JP6608922B2 - 光パターン化可能な組成物、パターン化高k薄膜誘電体及び関連デバイス - Google Patents
光パターン化可能な組成物、パターン化高k薄膜誘電体及び関連デバイス Download PDFInfo
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- JP6608922B2 JP6608922B2 JP2017520761A JP2017520761A JP6608922B2 JP 6608922 B2 JP6608922 B2 JP 6608922B2 JP 2017520761 A JP2017520761 A JP 2017520761A JP 2017520761 A JP2017520761 A JP 2017520761A JP 6608922 B2 JP6608922 B2 JP 6608922B2
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- thin film
- vinylidene fluoride
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
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- JPXGPRBLTIYFQG-UHFFFAOYSA-N heptan-4-yl acetate Chemical compound CCCC(CCC)OC(C)=O JPXGPRBLTIYFQG-UHFFFAOYSA-N 0.000 claims description 2
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- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
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- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Description
で示される5又は6員単環式及び5〜6二環式環系が挙げられる。かかるヘテロアリール環の例として、ピロリル、フリル、チエニル、ピリジル、ピリミジル、ピリダジニル、ピラジニル、トリアゾリル、テトラゾリル、ピラゾリル、イミダゾリル、イソチアゾリル、チアゾリル、チアジアゾリル、イソオキサゾリル、オキサゾリル、オキサジアゾリル、インドリル、イソインドリル、ベンゾフリル、ベンゾチエニル、キノリル、2-メチルキノリル、イソキノリル、キノキサリル、キナゾリル、ベンゾトリアゾリル、ベンゾイミダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾイソオキサゾリル、ベンゾオキサジアゾリル、ベンゾオキサゾリル、シンノリニル、1H-インダゾリル、2H-インダゾリル、インドリジニル、イソベンゾフイル、ナフチリジニル、フタラジニル、プテリジニル、プリニル、オキサゾロピリジニル、チアゾロピリジニル、イミダゾピリジニル、フロピリジニル、チエノピリジニル、ピリドピリミジニル、ピリドピラジニル、ピリドピリダジニル、チエノチアゾリル、チエノキサゾリル、チエノイミダゾリル基等が挙げられる。ヘテロアリール基の更なる例として、4,5,6,7-テトラヒドロインドリル、テトラヒドロキノリニル、ベンゾチエノピリジニル、ベンゾフロピリジニル基等が挙げられる。一部の実施形態では、ヘテロアリール基は、本明細書で記載のように置換されてもよい。
X1はH又はClであり、
X2、X3、及びX4は、H、F及びClからなる群から選択され、但し、X2、X3、及びX4の1つ以下がClであり、X2、X3、及びX4の全てがFであることはなく、
xは約30mol%〜約85mol%であり、yは約10mol%〜約65mol%であり、x+y≦100mol%である]
によって表すことができる。
YはC=C、CR2、NR、O、S、及びSeからなる群から選択され、RがH、C1〜6アルキル基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、
ZはNR、任意選択で置換されているピリジル基、又は共有結合からなる群から選択され、
Ra、Rb、Rc、及びRdは独立にH、C1〜6アルキル基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRaとRbが一緒になって及び/又はRcとRdが一緒になって窒素原子と結合してグアニジニル基、アミジニル基、又はトリアミノホスファゼニル基を形成することができ、
Re及びRfは独立にハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基であり、
Rg、Rh、Ri、及びRjは独立にH、ハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRgとRhが一緒になって又はRhとRiが一緒になって又はRiとRjが一緒になって炭素原子2個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
Rk、Rl、Rm、及びRnは独立にH、ハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRkとRlが一緒になって又はRlとRmが一緒になって又はRmとRnが一緒になって炭素原子2個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
