JPH03275723A - Organic polymer, photoconductive material using same polymer and production thereof - Google Patents
Organic polymer, photoconductive material using same polymer and production thereofInfo
- Publication number
- JPH03275723A JPH03275723A JP2074971A JP7497190A JPH03275723A JP H03275723 A JPH03275723 A JP H03275723A JP 2074971 A JP2074971 A JP 2074971A JP 7497190 A JP7497190 A JP 7497190A JP H03275723 A JPH03275723 A JP H03275723A
- Authority
- JP
- Japan
- Prior art keywords
- photoconductive material
- organic polymer
- organic
- polymer
- organic molecule
- 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
- 239000000463 material Substances 0.000 title claims abstract description 13
- 229920000620 organic polymer Polymers 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229920000642 polymer Polymers 0.000 title abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 4
- 229920005603 alternating copolymer Polymers 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 238000002425 crystallisation Methods 0.000 claims abstract 3
- 230000008025 crystallization Effects 0.000 claims abstract 3
- 239000004952 Polyamide Substances 0.000 claims abstract 2
- 239000004962 Polyamide-imide Substances 0.000 claims abstract 2
- 239000004642 Polyimide Substances 0.000 claims abstract 2
- 229920002647 polyamide Polymers 0.000 claims abstract 2
- 229920002312 polyamide-imide Polymers 0.000 claims abstract 2
- 229920001721 polyimide Polymers 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 229910052714 tellurium Inorganic materials 0.000 claims abstract 2
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 3
- 229920002614 Polyether block amide Polymers 0.000 claims 1
- 239000004697 Polyetherimide Substances 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 229920003055 poly(ester-imide) Polymers 0.000 claims 1
- 229920001601 polyetherimide Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 238000012648 alternating copolymerization Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 abstract 1
- 230000032258 transport Effects 0.000 description 6
- 239000000969 carrier Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 1
- ODPYDILFQYARBK-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2SC2=C1 ODPYDILFQYARBK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Photoreceptors In Electrophotography (AREA)
- Polyamides (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は結晶化の容易な有機高分子とこれを用いた光導
電材料及びその製造方法に関し、特に電子写真方式の複
写機や光プリンタなどにおける光導電体に好適な光導電
材料に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to an organic polymer that is easily crystallized, a photoconductive material using the same, and a method for producing the same. The present invention relates to a photoconductive material suitable for a conductor.
従来の技術
光導電性を持つ有機物質の開発は、電子写真方式の光導
電材料として近年盛んになった。有機先導電材料の中で
多くの知見の得られているものには、ポリヴイニル力ル
バゾール（以下、ＰＶＫと称す）がある、ＰＶＫにおけ
る正孔のキャリア輸送能力は高い（室温の正札移動度は
〜１０”’ｃｓ”／Ｖ ｓ ）。膜中のキャリアは高分
子主鎖に螺旋状につながるカルバゾール環を主鎖に沿っ
てホッピングするものと考えられている。BACKGROUND OF THE INVENTION In recent years, the development of photoconductive organic materials has become popular as photoconductive materials for electrophotography. One of the organic leading conductive materials for which much knowledge has been obtained is polyvinyl Rubazole (hereinafter referred to as PVK). PVK has a high hole carrier transport ability (the mobility at room temperature is ~ 10"'cs"/Vs). The carriers in the film are thought to hop along the carbazole ring that is spirally connected to the polymer main chain.
ＰＶＫ単体の高分子層では可視光全域に光吸収帯がない
、しかし電子受容性の有機物トリニトロフルオレノンを
ＰＶＫに等量添加するとカルバゾール環とキャリア電荷
の授受を行い、キャリア移動錯体を形成して感度領域が
可視域全体に広がる。A single polymer layer of PVK has no light absorption band in the entire visible light range, but when an equal amount of electron-accepting organic trinitrofluorenone is added to PVK, it exchanges carrier charge with the carbazole ring, forming a carrier transfer complex. Sensitivity range extends to the entire visible range.
現在では光を吸収してキャリアを発生するキャリア発生
層とキャリアを有効に輸送するキャリア輸送層とを積層
した機能分離型の光導電体が主流である。キャリア発生
材料にはＳｅ、Ａｓ、Ｓｅ、などの無機材料、あるいは
フタロシアニン系の有機蒸着層、スクアリュウム塩をバ
インダー中に分散させた塗布層などが用いられる。一方
、キャリア輸送材料には前出のＰＶＫ単体の他にトリフ
ェニルアミン誘導体をバインダー中に分散させた物など
多くの有機材料が開発されている。Currently, the mainstream is a functionally separated photoconductor in which a carrier generation layer that absorbs light and generates carriers and a carrier transport layer that effectively transports carriers are laminated. As the carrier generating material, an inorganic material such as Se, As, Se, etc., a phthalocyanine organic vapor deposited layer, a coating layer in which squalium salt is dispersed in a binder, etc. are used. On the other hand, many organic materials have been developed as carrier transport materials, such as those in which triphenylamine derivatives are dispersed in a binder, in addition to the above-mentioned PVK alone.
本出願人は、キャリア輸送能力の高い材料としてポリバ
ラフェニレンスルフィド（以下、ＰＰＳと称す）を提案
（特開昭６２−１６４５５６号公報）した、ＰＰＳは耐
熱性に優れた絶縁材料であるが、酸素中で熱処理するこ
とでキャリア輸送能力が大幅に向上すること（第３５回
応用物理学会関係連合講演会予稿集３１ｐ−Ａ−１１）
を見いだした。これは膜中に取込まれた酸素分子がＰＰ
Ｓ分子を弱結ぶ働きをし、アモルファス領域に入って結
合し結晶領域の結合を結付けるからであると考えられる
。そしてこのようなＰＰＳ中ではキャリアの伝達方向は
分子鎖に直交し、結晶領域で高いキャリア移動度を持つ
ものと推測される。The present applicant proposed polybara phenylene sulfide (hereinafter referred to as PPS) as a material with high carrier transport ability (Japanese Patent Application Laid-Open No. 164556/1983). PPS is an insulating material with excellent heat resistance. Carrier transport ability is significantly improved by heat treatment in oxygen (Proceedings of the 35th Japan Society of Applied Physics Association Conference Proceedings 31p-A-11)
I found it. This is because oxygen molecules taken into the film become PP.
This is thought to be because it acts to weakly bind S molecules, enters the amorphous region and bonds, and connects the bonds in the crystalline region. In such a PPS, the carrier propagation direction is perpendicular to the molecular chain, and it is presumed that the carrier mobility is high in the crystalline region.
ＰＰＳの各分子の長さを重合度５〜７程度に短く揃えた
オリゴ−フェニレンスルフィド（以下、ＯＰＳと称す）
は、蒸着法によって配向性と結晶性を著しく向上させる
ことがきる。この膜の光導電性は結晶領域の拡大によっ
て増加し、且つキャリア伝導の方向は分子長軸に直交す
ること（第４１回応用物理学会学術講演会予稿集５ｐ−
Ｚｌｌ−１５）が分った。従ってキャリア発生官能基を
ＯＰＳ中に組込んだ分子は配向性、結晶性の良好な膜状
態を実現すれば前記官能基の光吸収帯で吸収発生したキ
ャリアをＯＰＳ骨格で伝達させることが可能（特開昭６
３−２７４８７１号公報）である。Oligo-phenylene sulfide (hereinafter referred to as OPS) in which the length of each PPS molecule is shortened to a degree of polymerization of about 5 to 7.
The orientation and crystallinity can be significantly improved by vapor deposition. The photoconductivity of this film increases as the crystalline region expands, and the direction of carrier conduction is perpendicular to the long axis of the molecules (Proceedings of the 41st Japan Society of Applied Physics Academic Conference, p. 5-
Zll-15) was found. Therefore, if a molecule with a carrier-generating functional group incorporated into the OPS achieves a film state with good orientation and crystallinity, carriers absorbed and generated in the optical absorption band of the functional group can be transmitted through the OPS skeleton ( Tokukai Showa 6
3-274871).
Claims (6)
分子との交互共重合体であることを特徴とする有機高分
子。 （イ）▲数式、化学式、表等があります▼ （ｎ≧２ Ｘ：Ｏ、Ｓ、Ｓｅ、Ｔｅのいずれか Ｙ、Ｚ：芳香族又は置換芳香族の基）(1) An organic polymer characterized by being an alternating copolymer of an organic molecule represented by the following general formula (A) and another organic molecule. (B) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (n≧2 X: O, S, Se, Te, Y, Z: aromatic or substituted aromatic group)
ポリアミド、ポリエーテルイミド、ポリエステルイミド
、ポリエーテルアミドのいずれかであることを特徴とす
る請求項１記載の有機高分子。(2) The alternating copolymer is polyimide, polyamideimide,
The organic polymer according to claim 1, which is any one of polyamide, polyetherimide, polyesterimide, and polyetheramide.
る官能基を有し、且つこの有機高分子を結晶化したもの
であることを特徴とする光導電材料。(3) A photoconductive material characterized in that the organic polymer according to claim 1 has a functional group that generates photocarriers, and is obtained by crystallizing this organic polymer.
以上存在することを特徴とする請求項３記載の光導電材
料。(4) The photoconductive material according to claim 3, characterized in that there is at least one scattering peak in the X-ray diffraction intensity curve.
請求項３記載の光導電材料の製造方法。(5) The method for producing a photoconductive material according to claim 3, wherein the crystallization is performed by heat treatment.
ことを特徴とする請求項５記載の光導電材料の製造方法
。(6) The method for producing a photoconductive material according to claim 5, characterized in that the heating temperature of the heat treatment is increased in accordance with crystallization.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2074971A JP3014713B2 (en) | 1990-03-25 | 1990-03-25 | Photoconductive material and manufacturing method thereof |
| EP19910104437 EP0449117A3 (en) | 1990-03-23 | 1991-03-21 | Organic polymer and preparation and use thereof |
| US08/090,638 US5486442A (en) | 1990-03-23 | 1993-07-13 | Organic polymer and preparation and use in crystal spatial light modulator |
| US08/451,727 US5597889A (en) | 1990-03-23 | 1995-05-26 | Organic polymer and preparation and use thereof |
| US08/450,909 US5876891A (en) | 1990-03-23 | 1995-05-26 | Photosensitive material and process for the preparation thereof |
| US08/453,061 US5654367A (en) | 1990-03-23 | 1995-05-26 | Organic polymer and preparation and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2074971A JP3014713B2 (en) | 1990-03-25 | 1990-03-25 | Photoconductive material and manufacturing method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03275723A true JPH03275723A (en) | 1991-12-06 |
| JP3014713B2 JP3014713B2 (en) | 2000-02-28 |
Family
ID=13562692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2074971A Expired - Fee Related JP3014713B2 (en) | 1990-03-23 | 1990-03-25 | Photoconductive material and manufacturing method thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3014713B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0532779A (en) * | 1990-11-27 | 1993-02-09 | Nkk Corp | Polyimide resin having naphthalene skeleton |
| US6233027B1 (en) | 1997-01-07 | 2001-05-15 | Canon Kabushiki Kaisha | Liquid crystal device and process for production thereof |
| WO2019151288A1 (en) * | 2018-01-31 | 2019-08-08 | 東レ株式会社 | Polyarylene sulfide copolymer and method for producing same |
| CN113667123A (en) * | 2021-09-10 | 2021-11-19 | 中鼎凯瑞科技成都有限公司 | Polyarylene sulfide compound with ultraviolet fluorescent tracing function and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03266392A (en) * | 1990-03-14 | 1991-11-27 | Seikosha Co Ltd | Sealing of el board |
-
1990
- 1990-03-25 JP JP2074971A patent/JP3014713B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03266392A (en) * | 1990-03-14 | 1991-11-27 | Seikosha Co Ltd | Sealing of el board |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0532779A (en) * | 1990-11-27 | 1993-02-09 | Nkk Corp | Polyimide resin having naphthalene skeleton |
| US6233027B1 (en) | 1997-01-07 | 2001-05-15 | Canon Kabushiki Kaisha | Liquid crystal device and process for production thereof |
| WO2019151288A1 (en) * | 2018-01-31 | 2019-08-08 | 東レ株式会社 | Polyarylene sulfide copolymer and method for producing same |
| US11440997B2 (en) | 2018-01-31 | 2022-09-13 | Toray Industries, Inc. | Polyarylene sulfide copolymer and method of producing the same |
| CN113667123A (en) * | 2021-09-10 | 2021-11-19 | 中鼎凯瑞科技成都有限公司 | Polyarylene sulfide compound with ultraviolet fluorescent tracing function and preparation method thereof |
| CN113667123B (en) * | 2021-09-10 | 2023-11-07 | 中鼎凯瑞科技成都有限公司 | Polyarylene sulfide compound with ultraviolet fluorescence tracing function and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3014713B2 (en) | 2000-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |