CN102844903A - 有机半导体 - Google Patents
有机半导体 Download PDFInfo
- Publication number
- CN102844903A CN102844903A CN2011800204037A CN201180020403A CN102844903A CN 102844903 A CN102844903 A CN 102844903A CN 2011800204037 A CN2011800204037 A CN 2011800204037A CN 201180020403 A CN201180020403 A CN 201180020403A CN 102844903 A CN102844903 A CN 102844903A
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- China
- Prior art keywords
- independently
- compound
- semiconducting compound
- aryl
- alkynyl
- Prior art date
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- 239000004065 semiconductor Substances 0.000 title claims description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 230000003381 solubilizing effect Effects 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000009257 reactivity Effects 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 238000013459 approach Methods 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 7
- -1 akenyl Chemical group 0.000 abstract description 5
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000003368 amide group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000151 deposition Methods 0.000 description 11
- 239000003989 dielectric material Substances 0.000 description 11
- 230000004888 barrier function Effects 0.000 description 9
- 230000008021 deposition Effects 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 230000005669 field effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002161 passivation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002094 self assembled monolayer Substances 0.000 description 3
- 239000013545 self-assembled monolayer Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C)(C)CI1C*CC1 Chemical compound CC(C)(C)CI1C*CC1 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000002322 conducting polymer Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229910004205 SiNX Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- FAERCJFAEOYPRX-UHFFFAOYSA-M [Br-].CCCCCCCCC1=CC=C([Mg+])C=C1 Chemical compound [Br-].CCCCCCCCC1=CC=C([Mg+])C=C1 FAERCJFAEOYPRX-UHFFFAOYSA-M 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- UHPJWJRERDJHOJ-UHFFFAOYSA-N ethene;naphthalene-1-carboxylic acid Chemical compound C=C.C1=CC=C2C(C(=O)O)=CC=CC2=C1 UHPJWJRERDJHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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Abstract
包含结构(I)的半导体化合物,其中X1和X2独立地为S、Se、SiR1R2、O、CR3R4、C2R5R6、N、NR7,其中R1至R7独立地包含氢,直链、支化或环状烷基、烯基或炔基,烷氧基,芳基,甲硅烷基或氨基;其中Ar1至Ar4各自是任选的,并且在存在的情况下独立地包含芳基或杂芳基;并且其中Y1至Y4独立地包含氢,反应性基团,任选地取代的直链、支化或环状烷基、烷氧基、烯基、炔基、酰氨基或氨基,任选地取代的芳基或杂芳基,其中Y1至Y4的至少一个不包含氢。以及涉及该半导体化合物的方法和器件。
Description
技术领域
本发明总体上涉及有机半导体,特别是涉及用于形成薄膜晶体管的一部分的有机半导体。
背景技术
晶体管可分为两种主要类型:双极结晶体管和场效应晶体管。两种类型均具有包括三个电极的共同结构,其具有在沟道区域中设置于其间的半导体材料。双极结晶体管的三个电极称为发射极、集电极和基极,而在场效应晶体管中,三个电极称为源极、漏极和栅极。由于在发射极和集电极之间的电流通过在基极和发射极之间流动的电流进行控制,因此双极结晶体管可描述为电流操作器件。相反,由于源极和漏极之间流动的电流通过栅极和源极之间的电压进行控制,因此场效应晶体管可描述为电压操作器件。
根据是否包括分别传导正电荷载流子(空穴)或负电荷载流子(电子)的半导体材料,晶体管也可分成p型和n型。半导体材料可根据其接收、传导和给予电荷的能力进行选择。半导体材料接收、传导和给予空穴或电子的能力可通过将材料掺杂而增强。
例如,p型晶体管器件可通过选择在接收、传导和给予空穴方面有效的半导体材料,以及选择在从该半导体材料注入和接收空穴方面有效的源极和漏极材料而形成。电极中费米能级与半导体材料的HOMO能级的良好能级匹配能增强空穴注入和接收。相反,n型晶体管器件可通过选择在接收、传导和给予电子方面有效的半导体材料,和选择在向该半导体材料注入电子和自该半导体材料接收电子方面有效的源极和漏极材料而形成。电极中费米能级与半导体材料的LUMO能级的良好能级匹配能增强电子注入和接收。
晶体管可通过沉积薄膜中的部件以形成薄膜晶体管(TFT)来形成。当有机材料用作这种器件中的半导体材料时,其称为有机薄膜晶体管(OTFT)。
OTFTs可以通过低成本、低温方法如溶液加工进行制造。而且,OTFTs与柔性塑料基板兼容,提供了在卷对卷工艺中在柔性基板上大规模制造OTFTs的前景。
参见图2,底栅有机薄膜晶体管(OTFT)的一般结构包括沉积于基板10上的栅极12。介电材料的绝缘层11沉积在栅极12的上方,并且源极和漏极13、14沉积于介电材料的绝缘层11的上方。源极和漏极13、14间隔开以限定其间的位于栅极12上方的沟道区。有机半导体(OSC)材料15沉积于沟道区中,用于连接源极和漏极13、14。OSC材料15可以至少部分地在源极和漏极13、14上方延伸。
