KR20080063803A - 박막 트랜지스터용 ｎ-형 반도체 물질 - Google Patents
박막 트랜지스터용 ｎ-형 반도체 물질 Download PDFInfo
- Publication number
- KR20080063803A KR20080063803A KR1020087010409A KR20087010409A KR20080063803A KR 20080063803 A KR20080063803 A KR 20080063803A KR 1020087010409 A KR1020087010409 A KR 1020087010409A KR 20087010409 A KR20087010409 A KR 20087010409A KR 20080063803 A KR20080063803 A KR 20080063803A
- Authority
- KR
- South Korea
- Prior art keywords
- thin film
- organic
- naphthalene
- groups
- phenyl
- 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 95
- 239000000463 material Substances 0.000 title claims abstract description 72
- 239000010409 thin film Substances 0.000 title claims abstract description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000000758 substrate Substances 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 230000008021 deposition Effects 0.000 claims abstract description 18
- 238000000859 sublimation Methods 0.000 claims abstract description 6
- 230000008022 sublimation Effects 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 40
- 239000010408 film Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- -1 1,4,5,8-naphthalene tetracarboxylic diimide compound Chemical class 0.000 claims description 21
- 238000000151 deposition Methods 0.000 claims description 20
- 230000005669 field effect Effects 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002837 carbocyclic group Chemical group 0.000 claims description 13
- 125000000962 organic group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- GSOFREOFMHUMMZ-UHFFFAOYSA-N 3,4-dicarbamoylnaphthalene-1,2-dicarboxylic acid Chemical class 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 claims description 7
- BTNXSMTXAULNSF-UHFFFAOYSA-N 5,8-bis[(3-methylphenyl)carbamoyl]naphthalene-1,4-dicarboxylic acid Chemical compound CC1=CC=CC(N=C(O)C=2C3=C(C(O)=O)C=CC(=C3C(C(O)=NC=3C=C(C)C=CC=3)=CC=2)C(O)=O)=C1 BTNXSMTXAULNSF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
- 229920001940 conductive polymer Polymers 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000012777 electrically insulating material Substances 0.000 claims description 3
- XHWZJYCDZSHZAE-UHFFFAOYSA-N 5,8-bis[(4-methylphenyl)carbamoyl]naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC(C)=CC=C1N=C(O)C(C1=C(C(O)=O)C=CC(=C11)C(O)=O)=CC=C1C(O)=NC1=CC=C(C)C=C1 XHWZJYCDZSHZAE-UHFFFAOYSA-N 0.000 claims description 2
- 230000002411 adverse Effects 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- NZUCZKHIJBFZSF-UHFFFAOYSA-N 5-carbamoyl-8-[(3-methylphenyl)carbamoyl]naphthalene-1,4-dicarboxylic acid Chemical compound CC1=CC=CC(N=C(O)C=2C3=C(C(O)=O)C=CC(=C3C(C(O)=N)=CC=2)C(O)=O)=C1 NZUCZKHIJBFZSF-UHFFFAOYSA-N 0.000 claims 2
- 239000007772 electrode material Substances 0.000 claims 2
- CFKCMSPQZMKHOU-UHFFFAOYSA-N 5,8-bis[(2-methylphenyl)carbamoyl]naphthalene-1,4-dicarboxylic acid Chemical compound CC1=CC=CC=C1N=C(O)C(C1=C(C(O)=O)C=CC(=C11)C(O)=O)=CC=C1C(O)=NC1=CC=CC=C1C CFKCMSPQZMKHOU-UHFFFAOYSA-N 0.000 claims 1
- FLQXNSOIEZOPLV-UHFFFAOYSA-N 5,8-bis[(3-methylphenyl)methylcarbamoyl]naphthalene-1,4-dicarboxylic acid Chemical compound CC1=CC=CC(CN=C(O)C=2C3=C(C(O)=O)C=CC(=C3C(C(O)=NCC=3C=C(C)C=CC=3)=CC=2)C(O)=O)=C1 FLQXNSOIEZOPLV-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 21
- 229910000071 diazene Inorganic materials 0.000 abstract description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 abstract description 3
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract 1
- 230000037230 mobility Effects 0.000 description 43
- 239000010410 layer Substances 0.000 description 36
- 230000001976 improved effect Effects 0.000 description 15
- 150000002790 naphthalenes Chemical class 0.000 description 10
- 239000011368 organic material Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000295 complement effect Effects 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 229910021417 amorphous silicon Inorganic materials 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 239000012212 insulator Substances 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
- 238000012545 processing Methods 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 5
- 238000002061 vacuum sublimation Methods 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000011149 active material Substances 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WFBBFRRQLKLBQT-UHFFFAOYSA-N 5,8-bis(phenylcarbamoyl)naphthalene-1,4-dicarboxylic acid Chemical compound C=12C(C(=O)O)=CC=C(C(O)=O)C2=C(C(O)=NC=2C=CC=CC=2)C=CC=1C(O)=NC1=CC=CC=C1 WFBBFRRQLKLBQT-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910021419 crystalline silicon Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 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
- 230000009467 reduction Effects 0.000 description 3
- 239000002094 self assembled monolayer Substances 0.000 description 3
- 239000013545 self-assembled monolayer Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 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
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-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
- 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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 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
- 239000002800 charge carrier Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
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- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
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- 238000001459 lithography Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000813 microcontact printing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 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
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000001947 vapour-phase growth Methods 0.000 description 2
- 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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
- MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000252505 Characidae Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
