JP4275600B2 - ヒドラゾン化合物および該ヒドラゾン化合物を用いた電子写真感光体、ならびに該電子写真感光体を備える画像形成装置 - Google Patents
ヒドラゾン化合物および該ヒドラゾン化合物を用いた電子写真感光体、ならびに該電子写真感光体を備える画像形成装置 Download PDFInfo
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- JP4275600B2 JP4275600B2 JP2004259877A JP2004259877A JP4275600B2 JP 4275600 B2 JP4275600 B2 JP 4275600B2 JP 2004259877 A JP2004259877 A JP 2004259877A JP 2004259877 A JP2004259877 A JP 2004259877A JP 4275600 B2 JP4275600 B2 JP 4275600B2
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 238000002366 time-of-flight method Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000005671 trienes Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical group CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
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- 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
- G03G5/0666—Dyes containing a methine or polymethine group
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- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Description
Ray Tube;略称CRT)などを光源とする高速プリンタにも応用されている。電子写真技術の応用範囲の拡大に伴い、電子写真感光体に対する要求は、高度で幅広いものになりつつある。
(1)光および熱に対して安定であること、
(2)感光体を帯電させる際のコロナ放電によって発生するオゾン、窒素酸化物(一般式:NOx)および硝酸などの活性物質に対して安定であること、
(3)電荷輸送能力に優れること、
(4)有機溶剤およびバインダ樹脂との相溶性に優れること、
(5)製造が容易で安価であること
などが要求される。しかしながら、前述の特許文献1〜8などに開示の電荷輸送物質は、これらの要求の一部を満足するけれども、すべてを高いレベルで満足するには至っていない。
すなわち、本発明は、一般式(1)
前記感光層は、前記本発明のヒドラゾン化合物を含有することを特徴とする電子写真感光体である。
前記電荷輸送物質が、前記本発明のヒドラゾン化合物を含むことを特徴とする。
前記電荷輸送層における前記本発明のヒドラゾン化合物の重量(A)に対するバインダ樹脂の重量(B)の比率(B/A)が、1.2以上、3.0以下であることを特徴とする。
前記電子写真感光体を帯電させる帯電手段と、
帯電された前記電子写真感光体に対して露光を施す露光手段と、
露光によって形成される静電潜像を現像する現像手段とを備えることを特徴とする画像形成装置である。
炭素数1〜3のアルキル基としては、メチル基、エチル基、イソプロピル基、n−プロピル基が挙げられる。
一般式(2)で表されるヒドラゾン中間体は、たとえば下記一般式(2a)
(R6O)3P …(4a)
(式中、R6は一般式(4)における定義と同義である。)で表される亜リン酸化合物と、下記一般式(4b)
中間層15としては、各種樹脂材料から成る樹脂層、アルマイト層などが用いられる。
(製造例1)例示化合物No.1の製造
前述の一般式(2a)で表されるケトン化合物としてアセトフェノンを用い、一般式(2b)で表されるヒドラジン化合物としてN,N−ジフェニルヒドラジンを用い、以下のようにして脱水縮合反応を行ない、下記構造式(6)で表されるヒドラゾン中間体を製造した。
Mass Spectrometry;略称LC−MS)で分析した結果、目的化合物である構造式(7)で表されるヒドラゾン−ケトン中間体(分子量の計算値:358.18)にプロトンが付加した分子イオン[M+H]+に相当するピークが359.4に観測された。このことから、得られた化合物が構造式(7)で表されるヒドラゾン−ケトン中間体であることが確認された(収率:90.0%)。また、LC−MSの分析結果から、得られたヒドラゾン−ケトン中間体の純度が98.1%であることが判った。
理論値…C:83.81%、H:6.59%、N:6.11%
実測値…C:83.67%、H:6.44%、N:6.01%