或者,已知的是在有机薄膜晶体管的顶部提供栅极以形成所谓的顶栅有机薄膜晶体管。在这样的结构中,源极和漏极沉积于基板上并间隔开以限定其间的沟道区。有机半导体材料层沉积于沟道区中以连接源极和漏极,并且可以至少部分地在源极和漏极上方延伸。介电材料的绝缘层沉积于有机半导体材料上方,并且也可以至少部分地在源极和漏极上方延伸。栅极沉积于绝缘层上方并且位于沟道区上方。
有机薄膜晶体管可以制造于刚性或柔性基板上。刚性基板可选自玻璃或硅,并且柔性基板可包括薄的玻璃或塑料,如聚(对苯二甲酸乙二醇酯)(PET)、聚(萘二甲酸乙二醇酯)(PEN)、聚碳酸酯和聚酰亚胺。
有机半导体材料可通过使用合适的溶剂而变得可溶液加工。示例性的溶剂包括单烷基苯或多烷基苯,例如甲苯和二甲苯;四氢化萘和氯仿。优选的溶液沉积技术包括旋涂和喷墨印刷。其他溶液沉积技术包括浸渍涂布、辊印和丝网印刷。
限定在源极和漏极之间的沟道的长度可最高达500微米,但是优选该长度小于200微米,更优选小于100微米,最优选小于20微米。
栅极可选自宽范围的导电材料,例如金属(例如金)或金属化合物(例如氧化铟锡)。或者,导电聚合物可沉积为栅极。这种导电聚合物可使用例如旋涂或喷墨印刷技术以及上述其他溶液沉积技术从溶液沉积。
绝缘层包括从具有高电阻率的绝缘材料中选择的介电材料。尽管需要具有高k值的材料,但是电介质的介电常数k通常约为2-3,因为对于OTFT可获得的电容与k成正比,且漏电流ID与电容成正比。因而,为了以低的工作电压获得高的漏电流,在沟道区中具有薄的介电层的OTFTs是优选的。
介电材料可以是有机的或无机的。优选的无机材料包括SiO2、SiNx和旋涂玻璃(SOG)。优选的有机材料通常是聚合物,包括绝缘聚合物例如聚乙烯醇(PVA)、聚乙烯吡咯烷酮(PVP),丙烯酸酯例如聚甲基丙烯酸甲酯(PMMA)、氟化聚合物和苯并环丁烷类(BCBs),它们可从Dow Corning获得。绝缘层可以由材料的混合物形成或者包含多层结构。
介电材料可以通过现有技术中已知的热蒸发、真空处理或者层积技术进行沉积。或者,介电材料可以使用例如旋涂或喷墨印刷技术以及以上讨论的其它溶液沉积技术从溶液沉积。
如果介电材料从溶液沉积到有机半导体上,它不应当导致有机半导体的溶解。类似地,如果有机半导体从溶液沉积到介电材料上,介电材料不应当溶解。避免这种溶解的技术包括:使用正交溶剂,例如使用用于沉积最上层、不溶解下层的溶剂;以及使下层交联。
绝缘层的厚度优选小于2微米,更优选小于500nm。
有机半导体是一类具有大范围共轭的π体系的有机分子,该体系允许电子的移动。
用于制备这些分子的优选方法为记载于例如WO 2000/53656中的Suzuki反应(偶联或聚合反应)以及记载于例如T.Yamamoto,“Electrically Conducting And Thermally Stable π-Conjugated Poly(arylene)s Prepared by Organometallic Processes”,Progress inPolymer Science 1993,17,1153-1205中的Yamamoto聚合。这些技术均通过“金属插入”来进行,其中金属配合物催化剂的金属原子插入单体的离去基团和芳基之间。在Yamatomo聚合的情况下,使用镍配合物催化剂;在Suzuki反应的情况下,使用钯配合物催化剂。
例如,在通过Yamatomo聚合的线性聚合物的合成中,使用具有两个反应性卤素基团的单体。类似地,根据Suzuki反应方法,至少一个反应性基团是硼衍生物基团例如硼酸或硼酸酯,另一个反应性基团是卤素。优选的卤素是氯、溴和碘,最优选溴。
或者,可以在聚合或偶联反应(Stille反应)中使用甲锡烷基作为反应性基团。
有机半导体的性能通常通过测量其“电荷迁移率”(cm2V-1s-1)而进行评价,所述电荷迁移率可以涉及空穴或电子的迁移率。该测量涉及载荷子向跨材料施加的电场的漂移速度。
具有相对较高的迁移率的有机半导体往往是包含具有刚性平面结构的化合物的那些,所述刚性平面结构具有大范围共轭,该共轭允许固态下的有效的π-π叠加。
WO 2007/068618记载了多种有机半导体,其各自包含稠合芳环的阵列,所述稠合芳环具有被乙炔基团取代的中心苯环。
JP 2007/088222和WO 2007/116660记载了小分子、低聚物和聚合物形式的苯并二噻吩类及其衍生物作为有机半导体的用途。
