JP7129640B2 - 縮環ヘテロ5員環分子、p型半導体膜および電子デバイス - Google Patents
縮環ヘテロ5員環分子、p型半導体膜および電子デバイス Download PDFInfo
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- JP7129640B2 JP7129640B2 JP2020540212A JP2020540212A JP7129640B2 JP 7129640 B2 JP7129640 B2 JP 7129640B2 JP 2020540212 A JP2020540212 A JP 2020540212A JP 2020540212 A JP2020540212 A JP 2020540212A JP 7129640 B2 JP7129640 B2 JP 7129640B2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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Description
本開示の縮環ヘテロ5員環分子は、1分子中、3個または5個のヘテロ5員環を含む8個の芳香族環が縮合した構造を有している。ヘテロ5員環は、チオフェン環、セレノフェン環およびフラン環からなる群より選択されるヘテロ5員環であり、これらのヘテロ5員環はいずれも芳香族環に属するものである。本開示の縮環ヘテロ5員環分子が有する3個または5個のヘテロ5員環は、それぞれ独立して、上記群より選択されてよいが、正孔移動度のさらなる向上の観点から、縮環ヘテロ5員環分子が1分子中に有する全てのヘテロ5員環は同じヘテロ原子を有するヘテロ5員環であることが好ましい。本開示の縮環ヘテロ5員環分子に含まれるヘテロ5員環以外の芳香族環は通常、ベンゼン環である。従って、本開示の縮環ヘテロ5員環分子が有する8個の芳香族環は通常、3個のヘテロ5員環および5個のベンゼン環を縮合形態で含むか、または5個のヘテロ5員環および3個のベンゼン環を縮合形態で含む。縮合とは、隣接する2個の芳香族環が2個の炭素原子およびそれらの間に形成される結合(すなわち共有結合)を有すること、またはその状態のことである。
・組み合わせ:
Rb1~Rb3、Rb5~Ra9、およびRb11~Rb14は、それぞれ独立して、水素原子または炭素原子数1~10のアルキル基であり、より好ましくは水素原子である。Rb4およびRb10は、それぞれ独立して、水素原子、炭素原子数1~10のアルキル基、または炭素原子数6~18のアリール基であり、より好ましくは水素原子、炭素原子数3~8のアルキル基、または炭素原子数6~12のアリール基であり、さらに好ましくは水素原子である。
縮環ヘテロ5員環分子は公知の方法により製造することができる。例えば、目的とする縮環ヘテロ5員環分子が有する芳香族環部の一部を構成する原料(例えば、ナフタレン、後述の式(m-1)で表されるベンゾ[1,2-b:4,5-b’]ビス[b]ベンゾチオフェン、または後述の式(n-1)で表されるベンゾ[1,2-b:4,5-b’]ビス[b]ベンゾセレノフェン))を用いて、所望位置の水素原子のハロゲン化反応(例えば、ヨウ素化反応)および薗頭カップリング反応を繰り返す。所望位置とは、目的とする縮環ヘテロ5員環分子を得るために縮合ヘテロ5員環または縮合ベンゼン環を形成するべき位置という意味である。これにより、所望位置に縮合ヘテロ5員環および縮合ベンゼン環を形成することができ、結果として、目的とする縮環ヘテロ5員環分子を製造することができる。所望位置の水素原子がハロゲン化された中間体が単独では得られず、混合物として得られる場合は、カラムクロマトグラフィ等の公知の分離法により、分離および精製すればよい。
本開示の縮環ヘテロ5員環分子は、元素分析法、質量分析法およびC13-NMR(炭素13核磁気共鳴)により、同定することができる。
本開示の縮環ヘテロ5員環分子はより十分に優れた正孔移動度を示すため、分子系有機半導体材料または炭素系正孔輸送材料、特にp型半導体材料として有用である。このため、本開示の縮環ヘテロ5員環分子は、電子デバイス(電子素子)、例えば、トランジスタに用いることにより、電子デバイスの周波数特性を向上させることができる。
ゲート電極1;
前記ゲート電極1上に形成されるゲート絶縁膜2;
前記ゲート絶縁膜2上に離隔して形成されるソース電極3およびドレイン電極4;ならびに
前記ゲート絶縁膜2の露出領域、前記ソース電極3および前記ドレイン電極4と接触して形成された半導体膜5を含む。
絶縁性の下地基板12;
前記絶縁性の下地基板12上に離隔して形成されるソース電極13およびドレイン電極14;
前記絶縁性の下地基板12の露出領域、前記ソース電極13および前記ドレイン電極14と接触して形成された半導体膜15;
前記半導体膜15の上に形成されたゲート絶縁膜16;ならびに
前記ゲート絶縁膜16の上において、上面から見て、前記ソース電極13および前記ドレイン電極14の間となる位置に形成された、ゲート電極17を含む。
発明者らは、縮環ヘテロ5員環分子の正孔移動度の分子動力学および分子軌道計算による予測を実施した。移動度の計算方法は、デービッド・エバンス他、オーガニックエレクトロニクス第29巻(2016年)第50~56ページ(David R. Evans et al.,“Estimation of charge carrier mobility in amorphous organic materials using percolation corrected random-walk method”, Organic Electronics vol. 29 (2016) pages 50-56)記載の方法を適用した。すなわち、移動度の計算に必要となる、電荷ホッピングレート(κ)は、以下の式で与えられることが知られている。
まず、式(m-1)で表されるベンゾ[1,2-b:4,5-b’]ビス[b]ベンゾチオフェンを、文献(瀧宮、オーガニックレターズ、2007年第9巻、第4499~4502ページ(K. Takimiya, Org. Lett., 2007, 9, 4499-4502))に記載の方法で合成した。
(化合物(ii-se-1)の製造)
まず、式(n-1)で表されるベンゾ[1,2-b:4,5-b’]ビス[b]ベンゾセレノフェンを、論文(タキミヤ、オーガニックレターズ、2007年第9巻、第4499~4502ページ)に記載の方法で合成した。
(実施例1~2および比較例1)
化合物(i-s-1)、化合物(ii-se-1)または化合物(x-1)を用いて、図2に示すトランジスタ基本構造体11を製造した。
2、16 ゲート絶縁膜
3、13 ソース電極
4、14 ドレイン電極
5、15 半導体膜
10、11 トランジスタ基本構造体
12 下地基板
Claims (9)
- 1分子中8個の芳香族環を有し、前記8個の芳香族環は3個のヘテロ5員環を含み、かつ前記8個の芳香族環は1個または2個のナフタレン構造部を有する縮環ヘテロ5員環分子であって、
前記3個のヘテロ5員環は、それぞれ独立して、チオフェン環、セレノフェン環およびフラン環からなる群より選択され、
前記縮環ヘテロ5員環分子は、下記一般式(I)又は(II)で表され、
一般式(I)中、Ra 1 ~Ra 14 は、それぞれ独立して、水素原子、炭素原子数1~20のアルキル基または炭素原子数6~18のアリール基であり、M 1 ~M 3 は、それぞれ独立して、硫黄原子、セレン原子または酸素原子であり、
一般式(II)中、Rb 1 ~Rb 14 は、それぞれ独立して、水素原子、炭素原子数1~20のアルキル基または炭素原子数6~18のアリール基であり、M 1 ~M 3 は、それぞれ独立して、硫黄原子、セレン原子または酸素原子である、
縮環ヘテロ5員環分子。
- 前記3個のヘテロ5員環は全て同じヘテロ原子を有するヘテロ5員環である、請求項1に記載の縮環ヘテロ5員環分子。
- 前記8個の芳香族環が互いに縮合されて芳香族環部を構成し、
前記縮環ヘテロ5員環分子は、前記8個の芳香族環の全てが隣接する1個または2個のみの芳香族環と縮合している第一構造を有する、請求項1又は2に記載の縮環ヘテロ5員環
分子。 - 前記芳香族環部において、前記8個の芳香族環のうち前記第一構造の末端にある2個の芳香族環はともにベンゼン環である、請求項3に記載の縮環ヘテロ5員環分子。
- 前記芳香族環部において、前記8個の芳香族環のうち前記第一構造の末端にある2個の芳香族環はベンゼン環であり、
前記芳香族環部は、前記8個の芳香族環のうち2個の末端の芳香族環以外の全てのベンゼン環のそれぞれにおいて、前記ベンゼン環と隣接する一方の芳香族環と縮合している第一対の炭素原子と、前記ベンゼン環と隣接する他方の芳香族環と縮合している第二対の炭素原子とが、前記第一対の炭素原子と前記第二対の炭素原子との間に1つの炭素原子が介在した状態で配置されている構造を有する、
請求項3に記載の縮環ヘテロ5員環分子。 - 前記ヘテロ5員環に隣接する全ての芳香族環はベンゼン環である、請求項3または4に記載の縮環ヘテロ5員環分子。
- 請求項1~6のいずれかに記載の縮環ヘテロ5員環分子を含むp型半導体膜。
- 請求項7に記載のp型半導体膜を含む電子デバイス。
- ソース電極とドレイン電極とゲート電極と半導体膜とを備えるトランジスタを構成し、
前記半導体膜が請求項7に記載のp型半導体膜である、電子デバイス。
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