WO2009065479A1 - Conjugated copolymer - Google Patents
Conjugated copolymer Download PDFInfo
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- WO2009065479A1 WO2009065479A1 PCT/EP2008/008972 EP2008008972W WO2009065479A1 WO 2009065479 A1 WO2009065479 A1 WO 2009065479A1 EP 2008008972 W EP2008008972 W EP 2008008972W WO 2009065479 A1 WO2009065479 A1 WO 2009065479A1
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- WIPO (PCT)
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 36
- -1 i- propyl Chemical group 0.000 claims description 97
- 239000010410 layer Substances 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052785 arsenic Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 230000005669 field effect Effects 0.000 claims description 7
- 239000010408 film Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 238000013086 organic photovoltaic Methods 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000003003 spiro group Chemical group 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 239000011229 interlayer Substances 0.000 claims description 4
- 125000006608 n-octyloxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 239000003990 capacitor Substances 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 239000005518 polymer electrolyte Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 abstract description 12
- 125000005259 triarylamine group Chemical group 0.000 abstract description 9
- 239000004065 semiconductor Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 239000012212 insulator Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 238000000151 deposition Methods 0.000 description 9
- 238000007641 inkjet printing Methods 0.000 description 9
- 238000007639 printing Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000003989 dielectric material Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000010020 roller printing Methods 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000003618 dip coating Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 125000004001 thioalkyl group Chemical group 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000007606 doctor blade method Methods 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000007644 letterpress printing Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000007649 pad printing Methods 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 229920006301 statistical copolymer Polymers 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N 9,10-dihydrophenanthrene Chemical class C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 150000001642 boronic acid derivatives Chemical group 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000009396 hybridization Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
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- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
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- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical class [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 229920005548 perfluoropolymer Polymers 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000052 poly(p-xylylene) Polymers 0.000 description 2
- 229920003050 poly-cycloolefin Polymers 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920000306 polymethylpentene Polymers 0.000 description 2
- 239000011116 polymethylpentene Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
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- 150000003216 pyrazines Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- WWGXHTXOZKVJDN-UHFFFAOYSA-M sodium;n,n-diethylcarbamodithioate;trihydrate Chemical compound O.O.O.[Na+].CCN(CC)C([S-])=S WWGXHTXOZKVJDN-UHFFFAOYSA-M 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- 125000004862 thiobutyl group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N trimethylmethane Natural products CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
-
- 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
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
- H10K30/15—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2
- H10K30/152—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2 the wide bandgap semiconductor comprising zinc oxide, e.g. ZnO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; 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
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to a conjugated copolymer comprising indenofluorene and triarylamine units and to its use in organic electronic devices.
- organic semiconducting (OSC) materials in order to produce more versatile, lower cost electronic devices.
- OFETs organic field effect transistors
- OLEDs organic light emitting diodes
- PV photovoltaic
- sensors memory elements and logic circuits to name just a few.
- the organic semiconducting materials are typically present in the electronic device in the form of a thin layer, for example less than 1 micron thick.
- the performance of OFET devices is principally based upon the charge carrier mobility of the semiconducting material and the current on/off ratio, so the ideal semiconductor should have a low conductivity in the off state, combined with a high charge carrier mobility (> 1 x 10 '3 cm 2 V “1 s "1 ).
- the semiconducting material is relatively stable to oxidation i.e. it has a high ionisation potential, as oxidation leads to reduced device performance.
- Further requirements for the semiconducting material are a good processability, especially for large-scale production of thin layers and desired patterns, and high stability, film uniformity and integrity of the organic semiconductor layer.
- One aim of the present invention is to provide new organic semiconducting materials for use in electronic devices, which have advantageous properties, in particular good processability, high charge- carrier mobility, high on/off ratio, high oxidative stability and long lifetime in electronic devices. Another aim is to extend the pool of semiconducting materials availabel to the expert. Other aims of the present invention are immediately evident to the expert from the following detailed description.
- R 1"4 denote aromatic or aliphatic hydrocarbyl groups, and two adjacent groups R 1 ' 2 or R 3 ' 4 may also form a spiro group
- polymers are suitable for use as semiconducting materials in electronic devices like transistors, and as charge transport layer or interlayer in polymer light emitting diodes (PLEDs), as they have good processibility and at the same time show a high charge carrier mobility and high oxidative stability.
- PLEDs polymer light emitting diodes
- WO 2004/041901 describes polymers comprising aryl-substituted indenofluorenes and further units like triarylamine or heteroaryl moieties, and their use in OLED or OFET devices, but does not disclose a device as claimed in the present invention.
- WO 2005/024971 discloses an OLED device comprising a crosslinked buffer layer as electron blocking layer, and further discloses a polymer comprising 50 % indenofluorene and 50 % triarylamine units, but does not disclose a polymer as claimed in the present invention.
- Triarylamines have good hole transport ability. However, they have only moderate solubility in many organic solvents, which does negatively affect their processability in a film-forming process and leads to films with moderate uniformity. Indenofluorenes, on the other hand, are soluble in conventional organic solvents and thus show good processability, enabling the formation of films with high uniformity. However, they have been reported mainly to be efficient electron transporting and light-emitting moieties. It was therefore surprising that a polymer according to the present invention, wherein indenofluorene units are combined with hole transporting moieties like triarylamines, shows high charge carrier mobility and enables the preparation of electronic devices like transistors with high on/off ratios.
- the invention relates to a conjugated copolymer comprising > 50 mol% of one or more identical or different units of formula I
- one of A and A' is a single bond and the other is CR 1 R 2 ,
- one of B and B' is a single bond and the other is CR 3 R 4 ,
- X is halogen
- R 0 and R 00 are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
- Ar is a single bond or denotes mononuclear or polynuclear aryl or heterorayl
- n 1 ,
- Ar 1 which may be the same or different, denote, independently if in different repeat units, a single bond or an optionally substituted mononuclear or polynuclear aryl group,
- Ar 2 which may be the same or different, denote, independently if in different repeat units, an optionally substituted mononuclear or polynuclear aryl group,
- Ar 3 which may be the same or different, denote, independently if in different repeat units, an optionally substituted mononuclear or polynuclear aryl group, which may be optionally substituted by a bridging group linking different chain residues of formula III, and
- k 1 , 2 or 3.
