JP2001166516A5 - - Google Patents
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- JP2001166516A5 JP2001166516A5 JP1999353227A JP35322799A JP2001166516A5 JP 2001166516 A5 JP2001166516 A5 JP 2001166516A5 JP 1999353227 A JP1999353227 A JP 1999353227A JP 35322799 A JP35322799 A JP 35322799A JP 2001166516 A5 JP2001166516 A5 JP 2001166516A5
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- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 230000001133 acceleration Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000002344 surface layer Substances 0.000 description 4
- 230000001678 irradiating Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N Benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N Benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N Dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N Phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- 229950000688 Phenothiazine Drugs 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N Pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 239000012046 mixed solvent Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
Description
【特許請求の範囲】
【請求項１】 導電性支持体及び該導電性支持体上に設けられた感光層を有する電子写真感光体において、
該電子写真感光体の最表面層が、同一分子内に２つ以上の連鎖重合性官能基を有する正孔輸送性化合物を重合した化合物を含有し、
該最表面層の示差走査熱分析での発熱量が、６０ｍＪ／ｍｇ以下である
ことを特徴とする電子写真感光体。
【請求項２】 前記最表面層の示差走査熱分析での発熱量が、４０ｍＪ／ｍｇ以下である請求項１に記載の電子写真感光体。
【請求項３】 前記連鎖重合性官能基を有する正孔輸送性化合物が、下記一般式（１）で示される化合物である請求項１又は２に記載の電子写真感光体。
【化１】
（一般式（１）中、Ａは正孔輸送性基を示す。Ｐ１及びＰ２は連鎖重合性官能基を示す。Ｐ１とＰ２は同一でも異なっても良い。Ｚは置換基を有しても良い有機基を示す。ａ、ｂ及びｄは０又は１以上の整数を示し、ａ＋ｂ×ｄは２以上の整数を示す。また、ａが２以上の場合Ｐ１は同一でも異なっても良く、ｄが２以上の場合Ｐ２は同一でも異なっても良く、またｂが２以上の場合、Ｚ及びＰ２は同一でも異なっても良い。）
【請求項４】 前記一般式（１）中のＡの、ＡとＰ１ との結合部位及びＡとＺとの結合部位を水素原子に置き換えた正孔輸送性化合物が、下記一般式（２）で示される化合物、下記一般式（３）で示される化合物、下記一般式（４）で示される化合物、下記一般式（５）で示される化合物、下記一般式（７）で示される化合物、縮合環炭化水素、及び、縮合複素環（但し、下記一般式（７）で示される化合物、縮合環炭化水素、及び、縮合複素環は、下記一般式（８）で示される置換基を１つ以上有する。）からなる群から選ばれた少なくとも１種である請求項１に記載の電子写真感光体。
【化２】
（一般式（２）中、Ｒ１、Ｒ２及びＲ３は置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示す。但し、少なくともそのうち２つはアリール基を示す。また、Ｒ１、Ｒ２及びＲ３はそれぞれ同一であっても異なっていてもよい。）
【化３】
（一般式（３）中、Ｒ ４ 、Ｒ ５ 、Ｒ ８ 及びＲ ９ は置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示し、Ｒ ４ 、Ｒ ５ 、Ｒ ８ 及びＲ ９ はそれぞれ同一であっても異なっていてもよい。Ｒ ６ 及びＲ ７ は置換基を有しても良いアルキレン基又は置換基を有しても良いアリーレン基を示し、Ｒ ６ 及びＲ ７ は同一であっても異なっていてもよい。Ｑは置換基を有しても良い有機基を示す。）
【化４】
（一般式（４）中、Ｒ １０ 、Ｒ １１ 、Ｒ １２ 及びＲ １３ は置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示す。また、Ｒ １０ 、Ｒ １１ 、Ｒ １２ 及びＲ １３ はそれぞれ同一であっても異なっていてもよい。Ａｒ １ 及びＡｒ ２ は置換基を有しても良いアリーレン基を示し、それぞれ同一でも異なっても良い。ｍ １ は０又は１を示す。）
【化５】
｛（一般式（５）中、Ａｒ ３ 及びＡｒ ４ は置換基を有しても良いアリール基を示し、Ａｒ ３ 及びＡｒ ４ は同一でも異なっても良い。Ｒ １４ は置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示す。）但し、Ａｒ ３ 、Ａｒ ４ 及びＲ １４ のうち少なくとも１つは、下記一般式（６）で示される基を有する。
【化６】
（一般式（６）中、Ｒ １５ 及びＲ １６ は置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基、置換基を有しても良いアリール基又は水素原子を示し、Ｒ １５ 及びＲ １６ は同一であっても異なってもよい。Ａｒ ５ は置換基を有しても良いアリール基を示す。ｎ １ は０〜２の整数を示す。）｝
【化７】
