFAOYSA-K aluminum;4-phenylphenolate Chemical compound [Al+3].C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC([O-])=CC=C1C1=CC=CC=C1 VZSNNUDOANMGNX-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 150000003519 bicyclobutyls Chemical group 0.000 description 1
- 150000005350 bicyclononyls Chemical group 0.000 description 1
- 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 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product 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
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HQFQTTNMBUPQAY-UHFFFAOYSA-N cyclobutylhydrazine Chemical compound NNC1CCC1 HQFQTTNMBUPQAY-UHFFFAOYSA-N 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- BNZSBPKOMCJCNW-UHFFFAOYSA-N cyclobutylsulfanylcyclobutane Chemical compound C1CCC1SC1CCC1 BNZSBPKOMCJCNW-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 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
- ITIDSNKGTOBPBD-UHFFFAOYSA-N hydroxy-phenyl-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(=S)C1=CC=CC=C1 ITIDSNKGTOBPBD-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 150000002641 lithium Chemical group 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
- CWRUMZLXQIRXFL-UHFFFAOYSA-N lithium penta-1,3-diene Chemical compound [Li+].[CH2-]C=CC=C CWRUMZLXQIRXFL-UHFFFAOYSA-N 0.000 description 1
- DLENDKSMPIEGPF-UHFFFAOYSA-N lithium piperidine Chemical compound [Li+].C1CCNCC1 DLENDKSMPIEGPF-UHFFFAOYSA-N 0.000 description 1
- BNHFWQQYLUPDOG-UHFFFAOYSA-N lithium;1,2,2,3-tetramethylpiperidine Chemical compound [Li].CC1CCCN(C)C1(C)C BNHFWQQYLUPDOG-UHFFFAOYSA-N 0.000 description 1
- HIZMSKAWFIZQKV-UHFFFAOYSA-N lithium;2-methanidyloxy-2-methylpropane Chemical compound [Li+].CC(C)(C)O[CH2-] HIZMSKAWFIZQKV-UHFFFAOYSA-N 0.000 description 1
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WDDLHZXDSVMNRK-UHFFFAOYSA-N lithium;3-methanidylheptane Chemical compound [Li+].CCCCC([CH2-])CC WDDLHZXDSVMNRK-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
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical compound [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 description 1
- ATKCLEUSJFRRKA-UHFFFAOYSA-N lithium;prop-1-yne Chemical compound [Li+].CC#[C-] ATKCLEUSJFRRKA-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- FFERJQVZFBLPPP-UHFFFAOYSA-N lithium;trichloromethane Chemical compound [Li+].Cl[C-](Cl)Cl FFERJQVZFBLPPP-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BJMDYNHSWAKAMX-UHFFFAOYSA-N methyl(diphenyl)sulfanium Chemical compound C=1C=CC=CC=1[S+](C)C1=CC=CC=C1 BJMDYNHSWAKAMX-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- YPJRZWDWVBNDIW-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[4-[4-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-MBALSZOMSA-N 0.000 description 1
- NJWJVPXCXKIBJD-QURGRASLSA-N n,n-diphenyl-6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 NJWJVPXCXKIBJD-QURGRASLSA-N 0.000 description 1
- CLTPAQDLCMKBIS-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-1-ylamino)phenyl]phenyl]-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CLTPAQDLCMKBIS-UHFFFAOYSA-N 0.000 description 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 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
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical class CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- YAQFXAHJUXNNQQ-UHFFFAOYSA-N tributyl-(3-hexylthiophen-2-yl)stannane Chemical compound CCCCCCC=1C=CSC=1[Sn](CCCC)(CCCC)CCCC YAQFXAHJUXNNQQ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- AXIZEIIHNRROTM-UHFFFAOYSA-N tungsten ytterbium Chemical compound [Yb][W] AXIZEIIHNRROTM-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-N zinc;quinolin-8-ol Chemical compound [Zn+2].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- 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
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
本發明係提供一種以下述式(1)所示之噻吩衍生物。
(R1~R4表示烷基、烯基、炔基、烷氧基、烯基氧基、炔基氧基、烷基硫代基、炔基硫代基、芳基氧基、雜芳基氧基、芳基硫代基或雜芳基硫代基;R5~R8表示氫、烷基、烯基、炔基、烷氧基、烯基氧基、炔基氧基、烷基硫代基、炔基硫代基、芳基氧基、雜芳基氧基、芳基硫代基或雜芳基硫代基;R9~R12表示氫、烷基、烯基、炔基、烷氧基、烯基氧基、炔基氧基、烷基硫代基、炔基硫代基或芳基)。
Description
本發明係關於噻吩衍生物及其利用以及噻吩衍生物之製造方法,更詳言之,是關於藉由至少於3位具有取代基之2-噻吩基而可於2、3、4及5位被取代之噻吩衍生物、利用上述衍生物作為其電荷輸送性物質,以及噻吩衍生物之製造方法。
有機電致發光(以下稱為有機EL)元件中,發光層或電荷注入層方面,可使用由有機化合物所成的電荷輸送性薄膜。特別是,電洞注入層係擔任陽極與電洞輸送層或發光層之電荷的接受,且為用以達成有機EL元件之低電壓驅動及高亮度的重要機能。
電洞注入層之形成方法,可大致上分為蒸鍍法所代表的乾式製程與旋轉塗佈法所代表的濕式製程,相較於此等各製程,濕式製程者可有效率地於大面積上製造平坦性高的薄膜。因此,在有機EL顯示器的大面積化逐漸進展的現今,可望以濕式製程來形成電洞注入層。
有鑑於此,本發明者們正在開發具有可實現
適用於各種濕式製程同時在用於有機EL元件之電洞注入層時優異的EL元件特性之薄膜的電荷輸送性材料,以及對用於其中的有機溶劑溶解性良好的化合物(參考例如專利文獻1~4)。
[專利文獻1]國際公開第2008/032616號
[專利文獻2]國際公開第2008/129947號
[專利文獻3]國際公開第2006/025342號
[專利文獻4]國際公開第2010/058777號
本發明係與至今所開發而來的上述專利文獻之技術相同地,以提供一種新穎的噻吩衍生物為目的,該噻吩衍生物可實現對有機溶劑顯示出良好的溶解性,同時可予以薄膜化而適用於電洞注入層時具有優異的壽命特性之有機EL元件。
