TWI650373B - 有機電晶體製造用溶劑及其用途 - Google Patents
有機電晶體製造用溶劑及其用途 Download PDFInfo
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- TWI650373B TWI650373B TW103140168A TW103140168A TWI650373B TW I650373 B TWI650373 B TW I650373B TW 103140168 A TW103140168 A TW 103140168A TW 103140168 A TW103140168 A TW 103140168A TW I650373 B TWI650373 B TW I650373B
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- 239000002904 solvent Substances 0.000 title claims abstract description 112
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 45
- 239000004065 semiconductor Substances 0.000 claims abstract description 69
- 239000000463 material Substances 0.000 claims abstract description 68
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 24
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 18
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 18
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 14
- 125000005647 linker group Chemical group 0.000 claims description 14
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 claims description 8
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 claims description 7
- YZDGROPVYQGZTK-UHFFFAOYSA-N 3-methyl-2,3-dihydro-1-benzofuran Chemical compound C1=CC=C2C(C)COC2=C1 YZDGROPVYQGZTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- KILGIXRNINKGLK-UHFFFAOYSA-N 5,5-dimethoxycyclohexa-1,3-diene Chemical compound COC1(OC)CC=CC=C1 KILGIXRNINKGLK-UHFFFAOYSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 4
- -1 methylene, methylmethylene, dimethylmethylene, ethylidene, propylidene Chemical group 0.000 description 38
- 238000000034 method Methods 0.000 description 19
- 239000000758 substrate Substances 0.000 description 17
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 12
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
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- 239000004033 plastic Substances 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
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- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 150000001983 dialkylethers Chemical class 0.000 description 4
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 150000003997 cyclic ketones Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QPHFJZRSMXHTAW-UHFFFAOYSA-N 1-[2-(2-methoxypropoxy)propoxy]butane Chemical compound CCCCOCC(C)OCC(C)OC QPHFJZRSMXHTAW-UHFFFAOYSA-N 0.000 description 2
