JPS6381359A - Organic photoconductor - Google Patents
Organic photoconductorInfo
- Publication number
- JPS6381359A JPS6381359A JP22678086A JP22678086A JPS6381359A JP S6381359 A JPS6381359 A JP S6381359A JP 22678086 A JP22678086 A JP 22678086A JP 22678086 A JP22678086 A JP 22678086A JP S6381359 A JPS6381359 A JP S6381359A
- Authority
- JP
- Japan
- Prior art keywords
- phthalocyanine
- organic photoconductor
- dispersion
- binder resin
- basic monomer
- 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.)
- Pending
Links
- 239000011347 resin Substances 0.000 claims abstract description 12
- 229920005989 resin Polymers 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims abstract description 8
- 239000011230 binding agent Substances 0.000 claims abstract description 7
- 239000006185 dispersion Substances 0.000 abstract description 19
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 abstract description 9
- 239000000049 pigment Substances 0.000 abstract description 5
- 239000002245 particle Substances 0.000 abstract description 4
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 150000007524 organic acids Chemical class 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 230000035945 sensitivity Effects 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002964 rayon Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 229920005497 Acrypet® Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 108091008695 photoreceptors Proteins 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 235000000001 Phoenix pusilla Nutrition 0.000 description 1
- 244000290891 Phoenix pusilla Species 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003984 copper intrauterine device Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0696—Phthalocyanines
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真用の有機光導電体に関するものである
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an organic photoconductor for electrophotography.
Ｃ従来の技術〕
最近、電子写真用感光体は無機化合物の酸化亜鉛、硫化
カドミウム、無定形セレン等から有機物系の感光体の使
用に移ってきている。！１７ｔ、性能向上のために電荷
発生層と電荷移動層を有する二層型の機能分離型感光体
が主流となっている。この電荷発生層には可視光線域に
大きな吸収帯を持つ樹脂もしくけ可視光線域に大きな吸
収帯を持つ色素を分散した樹脂が使用されている。C. Prior Art Recently, the use of electrophotographic photoreceptors has shifted from inorganic compounds such as zinc oxide, cadmium sulfide, and amorphous selenium to organic photoreceptors. ! 17t, a two-layer functionally separated photoreceptor having a charge generation layer and a charge transfer layer has become mainstream in order to improve performance. This charge generation layer is made of a resin having a large absorption band in the visible light region and a resin in which a dye having a large absorption band in the visible light region is dispersed.
ここで使用される色素は顔料／ｌ”−主流であるが、電
荷発生層の膜厚ｈｉ Ｉ １１ｆｎ以下であるｔめに、
顔料粒子はサブミクロン以下のサイズでなければ均一で
良好な電荷発生層を形成することはむずかしい。The dye used here is mainly pigment/l'', but since the thickness of the charge generation layer is hi I 11fn or less,
Unless the pigment particles have a submicron size or less, it is difficult to form a uniform and good charge generation layer.
さらに、サブミクロンサイズの顔料粒子の樹脂への分散
はシェーカー等の分散器を長時間作動させる必要がある
。Furthermore, dispersion of submicron-sized pigment particles into the resin requires operating a disperser such as a shaker for a long time.
本発明は電荷発生物質であるスルホン化７タロシアニン
を塩基性単量体で処理をして樹脂への分散性を向上させ
たものである。そして、塩基性単を体で処理したフタロ
シアン誘導体６Ｓ ／（インダー樹脂中に分散された有
機光導電体がつくられる。In the present invention, sulfonated 7-thalocyanine, which is a charge generating substance, is treated with a basic monomer to improve its dispersibility in a resin. Then, an organic photoconductor is prepared in which a basic monomer is treated with a phthalocyanine derivative 6S/(inner resin).
スルホン化フタロシアニン有機酸として働キ、塩基性単
量体と有機塩を形成する。この結果１重合性の官能基を
有するフタロシアニン誘導体が調製される。この結長、
フタロシアニン誘導体のバインダー樹脂への分散性、密
着性を向上することがで鎗る。次に実施例にもとすいて
本発明の有機光導電体を詳細に説明するｈｔ、本発明は
実施例に示す組合わせのみに限定されるものではない。Sulfonated phthalocyanine acts as an organic acid and forms organic salts with basic monomers. As a result, a phthalocyanine derivative having a monopolymerizable functional group is prepared. This growth,
This improves the dispersibility and adhesion of the phthalocyanine derivative to the binder resin. Next, the organic photoconductor of the present invention will be described in detail with reference to Examples, but the present invention is not limited to the combinations shown in the Examples.
