JP2008189759A - 高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 - Google Patents
高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 Download PDFInfo
- Publication number
- JP2008189759A JP2008189759A JP2007024313A JP2007024313A JP2008189759A JP 2008189759 A JP2008189759 A JP 2008189759A JP 2007024313 A JP2007024313 A JP 2007024313A JP 2007024313 A JP2007024313 A JP 2007024313A JP 2008189759 A JP2008189759 A JP 2008189759A
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- substituted
- same
- different
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 267
- 150000001875 compounds Chemical class 0.000 title claims abstract description 206
- 239000000203 mixture Substances 0.000 title claims description 62
- 239000007788 liquid Substances 0.000 title claims description 47
- 239000010409 thin film Substances 0.000 title claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 81
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 20
- 125000000732 arylene group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000003277 amino group Chemical group 0.000 claims description 100
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 100
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 96
- 239000000463 material Substances 0.000 claims description 94
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 77
- 230000005525 hole transport Effects 0.000 claims description 75
- 239000002904 solvent Substances 0.000 claims description 70
- 125000004414 alkyl thio group Chemical group 0.000 claims description 62
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 60
- 125000004104 aryloxy group Chemical group 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 56
- 125000005110 aryl thio group Chemical group 0.000 claims description 56
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 53
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 53
- 125000002252 acyl group Chemical group 0.000 claims description 49
- 125000004423 acyloxy group Chemical group 0.000 claims description 49
- 125000003368 amide group Chemical group 0.000 claims description 49
- 125000005462 imide group Chemical group 0.000 claims description 49
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 26
- 239000004793 Polystyrene Substances 0.000 claims description 22
- 229920002223 polystyrene Polymers 0.000 claims description 22
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 13
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 5
- 125000000879 imine group Chemical group 0.000 claims 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 199
- -1 2-ethylhexyl group Chemical group 0.000 description 174
- 238000000034 method Methods 0.000 description 107
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 77
- 239000000243 solution Substances 0.000 description 65
- 239000010408 film Substances 0.000 description 51
- 125000001424 substituent group Chemical group 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 39
- 150000002466 imines Chemical group 0.000 description 38
- 0 Cc1c(*)c(C)nc2c(*)c(*)c(*)c(*)c12 Chemical compound Cc1c(*)c(C)nc2c(*)c(*)c(*)c(*)c12 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000000576 coating method Methods 0.000 description 28
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- 239000002994 raw material Substances 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 238000012643 polycondensation polymerization Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 21
- 239000008096 xylene Substances 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000000758 substrate Substances 0.000 description 20
- 239000000178 monomer Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 125000005037 alkyl phenyl group Chemical group 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 239000004065 semiconductor Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 12
- 239000012298 atmosphere Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 239000004327 boric acid Substances 0.000 description 12
- 230000005669 field effect Effects 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 238000007611 bar coating method Methods 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000007756 gravure coating Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 125000005228 aryl sulfonate group Chemical group 0.000 description 8
- 229920001940 conductive polymer Polymers 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 229910052711 selenium Inorganic materials 0.000 description 8
- 239000011669 selenium Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 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 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229920005596 polymer binder Polymers 0.000 description 7
- 239000002491 polymer binding agent Substances 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 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 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000005103 alkyl silyl group Chemical group 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 238000003618 dip coating Methods 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000007645 offset printing Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229960003540 oxyquinoline Drugs 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Chemical group 0.000 description 5
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 5
- 229920000767 polyaniline Polymers 0.000 description 5
- 229920000123 polythiophene Polymers 0.000 description 5
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000007650 screen-printing Methods 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- KBXGMZXLKCUSEB-UHFFFAOYSA-M sodium;[ethyl(oxidosulfinothioyl)amino]ethane Chemical compound [Na+].CCN(CC)S([O-])=S KBXGMZXLKCUSEB-UHFFFAOYSA-M 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- JCXLYAWYOTYWKM-UHFFFAOYSA-N (2,3,4-triphenylcyclopenta-1,3-dien-1-yl)benzene Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCXLYAWYOTYWKM-UHFFFAOYSA-N 0.000 description 4
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229920000292 Polyquinoline Polymers 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000003759 ester based solvent Substances 0.000 description 4
- UCHAYWNMEHMRRW-UHFFFAOYSA-N ethyl 5-[2,7-dibromo-9-(3-ethoxycarbonyl-4-hexoxyphenyl)fluoren-9-yl]-2-hexoxybenzoate Chemical compound C1=C(C(=O)OCC)C(OCCCCCC)=CC=C1C1(C=2C=C(C(OCCCCCC)=CC=2)C(=O)OCC)C2=CC(Br)=CC=C2C2=CC=C(Br)C=C21 UCHAYWNMEHMRRW-UHFFFAOYSA-N 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000005453 ketone based solvent Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229910001512 metal fluoride Inorganic materials 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000548 poly(silane) polymer Polymers 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- YHEHCZLBPYNMES-UHFFFAOYSA-N 2-[7-(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluoren-2-yl]-1,3,2-dioxaborolane Chemical compound C1=C2C(CCCCCCCC)(CCCCCCCC)C3=CC(B4OCCO4)=CC=C3C2=CC=C1B1OCCO1 YHEHCZLBPYNMES-UHFFFAOYSA-N 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Chemical group 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
- 239000004210 ether based solvent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- APCOQCLKCAFINS-UHFFFAOYSA-N n,n-bis(4-bromophenyl)-4-butan-2-ylaniline Chemical compound C1=CC(C(C)CC)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 APCOQCLKCAFINS-UHFFFAOYSA-N 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- QVGRURMQPVFYBL-UHFFFAOYSA-N (2,3,4-triphenylcyclobuta-1,3-dien-1-yl)benzene Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QVGRURMQPVFYBL-UHFFFAOYSA-N 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-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
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- ABFHEPUDNWQFIF-UHFFFAOYSA-N 1-n,4-n-bis(4-bromophenyl)-1-n,4-n-bis(4-butylphenyl)benzene-1,4-diamine Chemical compound C1=CC(CCCC)=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(Br)=CC=1)C=1C=CC(CCCC)=CC=1)C1=CC=C(Br)C=C1 ABFHEPUDNWQFIF-UHFFFAOYSA-N 0.000 description 2
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 2
- FTNASWGZFPKXBO-UHFFFAOYSA-N 2-[7,7-dioctyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c]fluoren-5-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CCCCCCCCC1(CCCCCCCC)C2=CC(B3OC(C)(C)C(C)(C)O3)=CC=C2C(C2=CC=CC=C22)=C1C=C2B1OC(C)(C)C(C)(C)O1 FTNASWGZFPKXBO-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- MJHXBIKPCCIAKM-UHFFFAOYSA-N 3,7-dibromo-2,8-dioctoxydibenzothiophene Chemical compound S1C2=CC(Br)=C(OCCCCCCCC)C=C2C2=C1C=C(Br)C(OCCCCCCCC)=C2 MJHXBIKPCCIAKM-UHFFFAOYSA-N 0.000 description 2
- URSCUKXAWPGJBM-UHFFFAOYSA-N 4,7-bis(5-bromo-4-methylthiophen-2-yl)-2,1,3-benzothiadiazole Chemical compound S1C(Br)=C(C)C=C1C(C1=NSN=C11)=CC=C1C1=CC(C)=C(Br)S1 URSCUKXAWPGJBM-UHFFFAOYSA-N 0.000 description 2
- FEOWHLLJXAECMU-UHFFFAOYSA-N 4,7-dibromo-2,1,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=NSN=C12 FEOWHLLJXAECMU-UHFFFAOYSA-N 0.000 description 2
- PGJZXRPMGQBMQE-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(4-tert-butyl-2,6-dimethylphenyl)aniline Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1C1=CC(N)=CC=C1C1=CC=C(N)C=C1 PGJZXRPMGQBMQE-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000846 In alloy Inorganic materials 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910005965 SO 2 Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 125000006383 alkylpyridyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 125000005619 boric acid group Chemical group 0.000 description 2
- 150000001642 boronic acid derivatives Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000004696 coordination complex Chemical group 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical group NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- WPWWHXPRJFDTTJ-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzamide Chemical group NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F WPWWHXPRJFDTTJ-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- OXFFIMLCSVJMHA-UHFFFAOYSA-N 2,7-dibromo-9,9-dihexylfluorene Chemical compound C1=C(Br)C=C2C(CCCCCC)(CCCCCC)C3=CC(Br)=CC=C3C2=C1 OXFFIMLCSVJMHA-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- QJOOPTDSSDVOAY-UHFFFAOYSA-N 2-[7-(1,3,2-dioxaborolan-2-yl)-9,9-dihexylfluoren-2-yl]-1,3,2-dioxaborolane Chemical compound C1=C2C(CCCCCC)(CCCCCC)C3=CC(B4OCCO4)=CC=C3C2=CC=C1B1OCCO1 QJOOPTDSSDVOAY-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 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
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- PMYJGTWUVVVOFO-UHFFFAOYSA-N 4-phenyl-3-furoxancarbonitrile Chemical compound N#CC1=[N+]([O-])ON=C1C1=CC=CC=C1 PMYJGTWUVVVOFO-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- ZCRNIAPQEXUJCM-UHFFFAOYSA-N CCC(C)C(C1)C=CC=C1Nc(cc1)ccc1C(C=C1)=CCC1N(c1ccc(C(C)(C)C)cc1)c(cc1)ccc1C#N Chemical compound CCC(C)C(C1)C=CC=C1Nc(cc1)ccc1C(C=C1)=CCC1N(c1ccc(C(C)(C)C)cc1)c(cc1)ccc1C#N ZCRNIAPQEXUJCM-UHFFFAOYSA-N 0.000 description 1
- RXYRKENAVGHDDH-UHFFFAOYSA-N CCCCCCCCC1(c(cc(C(C)(CC)CCC(CCC)(C=C)c(cc2)ccc2N(c(cc2)ccc2-c(cc2)ccc2N(c2cccc(C(C)(CC)CCC)c2)c2c(C)cc(C(C)(C)C)cc2C)c2c(C)cc(C(C)(C)C)cc2C)cc2)c2-c2ccc(C(C)(C)CC)cc12)I Chemical compound CCCCCCCCC1(c(cc(C(C)(CC)CCC(CCC)(C=C)c(cc2)ccc2N(c(cc2)ccc2-c(cc2)ccc2N(c2cccc(C(C)(CC)CCC)c2)c2c(C)cc(C(C)(C)C)cc2C)c2c(C)cc(C(C)(C)C)cc2C)cc2)c2-c2ccc(C(C)(C)CC)cc12)I RXYRKENAVGHDDH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-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
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910001128 Sn alloy Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004705 aldimines Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 229910052785 arsenic Chemical group 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical group BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical group CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 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 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis 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
- 239000003086 colorant Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical class CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- TWXWPPKDQOWNSX-UHFFFAOYSA-N dicyclohexylmethanone Chemical compound C1CCCCC1C(=O)C1CCCCC1 TWXWPPKDQOWNSX-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical group CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 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
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MSTLSCNJAHAQNU-UHFFFAOYSA-N heptylcyclohexane Chemical compound CCCCCCCC1CCCCC1 MSTLSCNJAHAQNU-UHFFFAOYSA-N 0.000 description 1
- 125000005446 heptyloxy 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])O* 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QHWAQXOSHHKCFK-UHFFFAOYSA-N hexylcyclohexane Chemical compound CCCCCCC1CCCCC1 QHWAQXOSHHKCFK-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy 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