或いはRgとRhが一緒になって結合しても、RmとRnが一緒になって結合しても、任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成しない場合は、RgとRnが一緒になってQ及び炭素原子4個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
nは0、1、2又は3である]
からなる群から選択される式のうちの1つによって表すことができる。
が挙げられる。
からなる群から選択される式の1つによって表すことができる。
ieno[3,2-b;4,5-b']dithiophene」、J.Mater.Chem.(2012);Mitsuiら「Naphtha[2,l-b:6,5-b']difurans: A Versatile Motif Available for Solution-Processed Single-Crystal Organic Field-Effect Transistors with High Hole Mobility」、J.Am. Chem.Soc、134:5448〜5451頁(2012);及びSubramanianら「Chromophore Fluorination Enhances Crystallization and Stability of Soluble Anthradithiophene Semiconductors」、J.Am.Chem.Soc、130(9):2706〜2707頁(2008)を参照されたい);及びフタルイミド系、ジケトピロロピロール系、及びイソインジゴ系共役ポリマー(国際公開第2010/117449号;Liら、「A High Mobility P-Type DPP-Thieno[3,2-b]thiophene Copolymer for Organic Thin-Film Transistors」、Adv. Mater.、22: 4862〜4866頁 (2010);Liら、「Annealing-Free High-Mobility Diketopyrrolopyrrole-Quaterthiophene Copolymer for Solution-Processed Organic Thin Film Transistors」、J.Am.Chem.Soc、133: 2198〜2204頁(2011);Bronsteinら、「Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices」、J.Am.Chem.Soc、133: 3272〜3275頁(2011);Chenら、「Highly pi-Extended Copolymers with Diketopyrrolopyrrole Moieties for High-Performance Field-Effect Transistors」、Adv.Mater.(2012);Meiら、「Siloxane-Terminated Solubilizing Side Chains:Bringing Conjugated Polymer Backbones Closer and Boosting Hole Mobilities in Thin-Film Transistors」、J.Am.Chem.Soc、133: 20130〜20133頁(2011);及びLeiら「High-Performance Air-Stable Organic Field-Effect Transistors: Isoindigo-Based Conjugated Polymers」、J.Am.Chem.Soc、133: 6099〜6101頁(2011)を参照されたい)が挙げられる。p型半導体の追加の例として、直鎖アセン、湾曲アセン、アリールビニレン、フェニレン、及びアルキル及び/又はアルコキシ基で置換されている縮合(ヘテロ)アレーンが挙げられる。
le,Solution-Processed n-Channel Organic Thin Film Transistors」、J.Am.Chem.Soc、132(11): 3697〜3699頁(2010)を参照されたい);ジシアノメチレン置換共役系(例えば、米国特許第7,928,249号及びQiaoら、「Diketopyrrolopyrrole-Containing Quinoidal Small Molecules for High-Performance, Air-Stable, and Solution-Processable n-Channel Organic Field-Effect Transistors」、J.Am.Chem.Soc、134、4084〜4087頁(2012)に記載のもの);チオン酸塩化芳香族ビスイミド(例えば、国際公開第2011/082234号に記載のもの);NDI含有ポリマー(例えば、米国特許出願公開第2010/0326527号に記載のもの);及びチオフェンイミドポリマー(例えば、国際公開第2012/156948号に記載のもの)が挙げられる。n型半導体の追加の例として、直鎖アセン、湾曲アセン、アリールビニレン、フェニレン、及びアルキルカルボニル、アリールカルボニル、及び/又はシアノ基で置換されている縮合(ヘテロ)アレーンが挙げられる。
iridium based emitter materials」、Int.J.Mol.Sci.,9(8):1527〜1547頁(2008);Tokitoら、「Phosphorescent organic light-emitting devices:triplet energy management」、Electrochemistry、76(1):24〜31頁(2008);Chen、「Evolution of Red Organic Light-Emitting Diodes:Materials and Devices」、Chem.Mater.、16(23):4389〜4400頁(2004);Liuら「Polyfluorenes with on-chain metal centers」、Adv.Poly.Sci.、212(Polyfluorenes):125〜144頁(2008);Danevら、「Vacuum deposited polyimide - a perfect matrix for nanocomposite materials」、J.Opto electron.Adv.Mater.、7(3):1179〜1190頁(2005);米国特許第5,747,183号、米国特許第5,683,823号、米国特許第6,626,722号、米国特許第7,074,502号、米国特許第7,671,241号及び米国特許第7,772,762号に記載されている。
