JP2007288034A - 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ - Google Patents
有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ Download PDFInfo
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- JP2007288034A JP2007288034A JP2006115410A JP2006115410A JP2007288034A JP 2007288034 A JP2007288034 A JP 2007288034A JP 2006115410 A JP2006115410 A JP 2006115410A JP 2006115410 A JP2006115410 A JP 2006115410A JP 2007288034 A JP2007288034 A JP 2007288034A
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- organic semiconductor
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- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
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- 239000010955 niobium Substances 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
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Abstract
Description
該芳香族縮合多環が下記一般式(1)で表される置換基を3つ以上有することを特徴とする有機半導体材料。
2.前記芳香族縮合多環が下記一般式(2)で表される部分構造を少なくとも一つ含んでいることを特徴とする前記1に記載の有機半導体材料。
3.前記芳香族縮合多環が前記一般式(2)で表される部分構造を二つ以上含んでいることを特徴とする前記1に記載の有機半導体材料。
5.前記一般式(1)のR、一般式(2)のR1、R2、一般式(3)のR3〜R6が、各々アルキル基、シクロアルキル基、アルケニル基、アルキニル基、芳香族炭化水素環基、芳香族複素環基、−Si(R‘)3または−Ge(R‘)3(R’は置換基を表す。)で表されることを特徴とする前記1〜4のいずれか1項に記載の有機半導体材料。
本発明に係る有機半導体材料について説明する。
本発明の有機半導体材料に係る、3環以上の環が縮合した芳香族縮合多環を部分構造として有し、該芳香族縮合多環が上記一般式(1)で表される置換基を3つ以上有する化合物について説明する。
本発明に係る芳香族縮合多環について説明する。
3環以上が縮合した芳香族炭化水素環としては、具体的には、ナフタセン環、アントラセン環、テトラセン環、ペンタセン環、ヘキサセン環、フェナントレン環、ピレン環、ベンゾピレン環、ベンゾアズレン環、クリセン環、ベンゾクリセン環、アセナフテン環、アセナフチレン環、トリフェニレン環、コロネン環、ベンゾコロネン環、ヘキサベンゾコロネン環、フルオレン環、ベンゾフルオレン環、フルオランテン環、ペリレン環、ナフトペリレン環、ペンタベンゾペリレン環、ベンゾペリレン環、ペンタフェン環、ピセン環、ピラントレン環、コロネン環、ナフトコロネン環、オバレン環、アンスラアントレン環等が挙げられる。
3環以上が縮合した芳香族複素環としては、好ましくはN、O及びSから選択されたヘテロ原子を縮合環を構成する元素として含有する芳香族複素縮合環であることが好ましく、具体的には、アクリジン環、ベンゾキノリン環、カルバゾール環、フェナジン環、フェナントリジン環、フェナントロリン環、カルボリン環、サイクラジン環、キンドリン環、テペニジン環、キニンドリン環、トリフェノジチアジン環、トリフェノジオキサジン環、フェナントラジン環、アクリンドリン環、アントラジン環、ペリミジン環、ジアザカルバゾール環(カルボリン環を構成する炭素原子の任意の一つが窒素原子で置き換わったものを表す)、フェナントロリン環、ジベンゾフラン環、ジベンゾチオフェン環、ナフトフラン環、ナフトチオフェン環、ベンゾジフラン環、ベンゾジチオフェン環、ナフトジフラン環、ナフトジチオフェン環、アントラフラン環、アントラジフラン環、アントラチオフェン環、アントラジチオフェン環、チアントレン環、フェノキサチイン環、チオファントレン環(ナフトチオフェン環)等が挙げられる。