- LIYRYVJXMPWPAS-UHFFFAOYSA-N 1-methoxy-2-propoxypropane Chemical compound CCCOC(C)COC LIYRYVJXMPWPAS-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- HGERSUQOJQWENV-UHFFFAOYSA-N 1-pentan-2-yloxypropan-2-ol Chemical compound CCCC(C)OCC(C)O HGERSUQOJQWENV-UHFFFAOYSA-N 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- RZXAHVCTRLTLNA-UHFFFAOYSA-N 2-(2-methoxypropoxy)-1-propoxypropane Chemical compound CCCOCC(C)OCC(C)OC RZXAHVCTRLTLNA-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- WRWGLRHYWHYHJG-UHFFFAOYSA-N 2-methyl-2,3-dihydrofuran Chemical compound CC1CC=CO1 WRWGLRHYWHYHJG-UHFFFAOYSA-N 0.000 description 2
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 2
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 2
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
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- 229940007550 benzyl acetate Drugs 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000000052 comparative effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- STZKQZZZZDAERV-UHFFFAOYSA-N cyclohex-2-en-1-ylmethyl acetate Chemical compound CC(=O)OCC1CCCC=C1 STZKQZZZZDAERV-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- MSDKIQILHSEFNE-UHFFFAOYSA-N methyl acetate;oxolane Chemical compound COC(C)=O.C1CCOC1 MSDKIQILHSEFNE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 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
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
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- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- BOGFHOWTVGAYFK-UHFFFAOYSA-N 1-[2-(2-propoxyethoxy)ethoxy]propane Chemical compound CCCOCCOCCOCCC BOGFHOWTVGAYFK-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 1
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 description 1
- JXFITNNCZLPZNX-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OC JXFITNNCZLPZNX-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
茲提供一種對有機半導體材料的溶解性優良、可形成結晶性高之有機電晶體的有機電晶體製造用溶劑。
本發明之有機電晶體製造用溶劑包含1種或2種以上的下述式(a)所示之溶劑A。式中,環Z表示選自下述的環:芳香族碳環、5~7員之脂環族碳環、及5~7員之雜環。R1表示選自下述的基:側氧基、側硫基(thioxy group)、-ORa基、-SRa基、-O(C=O)Ra基、-RbO(C=O)Ra基、及經取代或未經取代的胺基;R2表示選自下述的基:氫原子、C1-7烷基、芳基、及-ORa基。R1與R2可相互鍵結而與構成環Z的碳原子共同形成環。
Description
本發明係有關於一種對有機半導體材料的溶解性優良的有機電晶體製造用溶劑、及包含該有機電晶體製造用溶劑與有機半導體材料的有機電晶體製造用組成物。本案係主張2013年11月21日於日本申請之特願2013-241096號之優先權,將其內容援用於此。
有機電晶體係作為構成顯示器或電腦機器的重要半導體電子裝置經廣泛活用,現今,係使用多晶矽或非晶矽等無機物作為半導體材料來製造。在使用此類無機物之薄膜有機電晶體的製造中,需要真空製程或高溫製程,製造成本增加為其問題。又,由於包括高溫製程,可用之基板有其限制,目前主要使用玻璃基板等。然而,玻璃基板其耐熱性雖高,但不耐衝擊,而不易輕量化,且因缺乏柔軟性,而不易形成具可撓性的有機電晶體。
因此,近年來,利用有機半導體材料之有機電子裝置相關的研究開發快速進展。有機半導體材料可藉由採印刷法、旋轉塗布法等濕製程的簡便方法容易地形成薄膜,而有所謂相較於習知利用無機半導體材料的有機電晶體,可使製程溫度低溫化的優點。由此,可在
一般耐熱性較低的塑膠基板上形成、可實現顯示器等電子裝置的輕量化或低成本化,同時可活用塑膠基板的可撓性之用途等,可望多元化地拓展。