（一般式（７）中、Ｒ １７ 及びＲ １８ は置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示し、Ｒ １７ 及びＲ １８ は同一でも異なっても良い。Ａｒ ６ は置換基を有しても良いアリール基を示す。）
【化８】
（一般式（８）中、Ｒ １９ 及びＲ ２０ は置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基、置換基を有しても良いアリール基又は水素原子を示し、Ｒ １９ 及びＲ ２０ は同一であっても異なってもよい。Ａｒ ７ は置換基を有しても良いアリール基を示す。ｎ ２ は０〜２の整数を示す。）
【請求項５】 前記一般式（１）中のＺ又は前記一般式（３）中のＱが、置換基を有しても良いアルキレン基、置換基を有しても良いアリーレン基、ＣＲ２１＝ＣＲ２２（Ｒ２１及びＲ２２は置換基を有しても良いアルキル基、置換基を有しても良いアリール基又は水素原子を示し、Ｒ２１及びＲ２２は同一であっても異なっていても良い。）、Ｃ＝Ｏ、Ｓ＝Ｏ、ＳＯ２、酸素原子又は硫黄原子からなる群より選ばれた１つの、あるいは２つ以上が組み合わされてなる有機基である請求項３又は４に記載の電子写真感光体。
【請求項６】 前記一般式（１）中のＺ又は一般式（３）中のＱが、下記一般式（９）で示される基である請求項３乃至５のいずれかに記載の電子写真感光体。
【化９】
（一般式（９）中、Ｘ１〜Ｘ３は置換基を有しても良いアルキレン基、（ＣＲ２３＝ＣＲ２４）ｍ２、Ｃ＝Ｏ、Ｓ＝Ｏ、ＳＯ２、酸素原子又は硫黄原子を示し、Ａｒ８及びＡｒ９は置換基を有しても良いアリーレン基を示す。Ｒ２３及びＲ２４は置換基を有しても良いアルキル基、置換基を有しても良いアリール基又は水素原子を示し、Ｒ２３及びＲ２４は同一であっても異なっていても良い。ｍ２は１〜５の整数、ｐ、ｑ、ｒ、ｓ及びｔは０〜１０の整数を示す。但し、ｐ、ｑ、ｒ、ｓ及びｔは同時に０であることはない。）
【請求項７】 前記一般式（１）中のＺ又は一般式（３）中のＱが、下記一般式（１０）で示される基である請求項３乃至５のいずれかに記載の電子写真感光体。
【化１０】
（一般式（１０）中、Ａｒ１０は置換基を有しても良いアリーレン基を示す。Ｘ４及びＸ５は（ＣＨ２）ｍ３、（ＣＨ＝ＣＲ２５）ｍ４、Ｃ＝Ｏ又は酸素原子を示す。Ｒ２５は置換基を有しても良いアルキル基、置換基を有しても良いアリール基又は水素原子を示し、ｍ３は１〜１０の整数、ｍ４は１〜５の整数、ｕ、ｖ及びｗは０〜１０の整数を示す。但し、ｕ、ｖ及びｗは同時に０であることはない。）
【請求項８】 前記一般式（２）中のＲ１、Ｒ２及びＲ３が置換基を有しても良いアリール基である請求項４乃至７のいずれかに記載の電子写真感光体。
【請求項９】 前記一般式（３）中のＲ４、Ｒ５、Ｒ８及びＲ９のうち少なくとも２つが置換基を有しても良いアリール基であり、Ｒ ６及びＲ７ が置換基を有しても良いアリーレン基である請求項４乃至７のいずれかに記載の電子写真感光体。
【請求項１０】 前記一般式（３）中のＲ４、Ｒ５、Ｒ８及びＲ９が置換基を有しても良いアリール基である請求項９に記載の電子写真感光体。
【請求項１１】 前記一般式（４）中のＲ１０及びＲ１１が置換基を有しても良いアリール基である請求項４乃至７のいずれかに記載の電子写真感光体。
【請求項１２】 前記一般式（４）中のｍ１が１であり、Ｒ １０、Ｒ１１、Ｒ１２及びＲ１３が置換基を有しても良いアリール基である請求項１１に記載の電子写真感光体。
【請求項１３】 前記一般式（５）中のＲ１４が置換基を有しても良いアリール基である請求項４乃至７のいずれかに記載の電子写真感光体。
【請求項１４】 前記一般式（６）中のＲ１６が置換基を有しても良いアリール基である請求項１３に記載の電子写真感光体。
【請求項１５】 前記一般式（７）中のＲ１７及びＲ１８が置換基を有しても良いアリール基である請求項４乃至７のいずれかに記載の電子写真感光体。
【請求項１６】 前記一般式（８）中のＲ２０が置換基を有しても良いアリール基である請求項１５に記載の電子写真感光体。
【請求項１７】 前記連鎖重合性官能基Ｐ１ 及びＰ２の一方又は両方が、下記一般式（１１）で示される不飽和重合性官能基である請求項３乃至１６のいずれかに記載の電子写真感光体。
【化１１】
（一般式（１１）中、Ｅは水素原子、ハロゲン原子、置換基を有しても良いアルキル基、置換基を有しても良いアリール基、シアノ基、ニトロ基、アルコキシ基、−ＣＯＯＲ２６｛Ｒ２６は水素原子、ハロゲン原子、置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示す。｝又は−ＣＯＮＲ２７Ｒ２８｛Ｒ２７及びＲ２８は水素原子、ハロゲン原子、置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示し、互いに同一であっても異なっていてもよい。｝を示す。Ｗは置換基を有しても良いアリーレン基、置換基を有しても良いアルキレン基、−ＣＯＯ−、−ＣＨ２−、−Ｏ−、−ＯＯ−、−Ｓ−又は−ＣＯＮＲ２９−｛Ｒ２９は水素原子、ハロゲン原子、置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示す。｝を示す。ｆは０又は１を示す。）
【請求項１８】 前記連鎖重合性官能基Ｐ１ 及びＰ２の一方又は両方が、下記一般式（１２）で示される環状エーテル基である請求項３乃至１６のいずれかに記載の電子写真感光体。
【化１２】
（一般式（１２）中、Ｒ３０及びＲ３１は水素原子、置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示す。ｎは１〜１０の整数を示す。）
【請求項１９】 前記連鎖重合性官能基Ｐ１ 及びＰ２の一方又は両方が、下記一般式（１３）で示される脂環式エポキシ基である請求項３乃至１６のいずれかに記載の電子写真感光体。
【化１３】
（一般式（１３）中、Ｒ３２及びＲ３３は水素原子、置換基を有しても良いアルキル基、置換基を有しても良いアラルキル基又は置換基を有しても良いアリール基を示す。ｎは０〜１０の整数を示す。）
【請求項２０】 前記連鎖重合性官能基Ｐ１ 及びＰ２の一方又は両方が、下記構造式（１４）乃至（２０）のいずれかで示される基である請求項３乃至１６のいずれかに記載の電子写真感光体。
【化１４】
【化１５】
【請求項２１】 同一分子内に２つ以上の連鎖重合性官能基を有する正孔輸送性化合物の酸化電位が、０．４〜１．２（Ｖ）である請求項１乃至２０のいずれかに記載の電子写真感光体。