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-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
- 150000002739 metals Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- IZYYWFVULMDNMD-UHFFFAOYSA-N n-(4-bromophenyl)-n-[4-[4-(n-(4-bromophenyl)-4-methylanilino)phenyl]phenyl]-4-methylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 IZYYWFVULMDNMD-UHFFFAOYSA-N 0.000 description 1
- NWUBUZPZBVNZTE-UHFFFAOYSA-N n-[4-[4-(4-bromo-n-(4-tert-butyl-2,6-dimethylphenyl)anilino)phenyl]phenyl]-n-(4-bromophenyl)-4-tert-butyl-2,6-dimethylaniline Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(Br)=CC=1)C=1C(=CC(=CC=1C)C(C)(C)C)C)C1=CC=C(Br)C=C1 NWUBUZPZBVNZTE-UHFFFAOYSA-N 0.000 description 1
- ZHDORMMHAKXTPT-UHFFFAOYSA-N n-benzoylbenzamide Chemical group C=1C=CC=CC=1C(=O)NC(=O)C1=CC=CC=C1 ZHDORMMHAKXTPT-UHFFFAOYSA-N 0.000 description 1
- AIDQCFHFXWPAFG-UHFFFAOYSA-N n-formylformamide Chemical group O=CNC=O AIDQCFHFXWPAFG-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical group OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-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
- 239000000049 pigment Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical group CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 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
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 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
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/122—Copolymers statistical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/148—Side-chains having aromatic units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
- C08G2261/522—Luminescence fluorescent
- C08G2261/5222—Luminescence fluorescent electrofluorescent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
Landscapes
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
【解決手段】陽極及び陰極との間に発光層を有し且つ該発光層と該陽極との間に正孔輸送層を有する高分子発光素子であって、 前記正孔輸送層が、下記化合物(I)で示される繰返し単位、下記一般式(II)で示される繰返し単位及び下記一般式(III)で示される繰返し単位を含む高分子化合物を含有する層であることを特徴とする高分子発光素子。[化合物(I)]:フルオレン骨格を有する化合物[一般式(II)] −Ar1− (II)(式(II)中、Ar1は2価の芳香族アミンを表す。)[一般式(III)] −Ar2− (III)(式(III)中、Ar2はアリーレン基又は2価の複素環基を表す。)。
【選択図】なし
Description
前記正孔輸送層が、下記一般式(I)で示される繰返し単位、下記一般式(II)で示される繰返し単位及び下記一般式(III)で示される繰返し単位を含む高分子化合物を含有する層であることを特徴とするものである。
[一般式(I)]
[一般式(II)]
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
[一般式(III)]
−Ar2− (III)
(式(III)中、Ar2はアリーレン基又は2価の複素環基を表す。)。
[一般式(IV)]
R10が結合している炭素及びR18が結合している炭素、R12が結合している炭素及びR13が結合している炭素、R24が結合している炭素及びR34が結合している炭素、又は、R30が結合している炭素及びR31が結合している炭素がそれぞれ直接結合して或いは酸素原子又は硫黄原子を介して結合して環を形成していてもよく、このような環が形成される場合、R10及びR18、R12及びR13、R24及びR34、又は、R30及びR31はそれぞれ一緒になって、前記直接結合、前記酸素原子又は前記硫黄原子を表す。)。
[一般式(V)]
[一般式(VI)]
[一般式(VII)]
[一般式(I)]
[一般式(II)]
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
[一般式(VI)]
[一般式(I)]
[一般式(II)]
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
[一般式(VII)]
[一般式(IV)]
R10が結合している炭素及びR18が結合している炭素、R12が結合している炭素及びR13が結合している炭素、R24が結合している炭素及びR34が結合している炭素、又は、R30が結合している炭素及びR31が結合している炭素がそれぞれ直接結合して或いは酸素原子又は硫黄原子を介して結合して環を形成していてもよく、このような環が形成される場合、R10及びR18、R12及びR13、R24及びR34、又は、R30及びR31はそれぞれ一緒になって、前記直接結合、前記酸素原子又は前記硫黄原子を表す。)。
本発明の高分子発光素子は、陽極及び陰極との間に発光層を有し且つ該発光層と該陽極との間に正孔輸送層を有する高分子発光素子であって、
前記正孔輸送層が、下記一般式(I)で示される繰返し単位、下記一般式(II)で示される繰返し単位及び下記一般式(III)で示される繰返し単位を含む高分子化合物を含有する層であることを特徴とするものである。
[一般式(I)]
[一般式(II)]
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
[一般式(III)]
−Ar2− (III)
(式(III)中、Ar2はアリーレン基又は2価の複素環基を表す。)。
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
で示される繰返し単位を含む。
前記一般式401〜410中においてRとして選択され得るアルキル基、アルコキシ基、アルキルチオ基、アリール基、アリールオキシ基、アリールチオ基、アリールアルキル基、アリールアルコキシ基、アリールアルキルチオ基、アリールアルケニル基、アリールアルキニル基、置換アミノ基、置換シリル基、ハロゲン原子、アシル基、アシルオキシ基、イミン残基、アミド基、酸イミド基、1価の複素環基および置換カルボキシル基の定義及び具体例等は、前記一般式(I)中のR5、R6、R7及びR8において説明したそれらの定義、具体例等と同じである。
R10が結合している炭素及びR18が結合している炭素、R12が結合している炭素及びR13が結合している炭素、R24が結合している炭素及びR34が結合している炭素、又は、R30が結合している炭素及びR31が結合している炭素がそれぞれ直接結合して或いは酸素原子又は硫黄原子を介して結合して環を形成していてもよく、このような環が形成される場合、R10及びR18、R12及びR13、R24及びR34、又は、R30及びR31はそれぞれ一緒になって、前記直接結合、前記酸素原子又は前記硫黄原子を表す。)。
−Ar2− (III)
(式(III)中、Ar2はアリーレン基又は2価の複素環基を表す。)
で示される繰返し単位を含む。
(a)ヘテロ原子として、窒素を含む2価の複素環基:ピリジンージイル基(下記一般式101〜106で示される基)、ジアザフェニレン基(下記一般式107〜110で示される基)、キノリンジイル基(下記一般式111〜125で示される基)、キノキサリンジイル基(下記一般式126〜130で示される基)、アクリジンジイル基(下記一般式131〜134で示される基)、ビピリジルジイル基(下記一般式135〜137で示される基)、フェナントロリンジイル基(下記一般式138〜140で示される基)。
