TWI500615B - An organic semiconductor material containing an perylene tetracarboxylic acid diimide compound and an organic semiconductor element - Google Patents
An organic semiconductor material containing an perylene tetracarboxylic acid diimide compound and an organic semiconductor element Download PDFInfo
- Publication number
- TWI500615B TWI500615B TW100104327A TW100104327A TWI500615B TW I500615 B TWI500615 B TW I500615B TW 100104327 A TW100104327 A TW 100104327A TW 100104327 A TW100104327 A TW 100104327A TW I500615 B TWI500615 B TW I500615B
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- Taiwan
- Prior art keywords
- organic semiconductor
- group
- semiconductor material
- alkyl group
- compound
- Prior art date
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- -1 perylene tetracarboxylic acid diimide compound Chemical class 0.000 title claims description 110
- 239000004065 semiconductor Substances 0.000 title claims description 100
- 239000000463 material Substances 0.000 title claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910000071 diazene Inorganic materials 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052797 bismuth Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 39
- 239000002904 solvent Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- 238000000034 method Methods 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- 239000010408 film Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000000926 separation method Methods 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910021642 ultra pure water Inorganic materials 0.000 description 10
- 239000012498 ultrapure water Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 6
- 229910002113 barium titanate Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 229910052732 germanium Inorganic materials 0.000 description 5
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 3
- UAIJLTSVXNMMEG-UHFFFAOYSA-N 1-butoxybutyl acetate Chemical compound CCCCOC(CCC)OC(C)=O UAIJLTSVXNMMEG-UHFFFAOYSA-N 0.000 description 3
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 3
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 150000004060 quinone imines Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 2
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- QYUJKRHVFFYCRG-UHFFFAOYSA-N 3-butyloctan-1-amine Chemical compound C(CCC)C(CCN)CCCCC QYUJKRHVFFYCRG-UHFFFAOYSA-N 0.000 description 2
- XPFCZYUVICHKDS-UHFFFAOYSA-N 3-methylbutane-1,3-diol Chemical compound CC(C)(O)CCO XPFCZYUVICHKDS-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- GSTSKEDNAQCUTL-UHFFFAOYSA-N 7,9-dihexylpentadecan-8-one Chemical compound CCCCCCC(CCCCCC)C(=O)C(CCCCCC)CCCCCC GSTSKEDNAQCUTL-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OXNYRQCAMIFHEM-UHFFFAOYSA-K C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].[Sr+2].[Ba+2] Chemical compound C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].[Sr+2].[Ba+2] OXNYRQCAMIFHEM-UHFFFAOYSA-K 0.000 description 2