【請求項２２】 前記重合が、電子線によって行われる重合である請求項１乃至２１のいずれかに記載の電子写真感光体。
【請求項２３】 前記電子線の加速電圧が、２５０ｋＶ以下である請求項２２に記載の電子写真感光体。
【請求項２４】 前記電子線の線量が、１〜１００Ｍｒａｄである請求項２２又は２３に記載の電子写真感光体。
【請求項２５】 請求項１乃至２４のいずれかに記載の電子写真感光体と、該電子写真感光体を帯電させる帯電手段、静電潜像の形成された電子写真感光体をトナーで現像する現像手段、及び、転写工程後の電子写真感光体上に残余するトナーを回収するクリーニング手段からなる群より選ばれる少なくとも１つの手段とを共に一体に支持し、電子写真装置本体に着脱自在であることを特徴とするプロセスカートリッジ。
【請求項２６】 請求項１乃至２４のいずれかに記載の電子写真感光体、該電子写真感光体を帯電させる帯電手段、帯電した該電子写真感光体に対して露光を行い該電子写真感光体上に静電潜像を形成する露光手段、該電子写真感光体上に形成された静電潜像をトナーで現像する現像手段、及び、該電子写真感光体上のトナー像を転写材上に転写する転写手段を備えることを特徴とする電子写真装置。
[Claims]
1. Conductive supportAnd the conductive supportaboveProvidedIn an electrophotographic photosensitive member having a photosensitive layer,
The outermost surface layer of the electrophotographic photosensitive member is in the same molecule.2Contains a compound obtained by polymerizing a hole-transporting compound having one or more chain-growth functional groups.,
TheOutermost layerofThe calorific value in differential scanning calorimetry,60mJ/ Mg or less
An electrophotographic photosensitive member characterized by this.
2. The outermost surface layer.ofThe calorific value in differential scanning calorimetry,40mJThe electrophotographic photosensitive member according to claim 1, which is / mg or less.
3. The hole-transporting compound having a chain-growth functional group is represented by the following general formula (1).Is a compoundThe electrophotographic photosensitive member according to claim 1 or 2.
[Chemical 1]
(Generalformula(1)Among them, A represents a hole transporting group. P1And P2Indicates a chain-growth functional group. P1And P2May be the same or different. Z represents an organic group which may have a substituent. a, b and d indicate an integer of 0 or 1 or more, and a + b × d indicates an integer of 2 or more. Also, when a is 2 or more, P1May be the same or different, and if d is 2 or more, P2May be the same or different, and when b is 2 or more, Z and P2May be the same or different..)
4. BeforeGeneral formula (1)Of A inside, A and P1 Binding site withas well asWith AA hole-transporting compound in which the binding site with Z is replaced with a hydrogen atom,It is represented by the following general formula (2)Compounds, compounds represented by the following general formula (3), compounds represented by the following general formula (4), compounds represented by the following general formula (5), compounds represented by the following general formula (7), condensed ring hydrocarbons. , And the condensed heterocycle (however, the compound represented by the following general formula (7), the condensed ring hydrocarbon, and the condensed heterocycle have one or more substituents represented by the following general formula (8)). At least one selected from the group consisting ofClaimTo 1The electrophotographic photosensitive member of the description.
