JP2014029479A5 - - Google Patents
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- JP2014029479A5 JP2014029479A5 JP2013112111A JP2013112111A JP2014029479A5 JP 2014029479 A5 JP2014029479 A5 JP 2014029479A5 JP 2013112111 A JP2013112111 A JP 2013112111A JP 2013112111 A JP2013112111 A JP 2013112111A JP 2014029479 A5 JP2014029479 A5 JP 2014029479A5
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Description
本発明は、支持体、該支持体上に形成された下引き層、および該下引き層上に形成された感光層を有する電子写真感光体において、
該下引き層は、
(i)−NCO基および−NHCOX1基(X1は下記式(1)〜(7)のいずれかで示される基である。)からなる群より選択される基を3〜6個有する分子量(−NHCOX1基を有する場合は、X1基を除いて算出した分子量である。)が200〜1300のイソシアネート化合物、
(ii)下記式(B)で示される構造単位を有する樹脂、および
(iii)下記式(A1)で示される化合物、下記式(A2)で示される化合物、下記式(A3)で示される化合物、下記式(A4)で示される化合物、下記式(A5)で示される化合物、下記式(A6)で示される化合物、下記式(A7)で示される化合物および下記式(A8)で示される化合物からなる群より選択される少なくとも1種の化合物、を含む組成物の重合物を含有することを特徴とする電子写真感光体に関する。
The present invention relates to an electrophotographic photosensitive member having a support, an undercoat layer formed on the support, and a photosensitive layer formed on the undercoat layer.
The undercoat layer is
(I) Molecular weight having 3 to 6 groups selected from the group consisting of —NCO group and —NHCOX 1 group (X 1 is a group represented by any one of the following formulas (1) to (7)) (In the case of having -NHCOX 1 group, it is a molecular weight calculated by removing X 1 group.) Is an isocyanate compound of 200-1300,
(Ii) the following formula (B) resin having a structural units in which the majorIncr indicated by, and (iii) a compound represented by the following formula (A1), the compound represented by the following formula (A2), represented by the following formula (A3) A compound represented by the following formula (A4), a compound represented by the following formula (A5), a compound represented by the following formula (A6), a compound represented by the following formula (A7), and a compound represented by the following formula (A8). And a polymer of a composition containing at least one compound selected from the group consisting of the above compounds.
Claims (3)
該下引き層は、
(i)−NCO基および−NHCOX1基(X1は下記式(1)〜(7)のいずれかで示される基である。)からなる群より選択される基を3〜6個有する分子量(−NHCOX1基を有する場合は、X1基を除いて算出した分子量である。)が200〜1300のイソシアネート化合物、
(ii)下記式(B)で示される構造単位を有する樹脂、および
(iii)下記式(A1)で示される化合物、下記式(A2)で示される化合物、下記式(A3)で示される化合物、下記式(A4)で示される化合物、下記式(A5)で示される化合物、下記式(A6)で示される化合物、下記式(A7)で示される化合物および下記式(A8)で示される化合物からなる群より選択される少なくとも1種の電子輸送物質、
を含む組成物の重合物を含有することを特徴とする電子写真感光体。
(式(B)中、R11は水素原子またはアルキル基を示す。Yは、単結合またはフェニレン基を示す。W1は、ヒドロキシ基、チオール基、アミノ基、またはカルボキシル基を示す。)