本發明者們為了達成上述目的一再地鑽研探討的結果發現,特定的噻吩衍生物除了對有機溶劑顯示出高溶解性之外,將其與摻雜物一起溶解於有機溶劑所調製
而成的塗漆,由此塗漆所得的薄膜具有高電荷輸送性,且將該薄膜適用於有機EL元件的電洞注入層時,可以實現優異的壽命特性,遂而完成本發明。
即,本發明係提供下述噻吩衍生物及其利用,以及噻吩衍生物之製造方法。
1.一種噻吩衍生物,其特徵係下述式(1)所示者。
(式中,R1~R4各自獨立地表示可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基、可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基、可以Z2所取代之碳數6~20之芳基氧基、可以Z2所取代之碳數2~20之雜芳基氧基、可以Z2所取代之碳數6~20之芳基硫代基或可以Z2所取代之碳數2~20之雜芳基硫代基;R5~R8各自獨立地表示氫原子、可以Z1所取代之碳數
1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基、可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基、可以Z2所取代之碳數6~20之芳基氧基、可以Z2所取代之碳數2~20之雜芳基氧基、可以Z2所取代之碳數6~20之芳基硫代基或可以Z2所取代之碳數2~20之雜芳基硫代基;又,R5~R8不為氫原子時,R1與R5、R2與R6、R3與R7及/或R4與R8可各自互相地鍵結形成2價之基;R9~R12各自獨立地表示氫原子、可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基、可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基或可以Z2所取代之碳數6~20之芳基;Z1表示鹵素原子、碳數1~20之烷氧基、碳數2~20之烯基氧基、碳數2~20之炔基氧基、碳數1~20之烷基硫代基、碳數2~20之烯基硫代基、碳數2~20之炔基硫代基、碳數6~20之芳基、碳數6~20之芳基氧基、碳數2~20之
雜芳基氧基、碳數6~20之芳基硫代基或碳數2~20之雜芳基硫代基;Z2表示鹵素原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數1~20之烷氧基、碳數2~20之烯基氧基、碳數2~20之炔基氧基、碳數1~20之烷基硫代基、碳數2~20之烯基硫代基、碳數2~20之炔基硫代基、碳數6~20之芳基氧基、碳數2~20之雜芳基氧基、碳數6~20之芳基硫代基或碳數2~20之雜芳基硫代基)
2.如1之噻吩衍生物,其中,R1~R4各自獨立地表示可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基、可以Z2所取代之碳數6~20之芳基氧基、可以Z2所取代之碳數2~20之雜芳基氧基、可以Z2所取代之碳數6~20之芳基硫代基或可以Z2所取代之碳數2~20之雜芳基硫代基。
3.如1或2之噻吩衍生物,其中,R5~R8各自獨立地表示氫原子、可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基或可以Z1所取代之碳數1~20之烷氧基。
4.如1~3中任一項之噻吩衍生物,其中,R9~R12各自獨立地表示氫原子、可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基或可以Z1所取代
之碳數2~20之炔基。
5.一種如1之噻吩衍生物之製造方法,其特徵係使下述式(2)所示之噻吩化合物與式(3)~(6)所示之三烷基錫烷基噻吩化合物在觸媒存在下反應。
(式中,Hal各自獨立地表示鹵素原子或擬鹵素基、Ra各自獨立地表示碳數1~20之烷基。R1~R12係與上述相同)
6.一種電荷輸送性物質,其係由如1~4中任一項之噻吩衍生物所成者。
7.一種電荷輸送性塗漆,其係包含如1~4中任一項之噻吩衍生物、摻雜物及有機溶劑。
8.一種電荷輸送性薄膜,其係使用如7之電荷輸送性塗漆所製作者。
9.一種電荷輸送性薄膜,其係包含如1~4中任一項之噻吩衍生物者。
10.一種電子裝置,其係具備至少1層如8或9之電荷輸送性薄膜者。
11.一種有機電致發光元件,其係具備至少1層如8或9之電荷輸送性薄膜者。
12.如11之有機電致發光元件,其中,前述電荷輸
送性薄膜係電洞注入層或電洞輸送層。
本發明之噻吩衍生物容易溶於有機溶劑,使此與摻雜物一起溶解於有機溶劑,可輕易地調製電荷輸送性塗漆。
由本發明之電荷輸送性塗漆製作的薄膜,因顯示出高電荷輸送性之故,可適用為以有機EL元件為首的電子裝置用薄膜。特別是,將此薄膜適用於有機EL元件的電洞注入層,可獲得壽命特性優異的有機EL元件。
又,本發明之電荷輸送性塗漆即使是在使用旋轉塗佈法或狹縫塗佈法等可於大面積成膜之各種濕式製程時,因可再現性佳地製造電荷輸送性優異的薄膜之故,近年來,對於在有機EL元件的領域中之進展亦可充分地對應。
有關本發明之噻吩衍生物,係如下述式(1)所示。
式中,R1~R4各自獨立地表示可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基、可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基、可以Z2所取代之碳數6~20之芳基氧基、可以Z2所取代之碳數2~20之雜芳基氧基、可以Z2所取代之碳數6~20之芳基硫代基或可以Z2所取代之碳數2~20之雜芳基硫代基。
R5~R8各自獨立地表示氫原子、可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基、可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫
代基、可以Z2所取代之碳數6~20之芳基氧基、可以Z2所取代之碳數2~20之雜芳基氧基、可以Z2所取代之碳數6~20之芳基硫代基或可以Z2所取代之碳數2~20之雜芳基硫代基。
又,R5~R8不為氫原子時,R1與R5、R2與R6、R3與R7及/或R4與R8可互相鍵結而形成2價之基。
R9~R12各自獨立地表示氫原子、可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基、可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基或可以Z2所取代之碳數6~20之芳基。
Z1表示鹵素原子、碳數1~20之烷氧基、碳數2~20之烯基氧基、碳數2~20之炔基氧基、碳數1~20之烷基硫代基、碳數2~20之烯基硫代基、碳數2~20之炔基硫代基、碳數6~20之芳基、碳數6~20之芳基氧基、碳數2~20之雜芳基氧基、碳數6~20之芳基硫代基或碳數2~20之雜芳基硫代基。
Z2表示鹵素原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數1~20之烷氧基、碳數2~20之烯基氧基、碳數2~20之炔基氧基、碳數1~20之烷基硫代基、碳數2~20之烯基硫代基、碳數2~20
之炔基硫代基、碳數6~20之芳基氧基、碳數2~20之雜芳基氧基、碳數6~20之芳基硫代基或碳數2~20之雜芳基硫代基。
鹵素原子方面,可舉出氟、氯、溴、碘原子等。
碳數1~20之烷基可為直鏈狀、分枝狀、環狀之任一者。烷基的具體例方面,可舉出甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、s-丁基、t-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等之碳數1~20之直鏈狀或分枝鏈狀烷基;環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、雙環丁基、雙環戊基、雙環己基、雙環庚基、雙環辛基、雙環壬基、雙環癸基等之碳數3~20之環狀烷基等。
碳數2~20之烯基可為直鏈狀、分枝狀、環狀之任一者。烯基的具體例方面,可舉出乙烯基、n-1-丙烯基、n-2-丙烯基、1-甲基乙烯基、n-1-丁烯基、n-2-丁烯基、n-3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、n-1-戊烯基、n-1-癸烯基、n-1-廿烯基等。
碳數2~20之炔基可為直鏈狀、分枝狀、環狀之任一者。炔基的具體例方面,可舉出乙炔基、n-1-丙炔基、n-2-丙炔基、n-1-丁炔基、n-2-丁炔基、n-3-丁炔基、1-甲基-2-丙炔基、n-1-戊炔基、n-2-戊炔基、n-3-戊炔基、n-4-戊炔基、1-甲基-n-丁炔基、2-甲基-n-丁炔基、3-
甲基-n-丁炔基、1,1-二甲基-n-丙炔基、n-1-己炔基、n-1-癸炔基、n-1-十五炔基、n-1-廿炔基等。
碳數1~20之烷氧基可為直鏈狀、分枝狀、環狀之任一者。烷氧基的具體例方面,可舉出甲氧基、乙氧基、n-丙氧基、異丙氧基、n-丁氧基、異丁氧基、s-丁氧基、t-丁氧基、n-戊基氧基、n-己基氧基、n-庚基氧基、n-辛基氧基、n-壬基氧基、n-癸基氧基等之碳數1~20之直鏈狀或分枝鏈狀烷氧基;環丙基氧基、環丁基氧基、環戊基氧基、環己基氧基、環庚基氧基、環辛基氧基、環壬基氧基、環癸基氧基、雙環丁基氧基、雙環戊基氧基、雙環己基氧基、雙環庚基氧基、雙環辛基氧基、雙環壬基氧基、雙環癸基氧基等之碳數3~20之環狀烷氧基等。
碳數2~20之烯基氧基可為直鏈狀、分枝狀、環狀之任一者。烯基氧基的具體例方面,可舉出乙烯基氧基、n-1-丙烯基氧基、n-2-丙烯基氧基、1-甲基乙烯基氧基、n-1-丁烯基氧基、n-2-丁烯基氧基、n-3-丁烯基氧基、2-甲基-1-丙烯基氧基、2-甲基-2-丙烯基氧基、1-乙基乙烯基氧基、1-甲基-1-丙烯基氧基、1-甲基-2-丙烯基氧基、n-1-戊烯基氧基、n-1-癸烯基氧基、n-1-廿烯基氧基等。
碳數2~20之炔基氧基可為直鏈狀、分枝狀、環狀之任一者。炔基氧基的具體例方面,可舉出乙炔基氧基、n-1-丙炔基氧基、n-2-丙炔基氧基、n-1-丁炔基氧基、n-2-丁炔基氧基、n-3-丁炔基氧基、1-甲基-2-丙炔基
氧基、n-1-戊炔基氧基、n-2-戊炔基氧基、n-3-戊炔基氧基、n-4-戊炔基氧基、1-甲基-n-丁炔基氧基、2-甲基-n-丁炔基氧基、3-甲基-n-丁炔基氧基、1,1-二甲基-n-丙炔基氧基、n-1-己炔基氧基、n-1-癸炔基氧基、n-1-十五炔基氧基、n-1-廿炔基氧基等。
碳數1~20之烷基硫代基可為直鏈狀、分枝狀、環狀之任一者。烷基硫代基的具體例方面,可舉出甲基硫代基、乙基硫代基、n-丙基硫代基、異丙基硫代基、n-丁基硫代基、異丁基硫代基、s-丁基硫代基、t-丁基硫代基、n-戊基硫代基、n-己基硫代基、n-庚基硫代基、n-辛基硫代基、n-壬基硫代基、n-癸基硫代基等之碳數1~20之直鏈狀或分枝鏈狀烷基硫代基;環丙基硫代基、環丁基硫代基、環戊基硫代基、環己基硫代基、環庚基硫代基、環辛基硫代基、環壬基硫代基、環癸基硫代基、雙環丁基硫代基、雙環戊基硫代基、雙環己基硫代基、雙環庚基硫代基、雙環辛基硫代基、雙環壬基硫代基、雙環癸基硫代基等之碳數3~20之環狀烷基硫代基等。