[Chemical 2]
(Generalformula(2)Medium, R1, R2And R3Indicates an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent. However, at least two of them exhibit an aryl group. Also, R1, R2And R3May be the same or different..)
[3]
(In general formula (3), R 4 , R 5 , R 8 And R 9 Indicates an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent, and R 4 , R 5 , R 8 And R 9 May be the same or different. R 6 And R 7 Indicates an alkylene group which may have a substituent or an arylene group which may have a substituent, and R 6 And R 7 May be the same or different. Q indicates an organic group which may have a substituent. )
[4]
(In general formula (4), R 10 , R 11 , R 12 And R 13 Indicates an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent. Also, R 10 , R 11 , R 12 And R 13 May be the same or different. Ar 1 And Ar 2 Indicates an arylene group which may have a substituent, and may be the same or different from each other. m 1 Indicates 0 or 1. )
[5]
{(In general formula (5), Ar 3 And Ar 4 Indicates an aryl group that may have a substituent, Ar 3 And Ar 4 May be the same or different. R 14 Indicates an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent. ) However, Ar 3 , Ar 4 And R 14 At least one of them has a group represented by the following general formula (6).
[Chemical 6]
(In general formula (6), R 15 And R 16 Indicates an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. 15 And R 16 May be the same or different. Ar 5 Indicates an aryl group that may have a substituent. n 1 Indicates an integer from 0 to 2. )}
[7]
(In general formula (7), R 17 And R 18 Indicates an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent, and R 17 And R 18 May be the same or different. Ar 6 Indicates an aryl group that may have a substituent. )
[Chemical 8]
(In general formula (8), R 19 And R 20 Indicates an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. 19 And R 20 May be the same or different. Ar 7 Indicates an aryl group that may have a substituent. n 2 Indicates an integer from 0 to 2. )
Claim5] BeforeGeneral formula (1)During ~Z orSaidGeneral formula (3)During ~Q is,An alkylene group which may have a substituent, an arylene group which may have a substituent, CR21= CR22(R21And R22Indicates an alkyl group which may have a substituent, an aryl group which may have a substituent or a hydrogen atom, and R21And R22Are the sameThereAlso differentBeAlso good..), C = O, S = O, SO2, Oxygen atom or sulfur atomGroup consisting ofThanSelected 1Oneof,OrTwo or moreCombinedBecomeOrganic groupIsClaim 3Or 4The electrophotographic photosensitive member according to.
Claim6] BeforeGeneral formula (1)During ~Z or general formula (3)During ~Q is,It is represented by the following general formula (9).Is the basisClaim 3~ 5The electrophotographic photosensitive member according to any one of.
[Chemical 9]
(Generalformula(9)Medium, X1~ X3Is an alkylene group which may have a substituent, (CR23= CR24)m2, C = O, S = O, SO2, Oxygen atom or sulfur atom, Ar8And Ar9Indicates an arylene group which may have a substituent. R23And R24Indicates an alkyl group which may have a substituent, an aryl group which may have a substituent or a hydrogen atom, and R23And R24Are the sameThereAlso differentBeIs also good. m2Is an integer from 1 to 5, p, Q, r, s andt is0 to 0Indicates an integer of 10. However, p, Q, r, s andt cannot be 0 at the same time..)
Claim7] BeforeGeneral formula (1)During ~Z or general formula (3)During ~Q is,It is represented by the following general formula (10).Is the basisClaim 3~ 5The electrophotographic photosensitive member according to any one of.
[Chemical 10]
(Generalformula(10)Medium, Ar10Indicates an arylene group which may have a substituent. X4And X5Is (CH2)m3, (CH = CR25)m4, C = O or oxygen atom. R25Indicates an alkyl group which may have a substituent, an aryl group which may have a substituent or a hydrogen atom, and m3Is an integer from 1 to 10, m4Is an integer from 1 to 5, u, V andw represents an integer from 0 to 10. However, u, V andw cannot be 0 at the same time..)
Claim8] BeforeGeneral formula (2)During ~R1, R2And R34 is an aryl group which may have a substituent.~ 7The electrophotographic photosensitive member according to any one of.
Claim9] BeforeGeneral formula (3)During ~R4, R5, R8And R9At least two of them are aryl groups which may have a substituent., R 6And R7 ButClaim that it is an arylene group which may have a substituent.4-7The electrophotographic photosensitive member according to any one of.
Claim10] BeforeGeneral formula (3)During ~R4, R5, R8And R9Claims that is an aryl group which may have a substituent.9The electrophotographic photosensitive member according to.
Claim11] BeforeGeneral formula (4)During ~R10And R11Claims that is an aryl group which may have a substituent.4-7The electrophotographic photosensitive member according to any one of.
Claim12] BeforeGeneral formula (4)During ~M1Is 1, R 10, R11, R12And R13Claims that is an aryl group which may have a substituent.11The electrophotographic photosensitive member according to.
Claim13] BeforeGeneral formula (5)During ~R14Claims that is an aryl group which may have a substituent.4-7The electrophotographic photosensitive member according to any one of.
Claim14] BeforeGeneral formula (6)During ~R16Claims that is an aryl group which may have a substituent.13The electrophotographic photosensitive member according to.