製造例1において、グリニヤール反応に際し、構造式(8)で表されるシンナミルブロマイド(1.2モル当量)に代えて、下記構造式(9)で表される5−ブロモ−1−フェニル−1,3−ペンタジエン2.2g(1.2モル当量)を用いること以外は、製造例1と同様にして、黄色粉末状化合物3.30gを得た。
理論値…C:84.67%、H:6.71%、N:5.49%
実測値…C:84.51%、H:6.58%、N:5.38%
製造例1において、脱水縮合反応に際し、p−メトキシアセトフェノンに代えて、3,4−メチレンジオキシベンズアルデヒドを用いて同様の操作を行ない、下記構造式(10)で表されるヒドラゾン中間体を黄色結晶として得た(収率98%)。
であることが判った。また、得られた例示化合物No.7の元素分析値は以下のとおりであった。
理論値…C:81.06%、H:5.44%、N:6.30%
実測値…C:79.97%、H:5.31%、N:6.18%
製造例3において、3,4−メチレンジオキシベンズアルデヒドに代えて、3,4−メチレンジオキシアセトフェノンを用いて同様の操作を行ない、下記構造式(13)で表されるヒドラゾン−アルデヒド中間体を製造した。
理論値…C:82.33%、H:5.92%、N:6.27%
実測値…C:82.17%、H:5.78%、N:6.15%
製造例1において、一般式(2a)で表されるケトン化合物、一般式(2b)で表されるヒドラジン化合物、一般式(5a)で表されるハロゲン化アシル化合物および一般式(4b)で表されるハロゲン化アリル化合物として表2に示す各原料化合物を用いて同様の操作を行ない、例示化合物No.11を製造した。なお、表2には、例示化合物No.1および6の原料化合物も合わせて示す。
製造例3において、一般式(2a)で表されるケトン化合物、一般式(2b)で表されるヒドラゾン化合物、一般式(4)で表されるウィッティッヒ試薬として表3〜4に示す各原料化合物を用いて同様の操作を行ない、例示化合物No.2〜5,8〜10,12および14をそれぞれ製造した。なお、表3〜4には、例示化合物No.7および13の原料化合物も合わせて示す。また、表3〜4において、Etはエチル基を示す。
(実施例1)
電荷発生物質として下記構造式(15)で表されるアゾ化合物1重量部を、テトラヒドロフラン(略称THF)99重量部にフェノキシ樹脂(ユニオンカーバイド社製:PKHH)1重量部を溶解させて得た樹脂溶液に加えた後、ペイントシェーカで2時間分散させ、電荷発生層用塗布液を調製した。この電荷発生層用塗布液を、膜厚80μmのポリエステルフィルムの表面にアルミニウムを蒸着して成る導電性支持体のアルミニウム上に、ベーカアプリケータにて塗布した後、乾燥させ、膜厚0.3μmの電荷発生層を形成した。
電荷輸送物質として、例示化合物No.1に代えて、表1に示す例示化合物No.3,8または14を用いる以外は、実施例1と同様にして、実施例2〜4の電子写真感光体を作製した。
電荷輸送物質として、例示化合物No.1に代えて、下記構造式(16)で表される比較化合物Aを用いる以外は、実施例1と同様にして、比較例1の電子写真感光体を作製した。
電荷輸送物質として、例示化合物No.1に代えて、下記構造式(17)で表される比較化合物Bを用いる以外は、実施例1と同様にして、比較例2の電子写真感光体を作製した。
以上のようにして作製した実施例1〜4および比較例1,2の各感光体を用い、各感光体に用いた電荷輸送物質の電荷移動度を以下のようにして測定した。各感光体の電荷輸送層表面に金を蒸着し、室温下で減圧しながら、飛行時間(Time−of−Flight)法によって電荷移動度(cm2/V・sec)を測定し、この値を各感光体に用いた電荷輸送物質の電荷移動度とした。測定結果を表6に示す。なお、表6に示す電荷移動度の値は、電界強度が2.5×105V/cmのときの値である。
酸化アルミニウム(化学式:Al2O3)と二酸化ジルコニウム(化学式:ZrO2)とで表面処理された樹枝状の酸化チタン(石原産業株式会社製:TTO−D−1)9重量部と、共重合ナイロン樹脂(東レ株式会社製:CM8000)9重量部とを、1,3−ジオキソラン41重量部とメタノール41重量部との混合溶剤に加え、ペイントシェーカを用いて12時間分散させ、中間層用塗布液を調製した。調製した中間層用塗布液を、厚み0.2mmのアルミニウム製板状導電性支持体上に、ベーカアプリケータにて塗布した後、乾燥させ、膜厚1μmの中間層を形成した。
電荷輸送物質として、例示化合物No.1に代えて、表1に示す例示化合物No.4,5または9を用いる以外は、実施例5と同様にして、実施例6〜8の電子写真感光体を作製した。
電荷輸送物質として、例示化合物No.1に代えて、前述の構造式(16)で表される比較化合物Aまたは構造式(17)で表される比較化合物Bを用いる以外は、実施例5と同様にして、比較例3および4の電子写真感光体を作製した。
実施例5と同様にして、厚み0.2mmのアルミニウム製板状導電性支持体上に、膜厚1μmの中間層を形成した。
電荷発生物質として、構造式(18)で表されるアゾ化合物に代えて、X型無金属フタロシアニンを用いる以外は、実施例5と同様にして、実施例10の電子写真感光体を作製した。
電荷発生物質として、構造式(18)で表されるアゾ化合物に代えて、X型無金属フタロシアニンを用い、電荷輸送物質として、例示化合物No.1に代えて、表1に示す例示化合物No.2,11または13を用いる以外は、実施例5と同様にして、実施例11〜13の電子写真感光体を作製した。
