KR20080073303A - 반도체 물질로서의 나프탈렌계 테트라카복실릭 다이이미드 - Google Patents
반도체 물질로서의 나프탈렌계 테트라카복실릭 다이이미드 Download PDFInfo
- Publication number
- KR20080073303A KR20080073303A KR1020087012156A KR20087012156A KR20080073303A KR 20080073303 A KR20080073303 A KR 20080073303A KR 1020087012156 A KR1020087012156 A KR 1020087012156A KR 20087012156 A KR20087012156 A KR 20087012156A KR 20080073303 A KR20080073303 A KR 20080073303A
- Authority
- KR
- South Korea
- Prior art keywords
- thin film
- groups
- naphthalene
- organic
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 100
- 239000000463 material Substances 0.000 title claims abstract description 72
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 229910000071 diazene Inorganic materials 0.000 title claims abstract description 11
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000006158 tetracarboxylic acid group Chemical group 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 55
- 239000010409 thin film Substances 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000000758 substrate Substances 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000008021 deposition Effects 0.000 claims abstract description 12
- 150000003949 imides Chemical class 0.000 claims abstract description 8
- 238000000859 sublimation Methods 0.000 claims abstract description 5
- 230000008022 sublimation Effects 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 43
- 239000010408 film Substances 0.000 claims description 33
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- -1 diimide compound Chemical class 0.000 claims description 18
- 230000005669 field effect Effects 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 238000000151 deposition Methods 0.000 claims description 13
- 150000002790 naphthalenes Chemical class 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920001940 conductive polymer Polymers 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- MRMRHDNOSZTUHA-UHFFFAOYSA-N 5,8-bis(cyclohexylcarbamoyl)naphthalene-1,4-dicarboxylic acid Chemical compound C=12C(C(=O)O)=CC=C(C(O)=O)C2=C(C(O)=NC2CCCCC2)C=CC=1C(O)=NC1CCCCC1 MRMRHDNOSZTUHA-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000012777 electrically insulating material Substances 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- FVFFILYGNGPUQS-UHFFFAOYSA-N 5,8-bis(cyclopentylcarbamoyl)naphthalene-1,4-dicarboxylic acid Chemical compound C=12C(C(=O)O)=CC=C(C(O)=O)C2=C(C(=O)NC2CCCC2)C=CC=1C(=O)NC1CCCC1 FVFFILYGNGPUQS-UHFFFAOYSA-N 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract description 3
- 230000037230 mobility Effects 0.000 description 38
- 239000010410 layer Substances 0.000 description 36
- 230000006870 function Effects 0.000 description 9
- 229910021417 amorphous silicon Inorganic materials 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 150000008056 dicarboxyimides Chemical class 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000010931 gold Substances 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000295 complement effect Effects 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000012212 insulator Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- GSOFREOFMHUMMZ-UHFFFAOYSA-N 3,4-dicarbamoylnaphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=N)C(C(=N)O)=C(C(O)=O)C(C(O)=O)=C21 GSOFREOFMHUMMZ-UHFFFAOYSA-N 0.000 description 3
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910021419 crystalline silicon Inorganic materials 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920002530 polyetherether ketone Polymers 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000002094 self assembled monolayer Substances 0.000 description 3
- 239000013545 self-assembled monolayer Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 2
- JLTPSDHKZGWXTD-UHFFFAOYSA-N 2-[6-(dicyanomethylidene)naphthalen-2-ylidene]propanedinitrile Chemical compound N#CC(C#N)=C1C=CC2=CC(=C(C#N)C#N)C=CC2=C1 JLTPSDHKZGWXTD-UHFFFAOYSA-N 0.000 description 2