- the invention further relates to the use of the copolymers as described above and below in an organic electronic device as described above and below .
- the invention relates to an organic electronic device comprising a semiconducting layer comprising a conjugated copolymer as described above and below .
- the organic electronic device includes, without limitation, organic field effect transistors (OFET), thin film transistors (TFT), integrated circuits (IC), radio frequency identification (RFID) tags, photodetectors, sensors, logic circuits, memory elements, capacitors, organic photovoltaic (OPV) cells, charge injection layers, charge transport layers or interlayers in polymer light emitting diodes (PLEDs), Schottky diodes, planarising layers, antistatic films, polymer electrolyte membranes (PEM), conducting substrates or patterns, photoconductors, electrophotographic elements and organic light emitting diodes (OLED).
- OFET organic field effect transistors
- TFT thin film transistors
- IC integrated circuits
- RFID radio frequency identification
- PEV organic photovoltaic
- Figure 1 shows the source-drain current vs. gate voltage characteristic of an OFET prepared according to example 2.
- polymer generally means a molecule of high relative molecular mass, the structure of which essentially comprises the multiple repetition of units derived, actually or conceptually, from molecules of low relative molecular mass (PAC, 1996, 68, 2291 ).
- oligomer generally means a molecule of intermediate relative molecular mass, the structure of which essentially comprises a small plurality of units derived, actually or conceptually, from molecules of lower relative molecular mass (PAC, 1996, 68, 2291 ).
- a polymer means a compound having > 1 , preferably > 10 repeating units
- an oligomer means a compound with > 1 and ⁇ 20, preferably ⁇ 10, repeating units.
- the term "repeating unit” means the constitutional repeating unit (CRU), which is the smallest constitutional unit the repetition of which constitutes a regular macromolecule, a regular oligomer molecule, a regular block or a regular chain (PAC, 1996, 68, 2291 ).
- CRU constitutional repeating unit
- leaving group means an atom or group (charged or uncharged) that becomes detached from an atom in what is considered to be the residual or main part of the molecule taking part in a specified reaction (see also PAC, 1994, 66, 1134).
- conjugated means a compound containing mainly C atoms with sp 2 -hybridisation (or optionally also sp-hybridisation), which may also be replaced by hetero atoms. In the simplest case this is for example a compound with alternating C-C single and double (or triple) bonds, but does also include compounds with units like 1 ,3-phenylene. "Mainly” means in this connection that a compound with naturally (spontaneously) occurring defects, which may lead to interruption of the conjugation, is still regarded as a conjugated compound.
- the molecular weight is given as the number average molecular weight M n determined by gel permeation chromatography (GPC) against polystyrene standards.
- carbyl group denotes any monovalent or multivalent organic radical moiety which comprises at least one carbon atom either without any non-carbon atoms (like for example -C ⁇ C-), or optionally combined with at least one non-carbon atom such as N, O, S, P, Si, Se, As, Te or Ge (for example carbonyl etc.).
- hydrocarbyl group denotes a carbyl group that does additionally contain one or more H atoms and optionally contains one or more hetero atoms like for example N, O, S, P, Si, Se, As, Te or Ge.
- a carbyl or hydrocarbyl group comprising a chain of 3 or more C atoms may also be linear, branched and/or cyclic, including spiro and/or fused rings.
- Preferred carbyl and hydrocarbyl groups include alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy, each of which is optionally substituted and has 1 to 40, preferably 1 to 25, very preferably 1 to 18 C atoms, furthermore optionally substituted aryl or aryloxy having 6 to 40, preferably 6 to 25 C atoms, furthermore alkylaryloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy, each of which is optionally substituted and has 6 to 40, preferably 7 to 40 C atoms.
- the carbyl or hydrocarbyl group may be a saturated or unsaturated acyclic group, or a saturated or unsaturated cyclic group. Unsaturated acyclic or cyclic groups are preferred, especially aryl, alkenyl and alkynyl groups (especially ethynyl). Where the CrC 40 carbyl or hydrocarbyl group is acyclic, the group may be linear or branched.
- the CrC 4O carbyl or hydrocarbyl group includes for example: a CrC 40 alkyl group, a C 2 -C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 allyl group, a C 4 -C 40 alkyldienyl group, a C 4 -C 40 polyenyl group, a C 6 -Ci 8 aryl group, a C2-Ci 8 heteroaryl group, a C 6 -C 4 O alkylaryl group, a C 6 -C 4 O arylalkyl group, a C 4 - C 40 cycloalkyl group, a C 4 -C 40 cycloalkenyl group, and the like.
- Preferred among the foregoing groups are a C 1 -C ⁇ o alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C2 0 alkynyl group, a C3-C20 allyl group, a C4-C20 alkyldienyl group, a C 6 -Ci 2 aryl group, a C2-C12 heteroaryl group and a C 4 -C 2 O polyenyl group, respectively. Also included are combinations of groups having carbon atoms and groups having hetero atoms, like e.g. an alkynyl group, preferably ethynyl, that is substituted with a silyl group, preferably a trialkylsilyl group.
- R 0 and R 00 are preferably selected from H, straight-chain or branched alkyl with 1 to 12 C atoms or aryl with 6 to 12 C atoms.
- Halogen is F, Cl, Br or I.
- Preferred alkyl groups include, without limitation, methyl, ethyl, n-propyl, i- propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, cycloheptyl, n- octyl, cyclooctyl, dodecanyl, tetradecyl, hexadecyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, perfluorohexyl etc.
- Preferred alkenyl groups include, without limitation, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl etc.
- Preferred alkynyl groups include, without limitation, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl etc.
- Preferred alkoxy groups include, without limitation, methoxy, ethoxy, 2- methoxyethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t- butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy etc.
- Preferred amino groups include, without limitation, dimethylamino, methylamino, methylphenylamino, phenylamino, etc.