実施例ｔ
ジスルホン化銅７タロシアニン（大日本イン中Ｐａｓｔ
ｏｇｅｎ Ｂｌｖｅ日ＢＬ）３，９．アリル７ミン塩酸
塩５７３！、蒸留水１０ｆｒＬｔを混合溶解して多量の
メタノールに注ぎ、析出物を乾燥しｔ、これを鋼フタロ
シアニア −７１Ｊ ルア ｊン塩とする。鋼７タロシ
アニンーアリルアミン塩３ｇ、メタクリル酸メチル２ｆ
ｎｔ、アクリル樹脂（三菱レイヨン、アクリペラ））２
１１．アセトン２０ｍ１を混合して、■東洋精機製作所
、試験用分散機准４８８により分散し几。Example t Disulfonated copper 7 thalocyanine (Dainippon Inchu Past
ogen Blve Japan BL) 3,9. Allyl 7mine hydrochloride 573! , and 10 frL of distilled water were mixed and dissolved, poured into a large amount of methanol, and the precipitate was dried. Steel 7 talocyanine-allylamine salt 3g, methyl methacrylate 2f
nt, acrylic resin (Mitsubishi Rayon, Acrypela)) 2
11. Mix 20ml of acetone and disperse using Toyo Seiki Seisakusho's test dispersion machine 488.
このとき、均一分散するまでの時間は５時間であり几。At this time, it took 5 hours to achieve uniform dispersion.
ここで得られ之分散液を分散液１とする。The dispersion obtained here is referred to as Dispersion 1.
Ｐ−ジエチルアミノベンツアルデヒドジフェニルヒドラ
ゾン（亜南香料■）１０．９．ポリカーボネート（エン
ジニアリングプラスチック、し千サン）１０Ｉ、トルエ
ン３０ｍ１を混合溶解した。これを分散液２とする。導
電層を形成し几ポリエステルフィルム上に分散液１を塗
布して３００〜３１５ｎｍの紫外線を照射しながら６０
℃で乾燥し友。乾燥後の膜厚は０．５μｍとなるように
調製した。この膜層を電荷発生層とする。この上に分散
液２を乾燥後の膜厚が１５μｍになるように塗布し７′
２．、この膜層を電荷移動層とする。得られ几有機光導
電体を川口電機製作所Ｂ Ｐ −４２８を使用して、−
６ＫＶでコロナ放電を行ないタングステン球を光源とし
て表面電位減衰変測定を行なっ友。半減露光量３． Ｏ
１ｍ ５ｔｔａであっｔ０実施例２
実施例１の銅フタロシアニン−アリルアミン塩５１１、
スチレン１．５ｍｌ、ジビニルベンゼンＱ、５ｍｌアク
リル樹脂（三菱レイヨン、アクリペット）２ ′ｌ、ア
セトン２０ｍ１を混合して、実施例１と同様に分散し次
。このとき均一分散までの時間Ｆｉ４＠間であったｎ＋
：こで得られ九分散液を分散液３とする。導電層を形成
し几ポリエステルフィルム上忙分散液３を塗布して、５
６６ｎｍの紫外線を１時間照射してから６０℃で乾燥し
た。この電荷発生層の上に実施例１と同様にして電荷移
動層を形成して測定を行なった。半減露光量２．６１ｕ
’２．８ｅｃであった。P-diethylaminobenzaldehyde diphenylhydrazone (Anan Kaori ■) 10.9. 10I of polycarbonate (engineering plastic, Shisensan) and 30ml of toluene were mixed and dissolved. This will be referred to as Dispersion 2. After forming a conductive layer, dispersion 1 was coated on a polyester film and heated for 60 minutes while irradiating it with ultraviolet light of 300 to 315 nm.
Dry at ℃. The film thickness after drying was adjusted to 0.5 μm. This film layer is used as a charge generation layer. Dispersion 2 was applied on top of this so that the film thickness after drying was 15 μm.
2. , this film layer is used as a charge transfer layer. The obtained organic photoconductor was processed using Kawaguchi Electric Seisakusho B P-428.
We carried out corona discharge at 6KV and measured changes in surface potential decay using a tungsten bulb as a light source. Half exposure amount 3. O
1 m 5tta and t0 Example 2 Copper phthalocyanine-allylamine salt 511 of Example 1,
1.5 ml of styrene, divinylbenzene Q, 5 ml of acrylic resin (Mitsubishi Rayon, Acrypet), and 20 ml of acetone were mixed and dispersed in the same manner as in Example 1. At this time, the time until uniform dispersion was Fi4@ n+
: The nine dispersion obtained in this manner is referred to as dispersion 3. After forming a conductive layer, apply dispersion 3 on the polyester film, and then apply 5
It was irradiated with 66 nm ultraviolet light for 1 hour and then dried at 60°C. A charge transfer layer was formed on this charge generation layer in the same manner as in Example 1, and measurements were performed. Half-reduction exposure amount 2.61u
It was 2.8ec.