電荷発生物質として、構造式(18)で表されるアゾ化合物に代えて、X型無金属フタロシアニンを用い、電荷輸送物質として、例示化合物No.1に代えて、前述の構造式(16)で表される比較化合物Aまたは構造式(17)で表される比較化合物Bを用いる以外は、実施例5と同様にして、比較例5および6の電子写真感光体を作製した。
以上のようにして作製した実施例5〜13および比較例3〜6の各感光体について、静電複写紙試験装置(株式会社川口電機製作所製:EPA−8200)を用いて、初期特性および繰返し特性を評価した。評価は、温度22℃、相対湿度65%(65%RH)の常温/常湿(N/N:Normal Temperature/Normal Humidity)環境下および温度5℃、相対湿度20%(20%RH)の低温/低湿(L/L:Low Temperature/Low Humidity)環境下のそれぞれの環境下において行なった。
以上の測定結果を表7に示す。
酸化アルミニウム(Al2O3)と二酸化ジルコニウム(ZrO2)とで表面処理された樹枝状の酸化チタン(石原産業株式会社製:TTO−D−1)9重量部と、共重合ナイロン樹脂(東レ株式会社製:CM8000)9重量部とを、1,3−ジオキソラン41重量部とメタノール41重量部との混合溶剤に加えた後、ペイントシェーカにて8時間分散処理し、中間層用塗布液を調製した。この中間層塗布液を塗工槽に満たし、この塗工層に直径40mm、長手方向の長さ340mmのアルミニウム製円筒状導電性支持体を浸漬した後引上げ、乾燥させ、膜厚1.0μmの中間層を導電性支持体上に形成した。
以上のようにして、実施例14の電子写真感光体を作製した。
電荷輸送物質として、例示化合物No.1に代えて、表1に示す例示化合物No.6または7を用いる以外は、実施例14と同様にして、実施例15および16の電子写真感光体を作製した。
電荷輸送物質として、例示化合物No.1に代えて、前述の構造式(16)で表される比較化合物Aを用いる以外は、実施例14と同様にして、比較例7の電子写真感光体を作製した。
電荷輸送層の形成に際し、バインダ樹脂であるポリカーボネート樹脂の量を25重量部に変更する以外は、実施例14と同様にして、実施例17の電子写真感光体を作製した。
電荷輸送層の形成に際し、バインダ樹脂であるポリカーボネート樹脂の量を25重量部に変更し、電荷輸送物質として、例示化合物No.1に代えて、表1に示す例示化合物No.10または12を用いる以外は、実施例14と同様にして、実施例18および19の電子写真感光体を作製した。
電荷輸送層の形成に際し、バインダ樹脂であるポリカーボネート樹脂の量を10重量部に変更する以外は、実施例14と同様にして、実施例20の電子写真感光体を作製した。
電荷輸送層の形成に際し、バインダ樹脂であるポリカーボネート樹脂の量を31重量部に変更する以外は、実施例14と同様にして、電子写真感光体を作製した。ただし、実施例14と同量のTHFではポリカーボネート樹脂が完全には溶解せず、電荷輸送層用塗布液の粘度が高くなったので、THFを追加し、ポリカーボネート樹脂が完全に溶解した電荷輸送層用塗布液を調製し、これを用いて電荷輸送層を形成した。
以上のようにして作製した実施例14〜20および比較例7の各感光体を、市販のデジタル複写機AR−C150(商品名、シャープ株式会社製)を感光体の回転周速が毎秒117mmになるように改造した試験用複写機にそれぞれ搭載し、各感光体の耐刷性、電気特性および環境安定性を以下のようにして評価した。なお、前述のデジタル複写機AR−C150は、感光体表面の帯電を負に帯電して電子写真プロセスを行なう負帯電型の画像形成装置である。
試験用複写機を用い、所定のパターンのテスト画像を記録用紙4万枚に形成した後、搭載していた感光体を取出して感光層の膜厚d1[μm]を測定し、この値d1を作製時の感光層の膜厚d0から差引いた値(d0−d1)を膜減り量Δdとして求め、耐刷性の評価指標とした。なお、膜厚の測定は、光干渉法による瞬間マルチ測光システムMCPD−1100(商品名、大塚電子株式会社製)で行なった。
複写機内部に、画像形成過程における感光体の表面電位を測定できるように表面電位計(ジェンテック社製:CATE751)を設けた。前記複写機を用い、各感光体について、温度22℃、相対湿度65%のN/N環境下において、帯電器による帯電動作直後の感光体の表面電位を帯電電位V1[V]として測定した。また、レーザ光によって露光を施した直後の感光体の表面電位を残留電位VL[V]として測定し、これをN/N環境下における残留電位VLNとした。帯電電位V1の絶対値が大きい程、帯電性に優れると評価し、残留電位VLNの絶対値が小さい程、光応答性に優れると評価した。
これらの評価結果を表8に示す。
11 導電性支持体
12 電荷発生層
13 電荷輸送層
14,140 感光層
15 中間層
30 露光手段
31 露光手段からの光
32 帯電器
33 現像器
34 転写器
35 定着器
36 クリーナ
100 画像形成装置
Claims (7)
- 一般式(1)