- Aryl groups may be mononuclear, i.e. having only one aromatic ring (like for example phenyl or phenylene), or polynuclear, i.e. having two or more aromatic rings which may be fused (like for example napthyl or naphthylene), individually covalently linked (like for example biphenyl), and/or a combination of both fused and individually linked aromatic rings.
- the aryl group is an aromatic group which is substantially conjugated over substantially the whole group.
- Aryl and heteroaryl preferably denote a mono-, bi- or tricyclic aromatic or heteroaromatic group with up to 25 C atoms that may also comprise condensed rings and is optionally substituted.
- Preferred aryl groups include, without limitation, benzene, biphenylene, triphenylene, [1 ,1 ':3',1 "]terphenyl-2'-ylene, naphthalene, anthracene, binaphthylene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzpyrene, fluorene, indene, indenofluorene, spirobifluorene, etc.
- Preferred heteroaryl groups include, without limitation, 5-membered rings like pyrrole, pyrazole, imidazole, 1 ,2,3-triazole, 1 ,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 1 ,2-thiazole, 1 ,3- thiazole, 1 ,2,3-oxadiazole, 1 ,2,4-oxadiazole, 1 ,2,5-oxadiazole, 1 ,3,4- oxadiazole, 1 ,2,3-thiadiazole, 1 ,2,4-thiadiazole, 1 ,2,5-thiadiazole, 1 ,3,4- thiadiazole, 6-membered rings like pyridine, pyridazine, pyrimidine, pyrazine, 1 ,3,5-triazine, 1 ,2,4-triazine, 1 ,2,
- Preferred arylalkyl groups include, without limitation, 2-tolyl, 3-tolyl, 4-tolyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-di-i-propylphenyl, 2,6-di-t- butylphenyl, o-t-butylphenyl, m-t-butylphenyl, p-t-butylphenyl, 4- phenoxyphenyl, 4-fluorophenyl, 3-carbomethoxyphenyl, 4- carbomethoxyphenyl etc.
- Preferred alkylaryl groups include, without limitation, benzyl, ethylphenyl, 2-phenoxyethyl, propylphenyl, diphenylmethyl, triphenylmethyl or naphthalinylmethyl.
- Preferred aryloxy groups include, without limitation, phenoxy, naphthoxy, 4-phenylphenoxy, 4-methylphenoxy, biphenyloxy, anthracenyloxy, phenanthrenyloxy etc.
- the aryl, heteroaryl, carbyl and hydrocarbyl groups optionally comprise one or more subtituents, preferably selected from silyl, sulpho, sulphonyl, formyl, amino, imino, nitrilo, mercapto, cyano, nitro, halogen, C 6- 12 aryl, CM 2 alkoxy, hydroxy and/or combinations thereof.
- the optional substituents may comprise all chemically possible combinations in the same group and/or a plurality (preferably two) of the aforementioned groups (for example amino and sulphonyl if directly attached to each other represent a sulphamoyl radical).
- substituents are sleeted from alkyl, alkoxy, alkenyl, oxaalkyl, thioalkyl, fluoroalkyl and fluoroalkoxy groups as defined for the
- R 1"4 is an alkyl or alkoxy radical, i.e. where the terminal CH 2 group is replaced by -O-, this may be straight-chain or branched. It is preferably straight-chain, has 2 to 8 carbon atoms and accordingly is preferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, heptoxy, or octoxy, furthermore methyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradecoxy, for example. Especially preferred are n-hexyl and n-dodecyl.
- R 1"4 is fluoroalkyl or fluoroalkoxy, it is preferably a straight-chain group (O)CjF 2I+I , wherein i is an integer from 1 to 15, in particular CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9 , C 5 F 11 , C 6 Fi 3 , C 7 F-I 5 or C 8 Fi 7 , very preferably C 6 Fi 3 , or the corresponding fluoroalkoxy group.
- i is an integer from 1 to 15, in particular CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9 , C 5 F 11 , C 6 Fi 3 , C 7 F-I 5 or C 8 Fi 7 , very preferably C 6 Fi 3 , or the corresponding fluoroalkoxy group.
- the groups R 1 and R 2 and/or the groups R 3 and R 4 form a spiro group together with the fluorene group, it is preferably spirobifluorene.
- - Ar is either a single bond or an optionally substituted mononuclear or polynuclear aryl group, very preferably a single bond,
- - Ar is selected from optionally substituted indenofluorene, optionally substituted spirobifluorene, optionally substituted 9,10- dihydrophenanthrene or optionally substituted phenanthrene,
- - m is ⁇ 10, very preferably 1 , 2, 3, 4 or 5, most preferably 1 ,
- - A' is CR 1 R 2
- B is CR 3 R 4
- Ar is a single bond
- m is preferably 1
- - A' is CR 1 R 2
- B 1 is CR 3 R 4
- Ar is a single bond
- m is preferably 1
- - R 1"4 denote optionally substituted carbyl or hydrocarbyl, very preferably optionally substituted alkyl, aryl or heteroaryl.
- m > 1
- the meanings of B and B' in each indenofluorene group are selected independently of the other indenofluorene groups.
- the units of formula I may consist exclusively of fused cis-indenfluorene moieties, or may consist exclusively of fused trans-indenofluorene moieties, or may comprise alternating or random sequences of fused cis- and trans-indenofluorene moieties.
- the units of formula I are preferably selected from the following subformulae:
- R 1"4 are as defined in formula I 1 R and R 5"8 independently of each other have one of the meanings of R 1 given in formula I, r is 0, 1 , 2, 3 or 4, t is 0, 1 or 2 and u is 0, 1 , 2 or 3.
- L is H, halogen or optionally fluorinated, linear or branched alkyl or alkoxy with 1 to 12 C atoms, and is preferably H, F, methyl, i-propyl, t- butyl, n-pentoxy, or trifluoromethyl, and
- L 1 is optionally fluorinated, linear or branched alkyl or alkoxy with 1 to 12 C atoms, and is preferably n-octyl or n-octyloxy.
- Ar 1 and Ar 2 in formula Il are preferably selected from 1 ,4-phenylene wherein one, two or three CH groups are optionally replaced by N, and which are optionally substituted by one or more groups R 1 as defined above. Further preferred are units of formula Il wherein Ar 1 is a single bond.
