JP6622229B2 - N−フルオロアルキル置換されたジブロモナフタレンジイミドおよびそれらの半導体としての使用 - Google Patents
N−フルオロアルキル置換されたジブロモナフタレンジイミドおよびそれらの半導体としての使用 Download PDFInfo
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- JP6622229B2 JP6622229B2 JP2016573969A JP2016573969A JP6622229B2 JP 6622229 B2 JP6622229 B2 JP 6622229B2 JP 2016573969 A JP2016573969 A JP 2016573969A JP 2016573969 A JP2016573969 A JP 2016573969A JP 6622229 B2 JP6622229 B2 JP 6622229B2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K19/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic element specially adapted for rectifying, amplifying, oscillating or switching, covered by group H10K10/00
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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]
-
- 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]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Description
2,6−ジブロモ−N,N’−ビス(2,2,2−トリフルオロエチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)、
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロプロピル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)、および
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロペンチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
から選択される。
− 高い電荷輸送移動度、
− 空気安定性、
− 高い電流オン/オフ比、
− 溶剤ベースの方法で使用される上での適性
の少なくとも1つを有する。
− 前記基板上に堆積された有機半導体と、
− 導電性チャネルの導電性を制御するためのゲート構造と、
− 前記チャネルの2つの端部の導電性のソースおよびドレイン電極と、
を含み、前記有機半導体は、式Iの少なくとも1種の化合物からなるか、または式Iの化合物を含む、前記基板である。更に、前記有機電界効果トランジスタは、一般に誘電体を含む。
− 前記基板上のバッファ層上に堆積された有機半導体と、
− 導電性チャネルの導電性を制御するためのゲート構造と、
− 前記チャネルの2つの端部の導電性のソースおよびドレイン電極と、
を含み、前記有機半導体は、式Iの少なくとも1種の化合物からなるか、または式Iの化合物を含む、前記基板である。更に、前記有機電界効果トランジスタは、一般に誘電体を含む。
− シラン、ホスホン酸、カルボン酸、ヒドロキサム酸、例えばアルキルトリクロロシラン、例えばn−オクタデシルトリクロロシラン、トリアルコキシシラン基を有する化合物、例えばアルキルトリアルコキシシラン、例えばn−オクタデシルトリメトキシシラン、n−オクタデシルトリエトキシシラン、n−オクタデシルトリ(n−プロピル)オキシシラン、n−オクタデシルトリ(イソプロピル)オキシシラン、トリアルコキシアミノアルキルシラン、例えばトリエトキシアミノプロピルシランおよびN−[(3−トリエトキシシリル)プロピル]エチレンジアミン、トリアルコキシアルキル−3−グリシジルエーテルシラン、例えばトリエトキシプロピル−3−グリシジルエーテルシラン、トリアルコキシアリルシラン、例えばアリルトリメトキシシラン、トリアルコキシ(イソシアナトアルキル)シラン、トリアルコキシシリル(メタ)アクリロイルオキシアルカンおよびトリアルコキシシリル(メタ)アクリルアミドアルカン、例えば1−トリエトキシシリル−3−アクリロイルオキシプロパン、
− アミン、ホスフィンおよび硫黄含有化合物、特にチオール
である。
1.基板、誘電体、有機半導体、好ましくはゲート、誘電体、有機半導体、ソースおよびドレイン、これは「ボトムゲート・トップコンタクト型」としても知られる
2.基板、誘電体、有機半導体、好ましくは基板、ゲート、誘電体、ソースおよびドレイン、有機半導体、これは「ボトムゲート・ボトムコンタクト型」としても知られる
3.基板、有機半導体、誘電体、好ましくは基板、ソースおよびドレイン、有機半導体、誘電体、ゲート、これは「トップゲート・ボトムコンタクト型」としても知られる
4.基板、有機半導体、誘電体、好ましくは基板、有機半導体、ソースおよびドレイン、誘電体、ゲート、これは「トップゲート・トップコンタクト型」としても知られる。
− 電子伝導特性を有する層(電子輸送層、ETL)、
− いかなる放射の吸収も必要ない正孔伝導性材料を含む層(正孔輸送層、HTL)、
− 吸収してはならない励起子−および正孔ブロッキング層(例えばEBL)、および
− 倍増層
から選択される。
− 少なくとも部分的に透明な導電性層(最上部電極、アノード)(11)、
− 正孔伝導性層(正孔輸送層、HTL)(12)、
− ドナー材料を含む層(13)、
− アクセプター材料を含む層(14)、
− 励起子ブロッキングおよび/または電子伝導性層(15)、
− 第二の導電性層(背面電極、カソード)(16)
を有する。
− 少なくとも部分的に透明な導電性層(カソード)(11)、
− 励起子ブロッキングおよび/または電子伝導性層(12)、
− アクセプター材料を含む層(13)、
− ドナー材料を含む層(14)、
− 正孔伝導性層(正孔輸送層、HTL)(15)、
− 第二の導電性層(背面電極、アノード)(16)
を有する。
− 少なくとも部分的に透明な導電性層(アノード)(21)、
− 正孔伝導性層(正孔輸送層、HTL)(22)、
− ドナー材料とアクセプター材料とを含み、それらがバルクヘテロ接合の形でドナー−アクセプターヘテロ接合を形成する混合層(23)、
− 電子伝導性層(24)、
− 励起子ブロッキングおよび/または電子伝導性層(25)、
− 第二の導電性層(背面電極、カソード)(26)
を有する。
基R11、R12、R13、R14、R21、R22、R23およびR24は、それぞれ独立して、水素、ハロゲンまたはハロゲン以外の基であり、
Y1は、OまたはNRaであり、ここでRaは、水素またはオルガニル基であり、
Y2は、OまたはNRbであり、ここでRbは、水素またはオルガニル基であり、
