JP2008163306A - 正孔輸送ポリマー - Google Patents
正孔輸送ポリマー Download PDFInfo
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- JP2008163306A JP2008163306A JP2007218773A JP2007218773A JP2008163306A JP 2008163306 A JP2008163306 A JP 2008163306A JP 2007218773 A JP2007218773 A JP 2007218773A JP 2007218773 A JP2007218773 A JP 2007218773A JP 2008163306 A JP2008163306 A JP 2008163306A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 48
- 230000005525 hole transport Effects 0.000 title claims abstract description 42
- 239000000463 material Substances 0.000 claims abstract description 163
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 253
- 238000000151 deposition Methods 0.000 claims description 28
- 230000008021 deposition Effects 0.000 claims description 25
- 239000000872 buffer Substances 0.000 claims description 24
- 229920001577 copolymer Polymers 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000007740 vapor deposition Methods 0.000 claims description 15
- 239000007791 liquid phase Substances 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 238000002207 thermal evaporation Methods 0.000 claims description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 10
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000005259 triarylamine group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 238000001947 vapour-phase growth Methods 0.000 claims description 3
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
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- 238000010438 heat treatment Methods 0.000 description 31
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- 238000000034 method Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 230000008901 benefit Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
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- 150000002739 metals Chemical class 0.000 description 7
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- -1 —N (R 7 ) (R 8 ) Chemical group 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 0 C*1c2ccccc2-c2ccccc12 Chemical compound C*1c2ccccc2-c2ccccc12 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- XEPMXWGXLQIFJN-UHFFFAOYSA-K aluminum;2-carboxyquinolin-8-olate Chemical compound [Al+3].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 XEPMXWGXLQIFJN-UHFFFAOYSA-K 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
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- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- OLLHYWBEIYJYTK-UHFFFAOYSA-J 2-carboxyquinolin-8-olate zirconium(4+) Chemical compound [Zr+4].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 OLLHYWBEIYJYTK-UHFFFAOYSA-J 0.000 description 2
- IYKBMPHOPLFHAQ-UHFFFAOYSA-N 2-phenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=2C3=NC=CC=2)C3=N1 IYKBMPHOPLFHAQ-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- NFFQNURCKDTKTK-UHFFFAOYSA-K [Al+3].C1(=CC=CC=C1)C1=CC=C(C=C1)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-] Chemical compound [Al+3].C1(=CC=CC=C1)C1=CC=C(C=C1)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-] NFFQNURCKDTKTK-UHFFFAOYSA-K 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Chemical group 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