- Ar 1"3 in formula Il is preferably selected from phenyl wherein one, two or three CH groups are optionally replaced by N, and which is optionally substituted by one or more groups R 1 as defined above.
- k in formula Il is very preferably 1.
- Y in formula Il is very preferably N.
- the units of formula Il are preferably selected from the following subformulae:
- R and r are as defined above and s is 0, 1 , 2, 3, 4 or 5.
- L and L' are as defined above, L is preferably i-propyl, t-butyl or trifluoromethyl and L' is preferably n-octyl or n-octyloxy.
- the copolymers consist of one or more, preferably one, two or three, most preferably one, type of units of formula I and one or more, preferably one, two or three, most preferably one, type of units of formula II.
- the upper limit of the ratio of the units of formula I in the copolymer is preferably ⁇ 99 mol%, more preferably ⁇ 90 %.
- the lower limit of the ratio of the units of formula I in the copolymer is preferably > 55 mol%, more preferably > 65 mol%, most preferably > 75 mol%.
- the upper limit of the ratio of the units of formula Il in the copolymer is preferably ⁇ 45 mol%, more preferably ⁇ 35 mol%, most preferably ⁇ 25 mol%.
- the lower limit of the ratio of the units of formula Il in the copolymer is preferably > 1 mol%, most preferably > 10mol%.
- the copolymers may also comprise one or more, preferably one, additional type of units, preferably selected from units having hole or electron transporting properties.
- Additional units having electron transport properties are preferably selected from the following formulae
- R and R" are as defined above, and are preferably H, alkyl, aryl, perfluoroalkyl, thioalkyl, cyano, alkoxy, heteroaryl, alkylaryl or arylalkyl.
- R is preferably H, phenyl or alkyl having 1 , 2, 3, 4, 5 or 6 C atoms.
- R 1 is preferably n-octyl or n-octyloxy.
- copolymers of the present invention include statistical or random copolymers, alternating copolymers and block copolymers, as well as combinations thereof.
- random and block copolymers comprising, very preferably consisting of, > 50 mol% of one or more units of formula I and > 0 mol% and ⁇ 50 mol% of one or more units of formula II.
- copolymers exclusively consisting of > 50 mol% of one type of units of formula I and > 0 mol% and ⁇ 50 mol% of one type of units of formula II.
- copolymers are preferably selected of the following formula
- U 1 is a unit of formula I or its preferred subformulae
- U ⁇ is a unit of formula Il or its preferred subformulae
- Preferred polymers of formula 1 are selected from the following subformulae
- R ,1-4 1 R, R 1 , r, s, x and y are as defined above.
- the total number of repeating units n is preferaby > 10, very preferaby > 50, and preferably up to 2,000, very preferably up to 5,000, most preferaby up to 10,000.
- the polymers of the present invention may be prepared by any suitable method.
- they can be suitably prepared by aryl-aryl coupling reactions, such as Yamamoto coupling, Suzuki coupling, Stille coupling, Sonogashira coupling or Heck coupling. Suzuki coupling and Yamamoto coupling are especially preferred.
- the monomers which are polymerised to form the repeat units of the polymers of the present invention can be prepared according to suitable methods which are known to the expert and have been disclosed in the literature. Suitable and preferred methods for the preparation of the indenofluorene monomers of formula I are described for example in WO 2004/041901 A1 and WO 2006/015862 A1. Suitable and preferred methods for the preparation of the triarylamine monomers of formula Il are described for example in WO 99/54385 A1.
- the polymers are prepared from monomers comprising one of the above mentioned groups of formula UX, which are linked to two polymerisable groups P. Accordingly, for example indenofluorene and triarylamine monomers selected from the following formulae can be used:
- P and P are independently of each other a polymerisable or reactive group and A, A', B, B 1 , Ar, Y, Ar 1"3 , R, R 1"4 , k, m, r and s are as defined above.
- the other co-monomers can be built accordingly.
- Another aspect of the invention is a process for preparing a polymer by coupling one or more monomers based on a unit of formula I with one one or more monomers based on a unit of formula II, and optionally with one or more further units, for example selected from formulae IM-IX, in a polymerisation reaction.
- Preferred methods for polymerisation are those leading to C-C-coupling or C-N-coupling, like Suzuki polymerisation, as described for example in WO 00/53656, Yamamoto polymerisation, as described in for example in T. Yamamoto et al., Progress in Polymer Science 1993, 17, 1153-1205 or in WO 2004/022626 A1 , and StMIe coupling.
- monomers as described above having two reactive halide groups P 1 ' 2 is preferably used.
- a monomer as described above is used wherein at least one reactive group P 1 2 is a boronic acid or boronic acid derivative group.
- Suzuki polymerisation may be used to prepare statistical, alternating and block random copolymers.
- statistical or block copolymers may be prepared from the above monomers wherein one of the reactive groups P and P is halogen and the other reactive group is a boronic acid or boronic acid derivative group.
- the synthesis of statistical, alternating and block copolymers is described in detail for example in WO 03/048225 A2 or WO 2005/014688 A2.
- Suzuki polymerisation employs a Pd(O) complex or a Pd(II) salt.
- Preferred Pd(O) complexes are those bearing at least one phosphine ligand such as Pd(Ph ⁇ P) 4 .
- Another preferred phosphine ligand is ⁇ s ⁇ ortho- tolyl)phosphine, i.e. Pd(O-ToI) 4 .
- Preferred Pd(II) salts include palladium acetate, i.e. Pd(OAc) 2 .
- Suzuki polymerisation is performed in the presence of a base, for example sodium carbonate, potassium phosphate or an organic base such as tetraethylammonium carbonate.
- Yamamoto polymerisation employs a Ni(O) complex, for example bis(1 ,5- cyclooctadienyl) nickel(O).
- leaving groups of formula -O-SO 2 Z can be used wherein Z is as described above.
- Particular examples of such leaving groups are tosylate, mesylate and triflate.