- DUEAGRUAIPIJKL-UHFFFAOYSA-N CCCCCC(CCCC)CC(=O)OC Chemical compound CCCCCC(CCCC)CC(=O)OC DUEAGRUAIPIJKL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- ZVRGTKOYXFVJFA-UHFFFAOYSA-N acetic acid;2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(O)=O.CC(C)COCC(C)C ZVRGTKOYXFVJFA-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 238000000231 atomic layer deposition Methods 0.000 description 2
- 238000003877 atomic layer epitaxy Methods 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229910000420 cerium oxide Inorganic materials 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-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
- 238000001914 filtration Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- WTJKUFMLQFLJOT-UHFFFAOYSA-N heptadecan-9-one Chemical compound CCCCCCCCC(=O)CCCCCCCC WTJKUFMLQFLJOT-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 0.000 description 2
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000000422 delta-lactone group Chemical group 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- NKZSPGSOXYXWQA-UHFFFAOYSA-N dioxido(oxo)titanium;lead(2+) Chemical compound [Pb+2].[O-][Ti]([O-])=O NKZSPGSOXYXWQA-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- HONACFWHXHOMHL-UHFFFAOYSA-N ethyl acetate methyl acetate Chemical compound C(C)(=O)OC.C(C)(=O)OCC.C(C)(=O)OC HONACFWHXHOMHL-UHFFFAOYSA-N 0.000 description 1
- GNJARWZWODMTDR-UHFFFAOYSA-N ethyl dec-2-enoate Chemical compound CCCCCCCC=CC(=O)OCC GNJARWZWODMTDR-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SDAXRHHPNYTELL-UHFFFAOYSA-N heptanenitrile Chemical compound CCCCCCC#N SDAXRHHPNYTELL-UHFFFAOYSA-N 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- HFGPZNIAWCZYJU-UHFFFAOYSA-N lead zirconate titanate Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Zr+4].[Pb+2] HFGPZNIAWCZYJU-UHFFFAOYSA-N 0.000 description 1
- 229910052451 lead zirconate titanate Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- COQAIRYMVBNUKQ-UHFFFAOYSA-J magnesium;barium(2+);tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Mg+2].[Ba+2] COQAIRYMVBNUKQ-UHFFFAOYSA-J 0.000 description 1
- LZFCBBSYZJPPIV-UHFFFAOYSA-M magnesium;hexane;bromide Chemical compound [Mg+2].[Br-].CCCCC[CH2-] LZFCBBSYZJPPIV-UHFFFAOYSA-M 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- KICUISADAVMYCJ-UHFFFAOYSA-N methyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC KICUISADAVMYCJ-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- CJBQSBZJDJHMLF-UHFFFAOYSA-N methyl oct-2-enoate Chemical compound CCCCCC=CC(=O)OC CJBQSBZJDJHMLF-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