実施例３゜
ジスルホン化銅ブタロシアニン（大日本インキ１ｈｘｌ
ｔｔＯ（１ｅｎ Ｂｌｖｅ ＦＪＢＬ ） ３．９ 、
４−ビニルピリジン５−１蒸留水１０ｍ１を混合溶解し
て多量のアセトンに注ぎ、析出物を乾燥しｔ、これを鋼
フタロシアニン−ビニルピリジン塩とする。鋼７タロシ
アニンービニルビリジン塩３Ｉ、スチレン１５ｍ１、ジ
ビニルベンゼン［１，５ｆｒＬｔ、アクリル樹脂（三菱
レイヨン、アクリペット） ２ ｇ、 アセトン２Ｑ
ｔｔｓｌを混合して、実施例１と同様に分散した。この
とき均一分散までの時間は４時間でもつ友。ここで得ら
れ九分散液を分散液４とする。以下実施例２と同様にし
て電荷発生層、電荷移動層を形成Ｉ−て測定を行なった
。半減露光量２． ｏ ｌｖ、ｚ、 ｓｅｃであっち〔
参考例〕
ンスルホン化鋼７タロシアニン（大日本インキＩＰｔｘ
８ｔＯＱｅｎ Ｂｌｖｅ ８ＢＬ ）３ ｇ、アクリル
樹脂（三菱レイヨン、アクリペット）３１ アセトン２
０―を混合して、実施例１と同様にして分散した。この
とき均一分散までの時間は８時間であった。この分散液
を導電層を形成したポリエステルフィルム上に乾燥後の
膜厚が０．５μ毒となるように塗布し比ゆこの電荷発生
層の上に実施例１と同様にして電荷移動層を形成して測
定を行なった。半減露光量８ ｌｕｘ、 ｓｅｔであっ
た。Example 3 Disulfonated copper butalocyanine (Dainippon Ink 1hxl)
ttO (1en Blve FJBL) 3.9,
4-Vinylpyridine 5-1 is mixed and dissolved with 10ml of distilled water, poured into a large amount of acetone, and the precipitate is dried to obtain a steel phthalocyanine-vinylpyridine salt. Steel 7 talocyanine-vinyl pyridine salt 3I, styrene 15ml, divinylbenzene [1,5frLt, acrylic resin (Mitsubishi Rayon, Acrypet) 2g, acetone 2Q
ttsl was mixed and dispersed in the same manner as in Example 1. In this case, the time required for uniform dispersion is 4 hours. The nine dispersion liquid obtained here is referred to as dispersion liquid 4. Thereafter, a charge generation layer and a charge transfer layer were formed in the same manner as in Example 2, and measurements were performed. Half exposure amount 2. o lv, z, sec over there [
Reference example] Sulfonated steel 7 talocyanine (Dainippon Ink IPtx
8tOQen Blve 8BL) 3 g, acrylic resin (Mitsubishi Rayon, Acrypet) 31 acetone 2
0- was mixed and dispersed in the same manner as in Example 1. At this time, it took 8 hours to achieve uniform dispersion. This dispersion was applied onto the polyester film on which the conductive layer was formed so that the film thickness after drying would be 0.5μ, and a charge transfer layer was formed on the charge generation layer in the same manner as in Example 1. The measurements were carried out. The half-reduction exposure was 8 lux, set.
以上にように本発明による有機光導電体は７タロシアニ
ン誘導体を塩基性単量体で処理してから（処理したもの
を）バインダー樹脂に分散する（した）ことを特徴とし
ており１分散時間の短縮、７タロシアニン顔料粒子とバ
インダー樹脂の密着性の向上、及び有機光導電体として
の惑星を向上させることができる。As described above, the organic photoconductor of the present invention is characterized by treating the 7-thalocyanine derivative with a basic monomer and then dispersing the treated product in a binder resin, thereby reducing the dispersion time. , 7 It is possible to improve the adhesion between the talocyanine pigment particles and the binder resin, and to improve the planet as an organic photoconductor.
以 上that's all
Claims (1)
ー樹脂中に分散され構成されていることを特徴とする有
機光導電体。An organic photoconductor comprising a phthalocyanide derivative treated with a basic monomer dispersed in a binder resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22678086A JPS6381359A (en) | 1986-09-25 | 1986-09-25 | Organic photoconductor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22678086A JPS6381359A (en) | 1986-09-25 | 1986-09-25 | Organic photoconductor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6381359A true JPS6381359A (en) | 1988-04-12 |
Family
ID=16850493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22678086A Pending JPS6381359A (en) | 1986-09-25 | 1986-09-25 | Organic photoconductor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6381359A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5597675A (en) * | 1995-03-31 | 1997-01-28 | Imation Corp. | Dispersing polymers for phthalocyanine pigments used in organic photoconductors |
| US5600513A (en) * | 1993-03-04 | 1997-02-04 | Seiko Epson Corporation | Position detecting mechanisms for recording media |
-
1986
- 1986-09-25 JP JP22678086A patent/JPS6381359A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5600513A (en) * | 1993-03-04 | 1997-02-04 | Seiko Epson Corporation | Position detecting mechanisms for recording media |
| US5597675A (en) * | 1995-03-31 | 1997-01-28 | Imation Corp. | Dispersing polymers for phthalocyanine pigments used in organic photoconductors |
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