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- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
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- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical group C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- VMAUSAPAESMXAB-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)quinoxaline Chemical compound C1=CC(F)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(F)C=C1 VMAUSAPAESMXAB-UHFFFAOYSA-N 0.000 description 1
- CYKLQIOPIMZZBZ-UHFFFAOYSA-N 2,7-dibromo-9,9-dioctylfluorene Chemical compound C1=C(Br)C=C2C(CCCCCCCC)(CCCCCCCC)C3=CC(Br)=CC=C3C2=C1 CYKLQIOPIMZZBZ-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C(=CC=CC=1)C1(CCCCC1)C=1C(=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- 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
- 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
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
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- 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
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H—ELECTRICITY
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- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
【解決手段】重合させた後のポリマー主鎖を構成する位置にあり、かつ芳香環どうしを結合する位置にあるチッ素原子を含み、さらにフルオレン環および/または複素環を含有する芳香族π共役系モノマーから選ばれた少なくとも1種のモノマー、ただし、こららモノマーの少なくとも1種は架橋性反応基を含む、からなる正孔輸送能力をもったポリマー。
【選択図】図1
Description
RおよびYは、独立に、H、
R’は、架橋性基であり;
R”は、独立に、H、アルキル、フルオロアルキル、アリール、フルオロアリール、およびR’からなる群から選択され;
Xは、それぞれの場合に、同じまたは異なるものとすることができ、かつ脱離基であり;
Zは、C、Si、またはNであり;
Qは、(ZR”n)bであり;
aは、0から5までの整数であり;
bは、0から20までの整数であり;
cは、0から4までの整数であり;
qは、0から7までの整数であり;
nは、1から2までの整数である)。
RおよびYは、独立に、H、D、アルキル、フルオロアルキル、アリール、フルオロアリール、アルコキシ、アリールオキシ、NR”2、R’、
R’は、架橋性基であり;
R”は、独立に、H、アルキル、フルオロアルキル、アリール、フルオロアリール、およびR’からなる群から選択され;
Qは、(ZR”n)bであり;
Xは、それぞれの場合に、同じまたは異なるものとすることができ、かつ脱離基であり;
Zは、C、Si、またはNであり;
Eは、(ZR”n)b、O、S、Se、またはTeであり;
aは、0から5までの整数であり;
bは、0から20までの整数であり;
cは、0から4までの整数であり;
qは、0から7までの整数であり;
nは、1から2までの整数である)。
以下に示す実施形態の詳細に取り組む前に、いくつかの用語について定義しまたは解説する。
式Iを有するモノマーは、
式Iを有するモノマーのホモポリマーは、Yamamoto重合によって作製することができる。この合成方法では、非特許文献2に記載されているように、2個の脱離基を有するモノマーを、ビス(1,5−シクロオクタジエン)ニッケル(0)など化学量論量の0価のニッケル化合物と反応させる。そのようなホモポリマーは、アリールアミン末端基のみ有することになる。
RおよびYは、独立に、H、D、アルキル、フルオロアルキル、アリール、フルオロアリール、アルコキシ、アリールオキシ、NR”2、R’、
R’は、架橋性基であり;
R”は、独立に、H、アルキル、フルオロアルキル、アリール、フルオロアリール、およびR’からなる群から選択され;
Qは、(ZR”n)bであり;
Xは、脱離基であり;
Zは、C、Si、またはNであり;
Eは、(ZR”n)b、O、S、Se、またはTeであり;
aは、0から5までの整数であり;
bは、0から20までの整数であり;
cは、0から4までの整数であり;
qは、0から7までの整数であり;
nは、1から2までの整数である)。
本明細書に記載される少なくとも1種の化合物を含んだ1つまたは複数の層を有することから利益を得ることができる有機電子デバイスには、(1)電気エネルギーを放射線に変換するデバイス(例えば、発光ダイオード、発光ダイオードディスプレイ、またはダイオードレーザ)、(2)電子的プロセスによりシグナルを検出するデバイス(例えば、光検出器、光伝導セル、フォトレジスタ、光スイッチ、光トランジスタ、光電管、IR検出器)、(3)放射線を電気エネルギーに変換するデバイス(例えば、光起電力デバイスまたは太陽電池)、および(4)1つまたは複数の有機半導体層を含んだ1つまたは複数の電子構成要素を含むデバイス(例えば、トランジスタまたはダイオード)が含まれるが、これらに限定するものではない。本発明による組成物のその他の用途には、記憶装置、帯電防止フィルム、バイオセンサ、エレクトロクロミックデバイス、固体電解質キャパシタ、充電式バッテリなどのエネルギー貯蔵装置、および電磁遮蔽の適用例に用いられるコーティング材料が含まれる。
本明細書に記述される概念について、以下の実施例においてさらに記述するが、これらは、特許請求の範囲に記載される本発明の範囲を限定するものではない。
