JP4061561B2 - Material for organic molecular alignment thin film and method for producing organic molecular alignment thin film - Google Patents
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- 239000010409 thin film Substances 0.000 title claims description 47
- 239000000463 material Substances 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000010408 film Substances 0.000 claims description 10
- 238000001771 vacuum deposition Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 23
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005411 Van der Waals force Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
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Classifications
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- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
Description
【０００１】
【発明の属する技術分野】
本発明は、光導波路、光非線形素子、発光素子、薄膜トランジスター、光学フィルターなどの多くの光、電子、光電子デバイスなどに用いられる有機分子配向薄膜用材料およびそれを用いた有機分子配向薄膜の製造方法に関する。
【０００２】
【従来の技術】
光導波路、光非線形素子、発光素子、薄膜トランジスター、光学フィルターなどへの応用が期待されるものとして、擬一次元的な共役系を有する有機半導体であるπ共役系オリゴマーの研究が近年活発に行われている。
【０００３】
また、これらの薄膜に関する研究も、近年活発に行われている。これらを精密に配列させることができれば、光非線型性及びキャリア移動度の非常に大きい薄膜が作製できる可能性がある。したがって、高度に配向した有機配向薄膜からなる光、電子、光電子デバイスの実現が期待されている。
【０００４】
【発明が解決しようとする課題】
しかしながら、有機分子はファンデルワールス力により結合するものであり、その相互作用が非常に小さいために、高度に配向した薄膜を得ることは困難であった。
【０００５】
有機分子を用いた配向膜作製の例として、チオフェン６量体配向薄膜の作製を有機分子線蒸着法によって行う試みが、Jpn.J.Appl.Phys.33,L1031(1994)に記載されている。ここで、有機分子線蒸着法とは、通常の真空蒸着装置では到達できない１０−６Ｐａ以下の真空度で、０．１ｎｍ／ｍｉｎのオーダー以下の速度で蒸着を行う方法である。この方法を用いると高度に配向した薄膜は得られるが、蒸着速度を非常に遅くする必要があるため、配向膜の作製に時間がかかるとともに、高真空を実現するために高価な装置を用いなければならず、コスト高になってしまうという問題があった。
【０００６】
また、最近、ペンタセン(IEEE Electron Device Lett.18,87(1997)）およびジチエノチオフェン(Appl.Phys.Lett.71,3871(1997)）などの芳香族多環及び複素環を持つ構造において、配向性の高い薄膜が得られたとの報告がなされた。これらの薄膜のキャリア移動度は、０．０３〜０．７ｃｍ２／Ｖ・ｓと、有機膜の中では非常に大きな値である。しかしながら、ａ−Ｓｉ（アモルファス・シリコン）の移動度に追いつくには、さらに１〜２桁程度高い移動度を実現させる必要があり、そのためには分子の配向性をより向上させることにより分子間の相互作用を大きくし、分子間のキャリア移動を高速化する必要がある。
【０００７】
この発明は上述の点に鑑みてなされ、その目的は、有機分子線蒸着法によらず、通常の真空蒸着法によって、高度に配向した有機分子配向薄膜を作製することを可能にする材料を提供するとともに、その材料を用いて安価で量産性に優れた有機分子配向薄膜の製造方法を提供することにある。