- RHTASMVIGRWMCN-UHFFFAOYSA-N 5,8-bis(hexylcarbamoyl)naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)NCCCCCC)=CC=C(C(=O)NCCCCCC)C2=C1C(O)=O RHTASMVIGRWMCN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- BODUWJSFPLUDMP-UHFFFAOYSA-N benzo[lmn][3,8]phenanthroline-1,3,6,8(2h,7h)-tetrone Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=C2C(=O)NC(=O)C1=C32 BODUWJSFPLUDMP-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 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 2
- 229910052697 platinum Inorganic materials 0.000 description 2
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
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- 229910052709 silver Inorganic materials 0.000 description 2
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- 150000003573 thiols Chemical class 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
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- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- ZYZYQCACSQDPSB-UHFFFAOYSA-N 12,15-dioxatricyclo[8.6.0.02,7]hexadeca-1(10),2,4,6,8-pentaene-11,16-dione Chemical compound O=C1OCCOC(=O)C2=C1C=CC1=CC=CC=C21 ZYZYQCACSQDPSB-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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- DWLWGAWWEOVHEU-UHFFFAOYSA-N 5,8-bis(octylcarbamoyl)naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(O)=NCCCCCCCC)=CC=C(C(O)=NCCCCCCCC)C2=C1C(O)=O DWLWGAWWEOVHEU-UHFFFAOYSA-N 0.000 description 1
- JLTMBLAJAOSAKM-UHFFFAOYSA-N 5,8-bis[[4-(trifluoromethyl)phenyl]methylcarbamoyl]naphthalene-1,4-dicarboxylic acid Chemical compound C=12C(C(=O)O)=CC=C(C(O)=O)C2=C(C(O)=NCC=2C=CC(=CC=2)C(F)(F)F)C=CC=1C(O)=NCC1=CC=C(C(F)(F)F)C=C1 JLTMBLAJAOSAKM-UHFFFAOYSA-N 0.000 description 1
- RJCHVBHJXJDUNL-UHFFFAOYSA-N 5,8-dicarbamoylnaphthalene-1,4-dicarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=N)O)=CC=C(C(O)=N)C2=C1C(O)=O RJCHVBHJXJDUNL-UHFFFAOYSA-N 0.000 description 1
- NAZODJSYHDYJGP-UHFFFAOYSA-N 7,18-bis[2,6-di(propan-2-yl)phenyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone Chemical class CC(C)C1=CC=CC(C(C)C)=C1N(C(=O)C=1C2=C3C4=CC=1)C(=O)C2=CC=C3C(C=C1)=C2C4=CC=C3C(=O)N(C=4C(=CC=CC=4C(C)C)C(C)C)C(=O)C1=C23 NAZODJSYHDYJGP-UHFFFAOYSA-N 0.000 description 1
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 239000005083 Zinc sulfide Substances 0.000 description 1
- WOIHABYNKOEWFG-UHFFFAOYSA-N [Sr].[Ba] Chemical compound [Sr].[Ba] WOIHABYNKOEWFG-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 229910021523 barium zirconate Inorganic materials 0.000 description 1
- DQBAOWPVHRWLJC-UHFFFAOYSA-N barium(2+);dioxido(oxo)zirconium Chemical compound [Ba+2].[O-][Zr]([O-])=O DQBAOWPVHRWLJC-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 1
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- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- 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]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- 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
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- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31721—Of polyimide
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- Nanotechnology (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Organic Chemistry (AREA)
- Thin Film Transistor (AREA)
- Photovoltaic Devices (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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|---|---|---|---|
| US11/285,238 US7422777B2 (en) | 2005-11-22 | 2005-11-22 | N,N′-dicycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as n-type semiconductor materials for thin film transistors |
| US11/285,238 | 2005-11-22 |
Publications (1)
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| KR20080073303A true KR20080073303A (ko) | 2008-08-08 |
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| Country | Link |
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| EP (1) | EP1952453B1 (enExample) |