就有機半導體材料而言,周知透過使用例如稠五苯(pentacene)等的低分子半導體材料,可展現高半導體裝置性能。然而,稠五苯所代表的未經取代之多并苯(acene)系化合物的多數係因π共軛系所產生的強烈分子間交互作用而缺乏對溶劑的溶解性。因此,便無法調製高濃度的有機電晶體製造用組成物,而有以印刷法所形成的有機半導體其晶粒較小,若未外加高電壓則無法通電,甚而外加高電壓時絕緣膜發生剝離等問題。
此外,非專利文獻1、2中記載,作為有機半導體材料,係使用具噻吩骨架的供體受體型共聚物化合物。前述化合物因其強固的π-π堆積作用(stacking),基於高度的π電子重疊而顯示高移動度。然而,因強固的π-π堆積作用致結晶性高,缺乏對溶劑的溶解性為其問題。而且,前述文獻中記載使用1,2-二氯苯所代表的鹵化溶劑予以加熱溶解。然而,以1,2-二氯苯等使其溶解時,經常在室溫下發生凝膠化,對於採印刷法形成薄膜者屬不適合。又,鹵化溶劑有生態毒性之疑慮,亦存在作業安全上的問題。
[非專利文獻1]Adv. Mater. 2012, 24, p 4618-4622
[非專利文獻2]Adv. Mater. 2012, 24, p 6457-6461
從而,本發明之目的在於提供一種對有機半導體材料的溶解性優良、可形成結晶性高之有機電晶體的有機電晶體製造用溶劑。
本發明之其他目的在於提供一種包含前述有機電晶體製造用溶劑的有機電晶體製造用組成物。
本發明人等為解決上述課題而致力研究的結果發現,若使用特定的溶劑,縱使在較低溫度下亦可展現高有機半導體材料溶解性,在耐熱性比玻璃基板更低的塑膠基板上仍可藉由印刷法形成有機電晶體。另外發現,含有前述溶劑的有機電晶體製造用組成物,若予塗布於基板上,有機半導體材料即藉自組織化作用而結晶化。進而發現,若視需求對前述溶劑混合一般使用於電子材料用途的溶劑,則可進一步提升塗布性、乾燥性。本發明係基於此等見解而完成者。
亦即,本發明係提供一種有機電晶體製造用溶劑,其為有機半導體材料溶解用之溶劑,其包含1種或2種以上的下述式(a)所示之溶劑A;
[式中,環Z表示選自下述的環:芳香族碳環、5~7員之脂環族碳環、及5~7員之雜環;R1表示選自下述的基:
側氧基(=O)、側硫基(thioxy group)(=S)、-ORa基、-SRa基、-O(C=O)Ra基、-RbO(C=O)Ra基(Ra表示C1-7烷基、或芳基、或前述基經由單鍵或連結基鍵結而成的基,Rb表示C1-7伸烷基、或伸芳基、或前述基經由單鍵或連結基鍵結而成的基)、及經取代或未經取代的胺基;R2表示選自下述的基:氫原子、C1-7烷基、芳基、及-ORa基(Ra與前述相同);R1與R2可相互鍵結而與構成環Z的碳原子共同形成環]。
本發明又提供一種前述之有機電晶體製造用溶劑,其中溶劑A為選自2-甲基環戊酮、2-甲基環己酮、環己基甲基醚、環己胺、甲氧基苯、1,2-二甲氧基苯、2,3-二氫苯并呋喃、及2,3-二氫-3-甲基苯并呋喃中的至少1種。
本發明又提供一種前述之有機電晶體製造用溶劑,其中有機半導體材料為具有下述式(1)所示之構成單元的化合物:
(式中,L1、L2係相同或相異,表示選自下述的基:從芳香族碳環或雜芳香族碳環去除2個氫原子之基、伸乙烯基、伸乙炔基、及前述基的2個以上組合而成之2價基;R3、R4係相同或相異,表示選自下述的基:氫原子、可具
有取代基之C1-24烷基、芳基、及雜芳基;Y1、Y2係相同或相異,表示氧原子或硫原子;p、q係相同或相異,表示0以上之整數,且(p+q)為1以上之整數;p個L1可相同或相異;又,q個L2可相同或相異)。
本發明又提供一種前述之有機電晶體製造用溶劑,其中式(1)中之L1、L2係相同或相異,為選自下述式(L-1)~(L-22)的基:
本發明又提供一種前述之有機電晶體製造用溶劑,其中有機半導體材料為具有下述式(1-1)所示之構成單元的化合物:
(式中,R3~R12係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;R5與R6、R7與R8、R9與R10、R11與R12可各自相互鍵結而與構成噻吩環的碳原子共同形成環)。
本發明又提供一種有機電晶體製造用組成物,其包含有機半導體材料、及前述之有機電晶體製造用溶劑。
本發明又提供一種前述之有機電晶體製造用組成物,其中有機半導體材料為具有下述式(1)所示之構成單元的化合物:
(式中,L1、L2係相同或相異,表示選自下述的基:從芳香族碳環或雜芳香族碳環去除2個氫原子之基、伸乙烯基、伸乙炔基、及前述基的2個以上組合而成之2價基;R3、R4係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;Y1、Y2係相同或相異,表示氧原子或硫原子;p、q係相同或相異,表示0以上之整數,且(p+q)為1以上之整數)。
本發明又提供一種前述之有機電晶體製造用組成物,其中式(1)中之L1、L2係相同或相異,為選自下述式(L-1)~(L-22)的基:
本發明又提供一種前述之有機電晶體製造用組成物,其中有機半導體材料為具有下述式(1-1)所示之構成單元的化合物:
(式中,R3~R12係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;R5與R6、R7與R8、R9與R10、R11與R12可各自相互鍵結而與構成噻吩環的碳原子共同形成環)。
亦即,本發明係有關於以下者。
[1]一種有機電晶體製造用溶劑,其為有機半導體材料溶解用之溶劑,其包含1種或2種以上的式(a)所示之溶劑A。
[2]如[1]之有機電晶體製造用溶劑,其中溶劑A為選自環戊酮、C1-7(環)烷基環戊酮、環己酮、C1-7(環)烷基環己酮、環己基甲基醚、環己胺、苯甲醚(anisole)、1-甲氧基-2-甲基苯、苯并呋喃、2,3-二氫苯并呋喃、二氫甲基苯并呋喃、乙酸環己酯、乙酸二氫萜品酯(dihydroterpinyl acetate)、乙酸四氫苄酯、乙酸苄酯、乙酸四氫呋喃甲酯、二甲氧基苯、乙氧基苯、二丙二醇環戊基甲基醚、及N-甲基吡咯啶酮中的至少1種。
[3]如[1]之有機電晶體製造用溶劑,其中溶劑A為選自2-甲基環戊酮、2-甲基環己酮、環己基甲基醚、環己胺、甲氧基苯、1,2-二甲氧基苯、2,3-二氫苯并呋喃、及2,3-二氫-3-甲基苯并呋喃中的至少1種。