碳數2~20之烯基硫代基可為直鏈狀、分枝狀、環狀之任一者。烯基硫代基的具體例方面,可舉出乙烯基硫代基、n-1-丙烯基硫代基、n-2-丙烯基硫代基、1-甲基乙烯基硫代基、n-1-丁烯基硫代基、n-2-丁烯基硫代基、n-3-丁烯基硫代基、2-甲基-1-丙烯基硫代基、2-甲基-2-丙烯基硫代基、1-乙基乙烯基硫代基、1-甲基-1-丙烯基硫代基、1-甲基-2-丙烯基硫代基、n-1-戊烯基硫代基、n-
1-癸烯基硫代基、n-1-廿烯基硫代基等。
碳數2~20之炔基硫代基可為直鏈狀、分枝狀、環狀之任一者。炔基硫代基的具體例方面,可舉出乙炔基硫代基、n-1-丙炔基硫代基、n-2-丙炔基硫代基、n-1-丁炔基硫代基、n-2-丁炔基硫代基、n-3-丁炔基硫代基、1-甲基-2-丙炔基硫代基、n-1-戊炔基硫代基、n-2-戊炔基硫代基、n-3-戊炔基硫代基、n-4-戊炔基硫代基、1-甲基-n-丁炔基硫代基、2-甲基-n-丁炔基硫代基、3-甲基-n-丁炔基硫代基、1,1-二甲基-n-丙炔基硫代基、n-1-己炔基硫代基、n-1-癸炔基硫代基、n-1-十五炔基硫代基、n-1-廿炔基硫代基等。
烷基、烯基、炔基、烷氧基、烯基氧基、炔基氧基、烷基硫代基、烯基硫代基及炔基硫代基之碳數,係以12以下為佳,6以下更佳,4以下又再更佳。
碳數6~20之芳基的具體例方面,可舉出苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等。
碳數6~20之芳基氧基的具體例方面,可舉出苯基氧基、1-萘基氧基、2-萘基氧基、1-蒽基氧基、2-蒽基氧基、9-蒽基氧基、1-菲基氧基、2-菲基氧基、3-菲基氧基、4-菲基氧基、9-菲基氧基等。
碳數2~20之雜芳基氧基的具體例方面,可舉出2-噻吩基氧基、3-噻吩基氧基、2-喃基氧基、3-喃基氧基、2-噁唑基氧基、4-噁唑基氧基、5-噁唑基氧基、3-異
噁唑基氧基、4-異噁唑基氧基、5-異噁唑基氧基、2-噻唑基氧基、4-噻唑基氧基、5-噻唑基氧基、3-異噻唑基氧基、4-異噻唑基氧基、5-異噻唑基氧基、2-咪唑基氧基、4-咪唑基氧基、2-吡啶基氧基、3-吡啶基氧基、4-吡啶基氧基等。
碳數6~20之芳基硫代基的具體例方面,可舉出苯基硫代基、1-萘基硫代基、2-萘基硫代基、1-蒽基硫代基、2-蒽基硫代基、9-蒽基硫代基、1-菲基硫代基、2-菲基硫代基、3-菲基硫代基、4-菲基硫代基、9-菲基硫代基等。
碳數2~20之雜芳基硫代基的具體例方面,可舉出2-噻吩基硫代基、3-噻吩基硫代基、2-喃基硫代基、3-喃基硫代基、2-噁唑基硫代基、4-噁唑基硫代基、5-噁唑基硫代基、3-異噁唑基硫代基、4-異噁唑基硫代基、5-異噁唑基硫代基、2-噻唑基硫代基、4-噻唑基硫代基、5-噻唑基硫代基、3-異噻唑基硫代基、4-異噻唑基硫代基、5-異噻唑基硫代基、2-咪唑基硫代基、4-咪唑基硫代基、2-吡啶基硫代基、3-吡啶基硫代基、4-吡啶基硫代基等。
芳基、芳基氧基、雜芳基氧基、芳基硫代基及雜芳基硫代基之碳數係,14以下為佳,10以下更佳,6以下又再更佳。
R1~R4方面,可舉出可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z1所取代
之碳數1~20,特別是碳數2~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基、可以Z2所取代之碳數6~20之芳基氧基、可以Z2所取代之碳數2~20之雜芳基氧基、可以Z2所取代之碳數6~20之芳基硫代基或可以Z2所取代之碳數2~20之雜芳基硫代基為佳,可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z2所取代之碳數6~20之芳基氧基或可以Z2所取代之碳數2~20之雜芳基氧基更佳,可以Z1所取代之碳數1~20之烷氧基或可以Z2所取代之碳數6~20之芳基氧基又更佳。
又,R5~R8方面,係以氫原子、可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基、可以Z1所取代之碳數2~20之炔基或可以Z1所取代之碳數1~20之烷氧基為佳,又以氫原子、可以Z1所取代之碳數1~20之烷基或可以Z1所取代之碳數1~20之烷氧基更佳,氫原子或可以Z1所取代之碳數1~20之烷氧基又再更佳,氫原子為最佳。
R9~R12方面,係以氫原子、可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基或可以Z1所取代之碳數2~20之炔基為佳,以氫原子或可以Z1所取代之碳數1~20之烷基更佳,氫原子為最佳。
此外,R1~R12中,取代基之Z1方面,係以鹵素原子或碳數6~14之芳基為佳,鹵素原子或苯基更佳,
以不存在者(即非取代者)為最佳。
又,取代基之Z2方面,係以鹵素原子或碳數1~20之烷基為佳,鹵素原子或碳數1~4之烷基更佳,以不存在者(即非取代者)為最佳。
式(1)所示之噻吩衍生物,從合成之容易性的觀點來看,係以在3位具取代基之2-噻吩基全都有相同的構造者為佳。即,式(1)中R1~R4皆為相同的基,R5~R8皆為相同的基,且R9~R12皆為相同的基者為佳。
以下,列舉出式(1)所示之噻吩衍生物之具體例,但不受限於此等。此外,式中,Me、Et、Pr、Bu、Pen及Hex各自表示甲基、乙基、丙基、丁基、戊基及己基。
本發明之噻吩衍生物係,例如,可以使式(2)所示之噻吩化合物與式(3)~(6)所示之三烷基錫烷基噻吩化合物在觸媒存在下反應來製造。
(式中,Hal各自獨立地表示鹵素原子或擬鹵素基、Ra各自獨立地表示碳數1~20之烷基。R1~R12係與上述相同)
鹵素原子方面,可舉出與上述相同者。
擬鹵素基方面,可舉出甲烷磺醯基氧基、三氟甲烷磺醯基氧基、九氟丁烷磺醯基氧基等之(氟)烷基磺醯基氧基;苯磺醯基氧基、甲苯磺醯基氧基等之芳香族磺醯基氧基等。
三烷基錫烷基方面,可舉出三甲基錫烷基、三乙基錫烷基、三-n-丙基錫烷基、三異丙基錫烷基、三-n-丁基錫烷基、三-n-戊基錫烷基、三環己基錫烷基、三辛基錫烷基、n-丁基二甲基錫烷基等。
式(2)所示之噻吩化合物的具體例方面,可舉出四氯噻吩、四溴噻吩、四碘噻吩等,但不受限於此等。
式(3)~(6)所示之三烷基錫烷基噻吩化合
物方面,可舉出3-甲氧基-2-(三-n-丁基錫烷基)噻吩、3-甲基硫代基-2-(三-n-丁基錫烷基)噻吩、3-己基-(三-n-丁基錫烷基)噻吩、3,4-伸乙基二氧-2-(三-n-丁基錫烷基)噻吩等,但不受限於此等。
所置入的式(2)所示之噻吩化合物與式(3)~(5)所示之三烷基錫烷基噻吩化合物的比,相對於式(2)所示之噻吩化合物,係可使式(3)~(5)所示之噻吩化合物各自為1當量以上,又以1~1.2當量左右為佳。
上述反應中所用的觸媒方面,可舉例如氯化銅、溴化銅、碘化銅等之銅觸媒;肆(三苯基膦)鈀(Pd(PPh3)4)、雙(三苯基膦)二氯鈀(Pd(PPh3)2Cl2)、雙(亞苄基丙酮)鈀(Pd(dba)2)、參(亞苄基丙酮)二鈀(Pd2(dba)3)、雙(三-t-丁基膦)鈀(Pd(P-t-Bu3)2)等之鈀觸媒等。此等之觸媒可單獨使用1種或組合2種以上來使用。又,此等之觸媒亦可與公知而適當的配位子一起使用。
觸媒的使用量,相對於式(2)所示之噻吩化合物1mol,可為0.01~0.2mol左右,以0.05mol左右為佳。
又,使用配位子時,其使用量,相對於所用的金屬錯合物,可為0.1~5當量,1~2當量較佳。
上述反應可於溶劑中進行。使用溶劑時,其種類若對反應沒有不良影響的話,並無特別限制。具體例
方面,可舉出脂肪族烴類(戊烷、n-己烷、n-辛烷、n-癸烷、十氫萘等)、鹵素化脂肪族烴類(氯仿、二氯甲烷、二氯乙烷、四氯化碳等)、芳香族烴類(苯、硝基苯、甲苯、o-二甲苯、m-二甲苯、p-二甲苯、均三甲苯等)、鹵素化芳香族烴類(氯苯、溴苯、o-二氯苯、m-二氯苯、p-二氯苯等)、醚類(二乙基醚、二異丙基醚、t-丁基甲基醚、四氫呋喃、二氧陸圜、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、酮類(丙酮、甲基乙基酮、甲基異丁基酮、二-n-丁基酮、環己酮等)、醯胺類(N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等)、內醯胺及內酯類(N-甲基吡咯啶酮、γ-丁內酯等)、尿素類(N,N-二甲基四氫咪唑酮、四甲基脲等)、亞碸類(二甲基亞碸、環丁碸等)、腈類(乙腈、丙腈、丁腈等)等。此等之溶劑可單獨使用1種或混合2種以上使用。
反應溫度可於所用溶劑之融點~沸點為止之範圍下適當地設定即可,特別是以0~200℃左右為佳、20~150℃更佳。
反應結束後,可遵照常法進行後處理,得到目的之噻吩衍生物。
本發明之噻吩衍生物之合成中所用的式(3)~(6)所示之三烷基錫烷基噻吩化合物之製造方法雖未特別限定,但例如,可依下述反應式來予以合成(Scheme 1)。此外,下述反應式中,雖顯示出式(3)所示之三烷基錫烷基噻吩化合物之合成方法,式(4)~(6)所示之
三烷基錫烷基噻吩化合物亦仿效下述反應式,使對應的噻吩化合物鋰化(Lithiation),使其與鹵素化三烷基錫反應,得以同樣地合成。
(式中,R1、R5、R9及Ra係與上述相同。X表示鹵素原子)
特別是,此合成方法係因可將2及5位無取代,而於3位具有配位性取代基,且4位為無取代或以非配位性取代基所取代的噻吩化合物(式(7”))之2位高選擇性地鋰化,特別適用於式(7)所示之噻吩化合物之合成(Scheme 2)。
(式中,Ra、R及X係與上述相同。R13表示配位性取代基、R14表示氫原子或非配位性取代基)
所謂配位性取代基,係指氧、氮、硫原子等
具有可對鋰原子配位之原子的取代基,所謂非配位性取代基,意指不含該等原子之取代基。
配位性取代基方面,可舉出可以Z1所取代之碳數1~20之烷氧基、可以Z1所取代之碳數2~20之烯基氧基、可以Z1所取代之碳數2~20之炔基氧基、可以Z2所取代之碳數6~20之芳基氧基、可以Z2所取代之碳數2~20之雜芳基氧基、可以Z1所取代之碳數1~20之烷基硫代基、可以Z1所取代之碳數2~20之烯基硫代基、可以Z1所取代之碳數2~20之炔基硫代基、可以Z2所取代之碳數6~20之芳基硫代基或可以Z2所取代之碳數2~20之雜芳基硫代基。
非配位性取代基方面,可舉出可以Z1所取代之碳數1~20之烷基、可以Z1所取代之碳數2~20之烯基或可以Z1所取代之碳數2~20之炔基。
此等烷氧基、烯基氧基、炔基氧基、芳基氧基、雜芳基氧基、烷基硫代基、烯基硫代基、炔基硫代基、芳基硫代基、雜芳基硫代基、烷基、烯基及炔基以及此等之取代基之Z1及可以Z2方面,可舉出與上述相同者。
式(3”)所示之噻吩化合物方面,可舉出3-甲基噻吩、3-乙基噻吩、3-n-丙基噻吩、3-n-丁基噻吩、3-n-戊基噻吩、3-n-己基噻吩、3-甲氧基噻吩、3-乙氧基噻吩、3-n-丙氧基噻吩、3,4-二甲氧基噻吩、3,4-二乙氧基噻吩、3,4-伸乙基二氧噻吩、3-甲基硫代基噻吩等,但不
受限於此等。