この比較例は、Suzuki重合を使用したジスチリル基を有するフルオレンおよびトリアリールアミンのコポリマーの調製について示す。式Iを有するモノマーは、使用しなかった。
110 アノード層
120 正孔輸送層
130 光活性層
140 電荷輸送層
150 カソード層
Claims (14)
- 下記の式Iを有する少なくとも1種のモノマーから作製されたことを特徴とするポリマー。
[式中、
RおよびYは、独立に、H、
D、アルキル、フルオロアルキル、アリール、フルオロアリール、アルコキシ、アリールオキシ、NR”2、R’からなる群から選択され、
R’は、架橋性基であり;
R”は、独立に、H、アルキル、フルオロアルキル、アリール、フルオロアリール、およびR’からなる群から選択され;
Xは、それぞれの場合に、同じまたは異なっており、かつ脱離基であり;
Zは、C、N、またはSiであり;
Qは、(ZR”n)bであり;
aは、0から5までの整数であり;
bは、0から20までの整数であり;
cは、0から4までの整数であり;
qは、0から7までの整数であり;
nは、1から2までの整数である。] - 請求項1に記載のポリマーであって、
下記の式IIからVIIIまでからなる群から選択された少なくとも1種のコモノマーを含むが、ただし、コポリマーが、Yamamoto重合によって作製される、ポリマー。
[式中、
RおよびYは、独立に、H、D、アルキル、フルオロアルキル、アリール、フルオロアリール、アルコキシ、アリールオキシ、NR”2、R’、
からなる群から選択され、
R’は、架橋性基であり;
R”は、独立に、H、アルキル、フルオロアルキル、アリール、フルオロアリール、およびR’からなる群から選択され;
Qは、(ZR”n)bであり;
Xは、それぞれの場合に、同じまたは異なるものとすることができ、かつ脱離基であり;
Zは、C、N、またはSiであり;
Eは、(ZR”n)b、O、S、Se、またはTeであり;
aは、0から5までの整数であり;
bは、0から20までの整数であり;
cは、0から4までの整数であり;
qは、0から7までの整数であり;
nは、1から2までの整数である
ことを特徴とするポリマー。] - 請求項1に記載のポリマーであって、
ホモポリマーであることを特徴とするポリマー。 - 請求項1または2に記載の少なくとも1種のポリマーを含むことを特徴とする電子デバイス。
- 請求項1または2に記載の少なくとも1種のポリマーを含む、光活性層を含むことを特徴とする電子デバイス。
- 請求項7に記載のデバイスであって、
光活性層の液相成長によって製作されたことを特徴とするデバイス。 - 請求項7に記載のデバイスであって、
光活性層の気相成長または熱蒸発堆積によって製作されたことを特徴とするデバイス。 - 請求項6に記載のデバイスであって、
アノード、緩衝層、正孔輸送層、光活性層、電子輸送層、電子注入層、およびカソードも含むことを特徴とするデバイス。 - 請求項10に記載のデバイスであって、
緩衝層、正孔輸送層、および光活性層の液相成長によって製作されることを特徴とするデバイス。 - 請求項10に記載のデバイスであって、
電子輸送層、電子注入層、およびカソードの気相成長によって製作されることを特徴とするデバイス。 - 請求項6に記載のデバイスであって、
(i)ジスチリル基を有するフルオレンおよびトリアリールアミンのコポリマーと、(ii)式Xを有するコポリマーとの少なくとも1種を含む、少なくとも1種の正孔輸送材料を含むことを特徴とするデバイス。 - 請求項6に記載のデバイスであって、
いくつかの有機層の液相成長およびいくつかの有機層の気相成長によって製作されたことを特徴とするデバイス。
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US9156939B2 (en) | 2009-02-27 | 2015-10-13 | Merck Patent Gmbh | Polymer containing aldehyde groups, reaction and crosslinking of this polymer, crosslinked polymer, and electroluminescent device comprising this polymer |
KR101732199B1 (ko) * | 2009-02-27 | 2017-05-02 | 메르크 파텐트 게엠베하 | 알데히드기를 포함하는 중합체, 상기 중합체의 변환 및 가교, 가교된 중합체, 및 상기 중합체를 함유하는 전계발광 소자 |
US9728724B2 (en) | 2009-02-27 | 2017-08-08 | Merck Patent Gmbh | Polymer containing aldehyde groups, reaction and crosslinking of this polymer, crosslinked polymer, and electroluminescent device comprising this polymer |
JP2015511215A (ja) * | 2011-12-28 | 2015-04-16 | ソルヴェイ(ソシエテ アノニム) | 架橋性アリールアミン組成物 |
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JPWO2015146912A1 (ja) * | 2014-03-28 | 2017-04-13 | 日産化学工業株式会社 | フルオレン誘導体及びその利用 |
Also Published As
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US20120077955A1 (en) | 2012-03-29 |
EP2069419A2 (en) | 2009-06-17 |
EP1892259B1 (en) | 2009-10-07 |
WO2008024378A2 (en) | 2008-02-28 |
JP5271520B2 (ja) | 2013-08-21 |
CN101134814B (zh) | 2011-10-26 |
TW200835717A (en) | 2008-09-01 |
US8487055B2 (en) | 2013-07-16 |
CN101134814A (zh) | 2008-03-05 |
EP1892259A1 (en) | 2008-02-27 |
WO2008024378A3 (en) | 2008-04-10 |
KR20080018835A (ko) | 2008-02-28 |
US8242223B2 (en) | 2012-08-14 |
US20080071049A1 (en) | 2008-03-20 |
KR101332519B1 (ko) | 2013-11-22 |
DE602007002674D1 (de) | 2009-11-19 |
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