【０００８】
【課題を解決するための手段】
上記課題を解決するために、本発明の有機分子配向薄膜用材料は、下記一般式（IV）、
【００１２】
また、本発明の有機分子配向薄膜用材料は、下記一般式（Ｖ）、
【００１３】
さらに、本発明の有機分子配向薄膜用材料は、下記一般式（VI）、
【００１４】
また、上記課題を解決するために、本発明の有機分子配向薄膜の製造方法は、上記π共役系オリゴマー又はπ共役系分子のいずれかからなる有機分子配向薄膜用材料を用いて真空蒸着法により成膜することを特徴とする。
【００１５】
【発明の実施の形態】
本発明の有機分子配向薄膜用材料のπ共役系オリゴマー又はπ共役系分子を、下記化学式（Ｉ−１〜２０）、（II−１〜１０）、（III−１〜１２）、（IV−１〜１１）、（Ｖ−１〜４）及び（VI−１、２）に具体的に示す。
【００１６】
本発明の有機分子配向薄膜の製造方法においては、上記π共役系オリゴマー又はπ共役系分子を用いて、真空蒸着法により成膜する。かかる真空蒸着法は、例えば石英等の基板を抵抗加熱蒸着装置内に戴置し、真空槽内を、好ましくは１×１０−７〜５×１０−３Ｐａに減圧する。また、成長速度が、好ましくは０．０５〜２ｎｍ／ｓとなるようるつぼの温度を加熱する。膜厚は、好ましくは０．５〜３００ｎｍの範囲内である。
【００２４】
【実施例】
参考例１
石英を基板とし、抵抗加熱蒸着装置内に戴置し、前記化学式（Ｉ−１１）の化合物分子を成膜させた。成膜に際して真空槽内は５×１０−４Ｐａまで減圧した。成長速度が０．３ｎｍ／ｓとなるようるつぼの温度を加熱し、５０ｎｍの厚さに成膜した。
【００２５】
参考例２
参考例１の式（Ｉ−１１）の化合物を式（II−１）の化合物に代えた以外は、参考例１と同様にして、有機薄膜を作製した。
【００２６】
参考例３
参考例１の式（Ｉ−１１）の化合物を式（III−１）の化合物に代えた以外は、参考例１と同様にして、有機薄膜を作製した。
【００２７】
実施例１
参考例１の式（Ｉ−１１）の化合物を式（IV−１）の化合物に代えた以外は、参考例１と同様にして、有機薄膜を作製した。
【００２８】
実施例２
参考例１の式（Ｉ−１１）の化合物を式（Ｖ−１）の化合物に代えた以外は、参考例１と同様にして、有機薄膜を作製した。
【００２９】
実施例３
参考例１の式（Ｉ−１１）の化合物を式（VI−１）の化合物に代えた以外は、参考例１と同様にして、有機薄膜を作製した。
【００３０】
比較例１
参考例１の式（Ｉ−１１）の化合物を次式（VII−１）、
【００３１】
比較例２
参考例１の式（Ｉ−１１）の化合物を次式（VII−２）、
【００３２】
比較例３
参考例１の式（Ｉ−１１）の化合物を次式（VII−３）、
【００３３】
比較例４
参考例１の式（Ｉ−１１）の化合物を次式（VII−４）、
【００３４】
比較例５
参考例１の式（Ｉ−１１）の化合物を次式（VII−５）、
【００３５】
比較例６
参考例１の式（Ｉ−１１）の化合物を次式（VII−６）、
【００３６】
上述のようにして得られた有機薄膜の配向性の評価を偏光吸収測定により行った。測定されたｐ偏光時の吸収量対ｓ偏光時の吸収量の比Ｉｐ／Ｉｓを参考例１〜３、実施例１〜３及び比較例１〜６について夫々下記の表１、２に示す。
【００３７】
【表２】
表１及び２から、対応する番号の実施例と比較例とを夫々比較すると、各比較例のＩｐ／Ｉｓ比の値に対し、その分子内にビニレン基を挟み込んだ構造を有する各実施例の比の値が明らかに大きくなっていることがわかる。これは、オリゴマー、芳香族多環及び芳香族複素環の間にビニレン構造を挟み込むことにより、分子が非常に高度に配向し、その結果会合状態を形成していることを示唆している。
【００４０】
また、溶液中での吸収ピークを比較すると、参考例１〜３および実施例１〜３と対応する比較例１〜６とでは、各実施例の吸収ピークはそれぞれ各比較例の吸収ピークよりも長波長側に存在していた。これはすなわち、ビニレン基を分子内に挟み込むことにより、分子の共役長が増大したことを示している。
【００４１】
また、半経験的分子軌道計算（ＭＯＰＡＣ９３：富士通、Ｓｔｅｗａｒｔによる）を用いたチオフェンのねじれ角に対する生成エネルギーの値を図１に示すが、この結果より、隣接するチオフェンのねじれにくさは、ビニレン基＞チオフェン基＞フェニレン基の順番であった。一方、室温（３００Ｋ）における熱エネルギーは、０．６ｋｃａｌ／ｍｏｌに相当する。したがって図１より、チオフェン基又はフェニレン基を挟み込んだ場合には室温でも回転が起こり得るが、ビニレン基を挟み込んだ場合には回転はほとんど起こり得ないことが分かる。これはすなわち、ビニレン基を挟み込んだ分子構造が、他の構造と比較してねじれ角が変化しにくいということを意味する。