式(7”)所示之噻吩化合物方面,可舉出3-甲氧基噻吩、3-乙氧基噻吩、3-n-丙氧基噻吩、3-甲基硫代基噻吩等,但不受限於此等。
鋰化劑方面,可舉出有機鋰化合物,列舉例如n-丁基鋰、s-丁基鋰、t-丁基鋰、異丁基鋰、甲基鋰、n-丙基鋰、異丙基鋰、乙基鋰、n-己基鋰、三甲基矽烷基甲基鋰、丙炔基鋰、2-乙基己基鋰、2,4-戊二烯基鋰、烯丙基鋰、1,3-丁二烯基-2-鋰、t-丁氧基甲基鋰、1-甲氧基烯丙基鋰、三氯甲基鋰、戊基鋰、苯基鋰、2,6-二甲氧基苯基鋰等之烷基鋰或芳基鋰化合物、鋰六甲基二矽胺、鋰二異丙基醯胺、鋰哌啶、鋰二乙基醯胺、鋰四甲基哌啶、鋰雙(二甲基乙基矽烷基)醯胺、鋰二甲基醯胺、鋰二環己基醯胺等之鋰醯胺化合物,但不受限於此等。
鹵素化三烷基錫方面,若為可導入三烷基錫烷基者即可,並無特別限定,但若考慮取得容易性、操作性及反應性之平衡,則以三(n-丁基)錫氯化物較佳。此外,鹵素化三烷基錫,可以公知的方法(例如,Chem.Commun.,2001,1840-1841中記載的方法)來合成,亦可以市售品取得。
式(3”)所示之噻吩化合物或式(7”)所示之噻吩化合物與鋰化劑的置入比,相對於式(3”)所示之噻吩化合物或式(7”)所示之噻吩化合物,雖可使鋰化劑為1~1.5當量左右,但以1.1當量左右為佳。
又,式(3’)所示之噻吩化合物或式(7’)所示之噻吩化合物與鹵素化三烷基錫的置入比,相對於式(3’)所示之噻吩化合物或式(7’)所示之噻吩化合物,雖可使鹵素化三烷基錫為1~5當量左右,但以1.2當量左右為佳。
反應溫度可於所用溶劑之融點~沸點為止之範圍下適當地設定即可,特別是以-78~20℃左右為佳、-20~0℃更佳。
反應結束後係依常法進行後處理,可得目的之噻吩衍生物。
反應溶劑在不阻礙反應的限制之下,並無特別限定,以鏈狀或環狀醚為佳。特別是,Scheme 2中,從使2位的鋰化選擇性提昇而使式(7)所示噻吩化合物之產率提昇的觀點來看,係以鏈狀醚更佳,又以具有至少1個分枝鏈之鏈狀醚再更佳。
鏈狀醚方面,可舉出二乙基醚、二異丙基醚、二-n-丁基醚、t-丁基甲基醚、環戊基甲基醚等具有直鏈狀或分枝狀之鏈狀烷基或具有環狀烷基之對稱或非對稱的二烷基醚,但不受限於此等。環狀醚方面,可舉出四氫呋喃、四氫吡喃、環氧己烷、環氧庚烷等,但不受限於此等。
此等之中,特別是從2位的鋰化選擇性之觀點來看,係以二異丙基醚、t-丁基甲基醚、環戊基甲基醚為佳。
本發明之電荷輸送性塗漆雖為含有由式(1)所示之噻吩衍生物所成之電荷輸送性物質與有機溶劑者,但為了使電荷輸送能等提昇,亦可因應所需而含有摻雜物。
摻雜物方面,若為塗漆中所用可溶解於至少1種溶劑中者即可,並無特別限定,可使用無機系摻雜物、有機系摻雜物之任一者。
無機系摻雜物方面,可舉出氯化氫、硫酸、硝酸、磷酸等之無機酸;氯化鋁(III)(AlCl3)、四氯化鈦(IV)(TiCl4)、三溴化硼(BBr3)、三氟化硼醚錯合物(BF3‧OEt2)、氯化鐵(III)(FeCl3)、氯化銅(II)(CuCl2)、五氯化銻(V)(SbCl5)、五氟化銻(V)(SbF5)、五氟化砷(V)(AsF5)、五氟化磷(PF5)、參(4-溴苯基)鋁六氯銻酸鹽(TBPAH)等之金屬鹵素化物;Cl2、Br2、I2、ICl、ICl3、IBr、IF4等之鹵素;磷鉬酸、磷鎢酸等之異性聚合酸等。
有機系摻雜物方面,可舉出苯磺酸、對甲苯磺酸、p-苯乙烯磺酸、2-萘磺酸、4-羥基苯磺酸、5-磺酸基水揚酸、p-十二烷基苯磺酸、二己基苯磺酸、2,5-二己基苯磺酸、二丁基萘磺酸、6,7-二丁基-2-萘磺酸、十二烷基萘磺酸、3-十二烷基-2-萘磺酸、己基萘磺酸、4-己基-1-萘磺酸、辛基萘磺酸、2-辛基-1-萘磺酸、己基萘磺酸、7-己基-1-萘磺酸、6-己基-2-萘磺酸、二壬基萘磺酸、2,7-二壬基-4-萘磺酸、二壬基萘二磺酸、2,7-二壬基-4,5-萘二
磺酸、國際公開第2005/000832號記載之1,4-苯并二氧陸圜二磺酸化合物、國際公開第2006/025342號記載之芳基磺酸化合物、國際公開第2009/096352號記載之芳基磺酸化合物、聚苯乙烯磺酸等之芳基磺酸化合物;10-樟腦磺酸等之非芳基磺酸化合物;7,7,8,8-四氰基醌二甲烷(TCNQ)、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)等之有機氧化劑等。
此等無機系及有機系的摻雜物係可單獨使用1種或組合2種以上使用。
此等之摻雜物之中更以異性聚合酸較佳。摻雜物方面若使用異性聚合酸,不只是可由以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表之透明電極得到高電洞受容能,亦可由以鋁所代表的金屬陽極得到顯示高電洞受容能之電荷輸送性優異的薄膜。
所謂異性聚合酸,係代表性地為式(A1)所示之Keggin型或式(A2)所示之Dawson型的化學構造所示,具有雜原子位於分子之中心位置的構造,且為釩(V)、鉬(Mo)、鎢(W)等之含氧酸的同素聚合酸與異種元素之含氧酸所縮合而成的聚合酸。如此的異種元素之含氧酸方面,主要可舉出矽(Si)、磷(P)、砷(As)之含氧酸。
異性聚合酸的具體例方面,可舉出磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等。此等可單獨使用1種或組合2種以上來使用。此外,本發明所用的異性聚合酸可為市售品取得,又,可以公知的方法合成。
特別是,當摻雜物由1種的異性聚合酸所成時,該1種的異性聚合酸係以磷鎢酸或磷鉬酸者為佳,磷鎢酸者更佳。又,當摻雜物由2種類以上之異性聚合酸所成時,該2種類以上之異性聚合酸中,係以至少1種為磷鎢酸或磷鉬酸者佳,磷鎢酸者更佳。
此外,異性聚合酸係元素分析等之定量分析中,從一般式所示之構造不管是元素數目多的或少的,只要是可取得的市售品或依公知的合成方法所適當地合成者,皆可用於本發明。
即,例如,一般而言,磷鎢酸係以化學式H3(PW12O40)‧nH2O表示,磷鉬酸係以化學式H3(PMo12O40)‧nH2O表示,定量分析中,此式中的P(磷)、O(氧)或W(鎢)或Mo(鉬)之數目不管多或少,只要是市售品可取得者,或可以公知的合成方法適當地合成者,係可於本發明中使用。此時,本發明所規定之異性聚合酸之質量,並非為合成物或市售品中純粹的磷
鎢酸之質量(磷鎢酸含量),而是指以市售品可取得的形態及公知的合成法所能單離的形態中,包含水合水或其他雜質等之狀態下的全質量。
又,芳基磺酸化合物亦可適用為摻雜物。特別是以式(B1)或(B2)所示之芳基磺酸化合物為佳。
式(B1)中,A1雖表示-O-或-S-,但以-O-為佳。A2雖表示萘環或蒽環,但以萘環為佳。A3表示2~4價之全氟聯苯基、p表示A1與A3之鍵結數目,雖為滿足2≦p≦4之整數,但以A3為2價之全氟聯苯基,且p為2者佳。q表示鍵結於A2之磺酸基數目,雖為滿足1≦q≦4之整數,但以2較佳。
式(B2)中,A4~A8各自獨立地表示氫原子、鹵素原子、氰基、碳數1~20之烷基、碳數1~20之鹵素化烷基或碳數2~20之鹵素化烯基,但A4~A8之中至少3個為鹵素原子。r表示鍵結於萘環之磺酸基數目,雖為滿足1≦r≦4之整數,但以2~4為佳,2更佳。
碳數1~20之鹵素化烷基方面,可舉出三氟甲基、2,2,2-三氟乙基、1,1,2,2,2-五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1,1,2,2,3,3,3-七氟丙基、4,4,4-
三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、1,1,2,2,3,3,4,4,4-九氟丁基等。碳數2~20之鹵素化烯基方面,可舉出全氟乙烯基、1-全氟丙烯基、全氟烯丙基、全氟丁烯基等。
鹵素原子、碳數1~20之烷基的例方面,雖可舉出與上述相同者,但鹵素原子方面,係以氟原子為佳。
此等之中,又以A4~A8為氫原子、鹵素原子、氰基、碳數1~10之烷基、碳數1~10之鹵素化烷基或碳數2~10之鹵素化烯基,且A4~A8之中至少3個為氟原子者佳。又以氫原子、氟原子、氰基、碳數1~5之烷基、碳數1~5之氟化烷基或碳數2~5之氟化烯基,且A4~A8之中至少3個為氟原子者更佳。再者,以氫原子、氟原子、氰基、碳數1~5之全氟烷基或碳數1~5之全氟烯基,且A4、A5及A8為氟原子又再更佳。
此外,所謂全氟烷基,意指烷基的氫原子全部被氟原子取代了之基,所謂全氟烯基,意指烯基的氫原子全部被氟原子取代了之基。
本發明中之其他摻雜物方面,雖可舉出適當的芳基磺酸化合物之具體例,但不受限於此等。
本發明之電荷輸送性塗漆中包含摻雜物時,摻雜物之使用量雖因考慮摻雜物之種類、所期望的電荷輸送性之程度等來適當地決定之故而無法一概地規定,以質量比計,相對於本發明由噻吩衍生物所成之電荷輸送性物質(以下,單稱為電荷輸送性物質)1,大概為0.01~50左右的範圍內。
特別是使用異性聚合酸作為摻雜物時,相對於電荷輸送性物質1,係以使異性聚合酸在質量比計為0.5~30.0左右、較佳為1.0~20.0左右、更佳為2.0~15.0左右、又更佳為3.0~12.0左右、再更佳為4.0~11.0左右,而在使用有機EL元件時,可再現性佳地得到能賦予高亮度之電荷輸送性薄膜。
此外,使用芳基磺酸化合物作為摻雜物時,相對於電荷輸送性物質1,係以使芳基磺酸化合物以莫耳
比計為0.05~15.0、較佳為0.10~10.0、更佳為0.25~7.0、又更佳為0.50~5.0、再更佳為0.75~3.0,而在使用有機EL元件時,可再現性佳地得到能賦予高亮度之電荷輸送性薄膜。
再者,本發明之電荷輸送性塗漆亦可含有有機矽烷化合物。藉由含有有機矽烷,可提高電洞注入能,該電洞注入能係以朝位於與稱為電洞輸送層或發光層之陽極的反對側與電洞注入層相接所積層之層的電洞注入能,其結果乃得以實現更高亮度特性。
此有機矽烷化合物方面,可舉出二烷氧基矽烷化合物、三烷氧基矽烷化合物或四烷氧基矽烷化合物。此等可單獨使用1種或組合2種以上來使用。
特別是,在有機矽烷化合物方面,係以二烷氧基矽烷化合物或三烷氧基矽烷化合物為佳,三烷氧基矽烷化合物更佳。
二烷氧基矽烷化合物、三烷氧基矽烷化合物及四烷氧基矽烷化合物方面,可舉例如式(C1)~(C3)所示者。
SiR’2(OR)2 (C1)
SiR’(OR)3 (C2)
Si(OR)4 (C3)
式中,R各自獨立地表示可以Z3所取代之碳數1~20之烷基、可以Z3所取代之碳數2~20之烯基、可以Z3所取代之碳數2~20之炔基、可以Z4所取代之碳數6~20之芳基或可以Z4所取代之碳數2~20之雜芳基。R’各
自獨立地表示可以Z5所取代之碳數1~20之烷基、可以Z5所取代之碳數2~20之烯基、可以Z5所取代之碳數2~20之炔基、可以Z6所取代之碳數6~20之芳基或可以Z6所取代之碳數2~20之雜芳基。
Z3表示鹵素原子、可以Z7所取代之碳數6~20之芳基或可以Z7所取代之碳數2~20之雜芳基。
Z4表示鹵素原子、可以Z7所取代之碳數1~20之烷基、可以Z7所取代之碳數2~20之烯基或可以Z7所取代之碳數2~20之炔基。
Z5表示鹵素原子、可以Z7所取代之碳數6~20之芳基、可以Z7所取代之碳數2~20之雜芳基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、氫硫基、異氰酸酯基(-NCO)、胺基、-NHY1基或-NY2Y3基。