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- 238000001451 molecular beam epitaxy Methods 0.000 description 1
- DMEKUKDWAIXWSL-UHFFFAOYSA-N n,n-dimethyl-7-nitro-9h-fluoren-2-amine Chemical compound [O-][N+](=O)C1=CC=C2C3=CC=C(N(C)C)C=C3CC2=C1 DMEKUKDWAIXWSL-UHFFFAOYSA-N 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 229910000510 noble metal Inorganic materials 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- BTNXBLUGMAMSSH-UHFFFAOYSA-N octanedinitrile Chemical compound N#CCCCCCCC#N BTNXBLUGMAMSSH-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KWJPCZGVGLPKMD-UHFFFAOYSA-N propan-2-yl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(C)C KWJPCZGVGLPKMD-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical group 0.000 description 1
- 231100000701 toxic element Toxicity 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 229940036248 turpentine Drugs 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
- 239000013585 weight reducing agent Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
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Description
本發明係關於一種包含具有特定結構之苝四羧酸二醯亞胺化合物的有機半導體材料。本發明之有機半導體材料尤其適合於有機薄膜電晶體(OFET)元件中之有機半導體層之形成。
先前,電子裝置所使用之有機電致發光元件、光電轉換元件、有機薄膜電晶體(OFET)元件等半導體元件一直採用無機化合物。然而,使用無機化合物之半導體亦存在製造製程昂貴,難以大面積化,環境負擔較大等問題。
近年來,業界發現了可用於半導體之有機分子,其可期待廉價之製造製程(無需低溫下之製膜化或稀有元素)、元件之輕量化、材料之多樣性、大面積化/薄型化、環境負擔之減低(例如不含具有毒性之元素)、高積體化等,目前業界正積極進行研究。
對於OFET所使用之材料,要求較高之載子遷移率(元件之高性能化)與優異之溶解性(塗佈製程之容易性),存在難以兼具兩者之問題。
專利文獻1~3中揭示有苝四羧酸二醯亞胺衍生物。專利文獻4~7中揭示有具有支鏈烷基鏈之苝四羧酸二醯亞胺化合物。
專利文獻1:美國專利第4431806號說明書
專利文獻2:美國專利第4667036號說明書
專利文獻3:美國專利申請公開第2003/181721號說明書
專利文獻4:日本專利特開平06-032789號公報
專利文獻5:國際公開第2008/091670號
專利文獻6:國際公開第2007/093643號
專利文獻7:國際公開第2008/063609號
因此,本發明之目的在於提供一種具有優異之溶解性且可表現出高載子遷移率之有機半導體材料、以及使用其之有機半導體層及有機半導體元件。
本發明者反覆進行努力研究,結果發現:具有特定結構之苝四羧酸二醯亞胺化合物具有優異之溶解性,包含該苝四羧酸二醯亞胺化合物之有機半導體材料適合於塗佈製程。並且,本發明者進一步進行研究,結果得知該有機半導體材料顯示出高載子遷移率,且得知藉由使用該有機半導體材料來製造有機半導體元件,可實現上述目的。
本發明係基於上述知識見解研究而成者,其係提供含有至少一種下述通式(I)所表示之苝羧酸二醯亞胺化合物的有機半導體材料者。
(式中,R1
及R1'
表示氫原子、碳原子數1~30之未經取代之烷基或碳原子數1~30之經取代之烷基,該未經取代之烷基及該置換烷基中之亞甲基亦可表示-CH=CH-或-C≡C-;該經取代之烷基之取代基為烷氧基、烷硫基、芳基、芳氧基、芳硫基、雜環基、醯基、醯氧基、胺基、磺醯胺基、磺醯基、羧基、氰基、磺基、羥基、硝基、巰基、醯亞胺基、胺甲醯基、乙烯基、(甲基)丙烯醯基、環氧基或鹵素原子,於為具有碳原子之取代基之情形時,含有該取代基之R1
及R1'
所表示之基之總碳原子數為30以下)
又,本發明提供一種將上述有機半導體材料製膜而成之有機半導體層。
又,本發明提供一種具有至少一層上述有機半導體層之有機半導體元件。
根據本發明,可提供一種具有優異之溶解性且可表現出高載子遷移率之有機半導體材料。若使用本發明之有機半導體材料,則藉由優異之溶解性可使半導體製造中之塗佈製程變得容易,且藉由高載子遷移率可實現元件之高性能化。
以下,基於較佳實施形態,詳細地說明包含至少一種本發明之苝四羧酸二醯亞胺化合物的有機半導體材料、有機半導體層、及有機半導體元件。
本發明之有機半導體材料所使用之苝四羧酸二醯亞胺化合物係上述通式(I)所表示之化合物,苝骨架上無取代基,且溶解性優異。上述通式(I)中,R1
與R1'
可相同,亦可相互不同。
上述通式(I)中之R1
、R1'