(式(A1)〜(A8)中、R101〜R106、R201〜R210、R301〜R308、R401〜R408、R501〜R510、R601〜R606、R701〜R708、およびR801〜R810は、それぞれ独立に、下記式(A)で示される1価の基、水素原子、シアノ基、ニトロ基、ハロゲン原子、アルコキシカルボニル基、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基、置換もしくは無置換の複素環基を示す。ただし、R101〜R106の少なくとも1つ、R201〜R210の少なくとも1つ、R301〜R308の少なくとも1つ、R401〜R408の少なくとも1つ、R501〜R510の少なくとも1つ、R601〜R606の少なくとも1つ、R701〜R708の少なくとも1つ、およびR801〜R810の少なくとも1つは、下記式(A)で示される1価の基である。該アルキル基の炭素原子の1つは、O、S、NH、NR901(R901はアルキル基)で置き換わっても良い。該置換のアルキル基の置換基は、アルキル基、アリール基、アルコキシカルボニル基およびハロゲン原子からなる群より選択される基である。該置換のアリール基の置換基は、ハロゲン原子、ニトロ基、シアノ基、アルキル基およびハロゲン基置換アルキル基からなる群より選択される基である。Z201、Z301、Z401およびZ501は、それぞれ独立に、炭素原子、窒素原子、または酸素原子を示す。Z201が酸素原子である場合はR209およびR210は存在せず、Z201が窒素原子である場合はR210は存在しない。Z301が酸素原子である場合はR307およびR308は存在せず、Z301が窒素原子である場合はR308は存在しない。Z401が酸素原子である場合はR407およびR408は存在せず、Z401が窒素原子である場合はR408は存在しない。Z501が酸素原子である場合はR509およびR510は存在せず、Z501が窒素原子である場合はR510は存在しない。)
(式(A)中、α、β、およびγの少なくとも1つは置換基を有する基であり、該置換基は、ヒドロキシ基、チオール基、アミノ基、およびカルボキシル基からなる群より選択される少なくとも1種の基である。lおよびmは、それぞれ独立に、0または1であり、lとmの和は、0以上2以下である。
αは、主鎖の原子数が1〜6のアルキレン基、炭素数1〜6のアルキル基で置換された主鎖の原子数が1〜6のアルキレン基、ベンジル基で置換された主鎖の原子数1〜6のアルキレン基、アルコシキカルボニル基で置換された主鎖の原子数1〜6のアルキレン基、またはフェニル基で置換された主鎖の原子数が1〜6のアルキレン基を示し、これらの基は、置換基として、ヒドロキシ基、チオール基、アミノ基、カルボキシル基からなる群より選択される少なくとも1種の基を有しても良い。該アルキレン基の主鎖中の炭素原子の1つは、OまたはSまたはNHまたはNR19(R19はアルキル基である。)で置き換わっていても良い。
βは、フェニレン基、炭素数1〜6のアルキル基置換フェニレン基、ニトロ基置換フェニレン基、ハロゲン基置換フェニレン基、またはアルコキシ基置換フェニレン基を示し、これらの基は、置換基として、ヒドロキシ基、チオール基、アミノ基、カルボキシル基からなる群より選択される少なくとも1種の基を有しても良い。
γは、水素原子、主鎖の原子数が1〜6のアルキル基、または炭素数1〜6のアルキル基で置換された主鎖の原子数が1〜6のアルキル基を示し、これらの基は、置換基として、ヒドロキシ基、チオール基、アミノ基、およびカルボキシル基からなる群より選択される少なくとも1種の基を有しても良い。) In an electrophotographic photoreceptor having a support, an undercoat layer formed on the support, and a photosensitive layer formed on the undercoat layer,
The undercoat layer is
(I) Molecular weight having 3 to 6 groups selected from the group consisting of —NCO group and —NHCOX 1 group (X 1 is a group represented by any one of the following formulas (1) to (7)) (In the case of having -NHCOX 1 group, it is a molecular weight calculated by removing X 1 group.) Is an isocyanate compound of 200-1300,
(Ii) the following formula (B) resin having a structural units in which the majorIncr indicated by, and (iii) a compound represented by the following formula (A1), the compound represented by the following formula (A2), represented by the following formula (A3) A compound represented by the following formula (A4), a compound represented by the following formula (A5), a compound represented by the following formula (A6), a compound represented by the following formula (A7), and a compound represented by the following formula (A8). At least one electron transport material selected from the group consisting of:
An electrophotographic photosensitive member comprising a polymer of a composition comprising:
(In formula (B), R 11 represents a hydrogen atom or an alkyl group. Y represents a single bond or a phenylene group. W 1 represents a hydroxy group, a thiol group, an amino group, or a carboxyl group.)