ction with self-assembled layer: Interplay of energy barrier and tunneling distance on charge injection in organic light-emitting diodes」、Organic Electronics、12(4):602〜608頁(2011);Sungら、「AC Field-Induced Polymer Electroluminescence with Single Wall Carbon Nanotubes」、Nano Letters、11(3):966〜972頁(2011);Qiaoら、「Controlling charge balance and exciton recombination by bipolar host in single-layer organic light-emitting diodes」、Journal of Applied Physics、108(3):034508/1〜034508/8頁(2011);Khizar-ul-Haqら、「Blue organic light-emitting diodes with low driving voltage and enhanced power efficiency based on MoO3 as hole injection layer and optimized charge balance」、Journal of Non-Crystalline Solids、356(20-22):1012〜1015頁(2010);Qiら、「Analysis of metal-oxide -based charge generation layers used in stacked organic light-emitting diodes」、Journal of Applied Physics、107(1):014514/1〜014514/8頁(201);Huangら、「Materials and interface engineering in organic light-emitting diodes」、Organic Electronics、243〜261頁(2010);Helanderら、「Comparison of Alq3/alkali-metal fluoride/ Al cathodes for organic electroluminescent devices」、Journal of Applied Physics、104(9):094510/1〜094510/6頁(2008);Roy Choudhuryら、「LiF as an n-dopant in tris(8-hydroxyquinoline) aluminum thin films」、Advanced Materials、20(8):1456〜1461頁(2008);Vaccaら、「Poly(3,4-ethylenedioxythiophene):poly(4-styrenesulfonate) ratio: Structural,physical and hole injection properties in organic light emitting diodes」、Thin Solid Films、516(12):4232〜4237頁(2008);Yangら、「Improved fabrication process for enhancing light emission in single-layer organic light-emitting devices doped with organic salt」Japanese Journal of Applied Physics、47(2,Pt.1):1101〜1103頁(2008);Kimら、「UV-ozone surface treatment of indium-tin-oxide in organic light emitting diodes」、Journal of the Korean Physical Society、50(6):1858〜1861頁(2007); Pratら、「Stable,highly efficient and temperature resistant organic light-emitting devices」、Japanese Journal of Applied Physics、Part 1:Regular Papers、Brief Communications & Review Papers」46(4A):1727〜1730頁(2007);Luoら、「Improving the stability of organic light-emitting devices by using a hole-injection-tunable-anode-buffer-layer」、Journal of Applied Physics、101(5):054512/1〜054512/4頁(2007);Matsushimaら、「Charge-carrier injection characteristics at