(b)ヘテロ原子として酸素、ケイ素、窒素、硫黄、セレンなどを含みフルオレン構造を有する基(下記一般式141〜155で示される基)。
(c)ヘテロ原子として酸素、ケイ素、窒素、硫黄、セレン、ホウ素、リンなどを含む5員環複素環基(下記一般式156〜175で示される基)。
(d)ヘテロ原子として酸素、ケイ素、窒素、セレンなどを含む5員環縮合複素基(下記一般式176〜187で示される基)。
(e)ヘテロ原子として酸素、ケイ素、窒素、硫黄、セレンなどを含む5員環複素環基でそのヘテロ原子のα位で結合し2量体やオリゴマーになっている基(下記一般式188〜189で示される基)。
(f)ヘテロ原子として酸素、ケイ素、窒素、硫黄、セレンなどを含む5員環複素環基でそのヘテロ原子のα位でフェニル基に結合している基(下記一般式190〜196で示される基)。
(g)ヘテロ原子として酸素、窒素、硫黄、セレンなどを含む5員環縮合複素環基にフェニル基やフリル基、チエニル基が置換した基(下記一般式197〜202で示される基)。
(h)ヘテロ原子として酸素、窒素などを含む6員環複素環基(下記一般式203〜206で示される基)。
−Ara− (A)
(式中、Araはそれぞれ独立にアリーレン基又は2価の複素環基を示す。)
で示される繰り返し単位が好ましい。
また、前記一般式(E)で示される繰り返し単位の中央の5員環としては、例えば、チアジアゾール、オキサジアゾール、トリアゾール、チオフェン、フラン、シロール等が挙げられる。
Y1−A−Y2 (X)
(式中、−A−は、前記一般式(I)〜(III)で示される繰返し単位又は前記一般式(A)中のAraで示される繰返し単位を表し、Y1及びY2は同一でも又は異なっていてもよく、それぞれ縮合重合可能な置換基を表す。)
で示される化合物を原料の一つとして適宜選択して用い、中でも、前記一般式(X)中の−A−が前記一般式(I)、(II)及び(III)で示される繰返し単位である化合物をそれぞれ必須成分として含有させて、これを縮合重合させる方法を挙げることができる。
Y3−Ara−Y4 (XI)
(式中、Araは前述のものと同義であり、Y3及びY4はそれぞれ独立に縮合重合に関与する置換基を示す。)
で示される化合物が例示される。このようにして、前記Y1−A−Y2で示される化合物に加えて、前記Y3−Ara−Y4で示される化合物を縮合重合させることで、−Ara−で示される繰り返し単位を更に有する本発明にかかる高分子化合物を製造することができる。
このような縮合重合に関与する置換基(Y1、Y2、Y3、Y4、Y5及びY6)としては、ハロゲン原子、アルキルスルホネート基、アリールスルホネート基、アリールアルキルスルホネート基、ホウ酸エステル基、スルホニウムメチル基、ホスホニウムメチル基、ホスホネートメチル基、モノハロゲン化メチル基、−B(OH)2、ホルミル基、シアノ基又はビニル基等が挙げられる。
で示される基が例示される。
−CH2S+Me2X−、又は、−CH2S+Ph2X−
(Xはハロゲン原子を示し、Phはフェニル基を示す。)
で示される基が例示される。
−CH2P+Ph3X−
(Xはハロゲン原子を示す。)
で示される基が例示される。
−CH2PO(OR’)2
(Xはハロゲン原子を示し、R’はアルキル基、アリール基、アリールアルキル基を示す。)
で示される基が例示される。
a)陽極/正孔輸送層/発光層/陰極
(ここで、/は各層が隣接して積層されていることを示す。以下同じ。)。
b)陽極/正孔輸送層/発光層/電子輸送層/陰極。
このような電子輸送材料としては、オキサジアゾール誘導体、ベンゾキノン及びその誘導体、アントラキノン及びその誘導体、8−ヒドロキシキノリン及びその誘導体の金属錯体、ポリキノリン及びその誘導体、ポリキノキサリン及びその誘導体、ポリフルオレン及びその誘導体がより好ましく、2−(4−ビフェニリル)−5−(4−t−ブチルフェニル)−1,3,4−オキサジアゾール、ベンゾキノン、アントラキノン、トリス(8−キノリノール)アルミニウム、ポリキノリンが更に好ましい。
c)陽極/電荷注入層/正孔輸送層/発光層/陰極
d)陽極/正孔輸送層/発光層/電荷注入層/陰極
e)陽極/電荷注入層/正孔輸送層/発光層/電荷注入層/陰極
f)陽極/電荷注入層/正孔輸送層/発光層/電子輸送層/陰極
g)陽極/正孔輸送層/発光層/電子輸送層/電荷注入層/陰極
h)陽極/電荷注入層/正孔輸送層/発光層/電子輸送層/電荷注入層/陰極。
i)陽極/絶縁層/正孔輸送層/発光層/陰極
j)陽極/正孔輸送層/発光層/絶縁層/陰極
k)陽極/絶縁層/正孔輸送層/発光層/絶縁層/陰極
l)陽極/絶縁層/正孔輸送層/発光層/電子輸送層/陰極
m)陽極/正孔輸送層/発光層/電子輸送層/絶縁層/陰極
n)陽極/絶縁層/正孔輸送層/発光層/電子輸送層/絶縁層/陰極。
本発明の第一の高分子化合物は、前記一般式(I)で示される繰返し単位、前記一般式(II)で示される繰返し単位及び前記一般式(VI)で示される繰返し単位を含むことを特徴とするものである。
(合成例1)
下記構造式で示される繰り返し単位を含有する高分子化合物<P−1>を製造した。
下記構造式で示される繰り返し単位を含有する高分子化合物<P−2>(本発明の第一の高分子化合物)を製造した。
下記構造式で示される繰り返し単位を含有する高分子化合物<P−3>を製造した。
下記構造式で示される繰り返し単位を含有する高分子化合物<P−4>を製造した。
下記構造式で示される繰り返し単位を含有する高分子化合物<P−5>(本発明の第二の高分子化合物)を製造した。
赤色発光性の高分子化合物<P−6>を製造した。すなわち、先ず、不活性雰囲気下、2,7−ビス(1,3,2−ジオキサボロラン−2−イル)−9,9−ジヘキシルフルオレン(1.91g)、4,7−ビス(5−ブロモ−4−メチル−2−チエニル)−2,1,3−ベンゾチアジアゾール(0.10g)、4,7−ジブロモ−2,1,3−ベンゾチアジアゾール(0.35g)、ビス(4−ブロモフェニル)−(4−セカンダリブチルフェニル)−アミン(0.74g)、2,7−ジブロモ−9,9−ジヘキシルフルオレン(0.79g)、ビストリフェニルホスフィンパラジウムジクロライド(8.4mg)、Aliquat336(0.52g,アルドリッチ製)、トルエン(40ml)を混合し、得られた反応溶液を105℃に加熱した。次に、前記反応溶液に2MのNa2CO3水溶液(11ml)を滴下し、1.5時間還流させた後、フェニルホウ酸(40mg)を加え、さらに3時間還流させた。次いで前記反応溶液に1.8Mのジエチルジチアカルバミン酸ナトリウム水溶液(15ml)を加え、80℃で4時間撹拌した後、25℃に冷却し、次いで、水(50ml)で3回、3質量%酢酸水溶液(50ml)で4回、水(50ml)で3回洗浄した後、アルミナカラム、シリカゲルカラムを通すことにより精製して、トルエン溶液を得た。得られたトルエン溶液をメタノール(3L)に滴下し、1時間撹拌した後、得られた固体をろ取し乾燥させて、赤色発光性の高分子化合物<P−6>を得た。得られた高分子化合物<P−6>の収量は2.02gであった。また、高分子化合物<P−6>のポリスチレン換算重量平均分子量は、1.8×105であり、ポリスチレン換算数平均分子量は8.0×104であった。
(実施例3)
スパッタ法により150nmの厚みでITO膜を積層させたガラス基板の表面に、ポリ(3,4)エチレンジオキシチオフェン/ポリスチレンスルホン酸(Bayer製)の懸濁液をスピンコート法により、約65nmの厚みとなるようにして塗布し、第一膜を製膜し、ホットプレート上で200℃、15分間乾燥した。
〈素子構成〉
ITO(陽極)/第一膜(BaytronP:厚み約65nm)/正孔輸送層(高分子化合物<P−3>:厚み約10nm)/発光層(高分子化合物<P−6>:厚み約80nm)/Ba(陰極)/Al(陰極)。
実施例3で得られた高分子発光素子に電圧を印加して性能を評価した。実施例3で得られた高分子発光素子に10.0Vの電圧を印加すると、発光波長のピークトップが670nmである蛍光を発し、その時の輝度は2836cd/m2であった。また、発光効率は3.8Vで最大値を示し、0.70cd/Aであった。さらに、初期輝度1500cd/m2での輝度50%までの減少時間(輝度半減寿命)は、176.6時間であることが確認され、十分に長寿命の高分子発光素子が得られることが確認された。
スパッタ法により150nmの厚みでITO膜を積層させたガラス基板の表面に、ポリ(3,4)エチレンジオキシチオフェン/ポリスチレンスルホン酸(Bayer製)の懸濁液をスピンコート法により、約65nmの厚みとなるようにして塗布し、第一膜を製膜し、ホットプレート上で200℃、15分間乾燥した。
〈素子構成〉
ITO(陽極)/第一膜(BaytronP:厚み約65nm)/正孔輸送層(高分子化合物<P−4>:厚み約10nm)/発光層(高分子化合物<P−6>:厚み約80nm)/Ba(陰極)/Al(陰極)。
比較例2で得られた高分子発光素子に電圧を印加して性能を評価した。比較例2で得られた高分子発光素子に10.0Vの電圧を印加すると、発光波長のピークトップが665nmである蛍光を発し、その時の輝度は3090cd/m2であった。また、発光効率は4.6Vで最大値を示し、0.63cd/Aであった。さらに、初期輝度1500cd/m2での輝度50%までの減少時間(輝度半減寿命)は、82.6時間であることが確認され、その輝度半減寿命は十分ではなかった。
Claims (14)
- 陽極及び陰極との間に発光層を有し且つ該発光層と該陽極との間に正孔輸送層を有する高分子発光素子であって、