Scherf等人在Journal of Polymer Science A:Polymer Chemistry 46(22)7342至7353页记载了具有以下结构的聚合物:
然而,使得化合物可以形成这样的π-π叠加而需要的提高的共轭水平也可导致半导体的带隙和稳定性的降低,导致差的性能和短的寿命。
此外,由于获得大范围共轭所需的分子尺寸,这些化合物会高度不可溶,这对合成造成特别的问题,并使它们难以用于有效的晶体管生产方法例如喷墨印刷中。
发明内容
本发明旨在提供具有高的迁移率、良好的溶解性和良好的环境稳定性的有机半导体。
在第一方面,本发明提供包含以下结构的半导体化合物:
其中X1和X2独立地为S、Se、SiR1R2、O、CR3R4、C2R5R6、N、NR7,其中R1至R7独立地包含氢,优选地具有1至20个碳的直链、支化或环状烷基、烯基或炔基,烷氧基,芳基,甲硅烷基或氨基;
其中Ar1至Ar4各自是任选的,并且在存在的情况下独立地包含芳基或杂芳基;
并且其中Y1至Y4独立地包含氢,反应性基团,优选地具有1至20个碳原子的任选地取代的直链、支化或环状烷基、烷氧基、烯基、炔基、酰氨基或氨基,任选地取代的芳基或杂芳基,其中Y1至Y4的至少一个不包含氢。
本发明人已出人意料地发现,本发明提供的二维共轭框架当用作半导体材料的一部分时提供了出色的稳定性,增强了迁移率并且提供了低的带隙。
优选地,Ar1至Ar4在存在的情况下独立地包含具有选自S、O、Si、N、Se的杂原子的杂环基团。
优选地,Y1至Y4的至少一个,例如2个、3个或全部,包含增溶基团,例如优选地具有1至20个碳原子的任选地取代的直链、支化或环状烷基、烷氧基、烯基、炔基、酰氨基或氨基。
本发明人已出人意料地发现,该优选的增溶基团定位提供出色的增溶效果。因此,较短的和/或较小的增溶基团可以用于这些优选的位置上。这些较短的和/或较小的增溶基团不太能介入π-π叠加,从而除了改善的溶液可处理性以外潜在地提供改善的迁移率。
此外,增溶基团的定位所提供的改善的溶解性使得半导体物质的平面共轭结构可以进一步扩展,而这些物质保持可溶。
在一些实施方案中,该半导体化合物包含两个或更多个例如一对反应性或可聚合基团,例如Y1和Y3或者Y2和Y4可以包含反应性基团。反应性聚合物基团优选地独立地包含诸如卤素、硼酸、二硼酸、硼酸和二硼酸的酯、亚烷基或甲锡烷基的结构部分。另一方面,本发明包含具有以下结构的半导体低聚物或聚合物:
其中n为2至10,000的整数;
其中X1和X2独立地为S、Se、SiR1R2、O、CR3R4、C2R5R6、N、NR7,其中R1至R7独立地包含氢,优选地具有1至20个碳的直链、支化或环状烷基、烯基或炔基,烷氧基,芳基,甲硅烷基或氨基;
其中Ar1至Ar4各自是任选的,并且在存在的情况下独立地包含芳基或杂芳基;
并且其中Y1至Y4独立地包含氢,反应性基团,优选地具有1至20个碳原子的任选地取代的直链、支化或环状烷基、烷氧基、烯基、炔基、酰氨基或氨基,任选地取代的芳基或杂芳基,其中Y1至Y4的至少一个不包含氢。
该化合物可以为例如单体、低聚物、聚合物或共聚物。
优选地,n为2至10例如2至5的整数。
优选地,该化合物包含选自以下的结构:
其中F8包含以下结构:
另一方面,本发明提供包含半导体部分的电子器件,所述半导体部分包含本文中所述的化合物。
另一方面,本发明提供一种溶液,该溶液用于施加于基材表面以在基材上形成半导体部分,该溶液包含本文中所述的化合物。
再一方面,本发明提供电子器件的制造方法,该方法包括将本文中所述的溶液施加于基材上。
下面将参照下列附图描述本发明的实施方案。
附图说明
图1示出根据本发明的化合物的合成。
图2是根据现有技术的底栅有机薄膜晶体管的一般结构的示意图;
图3是根据本发明一个实施方案的包含制造于公共基板上的有机薄膜晶体管和相邻的有机发光器件的像素的示意图;
图4是根据本发明一个实施方案的与有机发光器件成叠置关系制造的有机薄膜晶体管的示意图。
具体实施方式
在整个以下说明中,类似的附图标记将用于指类似的部分。
根据本发明的有机半导体可通过图1中所示的合成方法进行制造。
得到的化合物是易溶的,并因而可以通过喷墨印刷施加于基板上,以提供薄膜晶体管中的半导电层15,例如如图2中所示,以提供根据本发明的一个方面的电子器件。