[4]如[1]至[3]中任一項之有機電晶體製造用溶劑,
其中有機電晶體製造用溶劑總量中之溶劑(A)的含量為50重量%以上。
[5]如[1]至[4]中任一項之有機電晶體製造用溶劑,其中有機半導體材料為具有式(1)所示之構成單元的化合物。
[6]如[5]之有機電晶體製造用溶劑,其中式(1)中之L1、L2係相同或相異,為選自式(L-1)~(L-22)的基。
[7]如[1]至[4]中任一項之有機電晶體製造用溶劑,其中有機半導體材料為具有式(1-1)所示之構成單元的化合物。
[8]一種有機電晶體製造用組成物,其包含有機半導體材料、及如[1]至[7]中任一項之有機電晶體製造用溶劑。
[9]如[8]之有機電晶體製造用組成物,其中有機半導體材料為具有式(1)所示之構成單元的化合物。
[10]如[9]之有機電晶體製造用組成物,其中式(1)中之L1、L2係相同或相異,為選自式(L-1)~(L-22)的基。
[11]如[8]之有機電晶體製造用組成物,其中有機半導體材料為具有式(1-1)所示之構成單元的化合物。
[12]如[8]之有機電晶體製造用組成物,其中有機半導體材料為具有式(1-1a)所示之構成單元的化合物及/或具有式(1-1b)所示之構成單元的化合物。
[13]如[8]至[12]中任一項之有機電晶體製造用組成物,其中相對於100重量份的有機電晶體製造用溶劑,含有0.01~10重量份之有機半導體材料。
[14]如[8]至[13]中任一項之有機電晶體製造用組成物,其中相對於100重量份的有機電晶體製造用溶劑,含有0.01~10重量份之作為有機半導體材料之具有式(1-1a)所示之構成單元的化合物及/或具有式(1-1b)所示之構成單元的化合物。
[15]如[8]至[14]中任一項之有機電晶體製造用組成物,其中含有有機電晶體製造用組成物總量的90.00~99.99重量%之有機電晶體製造用溶劑。
本發明之有機電晶體製造用溶劑,縱使在較低溫度下亦具有高有機半導體材料溶解性。因此,在耐熱性較玻璃基板低,但耐衝擊、輕量且可撓性的塑膠基板等上,亦可直接形成有機電晶體,並且可形成耐衝擊、輕量且可撓性的顯示器或電腦機器。又,可藉由採印刷法、旋轉塗布法等濕製程的簡便方法容易地製造有機電晶體,可達成本之大幅刪減。
而且,本發明之有機電晶體製造用組成物,若予塗布於基板上,有機半導體材料即藉自組織化作用而結晶化,因此可獲得具有高結晶性的有機電晶體。
[有機電晶體製造用溶劑]
本發明之有機電晶體製造用溶劑係用以溶解有機半
導體材料之溶劑,其特徵為包含1種或2種以上的下述式(a)所示之溶劑A;
[式中,環Z表示選自下述的環:芳香族碳環、5~7員之脂環族碳環、及5~7員之雜環;R1表示選自下述的基:側氧基(=O)、側硫基(=S)、-ORa基、-SRa基、-O(C=O)Ra基、-RbO(C=O)Ra基(Ra表示C1-7烷基、或芳基、或前述基經由單鍵或連結基鍵結而成的基,Rb表示C1-7伸烷基、或伸芳基、或前述基經由單鍵或連結基鍵結而成的基)、及經取代或未經取代的胺基;R2表示選自下述的基:氫原子、C1-7烷基、芳基、及-ORa基(Ra與前述相同);R1與R2可相互鍵結而與構成環Z的碳原子共同形成環]。
(溶劑A)
本發明之溶劑A為上述式(a)所示之包含至少1個雜原子的化合物。式(a)中,環Z表示選自下述的環:芳香族碳環、5~7員之脂環族碳環、及5~7員之雜環。作為前述環,可舉出例如苯環等碳數6~14之芳香族碳環;環戊烷環、環己烷環、環庚烷環等5~7員之脂環族碳環(尤為5~7員之烷環);吡咯啶環、氧戊環(oxolane ring)、硫戊環(thiolane ring)等5~7員之雜環。
式(a)中,R1表示選自下述的基:側氧基(=O)、側硫基(=S)、-ORa基、-SRa基、-O(C=O)Ra基、-RbO(C=O)Ra基(Ra表示C1-7烷基、或芳基、或前述基經由單鍵或連結基鍵結而成的基,Rb表示C1-7伸烷基、或伸芳
基、或前述基經由單鍵或連結基鍵結而成的基)、及經取代或未經取代的胺基。又,R2表示選自下述的基:氫原子、C1-7烷基、芳基、及-ORa基(Ra與前述相同)。
作為前述C1-7烷基,可舉出例如甲基、乙基、丙基、丁基、戊基、己基、庚基等直鏈狀或支鏈狀烷基、或環戊基等碳數3~7之環烷基。
作為前述C1-7伸烷基,可舉出例如亞甲基、甲基亞甲基、二甲基亞甲基、伸乙基、伸丙基、三亞甲基(trimethylene)等直鏈狀或支鏈狀伸烷基等。
作為前述芳基,可舉出例如苯基等C6-14芳基。
作為前述伸芳基,可舉出例如伸苯基等C6-14伸芳基。
作為前述連結基,可舉出例如伸烷基、羰基(-CO-)、醚鍵(-O-)、酯鍵(-COO-)、醯胺鍵(-CONH-)、碳酸酯鍵(-OCOO-)、及此等複數個連結而成的基等。前述伸烷基之碳數較佳為1~18,可舉出亞甲基、甲基亞甲基、二甲基亞甲基、伸乙基、伸丙基、三亞甲基等直鏈狀或支鏈狀伸烷基、或1,2-伸環戊基、1,3-伸環戊基、亞環戊基、1,2-伸環己基、1,3-伸環己基、1,4-伸環己基、亞環己基等2價脂環族烴基(尤為伸環烷基)等。
作為前述經取代或未經取代的胺基,可舉出例如胺基;甲胺基、乙胺基、異丙胺基、二甲胺基、二乙胺基等單或二(C1-3)烷胺基等。
作為R1與R2可相互鍵結而與構成環Z的碳原
子共同形成的環,可舉出例如環戊烷、環己烷、環庚烷、苯、甲基苯、噻吩、甲基噻吩、呋喃、甲基呋喃、二氫呋喃、甲基二氫呋喃等。
就式(a)所示之溶劑A的重量平均分子量而言,例如為350以下左右,較佳為70~250,特佳為80~200。
作為本發明之溶劑A,可舉出例如環戊酮、C1-7(環)烷基環戊酮(例如2-甲基環戊酮、2-乙基環戊酮、2-丙基環戊酮、2-丁基環戊酮、2-戊基環戊酮、2-環戊基環戊酮、2-己基環戊酮、2-庚基環戊酮)、環己酮、C1-7(環)烷基環己酮(例如2-甲基環己酮、2-乙基環己酮、2-丙基環己酮、2-丁基環己酮、2-戊基環己酮、2-己基環己酮、2-庚基環己酮、4-戊基環己酮)、環己基甲基醚、環己胺、苯甲醚(=甲氧基苯)、1-甲氧基-2-甲基苯、苯并呋喃、2,3-二氫苯并呋喃、二氫甲基苯并呋喃(例如2,3-二氫-3-甲基苯并呋喃)、乙酸環己酯、乙酸二氫萜品酯、乙酸四氫苄酯、乙酸苄酯、乙酸四氫呋喃甲酯、二甲氧基苯(例如1,2-二甲氧基苯)、乙氧基苯、二丙二醇環戊基甲基醚、及N-甲基吡咯啶酮等。此等可單獨使用1種、或組合使用2種以上。此外,前述(環)烷基係表示烷基或環烷基。