前記正孔輸送層が、下記一般式(I)で示される繰返し単位、下記一般式(II)で示される繰返し単位及び下記一般式(III)で示される繰返し単位を含む高分子化合物を含有する層であることを特徴とする高分子発光素子。
[一般式(I)]
[一般式(II)]
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
[一般式(III)]
−Ar2− (III)
(式(III)中、Ar2はアリーレン基又は2価の複素環基を表す。)。 - 前記一般式(II)中のAr1が、下記一般式(IV)で示される基であることを特徴とする請求項1に記載の高分子発光素子。
[一般式(IV)]
R10が結合している炭素及びR18が結合している炭素、R12が結合している炭素及びR13が結合している炭素、R24が結合している炭素及びR34が結合している炭素、又は、R30が結合している炭素及びR31が結合している炭素がそれぞれ直接結合して或いは酸素原子又は硫黄原子を介して結合して環を形成していてもよく、このような環が形成される場合、R10及びR18、R12及びR13、R24及びR34、又は、R30及びR31はそれぞれ一緒になって、前記直接結合、前記酸素原子又は前記硫黄原子を表す。)。 - 前記一般式(III)中のAr2が、下記一般式(V)で示される基であることを特徴とする請求項1又は2に記載の高分子発光素子。
[一般式(V)]
- 前記一般式(III)中のAr2が、下記一般式(VI)で示される基であることを特徴とする請求項1又は2に記載の高分子発光素子。
[一般式(VI)]
- 前記一般式(III)中のAr2が、下記一般式(VII)で示される基であることを特徴とする請求項1又は2に記載の高分子発光素子。
[一般式(VII)]
- 前記高分子化合物のポリスチレン換算の重量平均分子量が103〜107であることを特徴とする請求項1〜5のうちのいずれか一項に記載の高分子発光素子。
- 前記正孔輸送層が正孔輸送材料を更に含有する層であることを特徴とする請求項1〜6のうちのいずれか一項に記載の高分子発光素子。
- 下記一般式(I)で示される繰返し単位、下記一般式(II)で示される繰返し単位及び下記一般式(VI)で示される繰返し単位を含むことを特徴とする高分子化合物。
[一般式(I)]
[一般式(II)]
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
[一般式(VI)]
- 下記一般式(I)で示される繰返し単位、下記一般式(II)で示される繰返し単位及び下記一般式(VII)で示される繰返し単位を含むことを特徴とする高分子化合物。
[一般式(I)]
[一般式(II)]
−Ar1− (II)
(式(II)中、Ar1は2価の芳香族アミンを表す。)
[一般式(VII)]
- 前記一般式(II)中のAr1が、下記一般式(IV)で示される基であることを特徴とする請求項8又は9に記載の高分子化合物。
[一般式(IV)]
R10が結合している炭素及びR18が結合している炭素、R12が結合している炭素及びR13が結合している炭素、R24が結合している炭素及びR34が結合している炭素、又は、R30が結合している炭素及びR31が結合している炭素がそれぞれ直接結合して或いは酸素原子又は硫黄原子を介して結合して環を形成していてもよく、このような環が形成される場合、R10及びR18、R12及びR13、R24及びR34、又は、R30及びR31はそれぞれ一緒になって、前記直接結合、前記酸素原子又は前記硫黄原子を表す。)。 - ポリスチレン換算の重量平均分子量が103〜107であることを特徴とする請求項8〜10のうちのいずれか一項に記載の高分子化合物。
- 請求項8〜11のうちのいずれか一項に記載の高分子化合物と、発光材料及び正孔輸送材料からなる群から選ばれる少なくとも1種の材料とを含有することを特徴とする組成物。
- 請求項8〜11のうちのいずれか一項に記載の高分子化合物と、溶媒とを含有することを特徴とする液状組成物。
- 請求項8〜11のうちのいずれか一項に記載の高分子化合物を1種類以上含有することを特徴とする導電性薄膜。
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007024313A JP5144938B2 (ja) | 2007-02-02 | 2007-02-02 | 高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 |
EP12162121.3A EP2471833B1 (en) | 2007-02-02 | 2008-02-01 | Polymer, composition, liquid composition, and conductive thin film |
KR1020097016167A KR20090122914A (ko) | 2007-02-02 | 2008-02-01 | 고분자 발광 소자, 고분자 화합물, 조성물, 액상 조성물 및 도전성 박막 |
EP08704331A EP2110399A4 (en) | 2007-02-02 | 2008-02-01 | POLYMER ELECTROLUMINESCENT DEVICE, POLYMER COMPOUND, LIQUID COMPOSITION, AND CONDUCTIVE THIN FILM |
US12/525,154 US8384066B2 (en) | 2007-02-02 | 2008-02-01 | Polymer light-emitting device, polymer compound, composition, liquid composition, and conductive thin film |
PCT/JP2008/051622 WO2008093821A1 (ja) | 2007-02-02 | 2008-02-01 | 高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 |
EP12162124A EP2471834A1 (en) | 2007-02-02 | 2008-02-01 | New polymer, composition, liquid composition, and conductive thin film |
CN200880003586XA CN101600752B (zh) | 2007-02-02 | 2008-02-01 | 高分子发光元件、高分子化合物、组合物、液态组合物及导电性薄膜 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007024313A JP5144938B2 (ja) | 2007-02-02 | 2007-02-02 | 高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008189759A true JP2008189759A (ja) | 2008-08-21 |
JP5144938B2 JP5144938B2 (ja) | 2013-02-13 |
Family
ID=39674123
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007024313A Active JP5144938B2 (ja) | 2007-02-02 | 2007-02-02 | 高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8384066B2 (ja) |
EP (3) | EP2471834A1 (ja) |
JP (1) | JP5144938B2 (ja) |
KR (1) | KR20090122914A (ja) |
CN (1) | CN101600752B (ja) |
WO (1) | WO2008093821A1 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013136667A1 (ja) * | 2012-03-15 | 2013-09-19 | 凸版印刷株式会社 | 有機エレクトロルミネセンスデバイス及びその製造方法 |
JP2014503984A (ja) * | 2010-10-15 | 2014-02-13 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ポリマーおよび有機発光デバイス |
CN107615505A (zh) * | 2015-07-31 | 2018-01-19 | 积水化学工业株式会社 | 太阳能电池 |
WO2018016414A1 (ja) * | 2016-07-22 | 2018-01-25 | 住友化学株式会社 | 高分子化合物の製造方法 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101240694B1 (ko) * | 2004-12-03 | 2013-03-07 | 스미또모 가가꾸 가부시키가이샤 | 살리실레이트 치환 공액 중합체 및 장치 |
KR101413380B1 (ko) * | 2007-08-28 | 2014-06-30 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 반도체 다이의 제조방법, 상기 방법으로 제조된 반도체다이를 포함하는 반도체 소자 |
EP2249411A4 (en) | 2008-03-07 | 2014-03-26 | Sumitomo Chemical Co | LAYER STRUCTURE |
JP5581607B2 (ja) * | 2008-06-05 | 2014-09-03 | 住友化学株式会社 | 高分子化合物及びそれを用いた有機トランジスタ |