(Formula (A1) ~ (A8) in, R 101 ~R 106, R 201 ~R 210, R 301 ~R 308, R 401 ~R 408, R 501 ~R 510, R 601 ~R 606, R 701 ~ R 708 and R 801 to R 810 are each independently a monovalent group represented by the following formula (A), a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkoxycarbonyl group, a substituted or unsubstituted alkyl Group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, provided that at least one of R 101 to R 106 , at least one of R 201 to R 210 , and at least one of R 301 to R 308 1, at least one of R 401 to R 408 , at least one of R 501 to R 510 , at least one of R 601 to R 606 , At least one of R 701 to R 708 and at least one of R 801 to R 810 is a monovalent group represented by the following formula (A): one of the carbon atoms of the alkyl group is O, S, NH, NR 901 (R 901 is an alkyl group) may be replaced with a group selected from the group consisting of an alkyl group, an aryl group, an alkoxycarbonyl group and a halogen atom. The substituent of the substituted aryl group is a group selected from the group consisting of a halogen atom, a nitro group, a cyano group, an alkyl group, and a halogen group-substituted alkyl group: Z 201 , Z 301 , Z 401 and Z 501 are each independently if .Z 201 showing a carbon atom, a nitrogen atom or oxygen atom, is an oxygen atom absent R 209 and R 210, 201 is not present is R 307 and R 308 when a .Z 301 is oxygen atom R 210 is absent when a nitrogen atom, .Z if Z 301 is a nitrogen atom R 308 is absent 401 there absent R 407 and R 408 when an oxygen atom, if Z 401 is a nitrogen atom if .Z 501 not present R 408 is an oxygen atom absent R 509 and R 510 In the case where Z 501 is a nitrogen atom, R 510 is not present.)
(In Formula (A), at least one of α, β, and γ is a group having a substituent, and the substituent is selected from the group consisting of a hydroxy group, a thiol group, an amino group, and a carboxyl group. At least one group, l and m are each independently 0 or 1, and the sum of l and m is 0 or more and 2 or less.
α is an alkylene group having 1-6 atoms in the main chain, an alkylene group having 1-6 atoms in the main chain substituted with an alkyl group having 1-6 carbon atoms, or a main chain substituted with a benzyl group. An alkylene group having 1 to 6 atoms, an alkylene group having 1 to 6 atoms in the main chain substituted with an alkoxycarbonyl group, or an alkylene group having 1 to 6 atoms in the main chain substituted with a phenyl group These groups may have at least one group selected from the group consisting of a hydroxy group, a thiol group, an amino group, and a carboxyl group as a substituent. One of the carbon atoms in the main chain of the alkylene group may be replaced by O or S or NH or NR 19 (R 19 is an alkyl group).
β represents a phenylene group, an alkyl group-substituted phenylene group having 1 to 6 carbon atoms, a nitro group-substituted phenylene group, a halogen group-substituted phenylene group, or an alkoxy group-substituted phenylene group, and these groups are hydroxy groups as substituents , At least one group selected from the group consisting of a thiol group, an amino group, and a carboxyl group.