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- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
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Images
Classifications
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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
-
- 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
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- 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
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- 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
- 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
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
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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
- 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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- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Composite Materials (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Organic Chemistry (AREA)
- Thin Film Transistor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/263,111 US7629605B2 (en) | 2005-10-31 | 2005-10-31 | N-type semiconductor materials for thin film transistors |
| US11/263,111 | 2005-10-31 |
Publications (1)
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|---|---|
| KR20080063803A true KR20080063803A (ko) | 2008-07-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7629605B2 (enExample) |
| EP (1) | EP1943691A2 (enExample) |
| JP (1) | JP2009514223A (enExample) |
| KR (1) | KR20080063803A (enExample) |
| TW (1) | TW200729571A (enExample) |
| WO (1) | WO2007053303A2 (enExample) |
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 |
| KR20170028787A (ko) * | 2015-09-04 | 2017-03-14 | 삼성전자주식회사 | 유기 광전 소자 및 이미지 센서 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1980791B (zh) * | 2004-01-26 | 2012-08-22 | 西北大学 | 苝n-型半导体和相关器件 |
| US7629605B2 (en) * | 2005-10-31 | 2009-12-08 | Eastman Kodak Company | N-type semiconductor materials for thin film transistors |
| US7422777B2 (en) * | 2005-11-22 | 2008-09-09 | Eastman Kodak Company | N,N′-dicycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as n-type semiconductor materials for thin film transistors |
| 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 |
| 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 |
| WO2009108397A1 (en) * | 2008-01-07 | 2009-09-03 | The Johns Hopkins University | Devices having high dielectric-constant, ionically-polarizable materials |
| US7649199B2 (en) * | 2008-04-11 | 2010-01-19 | Eastman Kodak Company | N-type semiconductor materials in thin film transistors and electronic devices |
| US20110079773A1 (en) * | 2009-08-21 | 2011-04-07 | Wasielewski Michael R | Selectively Functionalized Rylene Imides and Diimides |
| US8411489B2 (en) | 2010-04-30 | 2013-04-02 | Eastman Kodak Company | Semiconducting devices and methods of preparing |
| US20110269966A1 (en) | 2010-04-30 | 2011-11-03 | Deepak Shukla | Semiconducting articles |
| US8530270B2 (en) | 2010-04-30 | 2013-09-10 | Eastman Kodak Company | Methods of preparing semiconductive compositions and devices |
| US8314265B2 (en) | 2010-04-30 | 2012-11-20 | Eastman Kodak Company | Aromatic amic acids or amic esters and compositions |
| US8404892B2 (en) | 2010-05-27 | 2013-03-26 | Eastman Kodak Company | Aromatic amic acid salts and compositions |
| 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 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2951349A1 (de) | 1979-12-20 | 1981-07-02 | Bayer Ag, 5090 Leverkusen | Naphthalintetracarbonsaeurediimide als elektrische halbleiter und photoleiter |
| US4442193A (en) * | 1983-02-22 | 1984-04-10 | Eastman Kodak Company | Photoconductive compositions and elements containing naphthalene bis-dicarboximide compounds |
| US4468444A (en) * | 1983-04-21 | 1984-08-28 | Eastman Kodak Company | Pyrylium-sensitized leuco base photoconductive compositions and elements containing naphthalene bis-dicarboximide compounds |
| EP0769532B1 (de) * | 1995-10-12 | 2002-03-13 | Ciba SC Holding AG | Naphthalinlactamimid-Fluoreszenzfarbstoffe |
| JP3373783B2 (ja) | 1998-05-29 | 2003-02-04 | 京セラミタ株式会社 | ナフタレンテトラカルボン酸ジイミド誘導体及び電子写真用感光体 |
| JP3559173B2 (ja) * | 1998-07-01 | 2004-08-25 | 京セラミタ株式会社 | 負帯電単層型電子写真感光体 |
| JP2000113504A (ja) * | 1998-10-05 | 2000-04-21 | Mitsui Chemicals Inc | 光記録媒体 |
| US6387727B1 (en) | 1999-03-29 | 2002-05-14 | Agere Systems Guardian Corp. | Device comprising n-channel semiconductor material |
| 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 |
| EP1434282A3 (en) * | 2002-12-26 | 2007-06-27 | Konica Minolta Holdings, Inc. | Protective layer for an organic thin-film transistor |
| WO2005066718A1 (ja) * | 2003-12-26 | 2005-07-21 | Canon Kabushiki Kaisha | 電子写真感光体、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 |
| US7629605B2 (en) * | 2005-10-31 | 2009-12-08 | Eastman Kodak Company | N-type semiconductor materials for thin film transistors |
-
2005
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2006
- 2006-10-16 JP JP2008537779A patent/JP2009514223A/ja active Pending
- 2006-10-16 WO PCT/US2006/040750 patent/WO2007053303A2/en not_active Ceased
- 2006-10-16 EP EP06817131A patent/EP1943691A2/en not_active Withdrawn
- 2006-10-16 KR KR1020087010409A patent/KR20080063803A/ko not_active Ceased
- 2006-10-30 TW TW095139948A patent/TW200729571A/zh unknown
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2009
- 2009-08-21 US US12/545,337 patent/US7807994B2/en not_active Expired - Fee Related
Cited By (3)
| 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 |
| KR20170028787A (ko) * | 2015-09-04 | 2017-03-14 | 삼성전자주식회사 | 유기 광전 소자 및 이미지 센서 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20090312553A1 (en) | 2009-12-17 |
| WO2007053303A3 (en) | 2007-06-21 |
| US20070096084A1 (en) | 2007-05-03 |
| US7629605B2 (en) | 2009-12-08 |
| US7807994B2 (en) | 2010-10-05 |
| EP1943691A2 (en) | 2008-07-16 |
| JP2009514223A (ja) | 2009-04-02 |
| WO2007053303A2 (en) | 2007-05-10 |
| TW200729571A (en) | 2007-08-01 |
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