所表示之碳原子數1~30之未經取代之烷基可為直鏈烷基,亦可為支鏈烷基,又,亦可為環狀烷基。作為該未經取代之烷基之具體例,可列舉:甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基、己基、庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、正壬基、正癸基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、1-乙基己基、2-乙基己基、3-乙基己基、1-丁基辛基、2-丁基辛基、3-丁基辛基、1-己基癸基、2-己基癸基、3-己基癸基、1-癸基十四烷基、2-癸基十四烷基、3-癸基十四烷基、環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基等。該等中,較佳為1-乙基己基、2-乙基己基、3-乙基己基、1-丁基辛基、2-丁基辛基、3-丁基辛基、1-己基癸基、2-己基癸基、3-己基癸基、1-癸基十四烷基、2-癸基十四烷基、3-癸基十四烷基等支鏈烷基。
作為上述通式(I)中之R1
、R1'
所表示之碳原子數1~30之經取代之烷基,可列舉對上述未經取代之烷基進行取代而成的基。作為取代上述未經取代之烷基的取代基,例如可列舉:甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基、異丁氧基、戊氧基、異戊氧基、第三戊氧基、己氧基、環己氧基、庚氧基、異庚氧基、第三庚氧基、正辛氧基、異辛氧基、第三辛氧基、2-乙基己氧基、壬氧基、癸氧基等烷氧基;甲硫基、乙硫基、丙硫基、異丙硫基、丁硫基、第二丁硫基、第三丁硫基、異丁硫基、戊硫基、異戊硫基、第三戊硫基、己硫基、環己硫基、庚硫基、異庚硫基、第三庚硫基、正辛硫基、異辛硫基、第三辛硫基、2-乙基己硫基等烷硫基;苯基、萘基等芳基;苯氧基、萘氧基等芳氧基;苯硫基、萘硫基等芳硫基;吡啶基、嘧啶基、噠基、哌啶基、吡喃基、吡唑基、三基、吡咯基、喹啉基、異喹啉基、咪唑基、苯并咪唑基、三唑基、呋喃基(furyl)、呋喃基(furanyl)、苯并呋喃基、噻吩基、苯硫基、苯并苯硫基、噻二唑基、噻唑基、苯并噻唑基、唑基、苯并唑基、異噻唑基、異唑基、吲哚基、2-吡咯啶酮-1-基、2-哌啶酮-1-基、2,4-二羥基咪唑啶-3-基、2,4-二羥基唑啶-3-基等雜環基;乙醯基、2-氯乙醯基、丙醯基、辛醯基、丙烯醯基、甲基丙烯醯基、苯基羰基(苯甲醯基)、鄰苯二甲醯基、4-三氟甲基苯甲醯基、三甲基乙醯基、水楊醯基、草醯基、硬脂醯基、甲氧羰基、乙氧羰基、第三丁氧羰基、正十八烷氧羰基、胺甲醯基等醯基;乙醯氧基、苯甲醯氧基等醯氧基;胺基、乙基胺基、二甲基胺基、二乙基胺基、丁基胺基、環戊基胺基、2-乙基己胺基、十二烷基胺基、苯胺基、氯苯基胺基、甲苯胺基、甲氧苯胺基、N-甲基苯胺基、二苯基胺基、萘基胺基、2-吡啶基胺基、甲氧羰基胺基、苯氧羰基胺基、乙醯基胺基、苯甲醯基胺基、甲醯基胺基、三甲基乙醯基胺基、月桂醯基胺基、胺甲醯基胺基、N,N-二甲基胺基羰基胺基、N,N-二乙基胺基羰基胺基、啉基羰基胺基、甲氧羰基胺基、乙氧羰基胺基、第三丁氧羰基胺基、正十八烷氧羰基胺基、N-甲基-甲氧羰基胺基、苯氧羰基胺基、胺磺醯基胺基、N,N-二甲基胺基磺醯基胺基、甲基磺醯基胺基、丁基磺醯基胺基、苯基磺醯基胺基等可經取代之胺基;氟、氯、溴、碘等鹵素原子;磺醯胺基、磺醯基、羧基、氰基、磺基、羥基、硝基、巰基、醯亞胺基、胺甲醯基、乙烯基、丙烯醯基、甲基丙烯醯基、環氧基,較佳為鹵素原子。再者,於以具有碳原子之取代基取代之情形時,含有該取代基之R1
、R1'
所表示之基之總碳原子數滿足30以下之範圍。又,於為經取代之烷基之情形時,較佳為具有支鏈結構之基。
上述通式(I)所表示之苝四羧酸二醯亞胺化合物中,較佳為R1
為下述通式(II)~(IV)中之任一者所表示之烷基且R1'
為下述通式(II')~(IV')中之任一者所表示之烷基的化合物。進而,就原料容易獲得方面而言,更佳為下述通式(II)~(IV)中之Ra
及Rb
以及下述通式(II')~(IV')中之Ra'
及Rb'
不具有取代基者。
又,上述通式(I)中之R1
及/或R1'
為經1個以上之氟原子取代之烷基的化合物,由於製成有機半導體元件時元件於空氣中之穩定性較高,故而較佳。
又,上述通式(I)中之R1
及R1'
之碳原子數為10~30、尤其是10~25之化合物,由於製成有機半導體元件時載子遷移率尤其優異,故而較佳。
又,就提高結晶性與增大分子間相互作用之觀點而言,較佳為上述通式(I)中之R1
及R1'
為未經取代之烷基的化合物。
(式中,Ra
、Rb
、Ra'
及Rb'
表示氫原子、碳原子數1~27之未經取代之烷基或碳原子數1~27之經取代之烷基,該未經取代之烷基及該經取代之烷基中之亞甲基亦可表示-CH=CH-或-C≡C-;該經取代之烷基之取代基與通式(I)中之取代基相同;其中,通式(II)~(IV)及(II')~(IV')所表示之烷基之總碳原子數為30以下)
作為上述通式(I)所表示之本發明所使用之苝四羧酸二醯亞胺化合物之具體例,可列舉下述化合物No.1~No.26,但並不限定於該等化合物。
上述通式(I)所表示之苝四羧酸二醯亞胺化合物之製造方法無任何限制,可藉由利用眾所周知之一般反應的方法而獲得。例如可如下述反應路徑般,藉由苝四羧酸二酐與胺之反應而製造。
本發明之有機半導體材料含有至少一種上述苝四羧酸二醯亞胺化合物即可。即,本發明之有機半導體材料可僅包含一種或兩種以上之上述苝四羧酸二醯亞胺化合物,亦可除上述苝四羧酸二醯亞胺化合物以外,視需要含有一種或兩種以上之溶劑等。
作為上述溶劑,並無特別限制,例如可列舉:水、醇系溶劑、二醇系溶劑、酮系溶劑、酯系溶劑、醚系溶劑、脂肪族或脂環族烴系溶劑、芳香族烴系溶劑、具有氰基之烴溶劑、鹵化烴系溶劑、其他溶劑等。
作為上述醇系溶劑,可列舉:甲醇、乙醇、丙醇、異丙醇、1-丁醇、異丁醇、2-丁醇、第三丁醇、戊醇、異戊醇、2-戊醇、新戊醇、第三戊醇、己醇、2-己醇、庚醇、2-庚醇、辛醇、2-乙基己醇、2-辛醇、環戊醇、環己醇、環庚醇、甲基環戊醇、甲基環己醇、甲基環庚醇、苄醇、乙二醇單甲基醚、乙二醇單乙基醚、丙二醇單甲基醚、丙二醇單乙基醚、二乙二醇單甲基醚、二乙二醇單乙基醚、三乙二醇單甲基醚、三乙二醇單乙基醚、2-(N,N-二甲基胺基)乙醇、3-(N,N-二甲基胺基)丙醇等。
作為上述二醇系溶劑,可列舉:乙二醇、丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、1,5-戊二醇、新戊二醇、異戊二醇(3-甲基-1,3-丁二醇)、1,2-己二醇、1,6-己二醇、3-甲基-1,5-戊二醇、1,2-辛二醇、辛二醇(2-乙基-1,3-己二醇)、2-丁基-2-乙基-1,3-丙二醇、2,5-二甲基-2,5-己二醇、1,2-環己二醇、1,4-環己二醇、1,4-環己二甲醇等。