Claim15] BeforeGeneral formula (7)During ~R17And R18Claims that is an aryl group which may have a substituent.4-7The electrophotographic photosensitive member according to any one of.
Claim16] BeforeGeneral formula (8)During ~R20Claims that is an aryl group which may have a substituent.15The electrophotographic photosensitive member according to.
Claim17] SaidChain-growth functional group P1 as well asP2One or both,followingGeneralClaim 3 which is an unsaturated polymerizable functional group represented by the formula (11).To 16The electrophotographic photosensitive member according to any one of.
[Chemical 11]
(Generalformula(11)Among them, E is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, a cyano group, a nitro group, an alkoxy group, and −COOR.26{R26Is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent.Is shown.} Or -CONR27R28{R27And R28Indicates a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aryl group which may have a substituent, and may be the same as or different from each other. May..} IndicatesSu.W is an arylene group which may have a substituent, an alkylene group which may have a substituent, -COO-, -CH.2-, -O-, -OO-, -S- or -CONR29− {R29Is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent.Is shown.} Is shown. f indicates 0 or 1.. )
Claim18] SaidChain-growth functional group P1 as well asP2One or both,followingGeneralClaim 3 which is a cyclic ether group represented by the formula (12)To 16The electrophotographic photosensitive member according to any one of.
[Chemical 12]
(Generalformula(12)Medium, R30And R31Indicates a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent.Su.n indicates an integer of 1 to 10...)
Claim19] SaidChain-growth functional group P1 as well asP2One or both,Claim 3 which is an alicyclic epoxy group represented by the following general formula (13).To 16The electrophotographic photosensitive member according to any one of.
[Chemical 13]
(Generalformula(13)Medium, R32And R33Indicates a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent.Su.n indicates an integer from 0 to 10...)
Claim20] SaidChain-growth functional group P1 as well asP2One or both,followingConstructionEquation (14)~ (20)IzuRekaIn the group shownA certain claim 3To 16The electrophotographic photosensitive member according to any one of.
[Chemical 14]
[15]
Claim21] In the same molecule2Hole-transporting compound with one or more chain-growth functional groupsAcidThe potential for conversion,Claim 1 which is 0.4 to 1.2 (V)~ 20The electrophotographic photosensitive member according to any one of.
Claim22] SaidPolymerization,Made by electron beamPolymerizationClaim 1~ 21The electrophotographic photosensitive member according to any one of.
Claim23] SaidThe acceleration voltage of the electron beam,250kClaims that are V or less22The electrophotographic photosensitive member according to.
Claim24] SaidThe dose of the electron beam,Claims of 1-100 Mrad22Or23The electrophotographic photosensitive member according to.
Claim25] Claim 1~ 24The electrophotographic photosensitive member according to any one ofWhen, A charging means for charging the electrophotographic photosensitive member, a developing means for developing an electrophotographic photosensitive member on which an electrostatic latent image is formed with toner, and,Selected from the group consisting of cleaning means for recovering the toner remaining on the electrophotographic photosensitive member after the transfer process.Ruat least1With one meansToA process cartridge that supports both together and is removable from the main body of the electrophotographic apparatus.
Claim26] Claim 1~ 24The electrophotographic photosensitive member according to any one of the above, a charging means for charging the electrophotographic photosensitive member, and charging.TheFor electrophotographic photosensitive membershandMake an exposureOn the electrophotographic photosensitive memberExposure means for forming an electrostatic latent image, The electricityChild photophotoreceptorUpToThe formed electrostatic latent imageDevelopment means for developing with toner, and, TheAn electrophotographic apparatus comprising a transfer means for transferring a toner image on an electrophotographic photosensitive member onto a transfer material.
【００１４】
【課題を解決するための手段】
本発明に従って、導電性支持体及び該導電性支持体上に設けられた感光層を有する電子写真感光体において、
該電子写真感光体の最表面層が、同一分子内に２つ以上の連鎖重合性官能基を有する正孔輸送性化合物を重合した化合物を含有し、
該最表面層の示差走査熱分析での発熱量が、６０ｍＪ／ｍｇ以下である
ことを特徴とする電子写真感光体が提供される。
0014.
[Means for solving problems]
In accordance with the present invention, in an electrophotographic photosensitive member having a conductive support and a photosensitive layer provided on the conductive support.
Outermost surface layer of the electrophotographic photosensitive member contains a compound of the hole transporting compound was polymerized with two or more chain polymerizable functional groups in the same molecule,
The amount of heat generated by the differential scanning calorimetry of the outermost surface layer, the electrophotographic photosensitive member, characterized in that it is 60 m J / mg or less is provided.
但し上記一般式（５）中、Ａｒ３、Ａｒ４及びＲ１４のうち少なくとも１つは、下記一般式（６）で示される基を有する。 However in the general formula (5), at least one of Ar 3, Ar 4 and R 14, which have a group represented by the following general formula (6).