organic/organic heterojunction interfaces in organic light-emitting diodes」、Chemical Physics Letters、435(4-6):327〜330頁(2007);Kimら、「Controllable work function of Li-Al alloy nanolayers for organic light-emitting devices」、Advanced Engineering Materials、7(11):1023〜1027頁(2005);Kato、「Designing Interfaces That Function to Facilitate Charge Injection in Organic Light-Emitting Diodes」、Journal of the American Chemical Society、127(33):11538〜11539頁(2005);Veinotら、「Toward the Ideal Organic Light-Emitting Diode. The Versatility and Utility of Interfacial Tailoring by Cross-Linked Siloxane Interlayers」、Accounts of Chemical Research、38(8):632〜643頁(2005);Oyamadaら、「Extremely low-voltage driving of organic light-emitting diodes with a Cs-doped phenyldipyrenylphosphine oxide layer as an electron-injection layer」、Applied Physics Letters、86(3):033503/1〜033503/3頁(2005);Hughesら、「Electron-transporting materials for organic electroluminescent and electrophosphorescent devices」、Journal of Materials Chemistry、15(1):94〜107頁(2005);D'Andradeら、「Efficient organic electrophosphorescent white-light-emitting device with a triple doped emissive layer」、Advanced Materials、16(7):624〜628頁(2004);Kannoら、「Development of OLED with high stability and luminance efficiency by co-doping methods for full color displays」、IEEE Journal of Selected Topics in Quantum Electronics、10(1):30〜36頁(2004);Hanら、「Transparent-cathode for top-emission organic light-emitting diodes」、Applied Physics Letters、82(16):2715〜2717頁(2003);Tutisら、「Internal electric field and charge distribution in multilayer organic light-emitting diodes」、Journal of Applied Physics、93(8):4594〜4602頁(2003);Mathaiら、「Controlled injection of holes into A1Q3 based OLEDs by means of an oxidized transport layer」、Materials Research Society Symposium Proceedings、708(Organic Optoelectronic Materials、Processing and Devices): 101〜106頁(2002);Croneら、「Charge injection and transport in single-layer organic light-emitting diodes」、Applied Physics Letters、73(21):3162〜3164頁(1998);及びParkら、「Charge injection and photooxidation of single conjugated polymer molecules」、Journal of the American Chemical Society、126(13):4116〜7頁(2004)を参照されたい。
この実施例は、本発明のP(VDF-TrFE-CFE)系光パターン化可能な組成物の多様な実施形態の光架橋性を実証する。多様な感光性非求核塩基及び架橋剤を含む配合物を試験し、架橋剤も感光性非求核塩基も含まない対照配合物、及び架橋剤のみを含み感光性非求核塩基を含まない対照配合物と比較した。
フォトマスクを通して紫外光に曝露された誘電体膜は、スピンコーティング用に使用された溶媒で現像された場合、フォトマスクに対してネガティブの明白なパターンを示した。図5aは、フォトマスクを介してP(VDF-TrFE-CFE)膜中に開かれ、十分に画定された端部を有する大きさ250μm×250μmのビアホールの光学顕微鏡像を示す。代表的なビアホールを横断する線走査を図5bに示す。
この実施例は、本発明のP(VDF-HFP)系光パターン化可能な組成物の多様な実施形態の光架橋性を実証する。多様な感光性非求核塩基及び架橋剤を含む配合物を試験し、架橋剤も感光性非求核塩基も含まない対照配合物と比較した。