作為上述酮系溶劑,可列舉:丙酮、乙基甲基酮、甲基異丙基酮、甲基丁基酮、甲基異丁基酮、甲基戊基酮、甲基己基酮、乙基丁基酮、二乙基酮、二丙基酮、二異丁基酮、甲基戊基酮、環己酮、甲基環己酮等。
作為上述酯系溶劑,甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯、乙酸異丙酯、乙酸丁酯、乙酸異丁酯、乙酸第二丁酯、乙酸第三丁酯、乙酸戊酯、乙酸異戊酯、乙酸第三戊酯、乙酸苯酯、丙酸甲酯、丙酸乙酯、丙酸異丙酯、丙酸丁酯、丙酸異丁酯、丙酸第二丁酯、丙酸第三丁酯、丙酸戊酯、丙酸異戊酯、丙酸第三戊酯、丙酸苯酯、2-乙基己酸甲酯、2-乙基己酸乙酯、2-乙基己酸丙酯、2-乙基己酸異丙酯、2-乙基己酸丁酯、乳酸甲酯、乳酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸甲酯、甲氧基丙酸乙酯、乙氧基丙酸乙酯、乙二醇單甲基醚乙酸酯、二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、乙二醇單異丙基醚乙酸酯、乙二醇單丁基醚乙酸酯、乙二醇單第二丁基醚乙酸酯、乙二醇單異丁基醚乙酸酯、乙二醇單第三丁基醚乙酸酯、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、丙二醇單異丙基醚乙酸酯、丙二醇單丁基醚乙酸酯、丙二醇單第二丁基醚乙酸酯、丙二醇單異丁基醚乙酸酯、丙二醇單第三丁基醚乙酸酯、丁二醇單甲基醚乙酸酯、丁二醇單乙基醚乙酸酯、丁二醇單丙基醚乙酸酯、丁二醇單異丙基醚乙酸酯、丁二醇單丁基醚乙酸酯、丁二醇單第二丁基醚乙酸酯、丁二醇單異丁基醚乙酸酯、丁二醇單第三丁基醚乙酸酯、乙醯乙酸甲酯、乙醯乙酸乙酯、丁酮酸甲酯、丁酮酸乙酯、γ-內酯、丙二酸二甲酯、琥珀酸二甲酯、丙二醇二乙酸酯、δ-內酯等。
作為上述醚系溶劑,可列舉:四氫呋喃、四氫吡喃、味啉、乙二醇二甲基醚、二乙二醇二甲基醚、二丙二醇二甲基醚、三乙二醇二甲基醚、二丁基醚、二乙基醚、二烷等。
作為上述脂肪族或脂環族烴系溶劑,可列舉:戊烷、己烷、環己烷、甲基環己烷、二甲基環己烷、乙基環己烷、庚烷、辛烷、十氫萘、溶劑石油腦、松節油、D-檸檬烯、蒎烯、礦油精、Swazol#310(Cosmo Matsuyama Oil(股份))、Solvesso#100(Exon Chemical(股份))等。
作為上述芳香族烴系溶劑,可列舉:苯、甲苯、乙苯、二甲苯、均三甲苯、二乙苯、異丙苯、異丁苯、異丙基甲苯、萘滿等。
作為上述具有氰基之烴溶劑,可列舉:乙腈、1-氰基丙烷、1-氰基丁烷、1-氰基己烷、氰基環己烷、氰基苯、1,3-二氰基丙烷、1,4-二氰基丁烷、1,6-二氰基己烷、1,4-二氰基環己烷、1,4-二氰基苯等。
作為上述鹵化烴系溶劑,可列舉:四氯化碳、氯仿、二氯甲烷、三氯乙烯、氯苯、二氯苯、三氯苯等。
作為上述其他有機溶劑,可列舉:N-甲基-2-吡咯啶酮、二甲基亞碸、二甲基甲醯胺、苯胺、三乙胺、吡啶、二硫化碳等。
該等中,作為較佳溶劑,可列舉:氯仿、二氯甲烷、甲苯、二甲苯、均三甲苯、四氫呋喃、四氫吡喃、氯苯、二氯苯、三氯苯等。
於使本發明之有機半導體材料含有上述溶劑之情形時,其含量只要不妨礙使用該有機半導體材料之有機半導體層之形成,則無特別限制,例如相對於上述通式(I)所表示之苝羧酸二醯亞胺化合物100質量份,可自100質量份以上之範圍適宜選擇,理想為自500~1000000質量份之範圍選擇。然而,上述苝羧酸二醯亞胺化合物由於溶解性較高,故而即使溶劑之含量相對少量,亦可製成塗佈性良好且有機半導體層之製作效率良好的有機半導體材料。就該觀點而言,上述溶劑之含量相對於上述通式(I)所表示之苝羧酸二醯亞胺化合物100質量份,較佳為自100~100000質量份之範圍選擇,更佳為自7000~20000質量份之範圍選擇。
本發明之有機半導體材料中,進而可無特別限制地使用可用於形成有機半導體元件中之有機半導體層的成分作為任意成分。作為該任意成分之例子,可列舉金屬氧化物等。於含有該等任意成分之情形時,該等任意成分之含量並無特別限制,就無損有機半導體層之功能的觀點而言,相對於上述通式(I)所表示之苝羧酸二醯亞胺化合物100質量份,較佳為設為30質量份以下之範圍。
本發明之有機半導體材料可用於形成有機電致發光元件、光電轉換元件、有機薄膜電晶體(OFET)元件等半導體元件中之有機半導體層。
本發明之有機半導體層係將本發明之有機半導體材料製膜而成的薄膜。本發明之有機半導體層除了使用本發明之有機半導體材料來形成以外,其餘可與先前之有機半導體層相同。本發明之有機半導體層之形成通常於支持體上進行。本發明之有機半導體層可為形成於支持體上之狀態,又,亦可任意地拆除支持體而製成有機半導體層之單獨層。再者,於本發明之有機半導體材料含有上述溶劑之情形時,本發明之有機半導體層係經過去除溶劑之步驟而成的層。
作為本發明之有機半導體層之製造方法,例如可列舉藉由如下製程於支持體上形成塗膜的方法:蒸鍍法、物理氣相沈積法(PVD)、化學氣相沈積法(CVD)、原子層沈積法(ALD)、原子層磊晶法(ALE)、分子束磊晶法(MBE)、氣相磊晶法(VPE)、濺鍍法、電漿聚合法等乾式製程;浸漬塗佈法、澆鑄法、氣刀塗佈法、淋幕式塗佈法、輥塗法、線棒塗佈法、凹版印刷塗佈法、旋轉塗佈法、蘭慕爾-布羅吉法(Langmuir Blodgett method)、印刷法、噴墨法或者擠壓塗佈法等濕式製程。旋轉塗佈法、澆鑄法、浸漬塗佈法、噴墨法、印刷法等由於可簡便地製造有機半導體層,故而較佳。
再者,上述乾式製程中,可適宜地使用上述通式(I)所表示之苝羧酸二醯亞胺化合物本身或將該化合物溶解或者分散至上述溶劑中而成的溶液形態之本發明之有機半導體材料。上述濕式製程中,可使用上述溶液形態之本發明之有機半導體材料。
本發明之有機半導體層之膜厚並無特別限制,一般為1 nm~100 μm,更佳為1 nm~500 nm。於膜厚小於1 nm之情形時,膜上容易產生缺陷,於大於100 μm之情形時,漏電流會增加,因而欠佳。
本發明之有機半導體層可藉由常法進行摻雜處理,亦可於有機半導體層之形成時或形成後導入摻雜劑。