US20100327735A1 (en) * | 2009-06-29 | 2010-12-30 | General Electric Company | Fluorene dimers and trimers |
US20110077373A1 (en) * | 2009-09-29 | 2011-03-31 | General Electric Company | Polymer and optoelectronic device comprising the same |
US9331284B2 (en) | 2010-01-28 | 2016-05-03 | Sumitomo Chemical Company, Limited | Polymer compound and light-emitting device using same |
GB2477426B (en) * | 2010-01-28 | 2016-02-24 | Sumitomo Chemical Co | Fluorene polymers and light emitting device using the same |
GB2485001A (en) * | 2010-10-19 | 2012-05-02 | Cambridge Display Tech Ltd | OLEDs |
KR20130090736A (ko) | 2012-02-06 | 2013-08-14 | 주식회사 엘지화학 | 헤테로 방향족 화합물 및 이를 포함하는 유기 태양전지 |
US20170044308A1 (en) * | 2014-02-14 | 2017-02-16 | Hitachi Chemical Company, Ltd. | Polymer or oligomer, hole transport material composition, and organic electronic element using same |
JP7326551B2 (ja) | 2018-08-06 | 2023-08-15 | 永大産業株式会社 | 採光建築材 |
CN114068826A (zh) * | 2020-08-03 | 2022-02-18 | 湖南鼎一致远科技发展有限公司 | 一种空穴传输层和色带及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003226744A (ja) * | 2001-11-09 | 2003-08-12 | Sumitomo Chem Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
WO2006060437A2 (en) * | 2004-12-03 | 2006-06-08 | Sumitomo Chemical Company, Limited | Salicylate substituted conjugated polymers and devices |
JP2007162009A (ja) * | 2005-11-18 | 2007-06-28 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3577427A (en) | 1968-09-05 | 1971-05-04 | Shell Oil Co | Bromination of 2,1,3,-benzothiadiazoles and benzofurazans |
US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
JPS6372665A (ja) | 1986-09-12 | 1988-04-02 | Fuji Xerox Co Ltd | 電子写真用電荷輸送材料の製造方法 |
JPS63175860A (ja) | 1987-01-16 | 1988-07-20 | Fuji Xerox Co Ltd | 電子写真感光体 |
JP2651237B2 (ja) | 1989-02-10 | 1997-09-10 | 出光興産株式会社 | 薄膜エレクトロルミネッセンス素子 |
JPH02135361A (ja) | 1988-11-16 | 1990-05-24 | Fuji Xerox Co Ltd | 電子写真感光体 |
JPH02135359A (ja) | 1988-11-16 | 1990-05-24 | Fuji Xerox Co Ltd | 電子写真感光体 |
JPH0337992A (ja) | 1989-07-04 | 1991-02-19 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子の製造方法 |
JPH03152184A (ja) | 1989-11-08 | 1991-06-28 | Nec Corp | 有機薄膜el素子 |
JPH05110069A (ja) | 1991-10-14 | 1993-04-30 | Mitsubishi Electric Corp | 電界効果トランジスタの製造方法 |
JP3367064B2 (ja) | 1995-02-01 | 2003-01-14 | 住友化学工業株式会社 | 高分子蛍光体とその製造方法および有機エレクトロルミネッセンス素子 |
US5830972A (en) | 1995-04-10 | 1998-11-03 | Sumitomo Chemical Company, Limited | Polysilane, its production process and starting materials therefor |
US5948552A (en) | 1996-08-27 | 1999-09-07 | Hewlett-Packard Company | Heat-resistant organic electroluminescent device |
US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
DE69924155T2 (de) | 1999-02-04 | 2006-04-13 | Dow Global Technologies, Inc., Midland | Fluoren-copolymere und daraus hergestellte vorrichtungen |
GB0028867D0 (en) | 2000-11-28 | 2001-01-10 | Avecia Ltd | Field effect translators,methods for the manufacture thereof and materials therefor |
TWI249542B (en) * | 2001-11-09 | 2006-02-21 | Sumitomo Chemical Co | Polymer compound and polymer light-emitting device using the same |
SG125077A1 (en) * | 2001-12-19 | 2006-09-29 | Sumitomo Chemical Co | Copolymer, polymer composition and polymer light-emitting device |
SG128438A1 (en) | 2002-03-15 | 2007-01-30 | Sumitomo Chemical Co | Polymer compound and polymer light emitting deviceusing the same |
JP5069401B2 (ja) | 2002-05-10 | 2012-11-07 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ポリマー及びその製造方法 |
JP4461762B2 (ja) * | 2002-10-30 | 2010-05-12 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
WO2005036666A2 (en) | 2003-09-16 | 2005-04-21 | Dow Global Technologies Inc. | Method of preparing an insoluble polymer film on a substrate from a soluble polymer containing labile solubilizing groups |
WO2005049689A2 (en) | 2003-11-17 | 2005-06-02 | Sumitomo Chemical Company, Limited | Crosslinkable substituted fluorene compounds and conjugated oligomers or polymers based thereon |
TW200530373A (en) | 2003-12-12 | 2005-09-16 | Sumitomo Chemical Co | Polymer and light-emitting element using said polymer |
WO2005070995A1 (ja) * | 2004-01-21 | 2005-08-04 | Sumitomo Chemical Company, Limited | 重合体およびそれを用いた高分子発光素子 |
JP5256568B2 (ja) | 2004-12-28 | 2013-08-07 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