- the organic electronic device is for example an organic field effect transistor (OFET), thin film transistor (TFT), integrated circuit (IC), radio frequency identification (RFID) tag, photodetector, sensor, logic circuit, memory element, capacitor, organic photovoltaic (OPV) cell, charge injection layer, charge transport layer, Schottky diode, planarising layer, antistatic film, polymer electrolyte membrane (PEM), conducting substrate or pattern, photoconductor, electrophotographic element, or organic light emitting diode (OLED).
- OFET organic field effect transistor
- TFT thin film transistor
- IC integrated circuit
- RFID radio frequency identification
- photodetector sensor
- logic circuit memory element
- capacitor organic photovoltaic cell
- charge injection layer charge transport layer
- Schottky diode planarising layer
- antistatic film polymer electrolyte membrane
- PEM polymer electrolyte membrane
- conducting substrate or pattern photoconductor
- electrophotographic element electrophotographic element
- OLED organic light emitting diode
- An OFET device preferably comprises: - optionally a substrate,
- the semiconductor layer comprises one or more copolymers as described above and below.
- the gate, source and drain electrodes and the insulating and semiconducting layer in the OFET device may be arranged in any sequence, provided that the source and drain electrode are separated from the gate electrode by the insulating layer, the gate electrode and the semiconductor layer both contact the insulating layer, and the source electrode and the drain electrode both contact the semiconducting layer.
- the electronic device is an OFET comprising a dielectric insulating layer, a gate electrode contacting one surface of the dielectric layer, a semiconductor layer contacting the surface of the dielectric layer facing away from the gate electrode, and drain electrode and source electrodes contacting the surface of the semiconductor layer facing away from the dielectric layer.
- the OFET is preferably a top gate device or a bottom gate device.
- the organic semiconductor layer is preferably less than 30 microns thick.
- the thickness may also be less than 1 micron.
- the layer thickness is typically 500 nm or less, for use in OLEDs typically 100nm or less. The exact thickness of the layer will depend, for example, upon the requirements of the electronic device in which the layer is used.
- the thickness of a functional layer in an electronic device according to the present invention can range from 1 nm (in case of a monolayer) to 10 ⁇ m, preferably from 1 nm to 1 ⁇ m, more preferably from 1 nm to 500 nm.
- the organic semiconductor layer can be deposited by any suitable method. Liquid coating is more desirable than vacuum deposition techniques. Solution deposition methods are especially preferred.
- Preferred deposition techniques include, without limitation, dip coating, spin coating, ink jet printing, letter-press printing, screen printing, doctor blade coating, roller printing, reverse-roller printing, offset lithography printing, flexographic printing, web printing, spray coating, brush coating or pad printing. Ink-jet printing is particularly preferred.
- the organic semiconductor layer is preferably deposited from a formulation, very preferably a solution or a dispersion, comprising the copolymers) and one or more organic solvents.
- suitable and preferred organic solvents include, without limitation, dichloromethane, trichloromethane, monochlorobenzene, o- dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1 ,4-dioxane, acetone, methylethylketone, 1 ,2- dichloroethane, 1 ,1 ,1-trichloroethane, 1 ,1 ,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetralin, decalin, indane and/or mixtures thereof.
- the total concentration of the copolymer(s) in the formulation is preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight.
- solutions are evaluated as one of the following categories: complete solution, borderline solution or insoluble.
- the contour line is drawn to outline the solubility parameter- hydrogen bonding limits dividing solubility and insolubility. 'Complete' solvents falling within the solubility area can be chosen from literature values such as published in "Crowley, J. D., Teague, G. S. Jr and Lowe, J.W. Jr., Journal of Paint Technology, 38, No 496, 296 (1966)".
- Solvent blends may also be used and can be identified as described in "Solvents, W.H.Ellis, Federation of Societies for Coatings Technology, p9-10, 1986". Such a procedure may lead to a blend of 'non' solvents that will dissolve both the polymers of the present invention, although it is desirable to have at least one true solvent in a blend.
- the solutions are preferably applied to prefabricated device substrates by ink jet printing or microdispensing.
- industrial piezoelectric print heads such as, but not limited to, those supplied by Aprion, Hitachi-Koki, InkJet Technology, On Target Technology, Picojet, Spectra, Trident, Xaar are used.
- semi-industrial heads such as those manufactured by Brother, Epson, Konica, Seiko Instruments Toshiba TEC or single nozzle microdispensers such as those produced by Microdrop and Microfab may be used.
- solvents for ink jet printing or microdispensing must fulfil the requirements stated above and must not have any detrimental effect on the chosen print head. Additionally, solvents should have boiling points >100°C, preferably >140°C and more preferably >150°C in order to prevent operability problems caused by the solution drying out inside the print head.
- suitable solvents include substituted and non-substituted xylene derivatives, di-C 1-2 -alkyl formamide, substituted and non-substituted anisoles and other phenol- ether derivatives, substituted heterocycles such as substituted pyridines, pyrazines, pyrimidines, pyrrolidinones, substituted and non-substituted ⁇ /, ⁇ /-di-Ci- 2 -alkylanilines and other fluorinated or chlorinated aromatics.
- a preferred solvent for depositing copolymers according to the present invention by ink jet printing comprises a benzene derivative which has a benzene ring substituted by one or more substituents wherein the total number of carbon atoms among the one or more substituents is at least three.
- the benzene derivative may be substituted with a propyl group or three methyl groups, in either case there being at least three carbon atoms in total.
- Such a solvent enables an ink jet fluid to be formed comprising the solvent with the polymer, which reduces or prevents clogging of the jets and separation of the components during spraying.
- the solvent(s) may include those selected from the following list of examples: dodecylbenzene, 1-methyl-4-tert-butylbenzene, terpineol limonene, isodurene, terpinolene, cymene, diethylbenzene.
- the solvent may be a solvent mixture, that is a combination of two or more solvents, each solvent preferably having a boiling point >100°C, more preferably >140°C. Such solvent(s) also enhance film formation in the layer deposited and reduce defects in the layer.
- the ink jet fluid (that is mixture of solvent, binder and semiconducting compound) preferably has a viscosity at 20°C of 1-10OmPa s, more preferably 1-50mPa s and most preferably 1-3OmPa s.