作為上述摻雜劑,可列舉:鹼金屬、鹼土金屬、稀土金屬、金屬氧化物、銨離子、鏻離子等施體性摻雜劑,鹵素化合物、過渡金屬化合物、電解質陰離子等受體性摻雜劑。
作為上述支持體,並無特別限定,例如可列舉:玻璃、樹脂基板、石英、單晶矽、多晶矽、非晶矽等。
本發明之有機半導體元件只要具有至少一層本發明之有機半導體層,則無特別限定,除此方面以外,其餘可與先前之有機半導體元件相同。將本發明之有機半導體元件之構成例以剖面圖之形式示於圖1及圖2。
圖1(a)表示下閘極-上接觸型,圖1(b)表示下閘極-下接觸型,圖1(c)及(d)表示上閘極-下接觸型,圖1(e)及(f)表示下閘極-上/下接觸型,圖1(g)表示垂直型靜電感應電晶體(SIT:Static Induction Transistor)。圖2係圖1(a)之下閘極-上接觸型之變形例。圖1及圖2中,11為本發明之有機半導體層。
作為閘電極15,鉑、金、銀等貴金屬材料;銅、鋁等金屬材料;碳等導電性材料;ITO、氧化錫、摻雜有氟之氧化錫等透明導電材料;經摻雜處理之導電性聚合物;經高濃度負型摻雜之矽晶圓、經高濃度正型摻雜之矽晶圓等,該等可單獨使用,亦可併用複數種。閘電極15層之厚度並無特別限定,較佳為500 nm以下,更佳為100 nm以下。
作為絕緣層14,可使用各種絕緣膜,例如可列舉:氧化矽、氧化鋁、鈦酸鋇鍶、鋯酸鈦酸鋇、鋯酸鈦酸鉛、鈦酸鉛鑭、鈦酸鍶、鈦酸鋇、氟化鋇鎂、鈦酸鉍、鈦酸鍶鉍、氧化鉭、鉭酸鍶鉍、鉭酸鈮酸鉍、氧化鈦、氧化釔、氮化矽、氮化鋁等。絕緣層14之厚度並無特別限定,較佳為500 nm以下,更佳為300 nm以下。絕緣層14較佳為薄膜,尤佳為厚度為100 nm以下。再者,12為汲電極,13為源電極,16為基板。
以下,藉由合成例、實施例及比較例進一步詳細地說明本發明。然而,本發明並不受以下實施例等之任何限制。又,以下之實施例中,實施例5~7為參考例。
合成例1~合成例8係本發明之有機半導體材料所使用之苝四羧酸二醯亞胺化合物之合成例。於實施例1~8及比較例1~3中,係使用合成例1~8中所獲得之化合物或比較化合物來製備溶液狀之有機半導體材料,使用該有機半導體材料製作有機半導體層及有機半導體元件,並對元件進行評價。
(步驟1)向含有2-乙基-1-己醇13.0g(100.0mmol)、吡啶45ml之溶液中,於冰浴冷卻下添加對甲苯磺醯氯22.8g(120.0mmol),於同溫度下反應1小時。添加鹽酸、甲苯進行油水分離,並萃取有機層。進而利用超純水清洗該萃取液,添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,藉由矽膠管柱層析法純化所獲得之殘渣(展開溶劑:己烷-乙酸乙酯),以68%之產率獲得甲苯磺醯體(淡黃色透明油狀物)。
(步驟2)添加上述甲苯磺醯體19.3g(68.0mmol)、二甲基甲醯胺57ml、鄰苯二甲醯亞胺鉀13.9g(74.8mmol),升溫至120℃並反應3小時。添加超純水、甲苯進行油水分離,並萃取有機層。進而再次萃取水層後,同樣地進行清洗,向合併之有機層中添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,藉由矽膠管柱層析法純化所獲得之殘渣(展開溶劑:己烷-乙酸乙酯),以64%之產率獲得作為鄰苯二甲醯亞胺體之無色透明油狀物質。
(步驟3)向含有上述鄰苯二甲醯亞胺體11.3g(44.0mmol)、甲醇220ml之溶液中滴加肼一水合物10.4g(131.0 mmol)。將反應溫度升溫至80℃後,反應2小時,添加氯仿、10%氫氧化鉀水溶液進行油水分離,並萃取有機層。再次萃取水層後,與有機層合併,進而利用10%氫氧化鉀水溶液清洗該萃取液,添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,以99%之產率獲得作為2-乙基-1-己胺之無色透明油狀物質。該2-乙基-1-己胺不進行純化而用於下一步驟之反應。
(步驟4)於氮氣環境下,添加苝四羧酸二酐500 mg(1.3 mmol)、正丁醇/超純水36 ml(體積比=1/1),超音波照射15分鐘。向該溶液中添加步驟3中所獲得之2-乙基-1-己胺1.5 g(6.4 mmol),於90℃下反應8小時。冷卻至室溫,添加濃鹽酸及甲苯進行油水分離。利用超純水清洗有機層後,利用硫酸鎂進行乾燥,並進行過濾、減壓濃縮,藉由矽膠管柱層析法進行純化(展開溶劑:甲苯),獲得紅色結晶630 mg(產率:59%)。藉由1
H-NMR確認紅色結晶係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.68(4H,d,J=7.9 Hz),8.61(4H,d,J=7.9 Hz),4.16(4H,dq,J=22.1,6.7 Hz),1.98(2H,s),1.43-1.33(16H,m),0.93(12H,dt,J=25.0,7.3 Hz)
除了將合成例1之步驟1中所使用之2-乙基-1-己醇變更為2-丁基-1-辛醇以外,藉由與合成例1相同之手法獲得紅色結晶400 mg(步驟4之產率:57%)。藉由1
H-NMR確認紅色結晶係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.67(8H,dd,J=23.2,7.9 Hz),4.15(4H,d,J=7.3 Hz),2.02(2H,s),1.30(36H,m),0.90-0.83(12H,m)
除了將合成例1之步驟1中所使用之2-乙基-1-己醇變更為2-己基-1-癸醇以外,藉由與合成例1相同之手法獲得紅色結晶630 mg(步驟4之產率:47%)。藉由1
H-NMR確認紅色結晶係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.67(4H,d,J=8.5 Hz),8.60(4H,d,J=7.9 Hz),4.15(4H,d,J=7.3 Hz),2.02(2H,s),1.31(50H,dd,J=48.8,15.9 Hz),0.86-0.83(12H,m)
(步驟1)於氮氣環境下,向含有溴化銅546 mg(3.8 mmol)、氯化鋰322 mg(7.6 mmol)、四氫呋喃70 ml之溶液中,於冰浴冷卻下添加辛烯酸甲酯5.9 g(38.0 mmol)、三甲基氯矽烷4.5 g(41.2 mmol),進而滴加丁基溴化鎂25.5 ml(51.0 mmol,四氫呋喃溶液,2 mol/L),於同溫度下反應1小時。添加氯化銨水溶液、己烷、乙酸乙酯進行油水分離,並萃取有機層。進而利用氯化鈉清洗該萃取液,添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,藉由矽膠管柱層析法純化所獲得之殘渣(展開溶劑:己烷-乙酸乙酯),以99%之產率獲得3-丁基辛烷酸甲酯(淡黃色透明油狀物)。