这样的有机薄膜晶体管(OTFT)的一种应用可以是驱动光学器件(优选有机光学器件)中的像素。这种光学器件的实例包括光响应器件,特别是光电检测器,以及发光器件,特别是有机发光器件。OTFTs特别适合用于有源矩阵有机发光器件,例如用于显示器应用中。
图3显示了包含有机薄膜晶体管100和相邻的有机发光器件(OLED)102的像素,它们制造在共同的基板104上。OTFT 100包含栅极106、介电层108、分别为110和112的源极和漏极,以及OSC层114。OLED 102包含阳极116、阴极118和提供于阳极116和阴极118之间的电致发光层120。其它层可以位于阳极116和阴极118之间,例如电荷传输层、电荷注入层或电荷阻挡层。在图3的实施方案中,阴极材料118的层横跨OTFT 100和OLED 102两者,并且提供绝缘层122以将阴极层118与OSC层122电隔离。OTFT 100和OLED 102的活性区域通过共同的围堰材料限定,所述围堰材料通过在基板104上沉积光致抗蚀剂124的层并将其图案化以在基板上限定OTFT 100和OLED 102区域而形成。
在图3中,漏极112直接与有机发光器件102的阳极116相连,以将有机发光器件102在发光和不发光状态之间切换。
在图4中所示的替代性布置中,有机薄膜晶体管200可以以相对于有机发光器件202的叠置关系进行制造。在这样的实施方案中,有机薄膜晶体管202按如上所述构建成顶栅或底栅结构。和图3的实施方案一样,OTFT200和OLED 202的活性区域通过光致抗蚀剂124的图案化层限定,然而在该叠置布置中,存在两个独立的围堰层124——一个用于OLED 202,一个用于OTFT 200。平面化层204(也称为钝化层)沉积在OTFT 200上方。示例性的钝化层204包括BCBs和聚对二甲苯类。有机发光器件202在钝化层204上方制造,并且有机发光器件202的阳极116通过导体206与OTFT 200的漏极112电连接,该导体穿过钝化层204和围堰层124。
中间体1
在氮气下,向1,5-二氯蒽醌(6.8g,24.6mmol)在干燥甲苯(100ml)中的悬浮液中滴加4-辛基苯基溴化镁的溶液[由4-辛基苯(20.9g,74.3mmol)和镁卷片(magnesium turnings)(2.14g,89.2mmol)在干燥THF(60ml)中制备]。
在加入完成后,将THF蒸除,并将深红色的溶液在回流下搅拌16小时。将混合物用AcOH:H2O[150:700ml]稀释,将甲苯在减压下除去,将残余物萃取到醚中并用NaOH(7.3g)和Na2SO4(60g,在400ml H2O中)的水溶液洗涤。然后将混合物用MgSO4干燥并在真空中浓缩。
向残余物在AcOH中的溶液(70ml)中加入HI(10ml),并将混合物在100℃搅拌30分钟。将得到的固体通过过滤分离,用水(500ml)洗涤并在50℃在真空下干燥。然后将其在己烷中在回流下加热,冷却,过滤并用乙腈制浆(slurry),得到黄色固体形式的目标产物[(7.7g,17%)m/z623(M+),588(M+-Cl),553(M+-2×Cl)],其具有以下结构:
实施例1
将中间体1(7.5g,12.0mmol)、KOH(16.1g,288mmol)和喹啉(216ml)的悬浮液在230℃加热3小时。使得到的红色溶液冷却至室温,用甲苯(300ml)稀释,并用水(2×150ml)、2M HCl(2×150ml)、盐水(2×150ml)洗涤,用MgSO4干燥并在真空中浓缩。
将红色固体转移到索格斯利特套管(33×100mm)中并用乙腈(600ml)萃取。产物通过升华纯化(260℃和2×10-6mbar的压力),得到暗红色固体形式的目标产物[(0.75g,11%,HPLC 99.3%),m/z 552(M++2×H)),550(M+),451,352],其具有以下结构:
实施例2
使用实施例1的化合物作为活性层,以顶栅、底触点器件的形式制作了有机场效应晶体管器件。通过在玻璃基材上剥离而限定金源漏触点。限定10-200μm长、2mm宽的沟道。通过从1.5%(w/v)均三甲苯溶液以1000rpm的转速用30秒将实施例1的化合物旋涂到清洁的基材上而制作器件。随后将膜在80℃的热板上干燥10分钟,并在金属块上冷却1分钟。