| JP (1) | JP2009516930A (enExample) |
| KR (1) | KR20080073303A (enExample) |
| TW (1) | TWI416721B (enExample) |
| WO (1) | WO2007061614A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014200249A1 (ko) * | 2013-06-12 | 2014-12-18 | 경상대학교산학협력단 | 나프탈렌 다이이미드 유도체 화합물 및 제조방법과 이를 포함하는 유기전자소자 |
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| CN1980791B (zh) * | 2004-01-26 | 2012-08-22 | 西北大学 | 苝n-型半导体和相关器件 |
| US7569693B2 (en) | 2006-06-12 | 2009-08-04 | Northwestern University | Naphthalene-based semiconductor materials and methods of preparing and use thereof |
| EP2089398A2 (en) * | 2006-10-25 | 2009-08-19 | Polyera Corporation | Organic semiconductor materials and methods of preparing and use thereof |
| US7902363B2 (en) | 2006-11-17 | 2011-03-08 | Polyera Corporation | Diimide-based semiconductor materials and methods of preparing and using the same |
| WO2008063583A1 (en) * | 2006-11-17 | 2008-05-29 | Polyera Corporation | Acene-based organic semiconductor materials and methods of preparing and using the same |
| US7804087B2 (en) * | 2006-12-07 | 2010-09-28 | Eastman Kodak Company | Configurationally controlled N,N'-Dicycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as N-type semiconductor materials for thin film transistors |
| WO2008085942A2 (en) * | 2007-01-08 | 2008-07-17 | Polyera Corporation | Methods for preparing arene-bis(dicarboximide)-based semiconducting materials and related intermediates for preparing same |
| WO2008091670A2 (en) * | 2007-01-24 | 2008-07-31 | Polyera Corporation | Organic semiconductor materials and precursors thereof |
| US7858970B2 (en) * | 2007-06-29 | 2010-12-28 | Eastman Kodak Company | Heterocycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as N-type semiconductor materials for thin film transistors |
| WO2009108397A1 (en) * | 2008-01-07 | 2009-09-03 | The Johns Hopkins University | Devices having high dielectric-constant, ionically-polarizable materials |
| EP2240970B1 (en) * | 2008-02-05 | 2018-03-14 | Basf Se | Perylene semiconductors and methods of preparation and use thereof |
| TWI427098B (zh) * | 2008-02-05 | 2014-02-21 | Basf Se | 由芮-(π-受體)共聚物製備之半導體材料 |
| US7649199B2 (en) | 2008-04-11 | 2010-01-19 | Eastman Kodak Company | N-type semiconductor materials in thin film transistors and electronic devices |
| KR101694877B1 (ko) * | 2009-10-16 | 2017-01-11 | 삼성전자주식회사 | 그라핀 소자 및 그 제조 방법 |
| US8212243B2 (en) * | 2010-01-22 | 2012-07-03 | Eastman Kodak Company | Organic semiconducting compositions and N-type semiconductor devices |
| US8309394B2 (en) * | 2010-01-22 | 2012-11-13 | Eastman Kodak Company | Method of making N-type semiconductor devices |
| US8530270B2 (en) | 2010-04-30 | 2013-09-10 | Eastman Kodak Company | Methods of preparing semiconductive compositions and devices |
| US8411489B2 (en) | 2010-04-30 | 2013-04-02 | Eastman Kodak Company | Semiconducting devices and methods of preparing |
| US8314265B2 (en) | 2010-04-30 | 2012-11-20 | Eastman Kodak Company | Aromatic amic acids or amic esters and compositions |
| US20110269966A1 (en) | 2010-04-30 | 2011-11-03 | Deepak Shukla | Semiconducting articles |
| US8450726B2 (en) * | 2010-05-27 | 2013-05-28 | Eastman Kodak Company | Articles containing coatings of amic acid salts |
| US8431433B2 (en) | 2010-05-27 | 2013-04-30 | Eastman Kodak Company | Methods of providing semiconductor layers from amic acid salts |
| US8404892B2 (en) | 2010-05-27 | 2013-03-26 | Eastman Kodak Company | Aromatic amic acid salts and compositions |
| DE102011013897A1 (de) * | 2011-03-11 | 2012-09-13 | Technische Universität Dresden | Organische Solarzelle |
| US8692238B2 (en) | 2012-04-25 | 2014-04-08 | Eastman Kodak Company | Semiconductor devices and methods of preparation |
| US8779415B2 (en) | 2012-11-08 | 2014-07-15 | Eastman Kodak Company | Devices containing organic polymeric multi-metallic composites |