Z1、Z2、Z3およびZ4は、それぞれOであり、
Y1がNRaである場合に、基Z1およびZ2の一方は、NRcであってもよく、ここで基RaおよびRcは、一緒になって、橋かけ基であってその両端の結合の間に2〜5個の原子を有する基であり、かつ
Y2がNRbである場合に、基Z3およびZ4の一方は、NRdであってもよく、ここで基RbおよびRdは、一緒になって、橋かけ基であってその両端の結合の間に2〜5個の原子を有する基である]のペリレンジイミドである。
1.担体、基板、
2.ベース電極(アノード)、
3.正孔注入層、
4.正孔輸送層、
5.発光層、
6.電子輸送層、
7.電子注入層、
8.最上部電極(カソード)、
9.接点、
10.カバー、封止。
例1(比較、国際公開第2007/074137号パンフレット(WO 2007/074137)の化合物(21)):
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロブチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)(式Iで示され、その式中、R1およびR2が2,2,3,3,3,4,4,4−ヘプタフルオロブチルである、化合物)
2,6−ジブロモ−N,N’−ビス(2,2,2−トリフルオロエチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)(式Iで示され、その式中、R1およびR2が2,2,2−トリフルオロエチルである、化合物)
N,N’−ビス(2,2,2−トリフルオロエチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
2,6−ジブロモ−N,N’−ビス(2,2,2−トリフルオロエチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロプロピル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)(式Iで示され、その式中、R1およびR2が2,2,3,3,3−ペンタフルオロプロピルである、化合物)
N,N’−ビス(1H,1H−ペルフルオロプロピル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロプロピル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロペンチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)(式Iで示され、その式中、R1およびR2が2,2,3,3,4,4,5,5,5−ノナフルオロペンチルである、化合物)
N,N’−ビス(1H,1H−ペルフルオロペンチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロペンチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
ボトムゲート・トップコンタクト構成における蒸着されたOFETの製造のための一般的手順
高ドープのp型シリコン(100)ウェハ(0.01Ω・cm〜0.02Ω・cm)を基板Aとして使用した。熱的成長された100nm厚のSiO2層(キャパシタンス34nF/cm2)を有する高ドープのp型シリコン(100)ウェハ(0.005Ω・cm〜0.02Ω・cm)を、基板Bとして使用した。
トップゲート・ボトムコンタクト構成における標準的な基板上での溶液加工されたOFETのための手順
酢酸エチル中0.5%の半導体の溶液を、50℃に温め、それを標準的なPET基板上に1000rpmでスピンコート(スピンコータ:Primus STT15)した。該標準的なPET基板は、シャドウマスクパターン形成された、50nm厚の金製のソースおよびドレイン接点を有するPETシート(Mitsubishi DN4600)からなるものであった。半導体の堆積の後に、Cytop CTL−809(9%)を、3500rpmで誘電体層(厚さ660nm、εr=2.1)としてスピンコートした。スピンコート直後に、該基板をホットプレート上に置き、100℃で10分間にわたりアニールした。最後に、50nm厚のゲート電極を、シャドウマスクを通じて金の熱的蒸発によってパターン形成させた。
ボトムゲート・ボトムコンタクト構成におけるシリコンウェハ上での溶液加工されたOFETのための手順
酢酸エチル中0.5%の半導体の溶液を、50℃に温め、それを未処理の標準的なシリコン基板上に1000rpmでスピンコート(スピンコータ:Primus STT15)した。該標準的なシリコン基板は、230nm厚の二酸化ケイ素層(εr=3.9)を有するとともに、30nm厚の金およびITO接着剤からなるリソグラフィーによりパターン形成されたソース/ドレイン接点を有するシリコンウェハからなっていた。
Claims (11)
- R1およびR2は、同じ意味を有する、請求項1に記載の化合物。
- 2,6−ジブロモ−N,N’−ビス(2,2,2−トリフルオロエチル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)、および
2,6−ジブロモ−N,N’−ビス(1H,1H−ペルフルオロプロピル)ナフタレン[1,8:4,5]ビス(ジカルボキシイミド)
から選択される、請求項1に記載の化合物。 - 請求項1から3までのいずれか1項に記載の一般式Iの化合物の、半導体としての使用。
- 請求項1から3までのいずれか1項に記載の化合物を含む薄膜半導体。
- 少なくとも1つのゲート構造と、ソース電極と、ドレイン電極とを有する基板と、半導体材料としての請求項1から3までのいずれか1項に記載の式Iの少なくとも1種の化合物とを含む有機電界効果トランジスタ。
- トップゲート・ボトムコンタクト構成を有する、請求項6に記載の有機電界効果トランジスタ。
- ボトムゲート・ボトムコンタクト構成を有する、請求項6に記載の有機電界効果トランジスタ。
- 複数の有機電界効果トランジスタを含む基板であって、該電界効果トランジスタの少なくとも幾つかが請求項1から3までのいずれか1項に記載の式Iの少なくとも1種の化合物を含む、前記基板。
- 請求項9に記載の少なくとも1つの基板を含む半導体ユニット。
- 請求項1から3までのいずれか1項に記載の式Iの少なくとも1種の化合物を含む有機太陽電池。
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WO2015193808A1 (en) | 2015-12-23 |
CN106459748B (zh) | 2019-08-23 |
JP2017521395A (ja) | 2017-08-03 |
TW201609727A (zh) | 2016-03-16 |
US20170117479A1 (en) | 2017-04-27 |
US10186664B2 (en) | 2019-01-22 |
CN106459748A (zh) | 2017-02-22 |
EP3158025B1 (en) | 2019-03-13 |
KR20170016862A (ko) | 2017-02-14 |
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