Z6表示鹵素原子、可以Z7所取代之碳數1~20之烷基、可以Z7所取代之碳數2~20之烯基、可以Z7所取代之碳數2~20之炔基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、氫硫基、異氰酸酯基(-NCO)、胺基、-NHY1基或-NY2Y3基。
Y1~Y3各自獨立地表示可以Z7所取代之碳數1~20之烷基、可以Z7所取代之碳數2~20之烯基、可以Z7所取代之碳數2~20之炔基、可以Z7所取代之碳數6~20之芳基或可以Z7所取代之碳數2~20之雜芳基。
Z7表示鹵素原子、胺基、硝基、氰基或氫硫基。
式(C1)~(C3)中之鹵素原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基及碳數6~20之芳基方面,可舉出與上述相同者。碳數2~20之雜芳基方面,可舉出2-噻吩基、3-噻吩基、2-喃基、3-喃基、2-噁唑基、4-噁唑基、5-噁唑基、3-異噁唑基、4-異噁唑基、5-異噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基等。
R及R’中,烷基、烯基及炔基之碳數,較佳為10以下,更佳為6以下,又更佳為4以下。又,芳基及雜芳基之碳數,較佳為14以下,更佳為10以下,又更佳為6以下。
R方面,係以可以Z3所取代之碳數1~20之烷基、可以Z3所取代之碳數2~20之烯基或可以Z4所取代之碳數6~20之芳基為佳,可以Z3所取代之碳數1~6之烷基、碳數2~6之烯基或可以Z4所取代之苯基更佳,可以Z3所取代之碳數1~4之烷基或可以Z4所取代之苯基又再更佳,可以Z3所取代之甲基或乙基又更佳。
又,R’方面,可舉出可以Z5所取代之碳數1~20之烷基或可以Z6所取代之碳數6~20之芳基為佳,可以Z5所取代之碳數1~10之烷基或可以Z6所取代之碳數6~14之芳基更佳,可以Z5所取代之碳數1~6之烷基或可以Z6所取代之碳數6~10之芳基又再更佳,可以Z5所取
代之碳數1~4之烷基或可以Z6所取代之苯基又更佳。
此外,複數的R可全部相同或相異,複數的R’亦可全部相同或相異。
Z3方面,係以鹵素原子或可以Z7所取代之碳數6~20之芳基為佳,以氟原子或可以Z7所取代之苯基更佳,以不存在者(即非取代者)為最佳。
又,Z4方面,係以鹵素原子或可以Z7所取代之碳數6~20之烷基為佳,氟原子或可以Z7所取代之碳數1~10之烷基更佳,以不存在者(即非取代者)為最佳。
此外,Z5方面,係以鹵素原子、可以Z7所取代之苯基、可以Z7所取代之喃基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、氫硫基、異氰酸酯基、胺基、可以Z7所取代之苯基胺基或可以Z7所取代之二苯基胺基為佳,鹵素原子更佳,以氟原子或不存在者(即非取代者)又再更佳。
又,Z6方面,係以鹵素原子、可以Z7所取代之碳數1~20之烷基、可以Z7所取代之喃基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、氫硫基、異氰酸酯基、胺基、可以Z7所取代之苯基胺基或可以Z7所取代之二苯基胺基為佳,鹵素原子更佳,以氟原子或不存在者(即非取代者)又再更佳。
然後,Z7方面,係以鹵素原子為佳,以氟原子或不存在者(即非取代者)更佳。
以下,雖列舉本發明中可使用的有機矽烷化
合物之具體例,但非受限於此等者。
二烷氧基矽烷化合物的具體例方面,可舉出二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基丙基二甲氧基矽烷、甲基丙基二乙氧基矽烷、二異丙基二甲氧基矽烷、苯基甲基二甲氧基矽烷、乙烯基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二乙氧基矽烷、3-(3,4-環氧環己基)乙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-巰基丙基甲基二甲氧基矽烷、γ-胺基丙基甲基二乙氧基矽烷、N-(2-胺基乙基)胺基丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷等。
三烷氧基矽烷化合物的具體例方面,可舉出甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、戊基三甲氧基矽烷、戊基三乙氧基矽烷、庚基三甲氧基矽烷、庚基三乙氧基矽烷、辛基三甲氧基矽烷、辛基三乙氧基矽烷、十二烷基三甲氧基矽烷、十二烷基三乙氧基矽烷、十六烷基三甲氧基矽烷、十六烷基三乙氧基矽烷、十八烷基三甲氧基矽烷、十八烷基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、γ-胺基丙基三甲氧基矽烷、3-胺基丙基三乙
氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-甲基丙烯醯氧基丙基三乙氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、十二烷基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、(三乙氧基矽烷基)環己烷、全氟辛基乙基三乙氧基矽烷、三乙氧基氟矽烷、十三氟-1,1,2,2-四氫辛基三乙氧基矽烷、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷、3-(七氟異丙氧基)丙基三乙氧基矽烷、十七氟-1,1,2,2-四氫癸基三乙氧基矽烷、三乙氧基-2-噻吩基矽烷、3-(三乙氧基矽烷基)呋喃等。
四烷氧基矽烷化合物的具體例方面,可舉出四甲氧基矽烷、四乙氧基矽烷、四丙氧基矽烷等。
此等之中,係以3,3,3-三氟丙基甲基二甲氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、3,3,3-三氟丙基三甲氧基矽烷、全氟辛基乙基三乙氧基矽烷、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷等為佳。
本發明之電荷輸送性塗漆中含有機矽烷化合物時,其含量若考慮維持所得之薄膜的高電荷輸送性之點,相對於電荷輸送性物質及摻雜物之總質量,通常為0.1~50質量%左右,但若考慮用以抑制所得之薄膜的電荷輸送性之降低,且對提高以與稱為電洞輸送層或發光層之陽極於反對側與電洞注入層相接之方式所積層之層的電洞注入能,較佳為0.5~40質量%左右、更佳為0.8~30質量%左右、又更佳為1~20質量%。
此外,本發明之電荷輸送性塗漆中,除了上述由噻吩衍生物所成之電荷輸送性物質之外,亦可使用公知的其他電荷輸送性物質。
調製電荷輸送性塗漆時所用的有機溶劑方面,可使用得以良好地溶解電荷輸送性物質及摻雜物之高溶解性溶劑。
如此的高溶解性溶劑方面,可使用例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-四氫咪唑酮、二乙二醇單甲基醚等之有機溶劑。此等之溶劑可單獨地使用1種或混合2種以上使用,其使用量相對於塗漆中使用的溶劑全體,可為5~100質量%。
此外,電荷輸送性物質及摻雜物係以皆可完全溶解於上述溶劑者或是成均一地分散之狀態者為佳,完全溶解者更佳。
又,本發明中,係因於塗漆中至少含有1種在25℃具有10~200mPa‧s特別是35~150mPa‧s之黏度、常壓(大氣壓)下沸點為50~300℃特別是150~250℃之高黏度有機溶劑,而得以使塗漆之黏度容易調整,其結果係可再現性佳地賦予平坦性高的薄膜,且可實現能因應所用塗佈方法之塗漆的調整。
高黏度有機溶劑方面,並無特別限定,可舉例如環己醇、乙二醇、乙二醇二環氧丙基醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁
二醇、2,3-丁二醇、1,4-丁二醇、丙二醇、己二醇等。此等之溶劑可單獨使用1種或混合2種以上使用。
對本發明之塗漆中所用的溶劑全體而言,高黏度有機溶劑之添加比例係以固體不析出之範圍內者佳,且只要固體不析出,添加比例係以5~80質量%為佳。
再者,以對基板之沾濕性的提昇、溶劑之表面張力的調整、極性的調整、沸點的調整等之目的下,係可使其他溶劑以相對於塗漆中使用之溶劑全體,較佳為1~90質量%、更佳為1~50質量%之比例混合。
如此的溶劑方面,可舉例如丙二醇單甲基醚、乙二醇單丁基醚、二乙二醇二乙基醚、二乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二乙二醇單乙基醚、二丙酮醇、γ-丁內酯、乙基乳酸酯、n-己基乙酸酯等,但不受限於此等。此等之溶劑可單獨使用1種或混合2種以上使用。
本發明之塗漆的黏度,雖是因應欲製作之薄膜的厚度等或固形分濃度而適當地設定者,但通常是在25℃下為1~50mPa‧s。
又,本發明中之電荷輸送性塗漆的固形分濃度,雖可考量塗漆的黏度及表面張力等或欲製作之薄膜的厚度等而來適當地設定即可,但通常為0.1~10.0質量%左右,若考慮使塗漆的塗佈性提昇的話,則較佳為0.5~5.0質量%、更佳為1.0~3.0質量%。
藉由將上述電荷輸送性塗漆塗佈於基材上予以燒成,而得以於基材上使電荷輸送性薄膜形成。
塗漆的塗佈方法方面,並無特別限定,可舉出浸漬法、旋轉塗佈法、轉錄印刷法、輥筒塗佈法、刷毛塗佈、噴墨法、噴霧法、狹縫塗佈法等,並以能因應塗佈方法而調節塗漆的黏度及表面張力者為佳。
又,使用本發明之塗漆時,燒成氛圍也無特別地限定,使其不只是在大氣氛圍中,即使是在氮等之惰性氣體或真空中,亦可獲得具有均一的成膜面及高電荷輸送性之薄膜。
燒成溫度方面,在考量所得之薄膜的用途、賦予所得之薄膜之電荷輸送性之程度等,雖可於100~260℃左右的範圍內適當地設定,但使用所得之薄膜作為有機EL元件的電洞注入層時,係以140~250℃左右為佳、145~240℃左右更佳。
此外,燒成時,在使更高的均一成膜性表現、於基材上使反應進行的目的之下,亦可附以2階段以上之溫度變化。加熱若可使用例如加熱板或烘箱等適當的機器進行即可。
電荷輸送性薄膜的膜厚雖未特別限定,但於有機EL元件內作為電洞注入層使用時,係以5~200nm為佳。使膜厚變化的方法方面,係有使塗漆中的固形分濃度變化、使塗佈時的基板上之溶液量變化等之方法。
使用本發明之電荷輸送性塗漆製作OLED元件時,其使用材料或製作方法方面,雖可舉出如下述者,但不受限於此等。
使用之電極基板係以預先實施以洗劑、醇、純水等之液體洗淨進行淨化者佳,例如,陽極基板係以使用前即以UV臭氧處理、氧-電漿處理等之表面處理者為佳。惟,陽極材料以有機物為主成分時,亦可不進行表面處理。
具有由本發明之電荷輸送性塗漆所得之薄膜而成的電洞注入層之OLED元件之製作方法的例係如下。
藉由上述之方法,係於陽極基板上塗佈本發明之電荷輸送性塗漆予以燒成,且於電極上製作電洞注入層。將此導入真空蒸鍍裝置內,依序電鍍電洞輸送層、發光層、電子輸送層、電子輸送層/電洞阻礙層、陰極金屬而為OLED元件。此外,因應所需而得以於發光層與電洞輸送層之間設置電子阻礙層。
