JP3094083B2 - Orientation method - Google Patents
Orientation methodInfo
- Publication number
- JP3094083B2 JP3094083B2 JP02341096A JP34109690A JP3094083B2 JP 3094083 B2 JP3094083 B2 JP 3094083B2 JP 02341096 A JP02341096 A JP 02341096A JP 34109690 A JP34109690 A JP 34109690A JP 3094083 B2 JP3094083 B2 JP 3094083B2
- Authority
- JP
- Japan
- Prior art keywords
- film
- poly
- polymer compound
- polymer
- conjugated
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 15
- 229920000642 polymer Polymers 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 Poly (2,5-pyridinediyl) Polymers 0.000 claims description 10
- 229920001721 polyimide Polymers 0.000 claims description 8
- 239000004642 Polyimide Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000000151 deposition Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- 229920000547 conjugated polymer Polymers 0.000 description 21
- 238000002835 absorbance Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- 230000005684 electric field Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000005669 field effect Effects 0.000 description 4
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 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
- 230000031700 light absorption Effects 0.000 description 1
- 238000005259 measurement Methods 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
- 239000000126 substance Substances 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
- 238000001771 vacuum deposition Methods 0.000 description 1
Landscapes
- Polarising Elements (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- 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)
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 [Industrial Application Field] The present invention can be used for field effect transistors, diodes, polarizers, etc., and has a pi-conjugated polymer compound along the main chain (hereinafter referred to as the main chain) A polymer compound having a pi-conjugated system is abbreviated as a pi-conjugated polymer).
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.Chem.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12009
26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。Pi-conjugated polymers such as poly (2,5-thienylene) (also called polythiophene) can be used for field effect transistors (Appl. Phys. Lett., Vol. 49, No. 1210).
(1986), "J. Am. Chem. Soc.", 109, 2197 (1987)
Year)). For example, poly (2,5-thienylene) between the source and the drain of a field effect transistor (Japanese Patent No. 12009)
By controlling the gate voltage through an insulating layer in the presence of a pi-conjugated polymer such as No. 26), 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
分子化学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 existing between the source and the drain usually has no directionality and exists in a random manner. Π-conjugated polymer with high degree (such as the 24th Symposium on Unresolved Problems in Polymer Chemistry, page 9 (sponsored by The Society of Polymer Science, Kanto Branch)). In order to remedy such drawbacks, the pie-conjugated polymer is oriented (for example, oriented so as to face the source and drain), and the characteristics of the pi-conjugated polymer are fully utilized to generate a large current. There is a need for the development of a field effect transistor that is capable of responding to higher frequency alternating currents by providing or improving carrier mobility between the 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。As a method for obtaining an oriented pi-conjugated polymer, a method of polymerizing a monomer molecule oriented by the Langmuir-Blodgett method is considered (magazine "Surface Technology", Vol. 40, p. 716 (1989)). The method uses a wet system that is difficult to handle and has the disadvantage of requiring a high degree of complexity.
また，一方，ポリ（2,5−ピリジンジイル）（特願昭6
3−236）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ではパイ共役高分
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, poly (2,5-pyridinediyl) (Japanese Patent Application No.
A pi-conjugated polymer such as 3-236) is coated on a film of a polymer compound such as polyvinyl alcohol, and the substrate polymer film is stretched. can get. That is, when linearly polarized light is applied to this film, when the stretching direction of the substrate polymer film and the direction of the oscillating electric field of the linearly polarized light coincide with each other, strong absorption of light occurs due to the π-π * transition of the pi-conjugated polymer. When the directions are orthogonal, only weak absorption occurs (Japanese Patent Application No. 1-226639). In the conventional technology for producing such a polarizer, the pi-conjugated system that can be used is limited to those that are soluble or fusible and can be applied on a substrate film, or when applied using a solution. Is a wet system, and has the drawback that the operation is complicated and quality control is difficult.
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。In order to overcome the above-mentioned problems of the prior art, in the present invention, a pi-conjugated polymer is deposited on an oriented substrate polymer film, and the pie-conjugated polymer is oriented on the substrate polymer film by a dry method. Use a method with excellent operability.
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１−305739）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−尾結合の他に頭−
結合，尾−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−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 polymer used is poly (2,5-thienylene), poly (2,5-pyridinediyl), poly (2,2'-
Various pi-conjugated polymers such as bipyridine-5,5'-diyl) (Japanese Patent Application No. 1-305739) and derivatives thereof can be mentioned, and there is no limitation on the type of pi-conjugated polymer to be used. A pi-conjugated polymer suitable for vacuum deposition is desired. Further, a copolymer such as a copolymer including a structural unit having a thiophene skeleton and a pyridine skeleton may be used. Further, in the present invention, poly (2,5-pyridinediyl)
And poly (2,5-thienylene) derivatives having a substituent at the 3-position generally have a head-tail bond in addition to a so-called head-tail bond.
It is considered that bonds, tail-to-tail bonds and the like exist, but the pi-conjugated polymer used in the present invention has no such structural limitation. In addition, poly (2,2'-bipyridine-
5,5′-diyl) is a poly (2,5
-Pyridinediyl), both of which have been found to have almost the same effect, for example, in providing the above polarizer.
基板に用いる膜状高分子化合物（上記においては基板
高分子フィルムとも記載）には特に制限がない。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工
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。There is no particular limitation on the film-like polymer compound used for the substrate (also referred to above as the substrate polymer film). In liquid crystal display devices, polyimide films, etc., which are used industrially to align liquid crystal molecules, have excellent heat resistance and mechanical strength, and the technology to orient them by rubbing has been industrially established. Particularly preferred.
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。The method for orienting the film-like polymer compound is not particularly limited, but a method of mechanically rubbing (so-called rubbing) the film-like polymer compound, a method of stretching and orienting the film-like polymer compound, and the like are preferable.
〔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体
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た膜状ポリイミド）上に蒸着し
た。[Example 1] Poly (2,5-thienylene) synthesized by the reaction of a 2,5-dihalogenated thiophene with a zero-valent nickel complex (Japanese Patent Application No. 63-159635 and magazine "Polym. J." 1990
) Was placed in a tantalum boat and heated in a vacuum to deposit it on a rubbed film-like polyimide (film-like polyimide formed on a glass plate).
この様にして得られたガラス板上の膜について，直線
偏光を照射し透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（パーレン
雑誌「Synth.Metals」38巻399頁（1990）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 the ultraviolet-visible spectrum was measured by a transmission method. As a result, when the direction of the oscillating electric field of the linearly polarized light and the direction rubbed in the rubbing process match, the poly (2,5
-Thienylene) shows an absorption peak with a large absorbance at 430 nm, which is the position of the absorption band (scheduled to be published in Parlen Magazine "Synth. Metals", vol. 38, p. 399 (1990)), but the directions are perpendicular to each other. Showed an absorption peak having a smaller absorbance (measured in the same sample). The ratio of the two absorbances was about 1.4. Thus, poly (2,5-thienylene) could be oriented in the direction in which rubbing was performed on the polyimide film.
ポリ（2,2′−ビピリジン−5,5′−ジイル）（特願平
１−305739,雑誌「Chem.Lett.」1990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。Poly (2,2'-bipyridine-5,5'-diyl) (Japanese Patent Application No. 1-305739, Magazine "Chem. Lett." 1990, p. 223) is used in place of poly (2,5-thienylene). In the same manner as in Example 1, poly (2,2'-biviridine-5,5'-diyl) was vacuum-deposited on the rubbed polyimide film. The UV-visible spectrum of the film thus obtained was 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), when the direction of the oscillating electric field of linearly polarized light and the direction rubbed in the rubbing treatment match, A larger absorbance was observed, whereas a smaller absorbance was observed when both directions were orthogonal. The ratio of these two absorbances was about 1.1. Thus, poly (2,
2′-bipyridine-5,5′-diyl) could be oriented in the direction of rubbing 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
ペクトルを測定したが,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。The UV-visible spectrum of the rubbed polyimide film used in Examples 1 and 2 was measured by applying linearly polarized light. In the measurement region of 300 to 650 nm, the direction of the oscillating electric field of the linearly polarized light and the rubbing treatment were measured. The shape of the absorption spectrum and the change in the absorbance were not observed even when the angle between the directions in which the step was performed was changed. Therefore, the above change in absorbance is attributable to the orientation of the vapor-deposited pi-conjugated polymer.
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。A substance in which the pi-conjugated polymer is oriented on the film-like polymer compound by depositing an industrially useful polymer compound having a pi-conjugated system along the main chain on the oriented film-like polymer compound. Can be obtained.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ０８Ｌ 79:04 81:00 (58)調査した分野(Int.Cl.7，ＤＢ名) C08J 5/18 C08G 61/12 C08G 73/06 C08J 7/04 H05K 3/14 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 identification code FI C08L 79:04 81:00 (58) Investigated field (Int.Cl. 7 , DB name) C08J 5/18 C08G 61/12 C08G 73/06 C08J 7/04 H05K 3/14
Claims (4)
物を方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 for orienting a polymer compound having a pi-conjugated system along the main chain by depositing a polymer compound having a pi-conjugated system along the main chain on the oriented film-like polymer compound.
化合物が下記一般式 （R,R′は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−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. The polymer compound having a pi-conjugated system along the main chain is represented by the following general formula: (R, R 'represents H or a substituent, and n represents a degree of polymerization.) Poly (2,5-thienylene) or a derivative thereof represented by the following formula: The method described in the section.
化合物が下記一般式 （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. The polymer compound having a pi-conjugated system along the main chain is represented by the following general formula: (R, R ′, R ″ represent each H or a substituent, and n represents the degree of polymerization.) Poly (2,5-pyridinediyl) or poly (2,2′-bipyridine-5) , 5'-diyl) or a derivative thereof.
ことを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 claim 1, 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 JPH04208567A (en) | 1992-07-30 |
| JP3094083B2 true 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) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60028802T2 (en) * | 1999-10-15 | 2007-05-24 | Agfa-Gevaert | LIQUID CRYSTAL ORIENTATION LAYER |
| JP5062945B2 (en) * | 2003-06-27 | 2012-10-31 | 株式会社リコー | Polymer |
| 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 |
| JP5577117B2 (en) * | 2010-03-05 | 2014-08-20 | 住友化学株式会社 | Pyridine compounds |
| JP2011081392A (en) * | 2010-10-29 | 2011-04-21 | Sumitomo Chemical Co Ltd | Uniaxially oriented conjugated polymer thin film pattern |
-
1990
- 1990-11-30 JP JP02341096A patent/JP3094083B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04208567A (en) | 1992-07-30 |
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