【００４２】
さらに、ビニレン基を結合した分子構造についての生成エネルギーがねじれ角が０度の時に最も小さいことから、この構造はもともとねじれが少ない状態で安定であることが分かる。すなわち、ビニレン基を挟み込んだ分子構造は、平坦性の非常によい分子骨格を持ち、したがって、上記構造は蒸着時においても分子が配列しやすく、分子配向膜を作製するのに適した構造といえる。
【００４３】
以上の結果より、ビニレン基を分子内に挟み込むことにより、分子の共役長を増大させつつ、高度に配向した結晶性薄膜を得ることができ、本発明の優位性は明らかである。
【００４４】
なお、前記化学式（Ｉ−１〜１０、１２〜２０）、（II−２〜１０）、（III−２〜１２）、（IV−２〜１１）、（Ｖ−２〜４）、（VI−２）に示す分子構造の有機分子においても同等の効果が得られた。
【００４５】
【発明の効果】
本発明の、チオフェンオリゴマー誘導体、フェニレンオリゴマー誘導体、芳香族多環及び芳香族複素環の間にビニレン基を挟み込んだ有機分子配向薄膜用材料により、分子の共役系を増大させつつ、通常の真空蒸着法を用いても、高度に配向した配向薄膜を得ることが可能となる。
【００４６】
また、分子を配向させるとキャリアの移動度が大きくなることが明らかになっており（例えばJ.Am.Chem.Soc.115,8716(1993)）、本発明に係る分子配向膜を薄膜トランジスターの活性層に使用することにより、非常に高いキャリア移動度が達成できることが期待される。
【００４７】
さらに、本発明の有機分子配向薄膜用材料を用いることにより、基板温度が室温であっても、また通常の真空蒸着で用いる程度の真空度及び蒸着速度においても、高度に配向した薄膜を、大面積で均一に作製することができる。したがって、低コストで量産性に優れた有機分子配向薄膜の作製が可能となる。
【図面の簡単な説明】
【図１】本発明の実施例に係る、（ａ）ビニレン基、（ｂ）チオフェン基、（ｃ）フェニレン基を、チオフェン２量体間に挟み込んだ構造の生成エネルギーの、隣接チオフェンとのねじれ角依存性を示す説明図である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a material for an organic molecular alignment thin film used for many light, electronic, optoelectronic devices and the like such as an optical waveguide, an optical nonlinear element, a light emitting element, a thin film transistor, and an optical filter, and production of an organic molecular alignment thin film using the same. Regarding the method.
[0002]
[Prior art]
In recent years, research on π-conjugated oligomers, which are organic semiconductors with quasi-one-dimensional conjugated systems, has been actively conducted as expected applications for optical waveguides, optical nonlinear elements, light-emitting elements, thin film transistors, optical filters, etc. It has been broken.
[0003]
In addition, research on these thin films has been actively conducted in recent years. If these can be arranged precisely, a thin film with very high optical nonlinearity and carrier mobility may be produced. Therefore, realization of optical, electronic, and optoelectronic devices composed of highly oriented organic alignment thin films is expected.
[0004]
[Problems to be solved by the invention]
However, organic molecules are bonded by van der Waals forces, and their interaction is very small, so it is difficult to obtain a highly oriented thin film.
[0005]
As an example of preparation of an alignment film using organic molecules, an attempt to prepare a thiophene hexamer alignment thin film by an organic molecular beam deposition method is described in Jpn. J. Appl. Phys. 33, L1031 (1994). . Here, the organic molecular beam vapor deposition method is a method of performing vapor deposition at a speed of the order of 0.1 nm / min or less at a degree of vacuum of 10 −6 Pa or less that cannot be achieved by a normal vacuum deposition apparatus. Using this method, a highly oriented thin film can be obtained, but the deposition rate must be very slow, so it takes time to produce the oriented film and an expensive apparatus must be used to achieve a high vacuum. There was a problem that it became expensive.
[0006]
Recently, in structures having aromatic polycycles and heterocycles such as pentacene (IEEE Electron Device Lett. 18, 87 (1997)) and dithienothiophene (Appl. Phys. Lett. 71,3871 (1997)), It was reported that a highly oriented thin film was obtained. The carrier mobility of these thin films is 0.03 to 0.7 cm 2 / V · s, which is a very large value in the organic film. However, in order to catch up with the mobility of a-Si (amorphous silicon), it is necessary to realize a mobility that is about 1 to 2 orders of magnitude higher. For this purpose, the molecular orientation is further improved to improve the intermolecular mobility. It is necessary to increase the interaction and speed up the carrier movement between molecules.
[0007]
The present invention has been made in view of the above points, and an object of the present invention is to provide a material that makes it possible to produce a highly oriented organic molecular alignment thin film by an ordinary vacuum evaporation method, not by an organic molecular beam evaporation method. In addition, an object of the present invention is to provide a method for producing an organic molecular alignment thin film that is inexpensive and excellent in mass productivity using the material.
[0008]
[Means for Solving the Problems]
In order to solve the above problems, the organic molecular alignment thin film material of the present invention has the following general formula (IV),
[0012]
The organic molecular alignment thin film material of the present invention has the following general formula (V),
[0013]
Furthermore, the organic molecular alignment thin film material of the present invention has the following general formula (VI),
[0014]
In order to solve the above-mentioned problems, the method for producing an organic molecular alignment thin film of the present invention is performed by a vacuum vapor deposition method using the organic molecular alignment thin film material comprising either the π-conjugated oligomer or the π-conjugated molecule. It is characterized by forming a film.
[0015]
DETAILED DESCRIPTION OF THE INVENTION
The π-conjugated oligomer or π-conjugated molecule of the organic molecular alignment thin film material of the present invention is represented by the following chemical formulas (I-1 to 20), (II-1 to 10), (III-1 to 12), (IV- 1 to 11), (V-1 to 4) and (VI-1 and 2) are specifically shown.
[0016]
In the method for producing an organic molecularly oriented thin film of the present invention, a film is formed by vacuum vapor deposition using the π-conjugated oligomer or π-conjugated molecule. In such a vacuum deposition method, for example, a substrate such as quartz is placed in a resistance heating deposition apparatus, and the inside of the vacuum chamber is preferably decompressed to 1 × 10 −7 to 5 × 10 −3 Pa. Further, the temperature of the crucible is heated so that the growth rate is preferably 0.05 to 2 nm / s. The film thickness is preferably in the range of 0.5 to 300 nm.
[0024]
【Example】
Reference example 1
Quartz was used as a substrate and placed in a resistance heating vapor deposition apparatus to form a compound molecule of the chemical formula (I-11). The vacuum chamber was depressurized to 5 × 10 −4 Pa during film formation. The temperature of the crucible was heated so that the growth rate was 0.3 nm / s, and a film was formed to a thickness of 50 nm.
[0025]
Reference example 2
An organic thin film was produced in the same manner as in Reference Example 1 except that the compound of Formula (I-11) in Reference Example 1 was replaced with the compound of Formula (II-1).
[0026]
Reference example 3
An organic thin film was produced in the same manner as in Reference Example 1 except that the compound of Formula (I-11) in Reference Example 1 was replaced with the compound of Formula (III-1).
[0027]
Example 1
An organic thin film was produced in the same manner as in Reference Example 1 except that the compound of Formula (I-11) in Reference Example 1 was replaced with the compound of Formula (IV-1).
[0028]
Example 2
An organic thin film was produced in the same manner as in Reference Example 1 except that the compound of Formula (I-11) in Reference Example 1 was replaced with the compound of Formula (V-1).
[0029]
Example 3
An organic thin film was produced in the same manner as in Reference Example 1 except that the compound of Formula (I-11) in Reference Example 1 was replaced with the compound of Formula (VI-1).
[0030]
Comparative Example 1
The compound of the formula (I-11) of Reference Example 1 is represented by the following formula (VII-1),
[0031]
Comparative Example 2
The compound of the formula (I-11) of Reference Example 1 is represented by the following formula (VII-2),
[0032]
Comparative Example 3
The compound of the formula (I-11) of Reference Example 1 is represented by the following formula (VII-3),
[0033]
Comparative Example 4
The compound of the formula (I-11) of Reference Example 1 is represented by the following formula (VII-4),
[0034]
Comparative Example 5
The compound of the formula (I-11) of Reference Example 1 is represented by the following formula (VII-5),
[0035]
Comparative Example 6
The compound of the formula (I-11) of Reference Example 1 is represented by the following formula (VII-6),
[0036]
The orientation of the organic thin film obtained as described above was evaluated by polarization absorption measurement. The measured ratios Ip / Is of absorption at the time of p-polarization to absorption at the time of s-polarization are shown in Tables 1 and 2 below for Reference Examples 1 to 3, Examples 1 to 3, and Comparative Examples 1 to 6, respectively.
[0037]
[Table 2]
From Tables 1 and 2, when Examples and Comparative Examples with corresponding numbers are respectively compared, the values of each Example having a structure in which a vinylene group is sandwiched in the molecule with respect to the Ip / Is ratio value of each Comparative Example. It can be seen that the ratio value is clearly increased. This suggests that the vinylene structure is sandwiched between oligomers, aromatic polycycles and aromatic heterocycles, so that the molecules are very highly oriented and consequently form an associated state.
[0040]
Moreover, when the absorption peak in a solution is compared, in Comparative Examples 1-6 corresponding to Reference Examples 1-3 and Examples 1-3, the absorption peak of each Example is respectively larger than the absorption peak of each Comparative Example. It existed on the long wavelength side. This indicates that the conjugation length of the molecule is increased by inserting the vinylene group into the molecule.
[0041]
In addition, the value of the generation energy with respect to the twist angle of thiophene using semiempirical molecular orbital calculation (MOPAC93: Fujitsu, Stewart) is shown in FIG. The order was> thiophene group> phenylene group. On the other hand, the thermal energy at room temperature (300 K) corresponds to 0.6 kcal / mol. Accordingly, it can be seen from FIG. 1 that when a thiophene group or a phenylene group is sandwiched, rotation can occur even at room temperature, but when a vinylene group is sandwiched, rotation hardly occurs. This means that the molecular structure sandwiching the vinylene group is less likely to change the twist angle compared to other structures.
[0042]
Furthermore, since the generation energy of the molecular structure bonded with the vinylene group is the smallest when the twist angle is 0 degree, it can be seen that this structure is originally stable with little twist. That is, the molecular structure sandwiching the vinylene group has a molecular skeleton with very good flatness. Therefore, the above structure can be said to be a structure suitable for producing a molecular alignment film because molecules are easily arranged even during vapor deposition. .
[0043]
From the above results, a highly oriented crystalline thin film can be obtained while increasing the conjugate length of the molecule by sandwiching the vinylene group in the molecule, and the superiority of the present invention is clear.
[0044]
The chemical formulas (I-1 to 10, 12 to 20), (II-2 to 10), (III-2 to 12), (IV-2 to 11), (V-2 to 4), (VI The same effect was also obtained with organic molecules having the molecular structure shown in -2).
[0045]
【The invention's effect】
Normal vacuum deposition while increasing the conjugated system of molecules by the organic molecular alignment thin film material in which a vinylene group is sandwiched between thiophene oligomer derivatives, phenylene oligomer derivatives, aromatic polycycles and aromatic heterocycles of the present invention. Even using the method, it is possible to obtain a highly oriented alignment thin film.
[0046]
Further, it has been clarified that when the molecules are oriented, the mobility of carriers increases (for example, J. Am. Chem. Soc. 115, 8716 (1993)). By using it in the active layer, it is expected that very high carrier mobility can be achieved.
[0047]
Furthermore, by using the organic molecular alignment thin film material of the present invention, a highly oriented thin film can be obtained even at a substrate temperature of room temperature or at a degree of vacuum and a vapor deposition rate that are used in normal vacuum vapor deposition. It can be produced uniformly in area. Therefore, it is possible to produce an organic molecular alignment thin film that is low in cost and excellent in mass productivity.
[Brief description of the drawings]
BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 shows the torsion between adjacent thiophenes and the formation energy of a structure in which (a) vinylene group, (b) thiophene group, and (c) phenylene group are sandwiched between thiophene dimers according to an embodiment of the present invention. It is explanatory drawing which shows angle dependence.
Claims (4)
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| JP4873515B2 (en) * | 2001-03-08 | 2012-02-08 | 独立行政法人科学技術振興機構 | Oriented growth method of organic semiconductor crystal and organic laser device using it |
| JP2003177052A (en) | 2001-12-13 | 2003-06-27 | Takata Corp | Apparatus for measuring sheet weight |
| DE50309671D1 (en) * | 2002-09-13 | 2008-06-05 | Starck H C Gmbh | Organic compounds with core-shell structure |
| ATE446961T1 (en) * | 2004-05-18 | 2009-11-15 | Merck Patent Gmbh | MONO-, OLIGO- AND POLYTHIENOÄ3,2-BUTHIOPHENE |
| EP1753768A1 (en) * | 2004-06-09 | 2007-02-21 | Merck Patent GmbH | POLYMERISABLE THIENO¬3,2-b|THIOPHENES |
| JP2006028054A (en) * | 2004-07-14 | 2006-02-02 | Konica Minolta Holdings Inc | Organic thin film transistor material, organic thin film transistor, field effect transistor and swichintg device |
| JP5155852B2 (en) * | 2005-04-15 | 2013-03-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Aryl-ethylene substituted aromatic compounds and their use as organic semiconductors |
| US8148720B2 (en) * | 2006-11-24 | 2012-04-03 | Idemitsu Kosan Co., Ltd. | Organic thin film transistor and organic thin film light-emitting transistor |
| US8330147B2 (en) * | 2006-12-04 | 2012-12-11 | Idemitsu Kosan, Co., Ltd. | Organic thin film transistor and organic thin film light emitting transistor having organic semiconductor compound with divalent aromatic hydrocarbon group and divalent aromatic heterocyclic group |
| US7718998B2 (en) * | 2006-12-14 | 2010-05-18 | Xerox Corporation | Thiophene electronic devices |
| WO2009125704A1 (en) * | 2008-04-10 | 2009-10-15 | 出光興産株式会社 | Compound for organic thin-film transistor and organic thin-film transistor using the compound |
| CN112159418B (en) * | 2020-09-11 | 2024-04-05 | 中国科学院宁波材料技术与工程研究所 | Conjugated organic molecule and organic solar cell |
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