一般式(2)において、R1、R2で、各々表される置換基は、一般式(1)において、Rで表される置換基と同義である。
一般式(3)において、R3〜R6で、各々表される置換基は、一般式(1)において、Rで表される置換基と同義である。
(a)前記一般式(1)のR、一般式(2)のR1、R2、一般式(3)のR3〜R5が、各々アルキル基、シクロアルキル基、アルケニル基、アルキニル基、芳香族炭化水素環基、芳香族複素環基、−Si(R‘)3または−Ge(R‘)3(ここで、R’は置換基を表す。)で表される場合、
(b)前記一般式(1)のR、一般式(2)のR1、R2、一般式(3)のR3〜R5が、各々芳香族炭化水素環基、芳香族複素環基、−Si(R)3または−Ge(R)3(ここで、Rは置換基を表す。)で表される場合、
(c)前記一般式(2)のR1、R2、一般式(3)のR3〜R5が、各々同一の置換基で表される場合、
(d)前記一般式(2)のR1、R2、一般式(3)のR3〜R5が、各々置換基を有するまたは2環以上が縮合した芳香族炭化水素環基または芳香族複素環基で表される場合、
等が挙げられる。
以下に例示化合物1の合成スキーム概要を示す。
本発明に係る有機半導体膜について説明する。
本発明の有機半導体膜は、本発明の有機半導体材料を下記に示す有機溶媒と混合して調製した、室温で溶液または分散液を用いて膜形成する工程を経て作製されることが好ましい。ここで、室温で溶液または分散液とは、有機半導体材料と有機溶媒とを10℃〜80
℃の条件下で混合した時に、溶液または分散液が形成されることが好ましく、分散液とは、有機半導体材料が粒子状に分散された状態を表すが、分散液中に、有機半導体材料が部分的溶解している状態も含まれる。
上記の溶液または分散液の調製に用いる有機溶媒としては、特に制限はなく、単一溶媒でも混合溶媒でもよいが、好ましくは、非ハロゲン系溶媒が用いられる。本発明に用いられる非ハロゲン系溶媒としては、ヘキサン、オクタンなどの脂肪族系、シクロヘキサンなどの脂環式系溶媒、ベンゼン、トルエン、キシレン等の芳香族系溶媒、テトラヒドロフラン、ジオキサン、エチレングリコールジエチルエーテル、アニソール、ベンジルエチルエーテル、エチルフェニルエーテル、ジフェニルエーテル、メチル−t−ブチルエーテル等のエーテル系溶媒、酢酸メチル、酢酸エチル、エチルセロソルブ等のエステル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、アセトン、メチルエチルケトン、シクロヘキサノン、2−ヘキサノン、2−ヘプタノン、3−ヘプタノン等のケトン系溶媒、その他ジメチルホルムアミド、ジメチルスルホキシド、ジエチルホルムアミド、1,3−ジオキソラン等が挙げられる。
本発明の有機半導体デバイス、有機薄膜トランジスタ(本願では、有機TFTともいう)について説明する。
ト電極を有するトップゲート型と、支持体上にまずゲート電極を有し、ゲート絶縁層を介して有機半導体チャネルで連結されたソース電極とドレイン電極を有するボトムゲート型に大別される。
オブ酸ビスマス、トリオキサイドイットリウムなどが挙げられる。それらのうち好ましいのは酸化ケイ素、酸化アルミニウム、酸化タンタル、酸化チタンである。窒化ケイ素、窒化アルミニウム等の無機窒化物も好適に用いることができる。
法等を用いて、有機半導体層1を形成し、その後ソース電極2、ドレイン電極3、絶縁層5、ゲート電極4を形成したものを表す。
本発明の有機半導体デバイスまたは有機薄膜トランジスタは、有機エレクトロルミネッセンス素子(有機EL素子ともいう)に具備することができ、有機EL素子は、例えば、陽極と陰極との間に有機EL層(有機層、有機化合物層ともいう)が挟まれた状態(挟持された状態ともいう)のものが挙げられるが、これらの構成としては、従来公知の層構成、有機EL層の材料等を用いて作製することが出来る。例えば、Nature,395巻,151〜154頁の文献等が参照出来る。
有機EL素子は、照明用や露光光源のような一種のランプとして使用しても良いし、画像を投影するタイプのプロジェクション装置や、静止画像や動画像を直接視認するタイプの表示装置(ディスプレイ)として使用しても良い。動画再生用の表示装置として使用する場合の駆動方式は単純マトリクス(パッシブマトリクス)方式でもアクティブマトリクス方式でもどちらでも良い。または、異なる発光色を有する本発明の有機EL素子を2種以上使用することにより、フルカラー表示装置を作製することが可能である。
タ12の駆動はオン状態が保たれて、次の走査信号の印加が行われるまで有機EL素子10の発光が継続する。順次走査により次に走査信号が印加されたとき、走査信号に同期した次の画像データ信号の電位に応じて駆動トランジスタ120が駆動して有機EL素子100が発光する。
《有機薄膜トランジスタ1の作製》
ゲート電極としての比抵抗0.01Ω・cmのSiウェハーに、厚さ2000Åの熱酸化膜を形成してゲート絶縁層とした後、オクタデシルトリクロロシランによる表面処理を行った。
比較化合物2(2,3,9,10−テトラヘキシルペンタセン)は、Organic Letters、vol.2(2000),p85に記載の方法で合成した。
比較化合物3は、J.Am.Chem.Soc.,vol.123(2001),p9486,supporting informationに記載の方法で合成した。
有機薄膜トランジスタ1の作製において、比較化合物1を比較化合物4に変更した以外は同様にして、有機薄膜トランジスタ3を作製した。
比較化合物4は、J.Am.Chem.Soc.,vol.127(2005),p4986,supporting informationに記載の方法で合成した。
有機薄膜トランジスタ1の作製において、比較化合物1を比較化合物4(ルブレン、アルドリッチ社製、市販試薬を昇華精製して用いた)に変更した以外は同様にして、有機薄膜トランジスタ4を作製した。
有機薄膜トランジスタ2の作製において、比較化合物1の代わりに、表1に記載の本発明の有機半導体材料に変更した以外は同様にして、有機薄膜トランジスタ6〜14を作製した。
得られた有機薄膜トランジスタ1〜14について、各素子のキャリア移動度とON/OFF値を、素子作成直後に測定した。なお、本発明では、I−V特性の飽和領域からキャリア移動度を求め、さらに、ドレインバイアス−50Vとし、ゲートバイアス−50V及び0Vにしたときのドレイン電流値の比率からON/OFF比を求めた。
2 ソース電極
3 ドレイン電極
4 ゲート電極
5 絶縁層
6 支持体
7 ゲートバスライン
8 ソースバスライン
10 有機TFTシート
11 有機TFT
12 出力素子
13 蓄積コンデンサ
14 垂直駆動回路
15 水平駆動回路
21 ディスプレイ
23 画素
25 走査線
26 データ線
27 電源ライン
100 有機EL素子
110 スイッチングトランジスタ
120 駆動トランジスタ
130 コンデンサ
A 表示部
B 制御部
Claims (12)
- 前記芳香族縮合多環が前記一般式(2)で表される部分構造を二つ以上含んでいることを特徴とする請求項1に記載の有機半導体材料。
- 前記一般式(1)のR、一般式(2)のR1、R2、一般式(3)のR3〜R6が、各々アルキル基、シクロアルキル基、アルケニル基、アルキニル基、芳香族炭化水素環基、芳香族複素環基、−Si(R‘)3または−Ge(R‘)3(R’は置換基を表す。)で表されることを特徴とする請求項1〜4のいずれか1項に記載の有機半導体材料。
- 前記一般式(1)のR、一般式(2)のR1、R2、一般式(3)のR3〜R6が、各々芳香族炭化水素環基、芳香族複素環基、−Si(R’)3または−Ge(R’)3(R’は置換基を表す。)を表すことを特徴とする請求項1〜4のいずれか1項に記載の有機半導体材料。
- 前記一般式(2)のR1、R2、一般式(3)のR3〜R6が、各々同一の置換基であることを特徴とする請求項2〜6のいずれか1項に記載の有機半導体材料。
- 前記一般式(2)のR1、R2、一般式(3)のR3〜R6が、各々置換基を有するまたは2環以上が縮合した芳香族炭化水素環基または芳香族複素環基であることを特徴とする請求項2〜7のいずれか1項に記載の有機半導体材料。
- 請求項1〜8のいずれか1項に記載の有機半導体材料を含有することを特徴とする有機半導体膜。
- 請求項1〜8のいずれか1項に記載の有機半導体材料を有機溶媒に溶解または分散し、得られた溶液または分散液を塗布・乾燥することによって形成されることを特徴とする有機半導体膜。
- 請求項1〜8のいずれか1項に記載の有機半導体材料を用いることを特徴とする有機半導体デバイス。
- 請求項1〜8のいずれか1項に記載の有機半導体材料を半導体層に用いることを特徴とする有機薄膜トランジスタ。
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WO2014142467A1 (ko) * | 2013-03-11 | 2014-09-18 | 덕산하이메탈(주) | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
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KR101918851B1 (ko) | 2017-06-22 | 2018-11-14 | 중앙대학교 산학협력단 | 반도체 특성을 갖는 전도성 고분자 박막의 제조방법 및 반도체 특성을 갖는 전도성 고분자 박막을 포함하는 박막 트랜지스터 |
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