陽極材料方面,可舉出以銦錫氧化物(ITO)、銦鋅氧化物(IZO)所代表的透明電極、由以鋁所代表的金屬或此等之合金等所構成之金屬陽極,係以平坦化處理者為佳。亦可使用具有高電荷輸送性之聚噻吩衍生物或聚苯胺衍生物。
此外,構成金屬陽極之其他金屬方面,可舉出鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、
鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉕、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或此等之合金等,但不受限於此等。
形成電洞輸送層之材料方面,可舉出(三苯基胺)二聚物衍生物、[(三苯基胺)二聚物]螺旋二聚物、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-聯苯胺(α-NPD)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-螺旋雙茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-螺旋雙茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-2,2’-二甲基聯苯胺、2,2’,7,7’-肆(N,N-二苯基胺基)-9,9-螺旋雙茀、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-茀、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-茀、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-茀、2,2’,7,7’-肆[N-萘基(苯基)-胺基]-9,9-螺旋雙茀、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙[N,N-雙(聯苯基-4-基)胺基]-9,9-螺旋雙茀、2,2’-雙(N,N-二苯基胺基)-9,9-螺旋雙茀、二-[4-(N,N-二(p-甲苯基)胺基)-苯基]
環己烷、2,2’,7,7’-四(N,N-二(p-甲苯基))胺基-9,9-螺旋雙茀、N,N,N’,N’-四-萘-2-基-聯苯胺、N,N,N’,N’-四-(3-甲基苯基)-3,3’-二甲基聯苯胺、N,N’-二(萘基)-N,N’-二(萘-2-基)-聯苯胺、N,N,N’,N’-四(萘基)-聯苯胺、N,N’-二(萘-2-基)-N,N’-二苯基聯苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(m-甲苯基)苯-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-二胺、參(4-(喹啉-8-基)苯基)胺、2,2’-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯、4,4’,4”-參[3-甲基苯基(苯基)胺基]三苯基胺(m-MTDATA)、4,4’,4”-參[1-萘基(苯基)胺基]三苯基胺(1-TNATA)等之三芳基胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’:5’,2”-聯三噻吩(BMA-3T)等之寡聚噻吩類等。
形成發光層之材料方面,可舉出參(8-羥基喹啉)鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)(p-苯基酚鹽)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-螺旋雙茀-2-基)-9,9-螺旋雙茀、2,7-雙(9,9-螺旋雙茀-2-基)-9,9-螺旋雙茀、2-[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2,2’-二芘基-9,9-螺旋雙茀、1,3,5-參(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-茀、2,2’-雙
(9,10-二苯基蒽)、2,7-二芘基-9,9-螺旋雙茀、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯基-4-基)并五苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、參[4-(芘基)-苯基]胺、10,10’-二(聯苯基-4-基)-9,9’-雙蒽、N,N’-二(萘-1-基)-N,N’-二苯基-[1,1’:4’,1”:4”,1'''-四苯基]-4,4'''-二胺、4,4’-二[10-(萘-1-基)蒽-9-基]聯苯、二苯并{[f,f’]-4,4’,7,7’-四苯基}二茚并[1,2,3-cd:1’,2’,3’-1m]苝、1-(7-(9,9’-雙蒽-10-基)-9,9-二甲基-9H-茀-2-基)芘、1-(7-(9,9’-雙蒽-10-基)-9,9-二己基-9H-茀-2-基)芘、1,3-雙(咔唑-9-基)苯、1,3,5-參(咔唑-9-基)苯、4,4’,4”-參(咔唑-9-基)三苯基胺、4,4’-雙(咔唑-9-基)聯苯基(CBP)、4,4’-雙(咔唑-9-基)-2,2’-二甲基聯苯、2,7-雙(咔唑-9-基)-9,9-二甲基茀、2,2’,7,7’-肆(咔唑-9-基)-9,9-螺旋雙茀、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)茀、9,9-雙[4-(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-螺旋雙茀、1,4-雙(三苯基矽烷基)苯、1,3-雙(三苯基矽烷基)苯、雙(4-N,N-二乙基胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基茀、4,4”-二(三苯基矽烷基)-p-三苯基、4,4’-二(三苯基矽烷基)聯苯、9-(4-t-丁基苯基)-3,6-雙(三苯基矽烷基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-茀-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基
(4-(9-苯基-9H-茀-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基)-9H-茀-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-螺旋雙茀-2-基-二苯基-膦氧化物、9,9’-(5-(三苯基矽烷基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(二苯基磷氧基)-9-苯基-9H-茀-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯并[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-啡啉、2,2’-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基磷氧基)二苯并[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷氧基)-9-(4-(二苯基磷氧基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等,亦可藉由與發光性摻雜物共蒸鍍形成發光層。
發光性摻雜物方面,可舉出3-(2-苯并噻唑基)-7-(二乙基胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯并噻唑基)喹啉酮并[9,9a,1gh]香豆素、喹吖酮、N,N’-二甲基-喹吖酮、參(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯丙酮酸)銥(III)(Ir(ppy)2(acac))、參[2-(p-甲苯基)吡啶]銥(III)(Ir(mppy)3)、9,10-雙[N,N-二(p-甲苯基)胺基]蒽、9,10-雙[苯基(m-甲苯基)胺基]蒽、雙[2-(2-羥基苯基)苯并噻唑]鋅(II)、N10,N10,N10,N10-四(p-甲
苯基)-9,9’-雙蒽-10,10’-二胺、N10,N10,N10,N10-四苯基-9,9’-雙蒽-10,10’-二胺、N10,N10-二苯基-N10,N10-二萘基-9,9’-雙蒽-10,10’-二胺、4,4’-雙(9-乙基-3-咔唑乙烯基)-1,1’-聯苯、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑基)乙烯基]苯、4,4’-雙[4-(二-p-甲苯基胺基)苯乙烯基]聯苯、4-(二-p-甲苯基胺基)-4’-[(二-p-甲苯基胺基)苯乙烯基]二苯乙烯、雙[3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)]銥(III)、4,4’-雙[4-(二苯基胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶)肆(1-吡唑基)硼酸酯銥(III)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-參(9,9-二甲基亞茀基)、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-茀-7-基}-9,9-二甲基-茀、N-(4-((E)-2-(6((E)-4-(二苯基胺基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯咪唑啉-2-亞基-C,C2)、mer-銥(III)參(1-苯基-3-甲基苯咪唑啉-2-亞基-C,C2)、2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-螺旋雙茀、6-甲基-2-(4-(9-(4-(6-甲基苯并[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯并[d]噻唑、1,4-二[4-(N,N-二苯基)胺基]苯乙烯基苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯基)苯、(E)-6-(4-(二苯基胺基)苯乙烯基)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶)(5-(吡啶-2-基)-1H-四唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苯甲基)二苯基膦酸)銥(III)、雙(3-三氟甲基-