JP4956918B2 (ja) * | 2005-06-03 | 2012-06-20 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
CN101511904A (zh) * | 2006-09-13 | 2009-08-19 | 住友化学株式会社 | 高分子化合物及高分子发光元件 |
JP5281800B2 (ja) * | 2007-02-01 | 2013-09-04 | 住友化学株式会社 | ブロック共重合体並びにそれを用いた組成物、液状組成物、発光性薄膜及び高分子発光素子 |
WO2008111658A1 (ja) * | 2007-03-09 | 2008-09-18 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを含む組成物 |
-
2007
- 2007-02-02 JP JP2007024313A patent/JP5144938B2/ja active Active
-
2008
- 2008-02-01 EP EP12162124A patent/EP2471834A1/en not_active Withdrawn
- 2008-02-01 EP EP08704331A patent/EP2110399A4/en not_active Withdrawn
- 2008-02-01 KR KR1020097016167A patent/KR20090122914A/ko not_active Application Discontinuation
- 2008-02-01 WO PCT/JP2008/051622 patent/WO2008093821A1/ja active Application Filing
- 2008-02-01 US US12/525,154 patent/US8384066B2/en active Active
- 2008-02-01 EP EP12162121.3A patent/EP2471833B1/en not_active Not-in-force
- 2008-02-01 CN CN200880003586XA patent/CN101600752B/zh not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003226744A (ja) * | 2001-11-09 | 2003-08-12 | Sumitomo Chem Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
WO2006060437A2 (en) * | 2004-12-03 | 2006-06-08 | Sumitomo Chemical Company, Limited | Salicylate substituted conjugated polymers and devices |
JP2008522011A (ja) * | 2004-12-03 | 2008-06-26 | 住友化学株式会社 | サリチラート置換共役ポリマー及びデバイス |
JP2007162009A (ja) * | 2005-11-18 | 2007-06-28 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014503984A (ja) * | 2010-10-15 | 2014-02-13 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ポリマーおよび有機発光デバイス |
WO2013136667A1 (ja) * | 2012-03-15 | 2013-09-19 | 凸版印刷株式会社 | 有機エレクトロルミネセンスデバイス及びその製造方法 |
JPWO2013136667A1 (ja) * | 2012-03-15 | 2015-08-03 | 凸版印刷株式会社 | 有機エレクトロルミネセンスデバイス及びその製造方法 |
CN107615505A (zh) * | 2015-07-31 | 2018-01-19 | 积水化学工业株式会社 | 太阳能电池 |
CN107615505B (zh) * | 2015-07-31 | 2021-10-15 | 积水化学工业株式会社 | 太阳能电池 |
WO2018016414A1 (ja) * | 2016-07-22 | 2018-01-25 | 住友化学株式会社 | 高分子化合物の製造方法 |
KR20190032428A (ko) * | 2016-07-22 | 2019-03-27 | 스미또모 가가꾸 가부시키가이샤 | 고분자 화합물의 제조 방법 |
JPWO2018016414A1 (ja) * | 2016-07-22 | 2019-05-09 | 住友化学株式会社 | 高分子化合物の製造方法 |
US10717809B2 (en) | 2016-07-22 | 2020-07-21 | Sumitomo Chemical Company, Limited | Production method of polymer compound |
KR102266665B1 (ko) | 2016-07-22 | 2021-06-21 | 스미또모 가가꾸 가부시키가이샤 | 고분자 화합물의 제조 방법 |
JP6992752B2 (ja) | 2016-07-22 | 2022-01-13 | 住友化学株式会社 | 高分子化合物の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP2110399A1 (en) | 2009-10-21 |
EP2471833A1 (en) | 2012-07-04 |
EP2110399A4 (en) | 2011-09-28 |
WO2008093821A1 (ja) | 2008-08-07 |
CN101600752A (zh) | 2009-12-09 |
KR20090122914A (ko) | 2009-12-01 |
EP2471834A1 (en) | 2012-07-04 |
JP5144938B2 (ja) | 2013-02-13 |
US8384066B2 (en) | 2013-02-26 |
EP2471833B1 (en) | 2013-08-28 |
US20100090206A1 (en) | 2010-04-15 |
CN101600752B (zh) | 2012-06-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5144938B2 (ja) | 高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 | |
JP5625271B2 (ja) | 高分子化合物及びそれを用いた発光素子 | |
US8298685B2 (en) | Block copolymer and polymer light-emitting device | |
JP5471048B2 (ja) | 共重合体及びそれを用いた高分子発光素子 | |
JP5446079B2 (ja) | 高分子化合物及びそれを用いた高分子発光素子 | |
JP5625272B2 (ja) | 1,3−ジエンを含む化合物及びその製造方法 | |
JP5281800B2 (ja) | ブロック共重合体並びにそれを用いた組成物、液状組成物、発光性薄膜及び高分子発光素子 | |
JP5281801B2 (ja) | ブロック共重合体および高分子発光素子 | |
JP5251043B2 (ja) | 高分子化合物および高分子発光素子 | |
JP5407122B2 (ja) | 高分子化合物および高分子発光素子 | |
JP5162868B2 (ja) | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 | |
JP6064433B2 (ja) | 高分子化合物およびそれを用いた発光素子 | |
JP4952032B2 (ja) | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 | |
JP5162856B2 (ja) | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 | |
JP2008106125A (ja) | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 | |
JP5239129B2 (ja) | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 | |
JP5217361B2 (ja) | 高分子化合物及びそれを用いた高分子発光素子 | |
JP2012041537A (ja) | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20091117 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20091117 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20121108 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20121126 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20151130 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5144938 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |