JPH04208567A - Orientation method - Google Patents
Orientation methodInfo
- Publication number
- JPH04208567A JPH04208567A JP2341096A JP34109690A JPH04208567A JP H04208567 A JPH04208567 A JP H04208567A JP 2341096 A JP2341096 A JP 2341096A JP 34109690 A JP34109690 A JP 34109690A JP H04208567 A JPH04208567 A JP H04208567A
- Authority
- JP
- Japan
- Prior art keywords
- conjugated
- poly
- film
- oriented
- polymer compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000000151 deposition Methods 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 16
- -1 poly(2,2'-bipyridine-5,5'-diyl) Polymers 0.000 claims description 10
- 229920001721 polyimide Polymers 0.000 claims description 7
- 239000004642 Polyimide Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000000758 substrate Substances 0.000 abstract description 9
- 238000001771 vacuum deposition Methods 0.000 abstract description 2
- 229920000547 conjugated polymer Polymers 0.000 description 20
- 238000002835 absorbance Methods 0.000 description 8
- 229920006254 polymer film Polymers 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000005669 field effect Effects 0.000 description 4
- 230000005684 electric field Effects 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000003908 quality control 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
- 150000003577 thiophenes Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polarising Elements (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は電界効果トランジスタ、ダイオード、偏光子な
どに用いることができ主鎖に沿うパイ共役系を有する高
分子化合物(以下、主鎖に沿うパイ共役系を有する高分
子化合物をパイ共役高分子と略称する)を配向させる技
術に関するものである。[Detailed Description of the Invention] [Field of Industrial Application] The present invention is a polymer compound that can be used for field effect transistors, diodes, polarizers, etc. and has a pi-conjugated system along the main chain (hereinafter referred to as This invention relates to a technique for orienting a polymer compound having a pi-conjugated system (abbreviated as a pi-conjugated polymer).
[従来の技術の問題点]
ポリ(2,5−チエニレン)(ポリチオフェンとも言う
)などのパイ共役高分子は電界効果トランジスタに用い
ることができる(雑誌「Appl.Phys.Lett
.」49巻1210頁(1986年)、「J.Am.C
hem.Soc.」、109巻2197頁(1987年
))。たとえば、電界効果トランジスタのソースとドレ
イン間にポリ(2,5−チエニレン)(日本特許第12
00926号)等のパイ共役高分子を存在させ、絶縁層
を通してゲート電圧をコントロールすることによりパイ
共役高分子の導電機能をコントロールしソースとドレイ
ン間の電流をコントロールすることができる。[Problems with conventional technology] Pi-conjugated polymers such as poly(2,5-thienylene) (also called polythiophene) can be used in field effect transistors (magazine "Appl. Phys. Lett.
.. ” vol. 49, p. 1210 (1986), “J.Am.C.
hem. Soc. ”, Vol. 109, p. 2197 (1987)). For example, poly(2,5-thienylene) (Japanese Patent No. 12) is used between the source and drain of a field effect transistor.
By making a pi-conjugated polymer such as No. 00926 exist and controlling the gate voltage through the insulating layer, the conductive function of the pi-conjugated polymer can be controlled and the current between the source and drain can be controlled.
しかし、特別な配向処理がなされていなければ、ソース
とドレインの間に存在するパイ共役高分子は通常方向性
を持たず無秩序に存在するため、一般的に主鎖方向に大
きな導電性と易動度を有するπ共役高分子(第24回高
分子化の未解決問題シンポジウム9頁(高分子学会関東
支部主催)等)の特性を十分に生かせない欠点を持って
いる。そして、このような欠点を改善するために、パイ
共役高分子を配向させて(たとえば、ソースとドレイン
の方向を向くように配向させて)、パイ共役高分子の特
性を十分に生かし大きな電流を与えたりソースとドレイ
ン間のキャリアーの移動度を向上させより高い周波数の
交流に応答できたりすることのできる電界効果トランジ
スタの開発が望まれている。However, unless a special orientation treatment is performed, the pi-conjugated polymer that exists between the source and drain usually has no directionality and exists in a disordered manner. It has the disadvantage that it cannot fully utilize the characteristics of π-conjugated polymers (such as the 24th Symposium on Unresolved Problems in Polymerization, p. 9 (sponsored by the Kanto branch of the Society of Polymer Science and Technology)). In order to improve these drawbacks, pi-conjugated polymers can be oriented (for example, oriented so that the source and drain are facing each other) to take full advantage of the characteristics of pi-conjugated polymers and generate large currents. It is desired to develop field effect transistors that can respond to higher frequency alternating current by increasing carrier mobility between source and drain.
配向したパイ共役高分子を得る手法としては、ラングミ
ュアー・ブロジェット法により配向させたモノマー分子
を重合させる手法などが考えられるが(雑誌「表面技術
」40巻716頁(1989年))、この方法は取扱い
が困難な湿式系を用い、また高度の複雑な技術を要求す
る欠点を有している。Possible methods for obtaining oriented pi-conjugated polymers include polymerizing oriented monomer molecules using the Langmuir-Blodgett method (Magazine "Surface Technology" Vol. 40, p. 716 (1989)); The method has the disadvantage of using a wet system that is difficult to handle and requiring highly complex technology.
また、一方、ポリ(2,5−ピリジンジイル)(特願昭
63−236)などのパイ共役高分子をポリビニルアル
コール等の高分子化合物のフィルム上に塗布し、この基
板高分子フィルムを延伸させて得たフィルムパイ共役高
分子が配向しており偏光子が得られる。すなわち、この
フィルムに直線偏光を当てた場合に基板高分子フィルム
の延伸方向と直線偏光の振動電場の方向が一致した時に
はパイ共役高分子のπ−π*遷移による光の強い吸収が
起こる一方両者の方向が直交する場合には弱い吸収しか
起こらない(特願平1−226639)。そして、この
ような偏光子を作製する従来の技術においては、用いる
ことのできるパイ共役系が可溶あるいは可融で基板フィ
ルム上に塗布できるものに限られたり、溶液を用いて塗
布する場合には湿式系であり操作が複雑で品質管理が困
難であったりする欠点を有している。On the other hand, a pi-conjugated polymer such as poly(2,5-pyridinediyl) (Japanese Patent Application No. 63-236) is coated on a film of a polymer compound such as polyvinyl alcohol, and this substrate polymer film is stretched. The obtained film has oriented pi-conjugated polymers, and a polarizer can be obtained. In other words, when linearly polarized light is applied to this film, when the stretching direction of the substrate polymer film matches the direction of the oscillating electric field of the linearly polarized light, strong absorption of light occurs due to the π-π* transition of the pi-conjugated polymer, while both If the directions are orthogonal, only weak absorption occurs (Japanese Patent Application No. 1-226639). In conventional techniques for producing such polarizers, the pi-conjugated systems that can be used are limited to those that are soluble or fusible and can be coated onto a substrate film, or when coating using a solution. Since it is a wet system, it has the drawbacks that the operation is complicated and quality control is difficult.
[問題を解決するための手段]
上記の従来の技術の問題点を克服するため、本発明にお
いては、パイ共役高分子を方向づけされた基板高分子フ
ィルム上に蒸着し乾式法により基板高分子フィルム上で
パイ共役高分子を配向させる操作性に優れた手法を用い
る。[Means for Solving the Problems] In order to overcome the problems of the above-mentioned conventional techniques, in the present invention, a pi-conjugated polymer is vapor-deposited on an oriented substrate polymer film, and the substrate polymer film is formed by a dry method. An easy-to-operate method for orienting pi-conjugated polymers is used.
使用するパイ共役高分子としてはポリ(2,5−チエニ
レン)、ポリ(2,5−ピリジンジイル)、ポリ(2,
2′−ビピリジン−5,5′−ジイル)(特願平1−3
05739)あるいはそれらの誘導体などの種々のパイ
共役高分子を挙げることができ、使用するパイ共役高分
子の種類に制限はない。真空蒸着に適しているパイ共役
高分子が望しい。また、チオフェン骨格とピリジン骨格
を有する構成単位から成る共重合体などの共重合体でも
よい。さらに、本発明においては、ポリ(2,5−ピリ
ジンジイル)や3位に置換基を有するポリ(2,5−チ
エニレン)誘導体等においては一般的にいわゆる頭一尾
結合の他に頭一頭結合、尾一尾結合等が存在するものと
考えられるが、本発明に用いられるパイ共役高分子にお
いてはこの様な構造上の制限はない。なお、ポリ(2,
2′−ビピリジン−5,5′−ジイル)は選択的に頭一
頭結合を持つポリ(2,5−ピリジンジイル)であると
見なすことができるが、この両者がたとえば上記偏光子
を与える場合においいてほとんど同じ効果を有すること
を確かめている。The pi-conjugated polymers used include poly(2,5-thienylene), poly(2,5-pyridinediyl), and poly(2,5-thienylene).
2'-bipyridine-5,5'-diyl) (Patent Application No. 1-3
05739) or derivatives thereof, and there is no restriction on the type of pi-conjugated polymer to be used. A pi-conjugated polymer suitable for vacuum deposition is desirable. Further, a copolymer such as a copolymer consisting of a structural unit having a thiophene skeleton and a pyridine skeleton may be used. Furthermore, in the present invention, in poly(2,5-pyridinediyl) and poly(2,5-thienylene) derivatives having a substituent at the 3-position, in addition to the so-called one-head bond, a one-head bond is generally used. , tail-to-tail bonds, etc. are considered to exist, but there are no such structural limitations in the pi-conjugated polymer used in the present invention. In addition, poly(2,
2'-bipyridine-5,5'-diyl) can be selectively considered to be poly(2,5-pyridinediyl) with a single head bond, but when both of them provide the above polarizer, for example, It has been confirmed that they have almost the same effect.
基板に用いる膜状高分子化合物(上記においては基板高
分子フィルム記載)には特に制限がない。There is no particular restriction on the film-like polymer compound (described as a substrate polymer film in the above) used for the substrate.
すでに液晶表示素子において、液晶分子を配向させるた
めに上業的に用いられているポリイミド膜などは耐熱性
、機械的強度にもすぐれ、ラビングなどにより方向づけ
を行なう技術も工業的に確立されているので特に好まし
い。Polyimide films, which are already used commercially to orient liquid crystal molecules in liquid crystal display devices, have excellent heat resistance and mechanical strength, and techniques for orienting them, such as by rubbing, have also been established industrially. Therefore, it is particularly preferable.
当該膜状高分子化合物を方向づける方法には特に制限が
ないが、膜状高分子化合物を機械的にこすり(いわゆる
ラビングを行ない)方向づけする方法や延伸して方向づ
けする方法などが好ましい。There are no particular limitations on the method for orienting the film-like polymer compound, but preferred are a method of mechanically rubbing the film-form polymer compound (so-called rubbing), a method of orientation by stretching, and the like.
[実施例]
[実施例1]
2,5−ジハロゲン化チオフェンとゼロ価ニッケル錯岩
の反応により合成したポリ(2,5−チエニレン)(特
願昭63−159635及び雑誌「Polym.J.」
22巻187頁(1990年))をタンタルボート中に
入れ、真空中で加熱することにより、ラビング処理を行
なってある膜状ポリイミド(ガラス板上に形成させ膜状
ポリイミド)上に蒸着した。[Example] [Example 1] Poly(2,5-thienylene) synthesized by reaction of 2,5-dihalogenated thiophene and zero-valent nickel complex (Japanese Patent Application No. 63-159635 and magazine "Polym.J.")
Vol. 22, p. 187 (1990)) was placed in a tantalum boat and heated in vacuum to deposit it on a polyimide film (film polyimide formed on a glass plate) that had been subjected to a rubbing process.
この様にして得られたガラス板上の膜について、直線偏
光を照射し対過法により紫外可視スペクトルを測定した
。その結果、直線偏光の振動電場の方向とラビング処理
においてこすった方向が一致する場合にはポリ(2,5
−チエニレン)の吸収帯の位置である430nm(雑誌
「Synth.Metals」38巻399頁(199
0)掲載予定)において大きな吸光度を持つ吸収ピーク
を示すのに対して、両者の方向が直交する場合にはこれ
よりも小さな吸光度を持つ吸収ピークを示した(同一の
サンプルにおいて測定)。上記2つの吸光度の比は約1
.4であった。このように、ポリ(2,5−チエニレン
)をポリイミド膜上でラビング処理を行なった方向に配
向させることができた。The film on the glass plate thus obtained was irradiated with linearly polarized light and its ultraviolet-visible spectrum was measured by the transmission method. As a result, if the direction of the oscillating electric field of linearly polarized light and the rubbing direction match, poly(2,5
-Thienylene) at 430 nm (Magazine "Synth.Metals" Vol. 38, p. 399 (199
0) Scheduled to be published) showed an absorption peak with large absorbance, whereas when the two directions were perpendicular to each other, an absorption peak with smaller absorbance was shown (measured on the same sample). The ratio of the above two absorbances is approximately 1
.. It was 4. In this way, poly(2,5-thienylene) could be oriented on the polyimide film in the direction of the rubbing treatment.
[実施例]
ポリ(2,2′−ビピリジン−5,5′−ジイル)(特
願平1−305739,雑誌「hem.Lett.」1
990年223頁)をポリ(2,5′−チエニレン)の
代りに用いる他は実施例1と同様にして、ラビング処理
を行なったポリイミド膜上にポリ(2,2′−ビビリジ
ン−5,5′−ジイル)を真空蒸着した。この様にして
得られた膜についても、実施例1と同様にして紫外可視
スペクトルを測定した。その結果、ポリ(2,2′−ビ
ピリジン−5,5′−ジイル)のπ−π*吸収帯の位置
において、直線偏光の振動電場の方向とラビング処理に
おいてこすった方向が一致する場合にはより大きな吸光
度が観測されるのに対し両者の方向が直交する場合には
より小さな吸光度が観測された。これら2つの吸光度の
比は約1.1であった。このように、ポリ(2,2′−
ビピリジン−5,5′−ジイル)をポリイミド膜上でラ
ビング処理を行なった方向に配向させることができた。[Example] Poly(2,2'-bipyridine-5,5'-diyl) (Japanese Patent Application No. 1-305739, Magazine "hem. Lett." 1
990, p. 223) was used instead of poly(2,5'-thienylene), poly(2,2'-biviridine-5,5 '-diyl) was vacuum deposited. The ultraviolet-visible spectrum of the film thus obtained was also measured in the same manner as in Example 1. As a result, at the position of the π-π* absorption band of poly(2,2'-bipyridine-5,5'-diyl), if the direction of the oscillating electric field of linearly polarized light and the direction of rubbing in the rubbing process match, A larger absorbance was observed, whereas a smaller absorbance was observed when the two directions were perpendicular. The ratio of these two absorbances was approximately 1.1. In this way, poly(2,2'-
Bipyridine-5,5'-diyl) could be oriented in the direction of the rubbing treatment on the polyimide film.
なお、実施例1及び2で用いたラビング処理を行なった
膜状ポリイミドについて直線偏光を当てて紫外可視スペ
トルを測定したが、300〜650nmの測定領域にお
いて、直線偏光の振動電場の方向とラビング処理を行な
った方向のなす角を変えても吸収スペクトルの形及び吸
光度の変化は観測されなかった。よって、上記の吸光度
の変化は蒸着パイ共役高分子の配向に帰因するものであ
る。Note that the ultraviolet-visible spectra were measured by applying linearly polarized light to the film-like polyimide that had been subjected to the rubbing treatment used in Examples 1 and 2. No change in the shape of the absorption spectrum or absorbance was observed even if the angle formed by the direction was changed. Therefore, the above change in absorbance is attributable to the orientation of the deposited pi-conjugated polymer.
[発明の効果]
主鎖に沿うパイ共役系を有する産業上有用な高分子化合
物を、方向づけされた膜状高分子化合物上に蒸着するこ
とにより、当該膜状高分子化合物上で当該パイ共役高分
子が配向した物質を得ることができる。[Effect of the invention] By depositing an industrially useful polymer compound having a pi-conjugated system along the main chain onto an oriented film-like polymer compound, the pi-conjugated polymer can be deposited on the film-like polymer compound. A substance with oriented molecules can be obtained.
Claims (4)
向づけされた膜状高分子化合物上に蒸着させることによ
り当該主鎖に沿うパイ共役系を有する高分子化合物を配
向させる方法。(1) A method of orienting a polymer compound having a pi-conjugated system along the main chain by vapor-depositing the polymer compound having a pi-conjugated system along the main chain onto an oriented film-like polymer compound.
が下記一般式 ▲数式、化学式、表等があります▼(R、R’はH又は
置換基を表す。 また、nは重合度を表す。) で表わされるポリ(2、5−チエニレン)又はその誘導
体であることを特徴とする特許請求の範囲第1項に記載
の方法。(2) A polymer compound having a pi-conjugated system along the main chain has the following general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (R and R' represent H or a substituent. Also, n represents the degree of polymerization. 2. The method according to claim 1, wherein the poly(2,5-thienylene) or a derivative thereof is represented by:
が下記一般式 ▲数式、化学式、表等があります▼又は▲数式、化学式
、表等があります▼ (R、R’、R”は各各H又は置換基を表わす。またn
は重合度を表わす。) で表わされるポリ(2、5−ピリジンジイル)又はポリ
(2、2’−ビピリジン−5、5’−ジイル)又はそれ
らの誘導体であることを特徴とする特許請求の範囲第1
項に記載の方法。(3) A polymer compound having a pi-conjugated system along the main chain has the following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (R, R', R" Represents each H or substituent, and n
represents the degree of polymerization. ) or poly(2,2'-bipyridine-5,5'-diyl) or derivatives thereof.
The method described in section.
特徴とする特許請求の範囲第1から第3項までのいずれ
かに記載の方法。(4) The method according to any one of claims 1 to 3, wherein the film-like polymer compound is a film-like polyimide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP02341096A JP3094083B2 (en) | 1990-11-30 | 1990-11-30 | Orientation method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP02341096A JP3094083B2 (en) | 1990-11-30 | 1990-11-30 | Orientation method |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04208567A true JPH04208567A (en) | 1992-07-30 |
JP3094083B2 JP3094083B2 (en) | 2000-10-03 |
Family
ID=18343223
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP02341096A Expired - Lifetime JP3094083B2 (en) | 1990-11-30 | 1990-11-30 | Orientation method |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3094083B2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003512647A (en) * | 1999-10-15 | 2003-04-02 | アグフア−ゲヴエルト,ナームローゼ・フエンノートシヤツプ | Liquid crystal alignment layer |
JP2005240001A (en) * | 2003-06-27 | 2005-09-08 | Ricoh Co Ltd | New arylamine polymer |
JP2007328368A (en) * | 2007-08-20 | 2007-12-20 | Sumitomo Chemical Co Ltd | Uniaxially oriented conjugating polymer thin film pattern |
JP2011081392A (en) * | 2010-10-29 | 2011-04-21 | Sumitomo Chemical Co Ltd | Uniaxially oriented conjugated polymer thin film pattern |
JP2011184320A (en) * | 2010-03-05 | 2011-09-22 | Sumitomo Chemical Co Ltd | Pyridine compound |
-
1990
- 1990-11-30 JP JP02341096A patent/JP3094083B2/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003512647A (en) * | 1999-10-15 | 2003-04-02 | アグフア−ゲヴエルト,ナームローゼ・フエンノートシヤツプ | Liquid crystal alignment layer |
JP2005240001A (en) * | 2003-06-27 | 2005-09-08 | Ricoh Co Ltd | New arylamine polymer |
JP2007328368A (en) * | 2007-08-20 | 2007-12-20 | Sumitomo Chemical Co Ltd | Uniaxially oriented conjugating polymer thin film pattern |
JP4656108B2 (en) * | 2007-08-20 | 2011-03-23 | 住友化学株式会社 | Method for producing uniaxially oriented conjugated polymer thin film pattern |
JP2011184320A (en) * | 2010-03-05 | 2011-09-22 | Sumitomo Chemical Co Ltd | Pyridine compound |
JP2011081392A (en) * | 2010-10-29 | 2011-04-21 | Sumitomo Chemical Co Ltd | Uniaxially oriented conjugated polymer thin film pattern |
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