- the organic semiconductor formulation can additionally comprise one or more further components like for example surface-active compounds, lubricating agents, wetting agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents which may be reactive or non-reactive, auxiliaries, colourants, dyes or pigments, sensitizers, stabilizers, nanoparticles or inhibitors.
- further components like for example surface-active compounds, lubricating agents, wetting agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents which may be reactive or non-reactive, auxiliaries, colourants, dyes or pigments, sensitizers, stabilizers, nanoparticles or inhibitors.
- the organic semiconductor layer or the formulation for its deposition comprises one or more organic binders to adjust its rheological properties, as described for example in WO 2005/055248 A1.
- the other components of the electronic device can be selected from standard materials, and can be manufactured and applied to the device by standard methods. Suitable materials and manufacturing methods for these components and layers are known to the the skilled person and are described in the literature.
- the deposition methods include liquid coating and vapour or vacuum deposition.
- Preferred deposition techniques include, without limitation, dip coating, spin coating, ink jet printing, letter-press printing, screen printing, doctor blade coating, roller printing, reverse-roller printing, offset lithography printing, flexographic printing, web printing, spray coating, brush coating or pad printing.
- Ink-jet printing is particularly preferred as it allows high resolution layers and devices to be prepared.
- Various substrates may be used for the fabrication of organic electronic devices, for example glass or plastics, plastics materials being preferred, examples including alkyd resins, allyl esters, benzocyclobutenes, butadiene-styrene, cellulose, cellulose acetate, epoxide, epoxy polymers, ethylene-chlorotrifluoro ethylene, ethylene-tetra-fluoroethylene, fibre glass enhanced plastic, fluorocarbon polymers, hexafluoropropylenevinylidene- fluoride copolymer, high density polyethylene, parylene, polyamide, polyimide, polyaramid, polydimethylsiloxane, polyethersulphone, poly- ethylene, polyethylenenaphthalate, polyethyleneterephthalate, polyketone, polymethylmethacrylate, polypropylene, ' polystyrene, polysulphone, polytetrafluoroethylene, polyurethanes, polyvinylchloride, silicone rubbers,
- Preferred substrate materials are polyethyleneterephthalate, polyimide, and polyethylenenaphthalate.
- the substrate may be any plastic material, metal or glass coated with the above materials.
- the substrate should preferably be homogenous to ensure good pattern definition.
- the substrate may also be uniformly pre-aligned by extruding, stretching, rubbing or by photochemical techniques to induce the orientation of the organic semiconductor in order to enhance carrier mobility.
- the electrodes can be deposited by liquid coating, such as spray-, dip-, web- or spin-coating, or by vacuum deposition or vapour deposition methods.
- Suitable electrode materials and deposition methods are known to the person skilled in the art.
- Suitable electrode materials include, without limitation, inorganic or organic materials, or composites of the two.
- suitable electrode materials include polyaniline, polypyrrole, PEDOT or doped conjugated polymers, further dispersions or pastes of graphite or particles of metal such as Au, Ag, Cu, Al, Ni or their mixtures as well as sputtercoated or evaporated metals, like e.g. Cu, Cr, Pt/Pd etc., and semiconductors like e.g. ITO.
- Organometallic precursors may also be used deposited from a liquid phase.
- the dielectric material for the insulator layer may be inorganic or organic or a composite of the two. It is preferred that the insulator is solution coated which allows ambient processing, but could be also deposited by various vacuum deposition techniques. When the insulator is being patterned, it may perform the function of interlayer insulation or act as gate insulator for an OFET.
- Preferred deposition techniques include, without limitation, dip coating, spin coating, ink jet printing, letter-press printing, screen printing, doctor blade coating, roller printing, reverse-roller printing, offset lithography printing, flexographic printing, web printing, spray coating, brush coating or pad printing. Ink-jet printing is particularly preferred as it allows high resolution layers and devices to be prepared.
- the dielectric material could be cross-linked or cured to achieve better resitivity against solvents and/or structural integrity and/or to enable patternability (photolithography)
- Preferred gate insulators are those that provide a low permittivity interface to the OSC.
- Suitable and preferred organic dielectric materials include, without limitation, fluorinated para-xylene , fluoropolyarylether, fluorinated polyimide polystyrene, poly( ⁇ -methylstyrene), poly( ⁇ -vinylnaphtalene), poly(vinyltoluene), polyethylene, cis-polybutadiene, polypropylene, polyisoprene, poly(4-methyl-1-pentene), poly (4-methylstyrene), poly(chorotrifluoroethylene), poly(2-methyl-1 ,3-butadiene), poly(p- xylylene), poly( ⁇ - ⁇ - ⁇ '- ⁇ tetrafluoro-p-xylylene), poly[1 ,1-(2-methyl propane)bis(4-phenyl)carbonate], poly(cyclohexyl methacrylate), poly(chlorostyrene), poly(2,6-dimethyl-1 ,4-phenylene ether),
- copolymers including regular, random or block copolymers like poly(ethylene/tetrafluoroethylene), poly(ethylene/chlorotrifluoro-ethylene), fluorinated ethylene/propylene copolymer, polystyrene-co- ⁇ - methylstyrene, ethylene/ethyl acrylate copolymer, poly(styrene/ 10%butadiene), poly(styrene/15%butadiene), poly(styrene/2,4 dimethylstyrene).
- regular, random or block copolymers like poly(ethylene/tetrafluoroethylene), poly(ethylene/chlorotrifluoro-ethylene), fluorinated ethylene/propylene copolymer, polystyrene-co- ⁇ - methylstyrene, ethylene/ethyl acrylate copolymer, poly(styrene/ 10%butadiene), poly(styrene/15%butadiene), poly(s
- polymers from the commercially availabe Topas ® series Ticona
- Suitable and preferred organic dielectric materials of this type include, without limitation, for example, polvinylalcohol, polyvinylphenol, polymethylmethacrylate, cyanoethylated polysaccharides such as cyanoethylpullulane, high permittivity flurorpolymers such as polyvinylidenefluoride, polyurethane polymers and poly( vinyl chloride/vinylacetate) polymers.