この実施例は、本発明のP(VDF-TRFE)系光パターン化可能な組成物の多様な実施形態の光架橋性を実証する。多様な感光性非求核塩基及び架橋剤を含む配合物を試験し、架橋剤も感光性非求核塩基も含まない対照配合物と比較した。
金属-絶縁体-金属(MIM)コンデンサ構造体を、本教示に記載の誘電体膜を使用して製作した。誘電体膜の静電容量を測定した。MIM構造体の製作では、ガラス上の多結晶ITOをボトム電極として使用し、ボトム電極上に誘電体膜をスピンコートして絶縁層を形成した。誘電体膜を光架橋するために、スピンコートされた膜を、Dymax Flood UVランプ(Model2000-EC)中で2分間曝露し、PGMEAによって現像した。
図9は、典型的なボトム-ゲートトップ-コンタクトOFETの構造を例示する。本発明の教示に記載の光架橋P(VDF-TrFE-CFE)(実施例1に記載した通りに調製された)膜を、ゲート誘電体としてボトム-ゲートトップ-コンタクトOFET内に組込んだ。具体的には、光架橋P(VDF-TrFE-CFE)膜を、ボトム-ゲートトップ-コンタクト試験用OFETデバイス中のゲート誘電体としてITO基板(これはゲート電極として機能する)上に形成した。比較デバイスを、(a)約600nmの元のP(VDF-TrFE-CFE)膜、及び(b)誘電定数約3.3.50nmを有する厚さ約600nmのポリ(メチルメタクリラート)(PMMA)系誘電体膜を用いて同様に作製した。活性半導体層は、真空チャンバ中の熱蒸発によって堆積したC8-BTBT(2,7-ジオクチル[l]ベンゾチエノ[3,2-b][l]ベンゾチオフェン)を含む。OFETを、シャドウマスクを通しての厚さ50nmの金ソース及びドレインコンタクトの蒸着によって完成させた。チャネルの長さ及び幅は、それぞれ100μm及び1000μmである。
図11は、典型的なトップ-ゲートボトム-コンタクトOFETの構造を例示する。本発明の教示に記載の光架橋P(VDF-TrFE-CFE)(実施例1に記載した通りに調製された)膜を、ゲート誘電体としてトップ-ゲートボトム-コンタクトOFET内に組込んだ。具体的には、スピンコートされた表面修飾層を有するポリエチレンナフタラート(PEN)膜を基板として使用した。ソース/ドレイン電極を、シャドウマスクを介しての厚さ50nmの銀ホイルの熱蒸発によって画定した。チャネルの長さ及び幅は、それぞれ、60μm及び1000μmである。半導体層の堆積前に、ソース/ドレイン電極を、チオール処理プロセスを使用して改変した。活性半導体層(約50〜100nm)は、シアノ分子官能化ペリレンジイミド半導体を含み、これを、スピンコーティングによって形成し、次いで5分間120℃のホットプレート上でアニールして溶媒残分を除去した。光架橋P(VDF-TrFE-CFE)膜(実施例1)を、ゲート誘電体として半導体層上に形成した。デバイスを、ゲート電極として厚さ50nmの銀ホイルの熱蒸発によって完成させた。比較デバイスを、(a)約600nmの元のP(VDF-TrFE-CFE)膜、及び(b)誘電定数約3.3.50nmを有する厚さ約600nmのポリ(メチルメタクリラート)(PMMA)系誘電体膜を用いて同様に作製した。
金属-絶縁体-金属(MIM)コンデンサ構造体を、光架橋P(VDF-TrFE-CFE)誘電体と接触した非強誘電性中間層誘電体(PMMA、k約3.3)を含む二層誘電体を用いて製作した。PMMAを、アニソール(又はPGMEA)溶液(20〜30mg/ml)から2000r.p.m.で60秒間スピンコーティングによって、続いて約110℃で10分間アニールして溶媒を乾燥することによって堆積した。誘電体膜の静電容量を測定した。MIM構造体の製作では(図13a)、ガラス上の多結晶性ITOを、ボトム電極として使用し、その電極上に誘電体膜をスピンコートして絶縁層を形成した。誘電体膜を光架橋するために、スピンコートされた膜を、Dymax Flood UVランプ(Model2000-EC)を使用して2分間曝露し、PGMEAによって現像した。比較のコンデンサ構造体を、単層光架橋P(VDF-TrFE-CFE)誘電体又は単層の元の(非架橋の)P(VDF-TrFE-CFE)誘電体いずれかを用いて製作した。
ボトム-ゲートトップ-コンタクトOFETを、(a)二層ゲート誘電体(光架橋P(VDF-TrFE-CFE)+PMMA)(図14a)又は(b)単層ゲート誘電体(光架橋P(VDF-TrFE-CFE))を用いて製作した。光架橋P(VDF-TrFE-CFE)膜は厚さが約600nmであるが、PMMA膜は、厚さが約50nmである。いずれの場合も、ゲート誘電体をITOコートガラス基板上に形成し、ゲート電極としてITOを用いた。活性半導体層は、真空チャンバ中の熱蒸発によって堆積したC8-BTBT(2,7-ジオクチル[l]ベンゾチエノ[3,2-b][l]ベンゾチオフェン)を含む。OFETを、シャドウマスクを通しての厚さ50nmの金ソース及びドレインコンタクトの蒸着によって完成させた。チャネルの長さ及び幅は、それぞれ100μm及び1000μmである。
トップ-ゲートボトム-コンタクトOFETを、(a)二層ゲート誘電体(光架橋P(VDF-TrFE-CFE)+PMMA)(図15a)又は(b)単層ゲート誘電体(光架橋P(VDF-TrFE-CFE))を用いて製作した。スピンコート表面修飾層を有するポリエチレンナフタラート(PEN)膜を基板として使用した。ソース/ドレイン電極を、シャドウマスクを介して厚さ50nmの銀の熱蒸発によって画定した。チャネルの長さ及び幅は、それぞれ、60μm及び1000μmであった。半導体層の堆積前に、ソース/ドレイン電極を、チオール処理プロセスを使用して改変した。PDICN2系半導体層(50〜100nm)を、スピンコーティングによって堆積し、次いで5分間120℃のホットプレート上でアニールして溶媒残分を除去した。中間層誘電体(厚さ約50〜100nm)を、光硬化性の非強誘電性ポリマー(PGMEA中約20〜30mg/ml、k約3.2)をスピンコーティングし、次いで、200mJ/cm2のUV硬化及び110℃で10分間実施されるアニール工程で溶媒を除去することによって堆積した。次いで、光架橋P(VDF-TrFE-CFE)膜(実施例1に記載されたようにして調製した)を中間層誘電体のトップ上に堆積して二層ゲート誘電体を提供した。デバイスを、ゲート電極として厚さ50nmの金を熱蒸発することによって仕上げた。