5-(2-吡啶基)吡唑)(苯甲基二苯基膦酸)銥(III)、雙(1-(2,4-二氟苯甲基)-3-甲基苯并咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)(4’,6’-二氟苯基吡啶)銥(III)、雙(4’,6’-二氟苯基吡啶)(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯)銥(III)、雙(4’,6’-二氟苯基吡啶)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥(III)、(Z)-6-均三甲苯基-N-(6-均三甲苯基喹啉-2(1H)-亞基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基胺基)苯乙烯基)-6-甲基-4H-吡喃-4-亞基)丙二腈、4-(二氰基亞甲基)-2-甲基-6-久洛尼啶-9-烯基-4H-吡喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基久洛尼啶-9-烯基)-4H-吡喃、4-(二氰基亞甲基)-2-t-丁基-6-(1,1,7,7-四甲基久洛尼啶-4-基-乙烯基)-4H-吡喃、參(二苯甲醯基甲烷)啡啉銪(III)、5,6,11,12-四苯基并四苯、雙(2-苯并[b]噻吩-2-基-吡啶)(乙醯丙酮酸)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮酸)銥(III)、雙[1-(9,9-二甲基-9H-茀-2-基)-異喹啉](乙醯丙酮酸)銥(III)、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯丙酮酸)銥(III)、參[4,4’-二-t-丁基-(2,2’)-二吡啶]釕(III)‧雙(六氟膦酸鹽)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基稠四苯、雙(2-苯基苯并噻唑)
(乙醯丙酮酸)銥(III)、5,10,15,20-四苯基四苯并卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯丙酮酸)銥(III)、參[2-(4-n-己基苯基)喹啉]銥(III)、參[2-苯基-4-甲基喹啉]銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑)(乙醯丙酮酸)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-克唏-2-酮酸)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、銥(III)雙(4-苯基噻吩并[3,2-c]吡啶并-N,C2)乙醯丙酮酸鹽、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯并[3,2,1-ij]喹啉-8-基)乙烯基)-4H-吡喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯丙酮酸)銥(III)、鉑(II)八乙基卟吩、雙(2-甲基二苯并[f,h]喹噁啉)(乙醯丙酮酸)銥(III)、參[(4-n-己基苯基)異喹啉]銥(III)等。
形成電子輸送層/電洞阻礙層之材料方面,可
舉出8-羥基喹啉-鋰、2,2’,2”-(1,3,5-石油醚甲苯基)-參(1-苯基-1-H-苯并咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-噁二唑、2,9-二甲基-4,7-二苯基-1,10-啡啉、4,7-二苯基-1,10-啡啉、雙(2-甲基-8-喹啉)-4-(苯基酚)鋁、1,3-雙[2-(2,2’-二吡啶-6-基)-1,3,4-氧雜二唑-5-基]苯、6,6’-雙[5-(聯苯基-4-基)-1,3,4-氧雜二唑-2-基]-2,2’-二吡啶、3-(4-聯苯基)-4-苯基-5-t-丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡啉、2,7-雙[2-(2,2’-二吡啶-6-基)-1,3,4-氧雜二唑-5-基]-9,9-二甲基茀、1,3-雙[2-(4-t-丁基苯基)-1,3,4-氧雜二唑-5-基]苯、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑[4,5f][1,10]啡啉、2-(萘-2-基)-4,7-二苯基-1,10-啡啉、苯基-二芘基膦氧化物、3,3’,5,5’-四[(m-吡啶基)-苯-3-基]聯苯、1,3,5-參[(3-吡啶基)-苯-3-基]苯、4,4’-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯、1,3-雙[3,5-二(吡啶-3-基)苯基]苯、雙(10-羥基苯并[h]喹啉)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
形成電子注入層之材料方面,可舉出酸化鋰(Li2O)、酸化鎂(MgO)、氧化鋁(Al2O3)、氟化鋰(LiF)、氟化鈉(NaF)、氟化鎂(MgF2)、氟化銫(CsF)、氟化鍶(SrF2)、三酸化鉬(MoO3)、鋁、Li(acac)、乙酸鋰、安息香酸鋰等。
陰極材料方面,可舉出鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
形成電子阻礙層之材料方面,可舉出參(苯基吡唑)銥等。
使用本發明之電荷輸送性塗漆的PLED元件之製作方法雖未特別限定,但可舉出以下的方法。
上述OLED元件製作中,取代電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作,係以藉由依序形成電洞輸送性高分子層、發光性高分子層,來製作具有以本發明之電荷輸送性塗漆所形成之電荷輸送性薄膜的PLED元件。
具體而言,係於陽極基板上塗佈本發明之電荷輸送性塗漆,藉由上述之方法來製作電洞注入層,並於其上依序形成電洞輸送性高分子層、發光性高分子層,進一步將陰極電極予以蒸鍍而為PLED元件。
使用之陰極及陽極材料方面,可使用與上述OLED元件製作時同樣者,可進行同樣的洗淨處理、表面處理。
電洞輸送性高分子層及發光性高分子層之形成法方面,可舉出在電洞輸送性高分子材料或發光性高分子材料或是於此等之中已加入摻雜物所成的材料中,加入溶劑而溶解,使其均一地分散,塗佈於電洞注入層或電洞輸送性高分子層之上後,各自燒成而成膜之方法。
電洞輸送性高分子材料方面,可舉出聚
[(9,9-二己基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,1’-伸聯苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺]-封端聚半矽氧烷、聚[(9,9-二辛基茀基-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯基胺)]等。
發光性高分子材料方面,可舉出聚(9,9-二烷基茀)(PDAF)等之聚茀衍生物、聚(2-甲氧基-5-(2’-乙基己氧基)-1,4-伸苯基伸乙烯基)(MEH-PPV)等之聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
溶劑方面,可舉出甲苯、二甲苯、氯仿等,溶解或均一分散法方面,可舉出攪拌、加熱攪拌、超音波分散等之方法。
塗佈方法方面,並無特別限定,可舉出噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉錄印刷法、輥筒塗佈法、刷毛塗佈等。此外,塗佈係於氮、氬等之惰性氣體下進行為佳。
燒成之方法方面,可舉出於惰性氣體下或真空中,以烘箱或加熱板加熱之方法。
此外,不只是由上述電荷輸送性塗漆所得之電荷輸送性薄膜,由本發明之噻吩衍生物所得之蒸鍍膜也
在電荷輸送性上表現優異,亦可依用途來使用以蒸鍍法所得之電荷輸送性薄膜。
以下,列舉合成例、實施例及比較例以更具體地說明本發明,但本發明並不受限於下述之實施例。此外,使用的裝置如下所示。
(1)液體層析:Agilent Technologies公司製、Agilent 1260 Infinity Binary LC系統
(2)NMR:日本電子股份公司製、JNM-ECP300 FT NMR SYSTEM
(3)基板洗淨:長州產業(股)製、基板洗淨裝置(減壓電漿方式)
(4)塗漆的塗佈:Mikasa(股)製、旋轉塗佈機MS-A100
(5)膜厚測定:(股)小坂研究所製、微細形狀測定機Surf coder ET-4000
(6)EL元件之製作:長州產業(股)製、多機能蒸鍍裝置系統C-E2L1G1-N
(7)EL元件的亮度等之測定:(有)TECH WORLD製、I-V-L測定系統
(8)EL元件的壽命測定:(股)EHC製、有機EL亮度壽命評價系統PEL-105S
基於下述反應式,合成3-甲氧基-2-(三-n-丁基錫烷基)噻吩(9)。
於燒瓶內置入3-甲氧基噻吩(8)5.01g,施予氮氣取代。其中,置入二異丙基醚100mL冷卻至0℃,再於其中滴下n-丁基鋰之己烷溶液(濃度1.64M)29.5mL。滴下後,使溫度維持在0℃持續攪拌30分鐘,之後,滴下三-n-丁基錫烷基氯化物14.5mL,使溫度維持在0℃再繼續攪拌3小時。
攪拌後,減壓下餾去溶劑,於所得之殘渣中加入n-己烷,濾掉所生成的不溶物,再度實施溶劑之減壓餾去及乾燥,得到含3-甲氧基-2-(三-n-丁基錫烷基)噻吩之混合物。
此混合物無須進一步純化,直接用來與之後步驟的化合物(10)進行反應。此外,使用1H-NMR及液體層析,確認混合物中的3-甲氧基-2-(三-n-丁基錫烷基)噻吩之含量為90.46%。
藉由以下之方法合成噻吩衍生物(11)。
於燒瓶內,將2,3,4,5-四溴噻吩(10)(東京化成工業(股)製)0.5g與3-甲氧基-2-(三-n-丁基錫烷基)噻吩(9)2.7g(4.8當量、純度90.46%)置入反應容器中,進行氮氣取代。於其中,加入二甲苯10mL、Pd(PPh3)4 0.073g(5mol%),在加熱迴流條件下攪拌23小時,攪拌結束後,將反應液冷卻至室溫。
於已冷卻的反應液中加入氯仿及離子交換水進行分液處理之後,將所得之有機層以離子交換水洗淨2次,接著,將其洗淨後之有機層以硫酸鈉予以乾燥之後,減壓下餾去溶劑。然後,於所得之殘渣中加入n-己烷予以漿料洗淨,過濾回收濾物。
之後,於燒瓶內,置入該濾物及甲苯5mL,在加熱迴流條件下攪拌濾物,確認溶解之後,將該溶液放冷至室溫為止。
放冷後,藉由過濾來回收析出物,進一步予以乾燥,
得到噻吩衍生物(11)(產量0.40g、產率60%)。1H-NMR之測定結果顯示如下。
1H-NMR(300MHz,CDCl3)δ[ppm]:7.20(d,2H,J=6.0Hz),7.02(d,2H,J=6.0Hz),6.80(d,2H,J=5.4Hz),6.74(d,2H,J=5.4Hz),3.94(s,6H),3.64(s,6H).