- Suitable and preferred inorganic dielectric materials of this type include, without limitation, for example composites of TiO 2 , Ta 2 O 5 , SrTiO 3 , Bi 4 Ti 3 Oi 2 , BaMgF 4 , barium zirconium titanate or barium strontium titanate.
- the insulator layer comprises, or consists of, an organic dielectric material having a low permittivity, preferably having a relative permittivity from 1.1 to below 3.0, as disclosed for example in WO 03/052841.
- Suitable and preferred materials for this embodiment include, without limitation, polypropylene, polyisobutylene, poly(4-methyl-1-pentene), polyisoprene, poly( vinyl cyclohexane), or a copolymer containing the monomer units of at least one of these materials, polycycloolefins like those from the Avatrel ® series and fluoropolymers, in particular those from the Cytop ® or* TeflonAF ® series.
- the insulator layer comprises a fluoropolymer, like e.g. the commercially available Cytop 809M® or Cytop 107M® (from Asahi Glass).
- the gate insulator layer is deposited, e.g. by spin-coating, doctor blading, wire bar coating, spray or dip coating or other known methods, from a formulation comprising an insulator material and one or more solvents with one or more fluoro atoms (fluorosolvents), preferably a perfluorosolvent.
- a suitable perfluorosolvent is e.g. FC75® (available from Acros, catalogue number 12380).
- Other suitable fluoropolymers and fluorosolvents are known in prior art, like for example the perfluoropolymers Teflon AF® 1600 or 2400 (from DuPont) or Fluoropel®
- an integrated circuit comprising a field effect transistor according to the present invention.
- photovoltaic cell comprising one or more copolymers as described above and below.
- An OPV device preferably comprises: - a low work function electrode (for example Aluminum),
- a high work function electrode for example ITO, one of which is transparent
- bilayer of consisting of a hole transporting and an electron transporting material; the bilayer can exist as two distinct layers, or a blended mixture (see for example Coakley, K. M. and McGehee, M. D.
- an optional conducting polymer layer such as for example PEDOT:PSS
- an optional coating on the high workfunction electrode such as LiF
- the hole transporting material in the blend exists of one of the copolymers as described above and below.
- the electron transporting material can be an inorganic material such as zinc oxide or cadmium selenide, or an organic material such as a fullerene derivate (for example PCBM, [(6,6)- phenyl C61 -butyric acid methyl ester] or a polymer see for example Coakley, K. M. and McGehee, M. D. Chem. Mater. 2004, 16, 4533). If the bilayer is a blend an optional annealing step may be necessary to optimize device performance. Unless the context clearly indicates otherwise, as used herein plural forms of the terms herein are to be construed as including the singular form and vice versa.
- the cloudy mixture is then degassed (stirred, bubbling N 2 ) for 1 hour.
- the oil bath is pre-heated to 105 0 C and a stock solution of catalyst is prepared [4.5 times the quantity required: palladium(ll) acetate (32.9 mg, 0.147 mmol) and tri(o-tolyl)phosphine (267.3 mg, 0.878 mmol) in degassed 1 ,4-dioxane (15.8 cm 3 ), which is degassed for 50 minutes in a sealed vial].
- the degassing glass tube is washed with 1 ,4-dioxane (6 cm 3 ) and toluene (6 cm 3 ) and then the flask is lowered into the preheated oil bath at 105 °C and after 10 minutes, the catalyst solution (3.5 cm 3 ) is added. The reaction mixture is then stirred vigourously for 2 hours in the dark. Tolyl boronate ester (31.3 mg, 0.193 mmol) is added followed by further catalyst solution (3.5 cm 3 ) and the mixture heated at 105 °C for 1 hour.
- a field effect transistor is prepared as follows: On a glass substrate patterned Au source and drain electrodes are provided by shadow masking. A self assembling monolayer of pentafluorobenzene-thiol (electrode injection layer) is spincoated onto the Au electrodes and washed with IPA. A semiconductor formulation is prepared by dissolving Example 1 in a concentration of 1 wt.% in mesitylene. The semiconductor solution is then spincoated onto the substrate at 500 rpm for 3 seconds followed by 2000rpm for 30s at room temperature in air and the solvent is evaporated. The insulator material (Cytop® 809M, available from Asahi Glass) is then spincoated onto the semiconductor giving a thickness of approximately 1 ⁇ m and the solvent is evaporated. A gold gate contact is defined over the device channel area by evaporation through a shadow mask.
- the transistor sample is mounted in a sample holder.
- Microprobe connections were made to the gate, drain and source electrodes using Karl Suss PH100 miniature probe-heads. These are linked to a Hewlett-Packard 4155B parameter analyser.
- the drain voltage is set to -5 V and the gate voltage is scanned from +20 to -60 V and back to +20 V in 1 V steps.
- the ISD (source-drain current) vs. VG (gate voltage) characteristic is shown in Figure 1.