(步驟2)於氮氣環境下,添加氫化鋁鋰2.7 g(70.0 mmol)、四氫呋喃69 ml,滴加上述3-丁基辛烷酸甲酯7.5 g(35.0 mmol)之四氫呋喃(25 ml)溶液,升溫至90℃並反應5小時。添加硫酸鈉、四氫呋喃,攪拌30分鐘,過濾後利用四氫呋喃清洗殘渣。向合併之有機層中添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,以99%之產率獲得醇體(淡黃色透明油狀物質)。該醇體不進行純化而用於下一步驟之反應。
(步驟3)向含有上述醇體6.2 g(33.3 mmol)、吡啶15 ml之溶液中,於冰浴冷卻下添加對甲苯磺醯氯7.6 g(40.0 mmol),於同溫度下反應1小時。添加鹽酸、甲苯進行油水分離,並萃取有機層。進而利用超純水清洗該萃取液,添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,藉由矽膠管柱層析法純化所獲得之殘渣(展開溶劑:己烷-乙酸乙酯),以56%之產率獲得甲苯磺醯體(淡黃色透明油狀物)。
(步驟4)添加上述甲苯磺醯體6.1 g(18.0 mmol)、二甲基甲醯胺14 ml、鄰苯二甲醯亞胺鉀4.0 g(21.6 mmol),升溫至150℃並反應3小時。添加超純水、甲苯進行油水分離,並萃取有機層。進而再次萃取水層後,同樣地進行清洗,向合併之有機層中添加硫酸鎂使之乾燥,繼而進行過濾、減壓濃縮,藉由矽膠管柱層析法純化所獲得之殘渣(展開溶劑:己烷-乙酸乙酯),以93%之產率獲得作為鄰苯二甲醯亞胺體之無色透明油狀物質。
(步驟5)向含有上述鄰苯二甲醯亞胺體5.1 g(16.4 mmol)、甲醇80 ml之溶液中滴加胼一水合物2.5 g(49.3 mmol)。將反應溫度升溫至100℃後,反應2小時,添加氯仿、10%氫氧化鉀水溶液進行油水分離,並萃取有機層。再次萃取水層後,與有機層合併,進而利用10%氫氧化鉀水溶液清洗該萃取液,添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,以88%之產率獲得作為3-丁基辛基胺之無色透明油狀物質。該3-丁基辛基胺不進行純化而用於下一步驟之反應。
(步驟6)添加苝四羧酸二酐1.0 g(2.6 mmol)、乙酸鋅370 mg(2.0 mmol)、咪唑10.4 g(153.0 mmol)及步驟5中所獲得之3-丁基辛基胺1.2 g(6.4 mmol),於160℃下反應2小時。冷卻至室溫,添加氯仿,藉由矽膠管柱層析法進行純化(展開溶劑:己烷-丙酮),獲得紅色結晶260 mg(產率:14%)。藉由1
H-NMR確認紅色結晶係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.62(4H,dd,J=7.9,2.4 Hz),8.52(4H,d,J=7.9 Hz),4.19-4.15(4H,m),1.71-1.65(2H,m),1.49-1.48(4H,m),1.37-1.24(28H,m),0.93-0.85(12H,m)
(步驟1)使含有7-十三烷酮3.2 g(16.0 mmol)、羥胺鹽酸鹽2.2 g(32.0 mmol)、乙醇46 ml、吡啶23 ml之溶液於70℃下反應2小時。添加鹽酸、己烷進行油水分離,並萃取有機層。進而利用鹽酸、超純水清洗該萃取液,添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,以86%之產率獲得酮肟體(淡黃色透明油狀物)。該酮肟體不進行純化而用於下一步驟之反應。
(步驟2)於氮氣環境下,添加上述酮肟體2.9 g(14.0 mmol)、甲苯91 ml,並滴加雙(2-甲氧基乙氧基)氫化鋁鈉9.5 ml(34 mmol),升溫至100℃並反應2小時。添加超純水、己烷進行油水分離,並萃取有機層。進而,利用5%氫氧化鈉水溶液清洗該有機層,添加硫酸鎂使之乾燥後,進行過濾、減壓濃縮,以88%之產率獲得作為胺體(1-己基庚基胺)之無色透明油狀物質。該胺體不進行純化而用於下一步驟之反應。
(步驟3)添加苝四羧酸二酐1.0 g(2.5 mmol)、乙酸鋅370 mg(2.0 mmol)、咪唑5.2 g(76.5 mmol)及步驟2中所獲得之1-己基庚基胺1.3 g(6.4 mmol),於160℃下反應2小時。冷卻至室溫,添加氯仿,藉由矽膠管柱層析法進行純化(展開溶劑:己烷-甲苯),獲得紅色結晶1.2 g(產率:63%)。藉由1
H-NMR確認紅色結晶係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.66-8.63(8H,m),5.21-5.13(2H,m),2.25-2.20(4H,m),1.84-182(4H,m),1.34-1.20(32H,m),0.81(12H,t,J=6.7 Hz)
除了將合成例5之步驟1中所使用之7-十三烷酮變更為9-十七烷酮以外,藉由與合成例5相同之手法獲得紅色固體1.6 g(步驟3之產率:72%)。藉由1
H-NMR確認紅色固體係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.61-8.58(8H,m),5.16-5.09(2H,m),2.20-2.16(4H,m),1.80-178(4H,m),1.26-1.15(48H,m),0.72(6H,t,J=6.7 Hz)
除了將合成例4之步驟1中所使用之辛烯酸甲酯與丁基溴化鎂變更為癸烯酸乙酯與己基溴化鎂以外,藉由與合成例4相同之手法獲得紅色結晶400 mg(步驟6之產率:97%)。藉由1
H-NMR確認紅色結晶係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.62(4H,d,J=7.9 Hz),8.54(4H,d,J=7.9 Hz),4.20-4.15(4H,m),1.71-1.65(2H,m),1.53-1.49(4H,m),1.35-1.28(44H,m),0.88-0.85(12H,m)