使噻吩衍生物(11)0.052g與磷鎢酸(關東化學(股)製)0.258g在氮氣氛圍下溶解於1,3-二甲基-2-四氫咪唑酮3.0g中。於所得之溶液中,加入五氟苯基三乙氧基矽烷0.009g予以攪拌,再於其中加入二乙二醇二甲基醚5.0g及丁二醇2g予以攪拌,調製電荷輸送性塗漆。
將實施例2所得的塗漆使用旋轉塗佈機塗佈於ITO基板之後,在50℃乾燥5分鐘,再於大氣氛圍下,在230℃燒成10分鐘,於ITO基板上形成了30nm之均一薄膜。ITO基板方面,係使用有銦錫氧化物(ITO)於表面上以膜厚150nm成型化之25mm×25mm×0.7t的玻璃基板,並於使用前藉由O2電漿洗淨裝置(150W、30秒鐘)去除表面上之雜質。
接著,對已形成薄膜之ITO基板,使用蒸鍍裝置(真
空度1.0×10-5Pa)依序積層α-NPD、Alq3、氟化鋰及鋁之薄膜,得到有機EL元件。此時,蒸鍍率係以α-NPD、Alq3及鋁為0.2nm/秒、氟化鋰為0.02nm/秒的條件下各自進行,使膜厚各自為30nm、40nm、0.5nm及120nm。
此外,為了防止因空氣中的氧、水等之影響所致的特性劣化,有機EL元件以封止基板予以封止之後,評價其特性。封止係以下述程序進行。
在氧濃度2ppm以下,露點-85℃以下之氮氣氛圍中,將有機EL元件收於封止基板之間,使封止基板藉由接著材(Nagase ChemteX(股)製、XNR5516Z-B1)予以貼合。此時,將捕水劑(Dynic(股)製、HD-071010W-40)與有機EL元件一起收於封止基板內。對已貼合的封止基板照射UV光(波長:365nm、照射量:6,000mJ/cm2)之後,於80℃進行1小時退火處理使接著材硬化。
除了使用PEDOT/PSS(H.C.Starck公司製AI4083)來取代實施例2所得的塗漆,在150℃燒成30分鐘來取代在230℃燒成10分鐘以外,其餘係以與實施例3同樣的方法製作元件。
進行所製作之元件的驅動電壓5V中之電流密度及亮度之測定以及耐久性試驗。將測定結果及亮度之半衰期(初期亮度5,000cd/m2)顯示於表1。
如表1中所示,已知具有由本發明之塗漆所得之電洞注入層的有機EL元件(實施例3),相較於使用一般的電荷輸送性材料之PEDOT/PSS時(比較例1),乃具有顯著優異的耐久性。
Claims (6)
- 一種噻吩衍生物,其特徵係以下述式(1)所示者,
- 如請求項1記載之噻吩衍生物,其中,R1~R4各自獨立地為碳數1~6之烷氧基。
- 如請求項1或2記載之噻吩衍生物,其中,R5~R8為氫原子。
- 如請求項1記載之噻吩衍生物,其係具有以下述(1-1)~(1-10)及(1-21)~(1-25)中任一者所示之構造,
- 如請求項4記載之噻吩衍生物,其係具有以下述(1-1)~(1-10)及(1-21)~(1-24)中任一者所示之構造,
- 如請求項1記載之噻吩衍生物,其係具有以下述(1-1)~(1-10)中任一者所示之構造,
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013127599 | 2013-06-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201518297A TW201518297A (zh) | 2015-05-16 |
TWI627169B true TWI627169B (zh) | 2018-06-21 |
Family
ID=52104553
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW103121013A TWI627169B (zh) | 2013-06-18 | 2014-06-18 | Thiophene derivative and utilization thereof and method for producing thiophene derivative |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP6128213B2 (zh) |
KR (1) | KR20160021181A (zh) |
CN (1) | CN105324370B (zh) |
TW (1) | TWI627169B (zh) |
WO (1) | WO2014203818A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6665853B2 (ja) * | 2015-03-13 | 2020-03-13 | 日産化学株式会社 | 有機エレクトロルミネッセンス素子用の電荷輸送性薄膜形成組成物、有機エレクトロルミネッセンス素子用の電荷輸送性薄膜及び有機エレクトロルミネッセンス素子 |
WO2016148184A1 (ja) * | 2015-03-17 | 2016-09-22 | 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 |
US20200032140A1 (en) * | 2017-04-05 | 2020-01-30 | Nissan Chemical Corporation | Charge-transporting varnish |
JP7351310B2 (ja) * | 2018-10-01 | 2023-09-27 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用の混合組成物 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102010399A (zh) * | 2010-11-11 | 2011-04-13 | 华东理工大学 | 含多噻吩基团的光致变色化合物 |
CN102219773A (zh) * | 2010-04-16 | 2011-10-19 | 中国科学院化学研究所 | 基于齐聚噻吩的x型二维或三维共轭分子及其制备方法和应用 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01107267A (ja) * | 1987-10-21 | 1989-04-25 | Mitsui Toatsu Chem Inc | 電子写真用感光体 |
CA2152922A1 (en) * | 1992-12-29 | 1994-07-07 | Georges Hadziioannou | Multi-bloc copolymer based tunable light emitting diode, polymers suitable therefor and oligomers |
US7862747B2 (en) | 2004-08-31 | 2011-01-04 | Nissan Chemical Industries, Ltd. | Arylsulfonic acid compound and use thereof as electron-acceptor material |
JP5262717B2 (ja) | 2006-09-13 | 2013-08-14 | 日産化学工業株式会社 | 電荷輸送性ワニス |
US8298444B2 (en) | 2007-04-12 | 2012-10-30 | Nissan Chemical Industries, Ltd. | Oligoaniline compound |
WO2010058777A1 (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 |
-
2014
- 2014-06-13 WO PCT/JP2014/065739 patent/WO2014203818A1/ja active Application Filing
- 2014-06-13 CN CN201480034762.1A patent/CN105324370B/zh not_active Expired - Fee Related
- 2014-06-13 JP JP2015522880A patent/JP6128213B2/ja not_active Expired - Fee Related
- 2014-06-13 KR KR1020167000082A patent/KR20160021181A/ko active IP Right Grant
- 2014-06-18 TW TW103121013A patent/TWI627169B/zh not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102219773A (zh) * | 2010-04-16 | 2011-10-19 | 中国科学院化学研究所 | 基于齐聚噻吩的x型二维或三维共轭分子及其制备方法和应用 |
CN102010399A (zh) * | 2010-11-11 | 2011-04-13 | 华东理工大学 | 含多噻吩基团的光致变色化合物 |
Also Published As
Publication number | Publication date |
---|---|
TW201518297A (zh) | 2015-05-16 |
JPWO2014203818A1 (ja) | 2017-02-23 |
CN105324370A (zh) | 2016-02-10 |
JP6128213B2 (ja) | 2017-05-17 |
CN105324370B (zh) | 2018-09-18 |
KR20160021181A (ko) | 2016-02-24 |
WO2014203818A1 (ja) | 2014-12-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI643913B (zh) | Charge transport varnish, charge transporting film and organic electroluminescent element | |
TW201602098A (zh) | 苯胺衍生物及其用途 | |
TWI821173B (zh) | 電荷輸送性塗漆 | |
TW201529537A (zh) | 電荷輸送性清漆、電荷輸送性薄膜、有機電致發光元件及電荷輸送性薄膜之製造方法 | |
TWI627169B (zh) | Thiophene derivative and utilization thereof and method for producing thiophene derivative | |
CN108884016B (zh) | 芳基胺衍生物及其用途 | |
TWI659944B (zh) | 電荷輸送性漆料及其利用 | |
TWI632174B (zh) | Aniline oligomer derivative, charge transport coating and organic electroluminescent element | |
TWI626228B (zh) | Triphenylamine derivatives and their utilization | |
CN106103411B (zh) | 苯胺衍生物及其利用 | |
TWI627158B (zh) | Arylsulfonic acid compounds and their utilization | |
TW201619163A (zh) | 電荷輸送性材料 | |
CN107428676B (zh) | 苯胺衍生物及其利用 | |
TWI659011B (zh) | 茀衍生物及其利用 | |
TWI603946B (zh) | Aniline derivatives, charge-transporting varnishes and organic electroluminescent devices | |
TW201716373A (zh) | 電荷輸送性清漆以及有機電致發光元件 | |
TWI672284B (zh) | 苯胺衍生物及其使用 | |
TWI646098B (zh) | 電荷輸送性清漆、電荷輸送性薄膜及有機電致發光元件 | |
TWI650385B (zh) | 電荷輸送性清漆 | |
TW201708225A (zh) | 有機電致發光元件用之電荷傳輸性薄膜形成組成物、有機電致發光元件用之電荷傳輸性薄膜及有機電致發光元件 | |
TW201529571A (zh) | 電荷輸送性清漆、電荷輸送性薄膜及有機電致發光元件 | |
TW201627272A (zh) | 電荷輸送性清漆 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Annulment or lapse of patent due to non-payment of fees |