| EP3155623B1 (en) | 2014-06-11 | 2019-05-08 | Eastman Kodak Company | Devices having dielectric layers with thiosulfate-containing polymers |
| JP2021082619A (ja) * | 2018-03-16 | 2021-05-27 | 国立大学法人大阪大学 | n型有機半導体材料及びそれを含有する有機半導体膜並びに有機薄膜トランジスタ |
| US12490574B2 (en) * | 2021-02-08 | 2025-12-02 | Uif (University Industry Foundation), Yonsei University | Skin-conformable biosignal monitoring sensor by applying organic-inorganic hybrid photo transistor and manufacturing method thereof |
Family Cites Families (20)
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| DE2636421A1 (de) | 1976-08-13 | 1978-02-16 | Basf Ag | Elektrisch leitfaehige perylenderivate |
| DE2951349A1 (de) | 1979-12-20 | 1981-07-02 | Bayer Ag, 5090 Leverkusen | Naphthalintetracarbonsaeurediimide als elektrische halbleiter und photoleiter |
| US4578334A (en) | 1984-11-23 | 1986-03-25 | Eastman Kodak Company | Multi-active photoconductive insulating elements and method for their manufacture |
| DE3526249A1 (de) | 1985-07-23 | 1987-01-29 | Hoechst Ag | Elektrophotographisches aufzeichnungsmaterial |
| US4719163A (en) | 1986-06-19 | 1988-01-12 | Eastman Kodak Company | Multi-active photoconductive insulating elements exhibiting far red sensitivity |
| US5468583A (en) * | 1994-12-28 | 1995-11-21 | Eastman Kodak Company | Cyclic bis-dicarboximide electron transport compounds for electrophotography |
| US6387727B1 (en) * | 1999-03-29 | 2002-05-14 | Agere Systems Guardian Corp. | Device comprising n-channel semiconductor material |
| JP3369515B2 (ja) * | 1999-07-28 | 2003-01-20 | 京セラミタ株式会社 | フタロシアニン結晶及びその製造方法と、これを含有した電子写真感光体 |
| DE20021356U1 (de) | 2000-12-18 | 2001-02-22 | Basf Ag, 67063 Ludwigshafen | Polyvinylchlorid mit kernhydrierten Phthalat-Weichmachern |
| US20020192397A1 (en) * | 2001-02-20 | 2002-12-19 | Fuji Photo Film Co., Ltd. | Polarizing plate protection film |
| US6844033B2 (en) * | 2001-03-01 | 2005-01-18 | Konica Corporation | Cellulose ester film, its manufacturing method, polarizing plate, and liquid crystal display |
| JP4792677B2 (ja) * | 2001-04-25 | 2011-10-12 | コニカミノルタホールディングス株式会社 | セルロースエステルフィルム |
| US6977275B2 (en) | 2002-01-16 | 2005-12-20 | Eastman Chemical Company | Carbohydrate esters and polyol esters as plasticizers for polymers, compositions and articles including such plasticizers and methods of using the same |
| JP2004014982A (ja) * | 2002-06-11 | 2004-01-15 | Konica Minolta Holdings Inc | 半導体回路および画像表示装置 |
| KR100513700B1 (ko) * | 2003-07-04 | 2005-09-09 | 삼성전자주식회사 | 나프탈렌테트라카르복시디이미드 유도체 및 이를 포함하는전자사진감광체 |
| JP2005208617A (ja) * | 2003-12-26 | 2005-08-04 | Canon Inc | 電子写真感光体、電子写真感光体の製造方法、プロセスカートリッジおよび電子写真装置 |
| CN1980791B (zh) * | 2004-01-26 | 2012-08-22 | 西北大学 | 苝n-型半导体和相关器件 |
| US7838871B2 (en) * | 2004-03-24 | 2010-11-23 | Samsung Mobile Display Co., Ltd. | Organic field-effect transistor, flat panel display device including the same, and a method of manufacturing the organic field-effect transistor |
| US7579619B2 (en) * | 2005-04-20 | 2009-08-25 | Eastman Kodak Company | N,N′-di(arylalkyl)-substituted naphthalene-based tetracarboxylic diimide compounds as n-type semiconductor materials for thin film transistors |
| US7629605B2 (en) * | 2005-10-31 | 2009-12-08 | Eastman Kodak Company | N-type semiconductor materials for thin film transistors |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014200249A1 (ko) * | 2013-06-12 | 2014-12-18 | 경상대학교산학협력단 | 나프탈렌 다이이미드 유도체 화합물 및 제조방법과 이를 포함하는 유기전자소자 |
| KR101490104B1 (ko) * | 2013-06-12 | 2015-03-25 | 경상대학교산학협력단 | 나프탈렌 다이이미드 유도체 화합물 및 제조방법과 이를 포함하는 유기전자소자 |
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| TW200733378A (en) | 2007-09-01 |
| US20070116895A1 (en) | 2007-05-24 |
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| US7422777B2 (en) | 2008-09-09 |
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| EP1952453B1 (en) | 2016-07-27 |
| JP2009516930A (ja) | 2009-04-23 |
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