於氮氣環境下,添加苝四羧酸二酐500 mg(1.3 mmol)、正丁醇/超純水25 ml(體積比=1/1),並超音波照射15分鐘。向該溶液中添加合成例3之步驟3中所獲得之2-己基-1-癸基胺616 mg(2.6 mmol)、1-十三烷基胺508 mg(2.6 mmol),於90℃下反應3小時。冷卻至室溫,添加濃鹽酸及甲苯進行油水分離。利用超純水清洗有機層後,利用硫酸鎂進行乾燥,進行過濾、減壓濃縮,藉由矽膠管柱層析法進行純化(展開溶劑:甲苯-甲醇),獲得紫紅色結晶331 mg(產率:42%)。藉由1
H-NMR確認紫紅色結晶係目標物。結果如下。
1
H-NMR(CDCl3
)δ:8.69(4H,dd,J=7.9,1.2 Hz),8.62(4H,d,J=7.9 Hz),4.21(2H,t,J=7.6 Hz),4.15(2H,d,J=7.3 Hz),2.03-2.01(1H,m),1.80-1.73(2H,m),1.39-1.30(44H,m),0.89-0.82(9H,m)
以相對於氯仿1 ml而為7 mg之比例溶解化合物No.1,獲得溶液狀之有機半導體材料。使用該有機半導體材料,按照以下順序製作具有圖2所示之層構成的有機薄膜電晶體(OTFT)元件。
對形成有厚度300 nm之矽酸化膜(絕緣層14)之負型摻雜矽基板(基板16、閘電極15)進行UV臭氧處理後,利用六甲基二矽氮烷(HMDS)進行處理,而製作自組裝膜(以下,將形成至自組裝膜為止者設為Si處理基板)。於空氣中,於Si處理基板上滴加含有化合物No.1之溶液狀之上述有機半導體材料,藉由旋轉塗佈法以厚度成為25~30 nm之方式形成有機半導體層11。於有機半導體層11之表面重疊經圖案化之鎳遮罩,並真空蒸鍍金,藉此形成成為電極之汲電極12及源電極13。該汲電極12及源電極13係設為通道寬度5 mm、通道長度20 μm。
所製作之OTFT元件隨著施加正閘極電壓,而顯示出增強汲極電流之正通道-增強型之運作特性。針對所製作之OTFT元件,自I-V特性之飽和區域求出載子遷移率(電荷遷移率),進而算出開/關比(於Vd設為80 V,Vg設為0~80 V時之汲極電流值的比)。又,亦測定於150℃、30分鐘之條件下加熱OTFT元件(退火處理)時之載子遷移率及開/關比。
除了將實施例1中所使用之化合物No.1變更為[表1]所示之化合物以外,藉由與實施例1相同之方法製作有機半導體材料,使用該有機半導體材料製作OTFT元件,並對其進行評價。
除了將實施例1中所使用之化合物No.1變更為N,N'-(2-乙基己基)-2,7-二氰基-3,4,9,10-苝四羧酸二醯亞胺(以下,亦稱為比較化合物No.1)以外,藉由與實施例1相同之手法製作OTFT元件,並對其進行評價。
除了將實施例1中所使用之化合物No.1變更為N,N'-(2-乙基己基)-2,7-二氟-3,4,9,10-苝四羧酸二醯亞胺(以下,亦稱為比較化合物No.2)以外,藉由與實施例1相同之手法製作OTFT元件,並對其進行評價。
除了將實施例1中所使用之化合物No.1變更為N,N'-[(+)-脫氫松香基]-3,4,9,10-苝四羧酸二醯亞胺(以下,亦稱為比較化合物No.3)以外,藉由與實施例1相同之手法製作OTFT元件,並對其進行評價。
將實施例1~8及比較例1~3之評價結果示於[表1]。
由[表1]之結果明確:使用含有具有特定結構之苝四羧酸二醯亞胺化合物的本發明之有機半導體材料而製作之OTFT元件,與使用含有比較化合物之有機半導體材料而製作之OTFT元件相比,電荷遷移率及開/關比更加優異。又,即使於退火處理後,本發明之有機半導體材料相對於含有比較化合物之有機半導體材料的優勢亦未改變。
按照以下順序製作具有圖2所示之層構成的有機薄膜電晶體(OTFT)元件。
於高真空(10-4
~10-3
Pa)下,以0.02 nm/sec之蒸鍍速度,於Si處理基板上積層30 nm之作為有機半導體材料之化合物No.3,而製成有機半導體層11。於該有機半導體層11之表面重疊經圖案化之鎳遮罩,使用金進行真空蒸鍍,藉此形成源電極13及汲電極12,而製成OTFT元件。該源電極13及汲電極12係形成為通道寬度5 mm、通道長度20 μm。
所製作之OTFT元件隨著施加正閘極電壓,而顯示出增強汲極電流之負通道-增強型之運作特性。針對所製作之OTFT元件,自I-V特性之飽和區域求出電荷遷移率,進而算出開/關比(Vd設為80 V,Vg設為80~0 V時之汲極電流值之比值),結果電荷遷移率為5.3×10-2
cm2
/Vs,開/關比為105
。又,於70℃、30分鐘之條件下加熱該OTFT元件後,同樣地進行評價,結果電荷遷移率為1.0×10-1
cm2
/Vs,開/關比為107
。
由實施例1~9之結果明確:包含至少一種本發明之苝羧酸二醯亞胺化合物之有機半導體材料不僅適合藉由濕式製程之製膜,亦可藉由真空蒸鍍等乾式製程進行製膜,藉由任何製程進行製膜而獲得的有機半導體元件均顯示出高載子遷移率。
11...有機半導體層
12...汲電極
13...源電極
14...絕緣層
15...閘電極
16...基板
圖1(a)係表示本發明之有機半導體元件之構成例(下閘極-上接觸型)的剖面圖;
圖1(b)係表示本發明之有機半導體元件之構成例(下閘極-下接觸型)的剖面圖;
圖1(c)係表示本發明之有機半導體元件之構成例(上閘極-下接觸型)的剖面圖;
圖1(d)係表示本發明之有機半導體元件之構成例(上閘極-下接觸型)的剖面圖;
圖1(e)係表示本發明之有機半導體元件之構成例(下閘極-上/下接觸型)的剖面圖;
圖1(f)係表示本發明之有機半導體元件之構成例(下閘極-上/下接觸型)的剖面圖;
圖1(g)係表示本發明之有機半導體元件之構成例[垂直型靜電感應電晶體(SIT:Static Induction Transistor)]的剖面圖;及
圖2係表示本發明之有機半導體元件之構成例(圖1(a)之下閘極-上接觸型之變形例即實施例中所製作之有機薄膜電晶體元件)的剖面圖。
11...有機半導體層
12...汲電極
13...源電極
14...絕緣層
15...閘電極
16...基板
Claims (3)
- 一種有機半導體材料,其包含至少一種下述通式(I)所表示之苝羧酸二醯亞胺化合物,
- 一種有機半導體層,其係將如請求項1之有機半導體材料製膜而成。
- 一種有機半導體元件,其具有至少一層如請求項2之有機半導體層。
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