将氟化介电材料从含氟溶剂旋涂到半导体层上,并在80℃的热板上干燥10分钟并在金属块上冷却1分钟。热蒸发80nm厚的铝层作为栅极。
在20μm沟道长度下,观察到的饱和最高迁移率为0.025cm2/Vs;获得4.5×104的开关比(从+20V至-40V的栅极偏压测得)。
通过在-40V Vg或-16V/100nm介电的栅-源场(gate-source field)的外推法,计算得到97kOhm-cm的接触电阻。
将会理解,包含OTFT和光活性区域(例如发光或光敏区域)的像素电路可以包含其它元件。特别是,图5和6的OLED像素电路通常除了所示的驱动晶体管还包含至少另一个晶体管和至少一个电容器。将会理解,此处所述的有机发光器件可以是顶部发光或底部发光器件。也就是说,该器件可以通过器件的阳极侧或阴极侧发光。在透明器件中,阳极和阴极都是透明的。将会理解,透明阴极器件不需要具有透明阳极(当然,除非想得到全透明器件),因此用于底部发光器件的透明阳极可以用反射材料层例如铝层替代或补充。
透明阴极对于有源矩阵器件是特别有利的,因为在这样的器件中穿过透明阳极的发光会至少部分地被位于发光像素下方的OTFT驱动电路阻挡,这可以从图4所示的实施方案中看出。
栅极、源极和漏极的厚度可以在5-200nm范围内,但是通常按原子力显微镜(AFM)测量为例如50nm。
其它层可以包括在器件结构中。例如,除了将自组装单层(SAM)提供在栅极、源极或漏极上,可以将SAM提供在基板、绝缘层和有机半导体材料上以在需要时提高结晶度、降低接触电阻、修补表面特性和提高粘合性。特别是,可以为沟道区中的介电表面提供包含结合区和有机区的单层,以改善器件性能,例如通过改善有机半导体的形貌(特别是聚合物配向和结晶度)和覆盖电荷陷阱,特别是对于高k介电表面。用于这种单层的示例性材料包括具有长的烷基链的氯硅烷或烷氧基硅烷,例如十八烷基三氯硅烷。
毫无疑问,本领域技术人员可以想到很多其它有效的替代方案。将会理解,本发明不限于所述实施方案,并包含对于本领域技术人员而言显而易见的、在所附权利要求范围内的变体。
Claims (14)
3.根据权利要求2的半导体化合物,其中该化合物是聚合物或共聚物。
4.根据权利要求2的半导体化合物,其中n为2至10的整数。
5.根据权利要求1至4任一项的半导体化合物,其中Ar1至Ar4独立地包含具有选自S、O、Si、N、Se的杂原子的杂环基团。
6.根据以上权利要求任一项的半导体化合物,其中Y1至Y4的至少一个包含增溶基团。
7.根据权利要求6的半导体化合物,其中Y1至Y4的增溶基团独立地包含任选地取代的直链、支化或环状烷基、烷氧基、烯基、炔基、酰氨基或氨基。
8.根据以上权利要求任一项的半导体化合物,其中该半导体化合物包含两个或更多个反应性或可聚合基团。
9.根据权利要求8的半导体化合物,其中Y1和Y3或者Y2和Y4包含反应性或可聚合基团。
10.根据权利要求8或权利要求9的半导体化合物,其中该反应性或可聚合基团独立地包含卤素、硼酸、二硼酸、硼酸和二硼酸的酯、亚烷基或甲锡烷基。
12.电子器件,其包含半导体部分,该半导体部分包含根据以上权利要求任一项的化合物。
13.溶液,该溶液用于施加于基材表面以在基材上形成半导体部分,该溶液包含根据以上权利要求任一项的化合物。
14.电子器件的制造方法,其包含将根据权利要求13的溶液施加于基材上。
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JP5724588B2 (ja) * | 2011-04-28 | 2015-05-27 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置および照明装置 |
US9985222B2 (en) * | 2014-06-23 | 2018-05-29 | Samsung Electronics Co., Ltd. | Organic compound, and organic thin film and electronic device |
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