で示されるヒドラゾン化合物。 - 導電性支持体と、前記導電性支持体上に設けられる感光層とを有する電子写真感光体であって、前記感光層は、請求項1記載のヒドラゾン化合物を含有することを特徴とする電子写真感光体。
- 前記感光層が、オキソチタニウムフタロシアニン化合物をさらに含有することを特徴とする請求項2記載の電子写真感光体。
- 前記感光層が、電荷発生物質を含有する電荷発生層と、電荷輸送物質を含有する電荷輸送層とを備え、前記電荷輸送物質が、前記ヒドラゾン化合物を含むことを特徴とする請求項2〜3のうちのいずれか1つに記載の電子写真感光体。
- 前記電荷輸送層が、さらにバインダ樹脂を含有し、前記電荷輸送層における前記ヒドラゾン化合物の重量(A)に対するバインダ樹脂の重量(B)の比率(B/A)が、1.2以上、3.0以下であることを特徴とする請求項4記載の電子写真感光体。
- 前記導電性支持体と前記感光層との間に、中間層を有することを特徴とする請求項2〜5のうちのいずれか1つに記載の電子写真感光体。
- 請求項2〜6のうちのいずれか1つに記載の電子写真感光体と、前記電子写真感光体を帯電させる帯電手段と、帯電された前記電子写真感光体に対して露光を施す露光手段と、露光によって形成される静電潜像を現像する現像手段とを備えることを特徴とする画像形成装置。
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CN200510103711.2A CN1325469C (zh) | 2004-09-07 | 2005-09-07 | 腙化合物及使用该腙化合物的电子照相感光体、以及具有该电子照相感光体的图像形成装置 |
US11/220,401 US7794907B2 (en) | 2004-09-07 | 2005-09-07 | Hydrazone compound, electrophotographic photoreceptor comprising the hydrazone compound, and image forming apparatus equipped with the electrophotographic photoreceptor |
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JP2009210676A (ja) * | 2008-03-03 | 2009-09-17 | Kyocera Mita Corp | 単層型電子写真感光体及び画像形成装置 |
JP4617369B2 (ja) * | 2008-04-08 | 2011-01-26 | シャープ株式会社 | 電子写真感光体およびそれを備えた画像形成装置 |
US20140012002A1 (en) * | 2012-07-04 | 2014-01-09 | Basf Se | Organic dyes comprising a hydrazone moiety and their use in dye-sensitized solar cells |
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US3824099A (en) * | 1973-01-15 | 1974-07-16 | Ibm | Sensitive electrophotographic plates |
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US4123269A (en) * | 1977-09-29 | 1978-10-31 | Xerox Corporation | Electrostatographic photosensitive device comprising hole injecting and hole transport layers |
US4150987A (en) * | 1977-10-17 | 1979-04-24 | International Business Machines Corporation | Hydrazone containing charge transport element and photoconductive process of using same |
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JPS58198043A (ja) | 1982-05-14 | 1983-11-17 | Ricoh Co Ltd | 電子写真用感光体 |
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JP2002055469A (ja) | 2000-08-09 | 2002-02-20 | Mitsubishi Paper Mills Ltd | 電子写真感光体 |
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WO2004087641A1 (ja) * | 2003-03-31 | 2004-10-14 | Daiichi Pharmaceutical Co., Ltd. | ヒドラゾン誘導体 |
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