4、4'、4''、4''' ドレイン電極
6、6'、6''、6''' 半導体層
8、8'、8''、8''' ゲート誘電体層
10、10'、10''、10''' ゲート電極
12、12'、12''、12''' 基板
1 透明基板
2 ゲート電極
3 ゲート誘電体
4 活性層
5 活性層
6 活性層
7 ソース電極
8 ドレイン電極
Claims (11)
- 電子、光学、又は光電子デバイスで使用するためのパターン化薄膜部品を形成する方法であって、
基板上に光パターン化可能な組成物を堆積して薄膜を形成する工程と、
前記薄膜を像様パターンで放射に曝露して、薄膜の非曝露領域を現像剤に可溶性にし、薄膜の曝露領域を現像剤に不溶性にする工程と、
前記薄膜の非曝露領域を現像剤によって除去してパターン化薄膜部品を形成する工程と
を含み、
前記光パターン化可能な組成物がフッ化ビニリデン系ポリマーと、感光性非求核塩基と、架橋剤とを含み、
前記フッ化ビニリデン系ポリマーがフッ化ビニリデンである第1の反復単位と、フッ化ビニル、トリフルオロエチレン、クロロフルオロエチレン、クロロトリフルオロエチレン、塩化ビニリデン、及びヘキサフルオロプロピレンからなる群から選択される第2の反復単位と、任意選択で、フッ化ビニル、クロロフルオロエチレン、クロロトリフルオロエチレン、塩化ビニリデン、及びヘキサフルオロプロピレンからなる群から選択される第2の反復単位と異なる第3の反復単位とを含み、
前記感光性非求核塩基が
YはC=C、CR2、NR、O、S、及びSeからなる群から選択され、RがH、C1〜6アルキル基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、
ZはNR、任意選択で置換されているピリジル基、又は共有結合からなる群から選択され、
Ra、Rb、Rc、及びRdは独立にH、C1〜6アルキル基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRaとRbが一緒になって及び/又はRcとRdが一緒になって窒素原子と結合してグアニジニル基又はトリアミノホスファゼニル基を形成することができ、
Re及びRfは独立にハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基であり、
Rg、Rh、Ri、及びRjは独立にH、ハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRgとRhが一緒になって又はRhとRiが一緒になって又はRiとRjが一緒になって炭素原子2個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
Rk、Rl、Rm、及びRnは独立にH、ハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRkとRlが一緒になって又はRlとRmが一緒になって又はRmとRnが一緒になって炭素原子2個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
或いはRgとRhが一緒になって結合しても、RmとRnが一緒になって結合しても、任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成しない場合は、RgとRnが一緒になってQ及び炭素原子4個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
nは0、1、2又は3である]
からなる群から選択される式のうちの1つによって表され、
前記架橋剤が熱的に活性化されず、過酸化物系でない、
方法。 - 前記感光性非求核塩基が
からなる群から選択される式のうちの1つによって表される、請求項1に記載の方法。 - 前記感光性非求核塩基が
- 前記フッ化ビニリデン系ポリマーが、フッ化ビニリデンとトリフルオロエチレンのコポリマー(P(VDF-TrFE))、フッ化ビニリデンとクロロトリフルオロエチレンのコポリマー(P(VDF-CTFE))、及びフッ化ビニリデンとヘキサフルオロプロピレンのコポリマー(P(VDF-HFP))からなる群から選択されるコポリマー、又はポリ(フッ化ビニリデン-トリフルオロエチレン-クロロトリフルオロエチレン)、ポリ(フッ化ビニリデン-トリフルオロエチレン-クロロフルオロエチレン)、ポリ(フッ化ビニリデン-トリフルオロエチレン-ヘキサフルオロプロピレン)、ポリ(フッ化ビニリデン-トリフルオロエチレン-フッ化ビニル)、及びポリ(フッ化ビニリデン-トリフルオロエチレン-塩化ビニリデン)からなる群から選択されるターポリマーである、請求項1に記載の方法。
- 部分フッ化ポリマーが式(I)
X1はH又はClであり、
X2、X3、及びX4は、H、F及びClからなる群から選択され、但し、X2、X3、及びX4の1つ以下がClであり、X2、X3、及びX4の全てがFであることはなく、
xは30mol%〜85mol%であり、
yは10mol%〜65mol%であり、
x+y≦100mol%である]
によって表される、請求項1に記載の方法。 - 前記架橋剤が、マレイミド、アミン、チオール、フェノール、シンナマート及びクマリン基からなる群から独立に選択される2つ以上の架橋基を含み、任意選択で前記架橋基が、ビスフェノール、ジアミン、ビスマレイミド、多官能性チオール、及びビス(シンナマート)からなる群から選択される、請求項1に記載の方法。