上記一般式（９）中、Ｘ１〜Ｘ３は置換基を有しても良いメチレン基、エチレン基及びプロピレン基等の炭素数２０以下のアルキレン基、（ＣＲ２３＝ＣＲ２４）ｍ２、Ｃ＝Ｏ、Ｓ＝Ｏ、ＳＯ２、酸素原子又は硫黄原子を示し、Ａｒ８及びＡｒ９は置換基を有しても良いアリーレン基（ベンゼン、ナフタレン、アントラセン、フェナンスレン、ピレン、チオフェン、フラン、ピリジン、キノリン、ベンゾキノリン、カルバゾール、フェノチアジン、ベンゾフラン、ベンゾチオフェン、ジベンゾフラン、ジベンゾチオフェン等より２個の水素原子を取り除いた基）を示す。Ｒ２３及びＲ２４は置換基を有しても良いメチル基、エチル基及びプロピル基等のアルキル基、置換基を有しても良いフェニル基、ナフチル基及びチオフェニル基等のアリール基又は水素原子を示し、Ｒ２３及びＲ２４は同一でも異なっても良い。ｍ２は１〜５の整数、ｐ、ｑ、ｒ、ｓ及びｔは０〜１０の整数を示す（但し、ｐ、ｑ、ｒ、ｓ及びｔは同時に０であることはない）。 In the above general formula (9), X 1 to X 3 are alkylene groups having 20 or less carbon atoms such as a methylene group, an ethylene group and a propylene group which may have a substituent, (CR 23 = CR 24 ) m2 , C. = O, S = O, SO 2 , indicating oxygen or sulfur atoms, Ar 8 and Ar 9 may have substituents on the arylene groups (benzene, naphthalene, anthracene, phenanthrene, pyrene, thiophene, furan, pyridine , A group from which two hydrogen atoms have been removed from quinoline, benzoquinoline, carbazole, phenothiazine, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene and the like). R 23 and R 24 are an alkyl group such as a methyl group, an ethyl group and a propyl group which may have a substituent, an aryl group such as a phenyl group, a naphthyl group and a thiophenyl group which may have a substituent, or a hydrogen atom. , And R 23 and R 24 may be the same or different. m 2 is an integer of 1 to 5, p , q, r, s and t are integers of 0 to 10 (however, p , q, r, s and t cannot be 0 at the same time).
上記一般式（１０）中、Ｘ４及びＸ５は（ＣＨ２）ｍ３、（ＣＨ＝ＣＲ２５）ｍ４、Ｃ＝Ｏ、又は酸素原子を示し、Ａｒ１０は置換基を有しても良いアリーレン基（ベンゼン、ナフタレン、アントラセン、フェナンスレン、ピレン、チオフェン、フラン、ピリジン、キノリン、ベンゾキノリン、カルバゾール、フェノチアジン、ベンゾフラン、ベンゾチオフェン、ジベンゾフラン、ジベンゾチオフェン等より２個の水素原子を取り除いた基）を示す。Ｒ２５は置換基を有しても良いメチル基、エチル基及びプロピル基等のアルキル基、置換基を有しても良いフェニル基、ナフチル基及びチオフェニル基等のアリール基又は水素原子を示す。ｍ３は１〜１０の整数、ｍ４は１〜５の整数、ｕ、ｖ及びｗは０〜１０の整数を示す（特に０又は１〜５の整数の時が特に好ましい。但し、ｕ、ｖ及びｗは同時に０であることはない）。 In the above general formula (10), X 4 and X 5 represent (CH 2 ) m3 , (CH = CR 25 ) m4 , C = O, or an oxygen atom, and Ar 10 may have a substituent. Shows a group (a group from which two hydrogen atoms have been removed from benzene, naphthalene, anthracene, phenanthrene, pyrene, thiophene, furan, pyridine, quinoline, benzoquinoline, carbazole, phenothiazine, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, etc.) .. R 25 represents an alkyl group such as a methyl group, an ethyl group and a propyl group which may have a substituent, an aryl group such as a phenyl group, a naphthyl group and a thiophenyl group which may have a substituent, or a hydrogen atom. m 3 is an integer of 1 to 10, m 4 is an integer of 1 to 5, u , v and w are integers of 0 to 10 (particularly 0 or an integer of 1 to 5 is particularly preferable, but u , v and w cannot be 0 at the same time).
電子線照射をする場合、加速器としてはスキャニング型、エレクトロカーテン型、ブロードビーム型及びパルス型及びラミナー型等いずれの形式も使用することができる。電子線を照射する場合に、本発明の電子写真感光体においては電気特性及び耐久性能を発現させる上で照射条件が非常に重要である。本発明において、加速電圧は２５０ｋＶ以下が好ましく、最適には１５０ｋＶ以下である。また、線量は好ましくは１Ｍｒａｄ〜１００Ｍｒａｄの範囲、より好ましくは３Ｍｒａｄ〜５０Ｍｒａｄの範囲である。加速電圧が２５０ｋＶを超えると電子写真感光体特性に対する電子線照射のダメージが増加する傾向にある。また、線量が１Ｍｒａｄよりも少ない場合には硬化が不十分となり易く、線量が１００Ｍｒａｄを超えた場合には電子写真感光体特性の劣化が起こり易いので注意が必要である。 In the case of electron beam irradiation, any type such as scanning type, electrocurtain type, broad beam type, pulse type and laminar type can be used as the accelerator. When irradiating an electron beam, the irradiation conditions are very important for exhibiting electrical characteristics and durability in the electrophotographic photosensitive member of the present invention. In the present invention, the acceleration voltage is preferably not more than 250 k V, and most preferably less than 0.99 k V. The dose is preferably in the range of 1 Mrad to 100 Mrad, more preferably in the range of 3 Mrad to 50 Mrad. Accelerating voltage tend to increase the damage of the electron beam irradiation for the electrophotographic photoreceptor characteristics exceeds 250 k V. Further, it should be noted that when the dose is less than 1 Mrad, curing is likely to be insufficient, and when the dose is more than 100 Mrad, the characteristics of the electrophotographic photosensitive member are likely to be deteriorated.
上記に記載したように、連鎖重合性官能基を有する正孔輸送性化合物を重合・硬化した電荷輸送層は下記の方法で示唆熱分析を行った場合、発熱量が６０ｍＪ／ｍｇ以下であり、好ましくは４０ｍＪ／ｍｇ以下である。この発熱は、主に電荷輸送層中の未反応の連鎖重合性官能基の反応による物と推定されるが、この発熱量の値が電子写真感光体の耐磨耗性は勿論、繰り返し使用や環境の変動による電位変動、更には転写メモリーやフォトメモリー等の各種メモリーにも極めて相関があり、上記値の場合が極めて良好な特性を発現することが判明した。 As described above, the charge transport layer obtained by polymerizing and curing the hole transporting compound having a chain-growth functional group has a calorific value of 60 mJ / mg or less when the differential thermal analysis is performed by the following method. , good Mashiku is less than or equal to 40m J / mg. This heat generation is presumed to be mainly due to the reaction of unreacted chain-growth functional groups in the charge transport layer, but the value of this heat generation amount is not only the wear resistance of the electrophotographic photosensitive member but also repeated use. It was found that there is an extremely high correlation between potential fluctuations due to environmental fluctuations and various memories such as transfer memory and photo memory, and that the above values exhibit extremely good characteristics.
次いで、化合物例Ｎｏ．６の正孔輸送性化合物６０部をモノクロロベンゼン５０部／ジクロロメタン３０部の混合溶媒中に溶解し、電荷輸送層用塗料を調製した。この塗料を前記の電荷発生層上にコーティングし、加速電圧１５０ｋＶ、線量７Ｍｒａｄの条件で電子線を照射し樹脂を硬化することによって、膜厚が１５μｍの電荷輸送層を形成し、電子写真感光体を得た。 Next, Compound Example No. The hole transporting compound 60 parts of 6 was dissolved in a mixed solvent of monochlorobenzene 50 parts / dichloromethane 30 parts, was manufactured by adjusting the coating material for the charge transport layer. The paint was coated on the charge generating layer of the acceleration voltage 0.99 k V, by curing by irradiating the resin with an electron beam under conditions of a dose 7 Mrad, thickness to form a charge transport layer of 15 [mu] m, electrophotographic A photoconductor was obtained.
表３及び表４より明らかなように、本発明の電子写真感光体では高感度、低残留電位であり、各種環境での電位変動も極めて小さく、安定した特性を有している。更に、転写メモリーやフォトメモリー等も極めて小さく優れた特性を発現することが明らかである。なお、これらの特性は電荷輸送層の示差走査熱量測定の発熱量と相関が見られ、発熱量が６０ｍＪ／ｍｇ以下の場合が良好で、４０ｍＪ／ｍｇ以下の場合が特に良好であることが明確である。 As is clear from Tables 3 and 4, the electrophotographic photosensitive member of the present invention has high sensitivity, low residual potential, extremely small potential fluctuation in various environments, and has stable characteristics. Furthermore, it is clear that the transfer memory, the photo memory, etc. are extremely small and exhibit excellent characteristics. Note that these properties observed correlation with the amount of heat generated differential scanning calorimetry of the charge transport layer, when the heat quantity is less than 60 m J / mg is good, if: 40 m J / mg are particularly good Is clear.
次いで、化合物例Ｎｏ．２６３の正孔輸送性化合物６０部をモノクロロベンゼン５０部／ジクロロメタン３０部の混合溶媒中に溶解し、電荷輸送層用塗料を調製した。この塗料を前記の電荷発生層上にコーティングし、加速電圧１５０ｋＶ、線量３０Ｍｒａｄの条件で電子線を照射し樹脂を硬化することによって、膜厚が１３μｍの電荷輸送層を形成し、電子写真感光体を得た。 Next, Compound Example No. 60 parts of the hole transporting compound of 263 was dissolved in a mixed solvent of 50 parts of monochlorobenzene / 30 parts of dichloromethane to prepare a coating material for a charge transport layer . The paint was coated on the above charge-generating layer, the acceleration voltage 0.99 k V, by curing by irradiating the resin with an electron beam under conditions of a dose 30 Mrad, thickness to form a charge transport layer of 13 .mu.m, electrophotographic A photoconductor was obtained.
これらの結果から、本発明の電子写真感光体は、ドットの再現性や文字の再現性に優れ高解像度の出力画像が得られることがわかる。また、欠陥がなく鮮明な画像が安定して得られた。これらの結果は、電荷輸送層の示差走査熱量測定の発熱量と相関が見られ、発熱量が６０ｍＪ／ｍｇ以下の場合が良好で、４０ｍＪ／ｍｇ以下の場合が特に良好であることが明確である。 From these results, it can be seen that the electrophotographic photosensitive member of the present invention is excellent in dot reproducibility and character reproducibility, and a high-resolution output image can be obtained. Moreover, a clear image without defects was stably obtained. These results are observed correlation with the amount of heat generated differential scanning calorimetry of the charge transport layer, when the heat quantity is less than 60 m J / mg is good, that the following cases 40 m J / mg are particularly good It's clear.
【０２５２】
【発明の効果】
本発明によれば、耐磨耗性が極めて良好であるばかりか、繰り返し使用や環境の変動によらず、安定して優れた電位特性を示し、転写メモリーやフォトメモリー等のメモリーも小さく、かつカブリ等の画像欠陥のない良好な画質を与えることができる。
[0252]
【Effect of the invention】
According to the present invention, not only the wear resistance is extremely good, but also stable and excellent potential characteristics are exhibited regardless of repeated use and environmental fluctuations, the memory such as a transfer memory and a photo memory is small, and fog is formed. It is possible to provide good image quality without image defects such as.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35322799A JP4136238B2 (en) | 1999-12-13 | 1999-12-13 | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35322799A JP4136238B2 (en) | 1999-12-13 | 1999-12-13 | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
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| Publication Number | Publication Date |
|---|---|
| JP2001166516A JP2001166516A (en) | 2001-06-22 |
| JP2001166516A5 true JP2001166516A5 (en) | 2007-01-25 |
| JP4136238B2 JP4136238B2 (en) | 2008-08-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP35322799A Expired - Lifetime JP4136238B2 (en) | 1999-12-13 | 1999-12-13 | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
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| JP (1) | JP4136238B2 (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4657900B2 (en) * | 2004-12-21 | 2011-03-23 | 株式会社リコー | Electrophotographic photosensitive member, image forming method using the same, image forming apparatus, and process cartridge for image forming apparatus |
| JP4796348B2 (en) * | 2005-07-27 | 2011-10-19 | 株式会社リコー | Electrostatic latent image carrier, image forming apparatus, image forming method, and process cartridge |
| WO2006121187A1 (en) | 2005-05-10 | 2006-11-16 | Ricoh Company, Ltd. | Acrylic ester compound and manufacturing intermediate thereof, method for manufacturing acrylic ester compound, and latent electrostatic image bearing member, image forming method, image forming apparatus and process cartridge |
| JP4699803B2 (en) * | 2005-05-10 | 2011-06-15 | 株式会社リコー | Acrylic acid ester compound and production method and production intermediate thereof |
| JP4699804B2 (en) * | 2005-05-11 | 2011-06-15 | 株式会社リコー | Acrylic acid ester compound and production method and production intermediate thereof |
| JP4813092B2 (en) * | 2005-05-19 | 2011-11-09 | 株式会社リコー | Electrophotographic photosensitive member, image forming method using the same, image forming apparatus, and process cartridge for image forming apparatus |
| JP5262014B2 (en) * | 2006-08-07 | 2013-08-14 | 三菱化学株式会社 | Organic compound having a crosslinking group, composition for organic electroluminescence device, and organic electroluminescence device |
| JP5049109B2 (en) * | 2006-12-11 | 2012-10-17 | 株式会社リコー | Electrophotographic photosensitive member, image forming method using the same, image forming apparatus, and process cartridge for image forming apparatus |
| JP5046678B2 (en) * | 2007-02-22 | 2012-10-10 | 株式会社リコー | Electrophotographic apparatus and process cartridge |
| US8846280B2 (en) | 2011-08-22 | 2014-09-30 | Fuji Xerox Co., Ltd. | Compound, charge transporting film, photoelectric conversion device, electrophotographic photoreceptor, process cartridge, and image forming apparatus |
| CN102952030B (en) | 2011-08-22 | 2016-02-24 | 富士施乐株式会社 | Compound, charge transport film, photoelectric conversion device and Electrophtography photosensor |
| JP6015264B2 (en) * | 2012-09-12 | 2016-10-26 | 富士ゼロックス株式会社 | Electrophotographic photosensitive member, process cartridge, and image forming apparatus |
| JP5892013B2 (en) | 2012-09-12 | 2016-03-23 | 富士ゼロックス株式会社 | Charge transport film, photoelectric conversion device, electrophotographic photosensitive member, process cartridge, and image forming apparatus |
| JP6741156B2 (en) * | 2017-06-12 | 2020-08-19 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photoreceptor, process cartridge, and image forming apparatus |
| CN112534356A (en) * | 2019-07-17 | 2021-03-19 | 富士电机株式会社 | Electrophotographic photoreceptor, method for producing the same, and electrophotographic apparatus |
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1999
- 1999-12-13 JP JP35322799A patent/JP4136238B2/en not_active Expired - Lifetime
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