JP5228907B2 - 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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- JP5228907B2 JP5228907B2 JP2008505037A JP2008505037A JP5228907B2 JP 5228907 B2 JP5228907 B2 JP 5228907B2 JP 2008505037 A JP2008505037 A JP 2008505037A JP 2008505037 A JP2008505037 A JP 2008505037A JP 5228907 B2 JP5228907 B2 JP 5228907B2
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- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/30—Germanium compounds
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Thin Film Transistor (AREA)
- Electroluminescent Light Sources (AREA)
Description
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 有機薄膜トランジスタシート
11 有機薄膜トランジスタ
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
101、201 基板
102 有機EL素子
102a、202 陽極
102b 有機EL層
102c、204 陰極
103 封止膜
205 駆動用素子
206 正孔輸送層
207 発光層
208 電子輸送層
601 基板
602 TFT
本発明の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は、上記一般式(1)で表される化合物を含有することが特徴である。本発明の有機半導体材料中、一般式(1)で表される化合物は、主成分であることが好ましい。ここで、主成分とは、有機半導体材料の全構成成分において、50質量%以上であることを意味する。
上記一般式(1)で表される部分構造を有する化合物の中でも、好ましく用いられるのは、上記一般式(2)で表される化合物である。
一般式(2)において、Z3、Z4で、各々形成される芳香族炭化水素環は、一般式(1)において、Z1、Z2で、各々掲載される芳香族炭化水素環と同義である。
下記スキームにより化合物10を合成した。
本発明の有機半導体膜、有機半導体デバイス、有機薄膜TFT(有機薄膜トランジスタ)について説明する。
《有機TFT(有機薄膜トランジスタ)素子3の作製》:比較例
ゲート電極としての比抵抗0.01Ω・cmのSiウェハーに、厚さ200nm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3のクロロホルム溶液をアプリケーターを用いて塗布し、自然乾燥することによりキャスト膜(厚さ50nm)を形成して、窒素雰囲気下で50℃、30分間の熱処理を施した。
有機TFT素子3の作製において、比較化合物3をそれぞれ比較化合物1、2及び4に各々変更した以外は同様にして、有機TFT素子1、2及び4を作製した。
有機TFT素子3の作製において、比較化合物3の代替として、表1に記載の、本発明の有機TFT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素子5〜14を各々作製した。
得られた有機TFT素子1〜14の各々について、作製直後と大気中で1ヶ月放置後の各素子のキャリア移動度とON/OFF比を各々求めた。
次に、本発明の有機半導体材料を用いた有機薄膜トランジスタの応用例として、有機薄膜トランジスタを用いた有機EL素子を説明する。
有機EL素子の作製は、Nature,395巻,151〜154頁に記載の方法を参考にして、図3に示したような封止構造を有するトップエミッション型の有機EL素子を作製した。尚、図3において、101は基板、102aは陽極、102bは有機EL層(具体的には、電子輸送層、発光層、正孔輸送層等が含まれる)、102cは陰極を示し、陽極102a、有機EL層102b、陰極102cにより、発光素子102が形成されている。103は封止膜を示す。尚、本発明の有機EL素子は、ボトムエミッション型でもトップエミッション型のどちらでもよい。
Claims (6)
- 下記一般式(2)で表される化合物の少なくとも1種を含有することを特徴とする有機半導体材料。
- 前記X1はSiを表し、前記X2はGeまたはSnを表すことを特徴とする請求項1記載の有機半導体材料。
- 前記一般式(2)で表される化合物が下記化合物9または下記化合物10であることを特徴とする請求項1又は2記載の有機半導体材料。
- 請求項1〜3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1〜3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1〜3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。
Priority Applications (1)
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JP2008505037A JP5228907B2 (ja) | 2006-03-10 | 2007-02-26 | 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 |
Applications Claiming Priority (4)
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JP2006065498 | 2006-03-10 | ||
JP2006065498 | 2006-03-10 | ||
JP2008505037A JP5228907B2 (ja) | 2006-03-10 | 2007-02-26 | 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 |
PCT/JP2007/053499 WO2007105473A1 (ja) | 2006-03-10 | 2007-02-26 | 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 |
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JP5228907B2 true JP5228907B2 (ja) | 2013-07-03 |
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Cited By (1)
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JP2014193861A (ja) * | 2007-03-07 | 2014-10-09 | Univ Kentucky Res Found | シリルエチニル化されたヘテロアセン類およびそれで作製された電子装置 |
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WO2008120839A1 (en) * | 2007-03-30 | 2008-10-09 | Gyeongsang National University Industrial And Academic Collaboration Foundation | Novel organic semiconductor compound, and organic thin film transistor using the same |
JP5452475B2 (ja) * | 2008-04-10 | 2014-03-26 | 出光興産株式会社 | 有機薄膜トランジスタ用化合物及びそれを用いた有機薄膜トランジスタ |
WO2009125721A1 (ja) * | 2008-04-10 | 2009-10-15 | 出光興産株式会社 | 有機薄膜トランジスタ用化合物及び有機薄膜トランジスタ |
JP2013544755A (ja) * | 2010-09-10 | 2013-12-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | アントラ[2,3−b:7,6−b’]ジチオフェン誘導体および有機半導体としてのそれらの使用 |
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JP2007088115A (ja) * | 2005-09-21 | 2007-04-05 | Konica Minolta Holdings Inc | 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 |
JP2007288033A (ja) * | 2006-04-19 | 2007-11-01 | Konica Minolta Holdings Inc | 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 |
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JPWO2006059486A1 (ja) * | 2004-12-02 | 2008-06-05 | コニカミノルタホールディングス株式会社 | 有機薄膜トランジスタ材料、有機薄膜トランジスタ、電界効果トランジスタ、スイッチング素子、有機半導体材料及び有機半導体膜 |
JP5041267B2 (ja) * | 2005-01-20 | 2012-10-03 | 富士電機株式会社 | 薄膜電界効果トランジスタ、およびその製造方法 |
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JP2007088115A (ja) * | 2005-09-21 | 2007-04-05 | Konica Minolta Holdings Inc | 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 |
JP2007288033A (ja) * | 2006-04-19 | 2007-11-01 | Konica Minolta Holdings Inc | 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 |
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