- 前記感光性非求核塩基及び前記架橋剤が、個別に、フッ化ビニリデン系ポリマーの10質量%未満で組成物中に存在する、請求項1に記載の方法。
- 前記光パターン化可能な組成物が、酢酸エチル、酢酸プロピル、酢酸ブチル、酢酸イソブチル、酢酸ペンチル、酢酸シクロヘキシル、酢酸ヘプチル、プロピオン酸エチル、プロピオン酸プロピル、プロピオン酸ブチル、プロピオン酸イソブチル、プロピレングリコールモノメチルエーテルアセタート(PGMEA)、乳酸メチル、乳酸エチル、γ-ブチロラクトン、アセトン、アセチルアセトン、メチルエチルケトン、メチルイソブチルケトン、2-ブタノン、2-ペンタノン、3-ペンタノン、2-ヘプタノン、3-ヘプタノン、シクロペンタノン、及びシクロヘキサノンからなる群から選択される有機溶媒を含む、請求項1に記載の方法。
- 前記パターン化薄膜部品に隣接して有機薄膜を形成する工程を含み、前記有機薄膜が非強誘電性ポリマーを含む、請求項1に記載の方法。
- ゲート誘電体としてパターン化薄膜部品を含む有機薄膜トランジスタであって、前記パターン化薄膜は、フッ化ビニリデン系ポリマーと、感光性非求核塩基と、架橋剤とを含む光パターン化可能な組成物由来の膜をゲート電極上に堆積することによって調製され、
前記フッ化ビニリデン系ポリマーがフッ化ビニリデンである第1の反復単位と、フッ化ビニル、トリフルオロエチレン、クロロフルオロエチレン、クロロトリフルオロエチレン、塩化ビニリデン、及びヘキサフルオロプロピレンからなる群から選択される第2の反復単位と、任意選択で、フッ化ビニル、クロロフルオロエチレン、クロロトリフルオロエチレン、塩化ビニリデン、及びヘキサフルオロプロピレンからなる群から選択される第2の反復単位と異なる第3の反復単位とを含み、
感光性非求核塩基が
YはC=C、CR2、NR、O、S、及びSeからなる群から選択され、RがH、C1〜6アルキル基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、
ZはNR、任意選択で置換されているピリジル基、又は共有結合からなる群から選択され、
Ra、Rb、Rc、及びRdは独立にH、C1〜6アルキル基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRaとRbが一緒になって及び/又はRcとRdが一緒になって窒素原子と結合してグアニジニル基又はトリアミノホスファゼニル基を形成することができ、
Re及びRfは独立にハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基であり、
Rg、Rh、Ri、及びRjは独立にH、ハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRgとRhが一緒になって又はRhとRiが一緒になって又はRiとRjが一緒になって炭素原子2個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
Rk、Rl、Rm、及びRnは独立にH、ハロ基、シアノ基、ニトロ基、C1〜6アルキル基、C1〜6ハロアルキル基、若しくはC1〜6アルコキシ基、任意選択で置換されているフェニル基、又は任意選択で置換されているベンジル基であり、或いはRkとRlが一緒になって又はRlとRmが一緒になって又はRmとRnが一緒になって炭素原子2個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
或いはRgとRhが一緒になって結合しても、RmとRnが一緒になって結合しても、任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成しない場合は、RgとRnが一緒になってQ及び炭素原子4個とその間で結合して任意選択で置換されているC6〜14アリール基又は任意選択で置換されている5〜14員ヘテロアリール基を形成することができ、
nは0、1、2又は3である]
からなる群から選択される式のうちの1つによって表され、
前記架橋剤が、マレイミド、アミン、チオール、フェノール、及びシンナマートからなる群から独立に選択される2つ以上の架橋基を含み、
基板と、ゲート電極と、ソース及びドレイン電極と、有機半導体層とを更に含み、前記ゲート誘電体が、前記ゲート電極と前記有機半導体層との間に位置する、
有機薄膜トランジスタ。 - 前記パターン化薄膜部品に隣接した非強誘電性ポリマーを含む有機薄膜を更に含み、前記有機薄膜は、電界が前記パターン化薄膜部品に印加された場合、有機薄膜が、パターン化薄膜部品中のフッ化ビニリデン系ポリマーの強誘電性ドメインの形成を防止し、前記有機薄膜が、前記パターン化薄膜部品と前記有機半導体層又はゲート電極のいずれかとの間に位置する、請求項10に記載の有機薄膜トランジスタ。
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KR102283518B1 (ko) | 2021-07-28 |
KR20170024007A (ko) | 2017-03-06 |
JP2017522613A (ja) | 2017-08-10 |
EP3161061A1 (en) | 2017-05-03 |
WO2015200872A1 (en) | 2015-12-30 |
CN106663736B (zh) | 2020-01-17 |
EP3161061B1 (en) | 2020-11-18 |
TW201606436A (zh) | 2016-02-16 |
TWI668516B (zh) | 2019-08-11 |
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