γ represents a hydrogen atom, an alkyl group having 1 to 6 atoms in the main chain, or an alkyl group having 1 to 6 atoms in the main chain substituted with an alkyl group having 1 to 6 carbon atoms. May have at least one group selected from the group consisting of a hydroxy group, a thiol group, an amino group, and a carboxyl group as a substituent. )
該製造方法が、
前記イソシアネート化合物、前記式(B)で示される構造単位を有する樹脂、および前記電子輸送物質を含有する下引き層用塗布液の塗膜を形成する工程、および
該塗膜を加熱乾燥させることによって前記下引き層を形成する工程を有することを特徴とする電子写真感光体の製造方法。 A method for producing the electrophotographic photosensitive member according to any one of claims 1 to 7,
The manufacturing method comprises:
The isocyanate compound to form a coating film of the undercoat layer coating liquid containing the resin, and the electron-transporting material having a structure units in which the majorIncr shown by the formula (B), and thereby the coating film is heated and dried A process for forming the undercoat layer by the method.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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JP2013112111A JP5826212B2 (en) | 2012-06-29 | 2013-05-28 | Method for producing electrophotographic photosensitive member |
CN201310270176.4A CN103529667B (en) | 2012-06-29 | 2013-06-28 | Electrophotographic photosensitive element, the production method of electrophotographic photosensitive element, handle box, electronic photographing device and imide compound |
KR1020130075259A KR101599580B1 (en) | 2012-06-29 | 2013-06-28 | Electrophotographic photosensitive member, method for producing electrophotographic photosensitive member, process cartridge, electrophotographic apparatus, and imide compound |
EP13174204.1A EP2680078B1 (en) | 2012-06-29 | 2013-06-28 | Electrophotographic photosensitive member, method for producing electrophotgraphic photosensitive member, process cartridge, electrophotographic apparatus, and imide compound |
US13/930,869 US8940465B2 (en) | 2012-06-29 | 2013-06-28 | Electrophotographic photosensitive member, method for producing electrophotographic photosensitive member, process cartridge, electrophotographic apparatus, and imide compound |
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JP2012147156 | 2012-06-29 | ||
JP2012147156 | 2012-06-29 | ||
JP2013112111A JP5826212B2 (en) | 2012-06-29 | 2013-05-28 | Method for producing electrophotographic photosensitive member |
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JP2014029479A JP2014029479A (en) | 2014-02-13 |
JP2014029479A5 true JP2014029479A5 (en) | 2014-10-23 |
JP5826212B2 JP5826212B2 (en) | 2015-12-02 |
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JP6049329B2 (en) * | 2012-06-29 | 2016-12-21 | キヤノン株式会社 | Electrophotographic photosensitive member, method for manufacturing electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
JP6300590B2 (en) * | 2014-03-18 | 2018-03-28 | キヤノン株式会社 | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
JP6544994B2 (en) * | 2014-07-09 | 2019-07-17 | キヤノン株式会社 | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus, and method of manufacturing electrophotographic photosensitive member |
JP6452452B2 (en) * | 2015-01-07 | 2019-01-16 | キヤノン株式会社 | Image forming method |
JP6508948B2 (en) * | 2015-01-26 | 2019-05-08 | キヤノン株式会社 | Electrophotographic photosensitive member, method of manufacturing electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
US9581920B2 (en) * | 2015-01-28 | 2017-02-28 | Canon Kabushiki Kaisha | Coating film-removing method for cylindrical substrate and manufacturing method for electrophotographic photosensitive member |
JP6789617B2 (en) | 2015-06-25 | 2020-11-25 | キヤノン株式会社 | Method for producing carboxylic acid anhydride, method for producing carboxylic acid imide, and method for producing electrophotographic photosensitive member |
US9851648B2 (en) * | 2015-06-25 | 2017-12-26 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
JP6708467B2 (en) * | 2016-04-07 | 2020-06-10 | キヤノン株式会社 | Method for removing coating film from cylindrical substrate and method for producing electrophotographic photoreceptor |
JP6833343B2 (en) * | 2016-05-09 | 2021-02-24 | キヤノン株式会社 | Electrophotographic photosensitive members, process cartridges and electrophotographic equipment |
JP7118793B2 (en) * | 2018-07-31 | 2022-08-16 | キヤノン株式会社 | Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus |
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US7371492B2 (en) * | 2005-07-28 | 2008-05-13 | Eastman Kodak Company | Vinyl polymer photoconductive elements |
US7541124B2 (en) * | 2005-08-19 | 2009-06-02 | Eastman Kodak Company | Condensation polymer photoconductive elements |
JP4971764B2 (en) * | 2005-11-30 | 2012-07-11 | キヤノン株式会社 | Electrophotographic photosensitive member, method for manufacturing electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
JP2007148293A (en) * | 2005-11-30 | 2007-06-14 | Canon Inc | Electrophotographic photoreceptor, process cartridge, and electrophotographic apparatus |
JP4649321B2 (en) * | 2005-11-30 | 2011-03-09 | キヤノン株式会社 | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
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