特別是,欲溶解作為有機半導體材料的以下所記載之具有式(1-1)所示之構成單元的化合物(其中具有式(1-1a)所示之構成單元的化合物)時,就溶劑A而言,選自2-甲基環戊酮、2-甲基環己酮、環己基甲基醚、環
己胺、苯甲醚(=甲氧基苯)、1,2-二甲氧基苯、2,3-二氫苯并呋喃、及2,3-二氫-3-甲基苯并呋喃中的至少1種,在前述有機半導體材料的溶解性優良方面係較佳者。
有機電晶體製造用溶劑中(100重量%)之溶劑A的含量(組合含有2種以上時為其總量)較佳為50重量%以上(例如50~100重量%),特佳為70重量%以上(例如70~100重量%)。溶劑A的含量低於上述範圍時,有有機半導體材料的溶解性降低之傾向。
(溶劑B)
本發明之有機電晶體製造用溶劑,除上述溶劑A以外,亦可併用一般使用於電子材料用途的溶劑,亦即與上述溶劑A相溶的溶劑(=溶劑B)。
作為溶劑B,可舉出例如(單、二、三)烷二醇單烷基醚、(單、二)烷二醇二烷基醚、(單、二)烷二醇烷基醚乙酸酯、(單、二)烷二醇二乙酸酯、乙酸烷基酯、C3-6醇、C3-6烷二醇、C3-6烷二醇單烷基醚、C3-6烷二醇烷基醚乙酸酯、C3-6烷二醇二乙酸酯、丙三醇三乙酸酯、羥基羧酸酯、羥基羧酸二酯、烷氧基羧酸酯、環狀酮、內酯、環狀醚、醯胺類、吡啶類、芳香族乙酸酯、胺類等。此等可單獨使用1種、或組合使用2種以上。
作為前述(單、二、三)烷二醇單烷基醚,可舉出例如乙二醇單甲基醚、乙二醇單乙基醚、乙二醇正丙基醚、乙二醇正丁基醚、二乙二醇單甲基醚、二乙二醇單乙基醚、二乙二醇正丙基醚、二乙二醇正丁基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇正丙基醚、
丙二醇正丁基醚、二丙二醇單甲基醚、二丙二醇單乙基醚、二丙二醇正丙基醚、二丙二醇正丁基醚、三丙二醇單甲基醚、三丙二醇正丁基醚等。
作為前述(單、二)烷二醇二烷基醚,可舉出例如乙二醇二甲基醚、乙二醇二乙基醚、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二丙基醚、二乙二醇二丁基醚、丙二醇二甲基醚、丙二醇二乙基醚、二丙二醇二甲基醚、二丙二醇二乙基醚、丙二醇甲基乙基醚、丙二醇甲基正丙基醚、丙二醇甲基正丁基醚、二丙二醇甲基乙基醚、二丙二醇甲基正丙基醚、二丙二醇甲基正丁基醚等。
作為前述(單、二)烷二醇烷基醚乙酸酯,可舉出例如乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、乙二醇單丙基醚乙酸酯、乙二醇單丁基醚乙酸酯、二乙二醇單甲基醚乙酸酯、二乙二醇單乙基醚乙酸酯、二乙二醇單丙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、丙二醇單丁基醚乙酸酯、二丙二醇單甲基醚乙酸酯、二丙二醇單乙基醚乙酸酯、二丙二醇單丙基醚乙酸酯、二丙二醇單丁基醚乙酸酯等。
作為前述(單、二)烷二醇二乙酸酯,可舉出例如乙二醇二乙酸酯、二乙二醇二乙酸酯、丙二醇二乙酸酯、二丙二醇二乙酸酯等。
作為前述乙酸烷基酯,可舉出例如乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸丁酯等。
作為前述C3-6醇,可舉出例如正丙醇、異丙醇、正丁醇、二級丁醇、三級丁醇、正戊醇、正己醇、2-己醇等。
作為前述C3-6烷二醇,可舉出例如1,3-丁二醇、1,4-丁二醇、1,6-己二醇等。
作為前述C3-6烷二醇單烷基醚,可舉出例如3-甲氧基丁醇等。
作為前述C3-6烷二醇烷基醚乙酸酯,可舉出例如3-甲氧基丁醇乙酸酯等。
作為前述C3-6烷二醇二乙酸酯,可舉出例如1,3-丁二醇二乙酸酯、1,4-丁二醇二乙酸酯、1,6-己二醇二乙酸酯等。
作為前述羥基羧酸酯,可舉出例如乳酸甲酯、乳酸乙酯等。
作為前述羥基羧酸二酯,可舉出例如乳酸甲酯乙酸酯、乳酸乙酯乙酸酯等。
作為前述烷氧基羧酸酯,可舉出例如甲氧基丙酸甲酯、乙氧基丙酸乙酯等。
作為前述環狀酮,可舉出例如4-酮基異佛酮等。
作為前述內酯類,可舉出例如β-丁內酯、γ-丁內酯、ε-己內酯、δ-戊內酯、γ-戊內酯、α-乙醯基-γ-丁內酯等。
作為前述環狀醚,可舉出例如四氫呋喃、四氫呋喃甲醇等。
作為前述醯胺類,可舉出例如二甲基甲醯胺等。
作為前述吡啶類,可舉出例如吡啶、甲基吡啶等。
作為前述芳香族乙酸酯,可舉出例如乙酸苯酯等。
作為前述胺類,可舉出例如二乙胺、三乙胺等。
在本發明中,藉由併用上述溶劑A與溶劑B,即可形成以高濃度含有有機半導體材料,且塗布性、乾燥性、安全性、分散性、溶解性等優良的有機電晶體製造用組成物。
為進一步提升塗布性,併用1種或2種以上選自前述(單、二、三)烷二醇單烷基醚、(單、二)烷二醇二烷基醚、(單、二)烷二醇烷基醚乙酸酯、(單、二)烷二醇二乙酸酯、及烷氧基羧酸酯的溶劑係屬有效。
為進一步提升顏料分散性,併用1種或2種以上選自丙二醇單甲基醚乙酸酯等單C3-6烷二醇烷基醚乙酸酯、及C3-6烷二醇烷基醚乙酸酯的溶劑係屬有效。
為進一步提升染料溶解性,併用1種或2種以上選自丙二醇單甲基醚等單C3-6烷二醇單烷基醚、丙二醇單甲基醚乙酸酯等單C3-6烷二醇烷基醚乙酸酯、C3-6烷二醇單烷基醚、C3-6烷二醇烷基醚乙酸酯、羥基羧酸酯、羥基羧酸二酯、C3-6醇、及C3-6烷二醇的溶劑係屬有效。
為進一步提升環氧樹脂或丙烯酸樹脂的溶解
性,併用1種或2種以上選自(單、二、三)烷二醇單烷基醚、(單、二)烷二醇二烷基醚、(單、二)烷二醇烷基醚乙酸酯、(單、二)烷二醇二乙酸酯、環狀酮、內酯類、環狀醚、醯胺類、吡啶類、芳香族乙酸酯、及胺類的溶劑係屬有效。
為進一步提升乾燥性,併用1種或2種以上選自丙二醇甲基正丙基醚、丙二醇甲基正丁基醚、二丙二醇甲基正丙基醚、二丙二醇甲基正丁基醚等(單、二)C3-6烷二醇C1-2烷基C3-4烷基醚、及乙酸烷基酯的溶劑係屬有效。
併用溶劑A與溶劑B時,其混合比(前者/後者(重量比))為例如95/5~50/50,較佳為95/5~70/30。比起溶劑A,溶劑B的比例較多時,有有機半導體材料的溶解性降低之傾向。此外,組合使用2種以上的溶劑作為溶劑A時為其合計量。就溶劑B而言亦同。
本發明之有機電晶體製造用溶劑由於含有溶劑A,在較低溫度下亦具有高有機半導體材料溶解性。例如,100℃下之具有前述式(1)所示之構成單元的化合物的溶解度,相對於100重量份的有機電晶體製造用溶劑而言為例如0.02重量份以上,較佳為0.03重量份以上,特佳為0.04重量份以上。溶解度的上限為例如5重量份,較佳為3重量份,特佳為2重量份。
(有機半導體材料)
本發明之有機電晶體製造用溶劑為有機半導體材料溶解用之溶劑。作為前述有機半導體材料,不特別限定
,惟在本發明中,下述式(1)所示具有包含可具有取代基之二酮吡咯并吡咯基的構成單元的化合物,在前述構成單元發揮作為受體基之作用、可與供體基藉由供體受體間之分子間電子交互作用所產生的強烈π-堆積作用而秩序良好地形成排列/配向之結構方面係較佳者。作為下述式(1)所示之構成單元的重複數,係為例如2~5000左右。
式(1)中,R3、R4係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基。作為前述C1-24烷基,可舉出例如甲基、乙基、丙基、丁基、戊基、己基、庚基、癸基、十二基、十八
基、二十基等碳數1~24之直鏈狀或支鏈狀烷基。作為前述芳基,可舉出例如苯基等C6-14芳基。作為前述雜芳基,可舉出例如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、2-唑基、2-噻唑基、2-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基、2-苯并呋喃基、2-苯并噻吩基、及2-噻吩并噻吩基等。作為前述基可具有之取代基,可舉出例如羥基、羧基等。
L1、L2係相同或相異,表示選自下述的基:從芳香族碳環或雜芳香族碳環去除2個氫原子之基、伸乙烯基、伸乙炔基、及前述基的2個以上組合而成之2價基。
作為前述芳香族碳環,可舉出例如苯、萘、蒽、菲、稠四苯(tetracene)、(chrysene)、芘、聯伸三苯(triphenylene)、稠五苯等。
作為前述雜芳香族碳環,可舉出例如吡咯、吡啶、呋喃、噻吩、硒吩、咪唑、吡唑、唑、1,3-噻唑、咪唑啉、吡、啉、噻、1,3,4-噻二唑等。
就本發明之L1、L2而言,其中,較佳為選自下述式(L-1)~(L-22)的基。
上述式中,R’係相同或相異,表示選自下述的基:氫原子、可具有取代基之烷基、芳基、雜芳基、烷氧基、硫烷基、三烷基矽基、鹵素原子、氰基、及硝基。當上述式所示之基包含2個以上的R’時,2個以上的R’可相互鍵結而與構成前述基的碳原子共同形成環。
作為前述烷基,表示如甲基、乙基、丙基、丁基、戊基、己基等碳數1~24之直鏈狀或支鏈狀烷基。
作為前述芳基,可舉出例如苯基等C6-14芳基。
作為前述雜芳基,可舉出例如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、2-唑基、2-噻唑基、2-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基、2-苯并呋喃基、2-苯并噻吩基、及2-噻吩并噻吩基等。
作為前述烷氧基,可舉出例如甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、三級丁氧基、戊氧基、己氧基等C1-24烷氧基等。
作為前述硫烷基,可舉出例如硫甲基、硫乙基、硫丙基、硫異丙基、硫丁基、硫異丁基、硫二級丁基、硫三級丁基、硫戊基、硫己基等硫C1-24烷基。
作為前述三烷基矽基,可舉出例如三甲基矽基、三級丁基二甲基矽基、三苯甲基矽基、三苯基矽基等三(C1-24)烷基及/或芳基矽基等。
作為前述鹵素原子,可舉出氟原子、氯原子、溴原子、碘原子等。
作為前述基可具有之取代基,可舉出例如可由保護基保護之羥基、可由保護基保護之羥甲基、可由保護基保護之胺基、可由保護基保護之羧基、可由保護基保護之磺酸基、鹵素原子、側氧基、氰基、硝基、雜環基、烴基、鹵烷基等。前述保護基可使用有機合成領域慣用之保護基。
作為2個以上的R’可相互鍵結而與構成L1、L2的碳原子共同形成的環,可舉出例如環戊烷、環己烷、環庚烷、苯、甲基苯、噻吩、甲基噻吩、呋喃、甲基呋
喃、二氫呋喃、甲基二氫呋喃等。
上述式中,r表示例如1~3之整數。
就具有前述式(1)所示之構成單元的化合物而言,其中,與可具有取代基之二酮吡咯并吡咯基共同具有從噻吩去除2個氫原子之基、及伸乙烯基的有機半導體材料,在藉由供體受體間之分子間電子交互作用所產生的強烈π-堆積作用而秩序良好地形成排列/配向之結構方面係較佳者,可舉出例如具有下述式(1-1)所示之構成單元的化合物。
上述式中,R3~R12係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基。R5與R6、R7與R8、R9與R10、R11與R12可各自相互鍵結而與構成噻吩環的碳原子共同形成環。作為R3~R12中可具有取代基之C1-24烷基、芳基、雜芳基、及構成噻吩環的碳原子共同形成的環,可舉出與上述R’之例同樣的實例。
就本發明之有機半導體材料而言,上述式(1-1)中之R5~R12較佳為氫原子,尤以使用具有下述式(1-1a)及/或下述式(1-1b)所示之構成單元的化合物,在可得高配向性之有機電晶體方面係較佳。
就具有前述式(1)所示之構成單元的化合物的重量平均分子量而言,為例如500萬以下左右,較佳為1000~100萬,特佳為5000~50萬。
[有機電晶體製造用組成物]
本發明之有機電晶體製造用組成物係以包含上述有機半導體材料及有機電晶體製造用溶劑為特徵。
本發明之有機電晶體製造用組成物可藉由例如將上述有機半導體材料、與上述有機電晶體製造用溶劑混合,並在大氣下,於70~150℃左右的溫度加熱約0.1~2小時來調製。
本發明之有機電晶體製造用組成物中之有機半導體材料的含量,例如使用具有前述式(1)所示之構成單元的化合物作為有機半導體材料時,相對於100重量份
的有機電晶體製造用溶劑而言為例如0.02重量份以上,較佳為0.03重量份以上,特佳為0.04重量份以上。上限為例如5重量份,較佳為3重量份,特佳為2重量份。
使用具有前述式(1-1a)及/或(1-1b)所示之構成單元的化合物作為有機半導體材料時(混合使用2種以上時為其總量),相對於100重量份的有機電晶體製造用溶劑而言為例如0.01重量份以上,較佳為0.05重量份以上,再佳為0.1重量份以上,特佳為0.2重量份以上。上限為例如10重量份,較佳為7重量份,特佳為5重量份。
本發明之有機電晶體製造用組成物中之有機電晶體製造用溶劑的含量為例如99.99重量%以下。其下限為例如90.00重量%,較佳為93.00重量%,特佳為95.00重量%;上限較佳為99.95重量%,特佳為99.90重量%。
基於可促進有機半導體材料之自組織化作用所致的結晶化,本發明之有機電晶體製造用組成物所含之有機電晶體製造用溶劑含量,相對於有機半導體材料(例如具有前述式(1)所示之構成單元的化合物)而言,較佳為例如10倍(重量)以上,更佳為13倍(重量)以上,特佳為20倍(重量)以上。上限為例如10000倍(重量),較佳為2000倍(重量),更佳為1000倍(重量),特佳為500倍(重量)。
本發明之有機電晶體製造用組成物中,除上述有機半導體材料與上述有機電晶體製造用溶劑以外,尚可視需求適當摻合一般的有機電晶體製造用組成物所含之成分(例如環氧樹脂、丙烯酸樹脂、纖維素樹脂、丁醛樹脂等)。
本發明之有機電晶體製造用組成物,縱使在較低溫度下亦可溶解有機半導體材料成高濃度。因此,在耐熱性較玻璃基板低,但耐衝擊、輕量且具可撓性的塑膠基板等上亦可直接形成有機電晶體,可形成耐衝擊、輕量且具可撓性的顯示器或電腦機器。又,本發明之有機電晶體製造用組成物由於包含本發明之有機電晶體製造用溶劑,若予塗布於基板上,則有機半導體材料即藉自組織化作用而結晶化,因而可獲得具有高結晶性的有機電晶體。更者,可藉由採印刷法、旋轉塗布法等濕製程的簡便方法容易地形成有機電晶體,可達成本之大幅刪減。
以下,根據實施例對本發明更具體地加以說明,惟本發明非受此等實施例所限定。
實施例1
使用作為有機半導體材料之具有式(1-1a)所示之構成單元的化合物(商品名「PDVT-8」;1-Material(股)製),於20℃環境下,使用作為有機電晶體製造用溶劑之2,3-二氫苯并呋喃(DHBF),調製成有機半導體材料濃度為0.05~0.40重量%的有機電晶體製造用組成物。
對所得有機電晶體製造用組成物在氮氣環境、遮光條件下,於120℃加熱約2小時,以目視確認是否可溶解。此外,就溶解性,係將以目視未確認不溶物的情形評為「○:溶解」、可確認不溶物的情形評為「×:不溶解」。以下亦同。
又,針對完全溶解的有機電晶體製造用組成物,在20℃、氮氣環境、遮光條件下予以靜置,測定析出物出現為止的時間。
實施例2~7、比較例1
除使用表1所示溶劑來替代2,3-二氫苯并呋喃(DHBF)以外,係以與實施例1同樣的方式調製有機電晶體製造用組成物,並評定有機半導體材料的溶解性。
O-DCB:1,2-二氯苯(東京化成工業(股)製)
DHBF:2,3-二氫苯并呋喃(東京化成工業(股)製;分子量:120.15)
CHXME:環己基甲基醚(和光純藥工業(股)製;分子量:114.19)
MANON:2-甲基環己酮(和光純藥工業(股)製;分子量:112.17)
MOB:甲氧基苯(東京化成工業(股)製;分子量:108.14)
DHMDF:2,3-二氫-3-甲基苯并呋喃(東京化成工業(股)製;分子量:134.18)
DMOB:1,2-二甲氧基苯(東京化成工業(股)製;分子量:138.16)
CHA:環己胺(和光純藥工業(股)製;分子量:99.17)
實施例8、比較例2
使用作為有機半導體材料之具有式(1-1b)所示之構成單元的化合物(商品名「PDVT-10」;1-Material(股)製),於20℃環境下,使用表2所示溶劑,調製成有機半導體材料濃度為0.10重量%的有機電晶體製造用組成物。對所得有機電晶體製造用組成物在氮氣環境、遮光條件下,於120℃加熱約2小時,以目視確認是否可溶解。
又,針對完全溶解的有機電晶體製造用組成物,在20℃、氮氣環境、遮光條件下予以靜置,測定析出物出現為止的時間。
O-DCB:1,2-二氯苯(東京化成工業(股)製)
DHBF:2,3-二氫苯并呋喃(東京化成工業(股)製;分子量:120.15)
本發明之有機電晶體製造用溶劑,縱使在較低溫度下亦具有高有機半導體材料溶解性。因此,在耐熱性較玻璃基板低,但耐衝擊、輕量且具可撓性的塑膠基板等上亦可直接形成有機電晶體,可形成耐衝擊、輕
量且具可撓性的顯示器或電腦機器。又,可藉由採印刷法、旋轉塗布法等濕製程的簡便方法容易地製造有機電晶體,可達成本之大幅刪減。
而且,本發明之有機電晶體製造用組成物,若予塗布於基板上,有機半導體材料即藉自組織化作用而結晶化,因此可獲得具有高結晶性的有機電晶體。
Claims (11)
- 一種有機電晶體製造用溶劑,其為有機半導體材料溶解用之溶劑,其包含1種或2種以上的下述式(a)所示之溶劑A;式中,環Z表示選自下述的環:芳香族碳環、5~7員之脂環族碳環、及5~7員之雜環;R1表示選自下述的基:側氧基(=O)、側硫基(thioxy group)(=S)、-ORa基、-SRa基、-O(C=O)Ra基、-RbO(C=O)Ra基、及經取代或未經取代的胺基,其中Ra表示C1-7烷基、或芳基、或前述基經由單鍵或連結基鍵結而成的基,Rb表示C1-7伸烷基、或伸芳基、或前述基經由單鍵或連結基鍵結而成的基;R2表示選自下述的基:氫原子、C1-7烷基、芳基、及-ORa基,其中Ra與前述相同;R1與R2可相互鍵結而與構成環Z的碳原子共同形成環,且,其中該有機半導體材料為具有下述式(1)所示之構成單元的化合物:式中,L1、L2係相同或相異,表示選自下述的基:從芳香族碳環或雜芳香族碳環去除2個氫原子之基、伸乙烯基、伸乙炔基、及前述基的2個以上組合而成之2價基;R3、R4係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;Y1、Y2係相同或相異,表示氧原子或硫原子;p、q係相同或相異,表示0以上之整數,且(p+q)為1以上之整數;p個L1可相同或相異;又,q個L2可相同或相異。