- the field effect mobility values are calculated from the gradient of the ISD vs. VQ characteristic in the linear regime (Lin mob) and the saturation regime (Sat mob). All measurements are performed in air at room temperature. The results are summarized below:
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Abstract
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Priority Applications (7)
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CN200880116937.8A CN101868490B (en) | 2007-11-21 | 2008-10-23 | Conjugated copolymer |
EP08851568A EP2222749A1 (en) | 2007-11-21 | 2008-10-23 | Conjugated copolymer |
US12/743,673 US8586684B2 (en) | 2007-11-21 | 2008-10-23 | Conjugated copolymer |
KR1020107013776A KR101532458B1 (en) | 2007-11-21 | 2008-10-23 | Conjugated copolymer |
JP2010534384A JP2011505439A (en) | 2007-11-21 | 2008-10-23 | Conjugated copolymer |
GB1009961.2A GB2467498B (en) | 2007-11-21 | 2008-10-23 | Conjugated copolymer |
HK10111122.6A HK1144695A1 (en) | 2007-11-21 | 2010-11-30 | Conjugated copolymer |
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EP07022611.3 | 2007-11-21 | ||
EP07022611 | 2007-11-21 |
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US (1) | US8586684B2 (en) |
EP (1) | EP2222749A1 (en) |
JP (1) | JP2011505439A (en) |
KR (1) | KR101532458B1 (en) |
CN (1) | CN101868490B (en) |
GB (1) | GB2467498B (en) |
HK (1) | HK1144695A1 (en) |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010149261A1 (en) * | 2009-06-26 | 2010-12-29 | Merck Patent Gmbh | Polymers containing structural units that comprise alkyl alkoxy groups, blends containing said polymers, and optoelectronic devices containing said polymers and blends |
WO2011098205A1 (en) * | 2010-02-12 | 2011-08-18 | Merck Patent Gmbh | Electroluminescent polymers, methods for producing same and use thereof |
US20130069020A1 (en) * | 2010-05-27 | 2013-03-21 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Formulation and method for preparation of organic electronic devices |
US8586684B2 (en) | 2007-11-21 | 2013-11-19 | Merck Patent Gmbh | Conjugated copolymer |
Families Citing this family (6)
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KR101344576B1 (en) * | 2009-04-01 | 2013-12-26 | 에이손 테쿠노로지 가부시키가이샤 | Organic electroluminescent element |
KR20120086319A (en) * | 2009-10-19 | 2012-08-02 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Triarylamine compounds for electronic applications |
GB201108865D0 (en) * | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Semiconductor compounds |
GB201108864D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Transistors and methods of making them |
TW201339138A (en) * | 2012-01-20 | 2013-10-01 | Univ Southern California | Synthesis of aza-acenes as novel n-type materials for organic electronics |
JP6078998B2 (en) * | 2012-06-20 | 2017-02-15 | 住友化学株式会社 | Polymer compound and light emitting device using the same |
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WO2004106409A1 (en) | 2003-05-30 | 2004-12-09 | Covion Organic Semiconductors Gmbh | Polymer |
WO2005024971A1 (en) * | 2003-09-04 | 2005-03-17 | Merck Patent Gmbh | Electronic devices comprising an organic conductor and semiconductor as well as an intermediate buffer layer made of a crosslinked polymer |
WO2006015862A1 (en) | 2004-08-11 | 2006-02-16 | Merck Patent Gmbh | Polymers for use in organic electroluminescent devices |
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WO2008011953A1 (en) * | 2006-07-25 | 2008-01-31 | Merck Patent Gmbh | Polymer blends and their use in organic light emitting devices |
Family Cites Families (1)
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KR101532458B1 (en) | 2007-11-21 | 2015-06-29 | 메르크 파텐트 게엠베하 | Conjugated copolymer |
-
2008
- 2008-10-23 KR KR1020107013776A patent/KR101532458B1/en active IP Right Grant
- 2008-10-23 WO PCT/EP2008/008972 patent/WO2009065479A1/en active Application Filing
- 2008-10-23 EP EP08851568A patent/EP2222749A1/en not_active Withdrawn
- 2008-10-23 JP JP2010534384A patent/JP2011505439A/en not_active Withdrawn
- 2008-10-23 GB GB1009961.2A patent/GB2467498B/en active Active
- 2008-10-23 CN CN200880116937.8A patent/CN101868490B/en active Active
- 2008-10-23 US US12/743,673 patent/US8586684B2/en active Active
- 2008-11-18 TW TW097144526A patent/TWI445731B/en not_active IP Right Cessation
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WO2004106409A1 (en) | 2003-05-30 | 2004-12-09 | Covion Organic Semiconductors Gmbh | Polymer |
WO2005024971A1 (en) * | 2003-09-04 | 2005-03-17 | Merck Patent Gmbh | Electronic devices comprising an organic conductor and semiconductor as well as an intermediate buffer layer made of a crosslinked polymer |
WO2006015862A1 (en) | 2004-08-11 | 2006-02-16 | Merck Patent Gmbh | Polymers for use in organic electroluminescent devices |
WO2007131582A1 (en) * | 2006-05-12 | 2007-11-22 | Merck Patent Gmbh | Indenofluorene polymer based organic semiconductor materials |
WO2008011953A1 (en) * | 2006-07-25 | 2008-01-31 | Merck Patent Gmbh | Polymer blends and their use in organic light emitting devices |
Cited By (8)
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US8586684B2 (en) | 2007-11-21 | 2013-11-19 | Merck Patent Gmbh | Conjugated copolymer |
WO2010149261A1 (en) * | 2009-06-26 | 2010-12-29 | Merck Patent Gmbh | Polymers containing structural units that comprise alkyl alkoxy groups, blends containing said polymers, and optoelectronic devices containing said polymers and blends |
US9175132B2 (en) | 2009-06-26 | 2015-11-03 | Merck Patent Gmbh | Polymers comprising structural units which contain alkylalkoxy groups, blends comprising these polymers, and opto-electronic devices comprising these polymers and blends |
WO2011098205A1 (en) * | 2010-02-12 | 2011-08-18 | Merck Patent Gmbh | Electroluminescent polymers, methods for producing same and use thereof |
US9534077B2 (en) | 2010-02-12 | 2017-01-03 | Merck Patent Gmbh | Electroluminescent polymers, process for the preparation thereof, and use thereof |
US20130069020A1 (en) * | 2010-05-27 | 2013-03-21 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Formulation and method for preparation of organic electronic devices |
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US8586684B2 (en) | 2013-11-19 |
JP2011505439A (en) | 2011-02-24 |
TWI445731B (en) | 2014-07-21 |
KR20100100897A (en) | 2010-09-15 |
CN101868490A (en) | 2010-10-20 |
GB2467498B (en) | 2012-11-28 |
GB2467498A (en) | 2010-08-04 |
CN101868490B (en) | 2014-06-04 |
EP2222749A1 (en) | 2010-09-01 |
HK1144695A1 (en) | 2011-03-04 |
KR101532458B1 (en) | 2015-06-29 |
US20100256328A1 (en) | 2010-10-07 |
GB201009961D0 (en) | 2010-07-21 |
TW200942560A (en) | 2009-10-16 |
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