- 如請求項1之有機電晶體製造用溶劑,其中溶劑A為選自2-甲基環戊酮、2-甲基環己酮、環己基甲基醚、環己胺、甲氧基苯、1,2-二甲氧基苯、2,3-二氫苯并呋喃、及2,3-二氫-3-甲基苯并呋喃中的至少1種。
- 如請求項1之有機電晶體製造用溶劑,其中式(1)中之L1、L2係相同或相異,為選自下述式(L-1)~(L-22)的基: 式中,R’係相同或相異,表示選自下述的基:氫原子、可具有取代基之烷基、芳基、雜芳基、烷氧基、硫烷基、三烷基矽基、鹵素原子、氰基、及硝基;當L1、L2包含2個以上的R’時,2個以上的R’可相互鍵結而與構成L1、L2的碳原子共同形成環;r為1~3的整數。
- 如請求項1至3中任一項之有機電晶體製造用溶劑,其中有機半導體材料為具有下述式(1-1)所示之構成單元的化合物:式中,R3~R12係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;R5與R6、R7與R8、R9與R10、R11與R12可各自相互鍵結而與構成噻吩環的碳原子共同形成環。
- 一種有機電晶體製造用組成物,其包含有機半導體材料、及有機電晶體製造用溶劑,其中,該有機半導體材料為具有下述式(1)所示之構成單元的化合物:式中,L1、L2係相同或相異,表示選自下述的基:從芳香族碳環或雜芳香族碳環去除2個氫原子之基、伸乙烯基、伸乙炔基、及前述基的2個以上組合而成之2價基;R3、R4係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;Y1、Y2係相同或相異,表示氧原子或硫原子;p、q係相同或相異,表示0以上之整數,且(p+q)為1以上之整數,該有機電晶體製造用溶劑包含1種或2種以上的下述式(a)所示之溶劑A:式中,環Z表示選自下述的環:芳香族碳環、5~7員之脂環族碳環、及5~7員之雜環;R1表示選自下述的基:側氧基(=O)、側硫基(=S)、-ORa基、-SRa基、-O(C=O)Ra基、-RbO(C=O)Ra基、及經取代或未經取代的胺基,其中Ra表示C1-7烷基、或芳基、或前述基經由單鍵或連結基鍵結而成的基,Rb表示C1-7伸烷基、或伸芳基、或前述基經由單鍵或連結基鍵結而成的基;R2表示選自下述的基:氫原子、C1-7烷基、芳基、及-ORa基,其中Ra與前述相同;R1與R2可相互鍵結而與構成環Z的碳原子共同形成環。
- 如請求項5之有機電晶體製造用組成物,其中式(1)中之L1、L2係相同或相異,為選自下述式(L-1)~(L-22)的基: 式中,R’係相同或相異,表示選自下述的基:氫原子、可具有取代基之烷基、芳基、雜芳基、烷氧基、硫烷基、三烷基矽基、鹵素原子、氰基、及硝基;當L1、L2包含2個以上的R’時,2個以上的R’可相互鍵結而與構成L1、L2的碳原子共同形成環;r為1~3的整數。
- 如請求項5之有機電晶體製造用組成物,其中有機半導體材料為具有下述式(1-1)所示之構成單元的化合物:式中,R3~R12係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;R5與R6、R7與R8、R9與R10、R11與R12可各自相互鍵結而與構成噻吩環的碳原子共同形成環。
- 一種有機電晶體製造用溶劑之作為具有以下述式(1)所示之構成單元的化合物之溶解用溶劑的用途,其中該有機電晶體製造用溶劑包含1種或2種以上的下述式(a)所示之溶劑A;式中,環Z表示選自下述的環:芳香族碳環、5~7員之脂環族碳環、及5~7員之雜環;R1表示選自下述的基:側氧基(=O)、側硫基(=S)、-ORa基、-SRa基、-O(C=O)Ra基、-RbO(C=O)Ra基、及經取代或未經取代的胺基,其中Ra表示C1-7烷基、或芳基、或前述基經由單鍵或連結基鍵結而成的基,Rb表示C1-7伸烷基、或伸芳基、或前述基經由單鍵或連結基鍵結而成的基;R2表示選自下述的基:氫原子、C1-7烷基、芳基、及-ORa基,其中Ra與前述相同;R1與R2可相互鍵結而與構成環Z的碳原子共同形成環;具有以下述式(1)所示之構成單元式中,L1、L2係相同或相異,表示選自下述的基:從芳香族碳環或雜芳香族碳環去除2個氫原子之基、伸乙烯基、伸乙炔基、及前述基的2個以上組合而成之2價基;R3、R4係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;Y1、Y2係相同或相異,表示氧原子或硫原子;p、q係相同或相異,表示0以上之整數,且(p+q)為1以上之整數;p個L1可相同或相異;又,q個L2可相同或相異。
- 如請求項8之溶解用溶劑的用途,其中溶劑A為選自2-甲基環戊酮、2-甲基環己酮、環己基甲基醚、環己胺、甲氧基苯、1,2-二甲氧基苯、2,3-二氫苯并呋喃、及2,3-二氫-3-甲基苯并呋喃中的至少1種。
- 如請求項8之溶解用溶劑的用途,其中式(1)中之L1、L2係相同或相異,為選自下述式(L-1)~(L-22)的基: 式中,R’係相同或相異,表示選自下述的基:氫原子、可具有取代基之烷基、芳基、雜芳基、烷氧基、硫烷基、三烷基矽基、鹵素原子、氰基、及硝基;當L1、L2包含2個以上的R’時,2個以上的R’可相互鍵結而與構成L1、L2的碳原子共同形成環;r為1~3的整數。
- 如請求項8之溶解用溶劑的用途,其中具有以式(1)所示之構成單元之化合物為具有下述式(1-1)所示之構成單元的化合物:式中,R3~R12係相同或相異,表示選自下述的基:氫原子、可具有取代基之C1-24烷基、芳基、及雜芳基;R5與R6、R7與R8、R9與R10、R11與R12可各自相互鍵結而與構成噻吩環的碳原子共同形成環。
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