JP2000147804A5 - - Google Patents
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- JP2000147804A5 JP2000147804A5 JP1998322741A JP32274198A JP2000147804A5 JP 2000147804 A5 JP2000147804 A5 JP 2000147804A5 JP 1998322741 A JP1998322741 A JP 1998322741A JP 32274198 A JP32274198 A JP 32274198A JP 2000147804 A5 JP2000147804 A5 JP 2000147804A5
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- 125000001424 substituent group Chemical group 0.000 description 123
- 125000003118 aryl group Chemical group 0.000 description 55
- 125000000217 alkyl group Chemical group 0.000 description 29
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 27
- 125000003710 aryl alkyl group Chemical group 0.000 description 22
- 125000000732 arylene group Chemical group 0.000 description 17
- 125000001544 thienyl group Chemical group 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- 125000001624 naphthyl group Chemical group 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 12
- -1 group Chemical group 0.000 description 12
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 125000001725 pyrenyl group Chemical group 0.000 description 10
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N Benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 8
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 8
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 125000005561 phenanthryl group Chemical group 0.000 description 8
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000004076 pyridyl group Chemical group 0.000 description 8
- 125000005493 quinolyl group Chemical group 0.000 description 8
- 125000004432 carbon atoms Chemical group C* 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 7
- 125000004430 oxygen atoms Chemical group O* 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 125000004434 sulfur atoms Chemical group 0.000 description 7
- 125000005842 heteroatoms Chemical group 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N Benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N Phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- 229950000688 Phenothiazine Drugs 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N Pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N Dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000004292 cyclic ethers Chemical group 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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、
該感光層が、電荷発生層及び電荷輸送層をこの順に又は逆順に積層した構成であり、
該電荷発生層が、電荷発生材料と、連鎖重合性官能基を有する正孔輸送性化合物を熱又は紫外線による重合又は架橋によって硬化させたものとを含む
ことを特徴とする電子写真感光体。
【請求項２】 前記連鎖重合性官能基を有する正孔輸送性化合物が、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】
（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 及びＰ２はそれぞれ同一であっても異なっていてもよい。Ｚは置換基を有してもよい有機残基を示す。Ｙは水素原子を示す。ａ、ｂ及びｄは０又は１以上の整数を示す。但し、ａ＝０の場合はｂ＋ｄは３以上の整数であり、ｂ又はｄが０の場合はａは２以上の整数であり、その他の場合はａ＋ｂ＋ｄは３以上の整数である。また、ａが２以上の場合はＰ１は同一であっても異なっていてもよい。ｄが２以上の場合はＰ２は同一であっても異なっていてもよい。ｂが２以上の場合はＺは同一であっても異なっていてもよい。）
【請求項４】 前記一般式（１）中のＡの、Ｐ１ との結合部位及びＺとの結合部位をそれぞれ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）、（３）、（４）、（５）、（６）及び（７）のいずれかで示される化合物、縮合環炭化水素或いは縮合複合環（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合環は下記一般式（８）で示される置換基を１つ以上有する。）である請求項３に記載の電子写真感光体。
【化２】
（式（２）中、Ｒ１、Ｒ２及びＲ３は置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。但し、Ｒ １ 、Ｒ ２ 及びＲ ３ のうちの少なくとも２つはアリール基を示す。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】
（式（３）中、Ｒ ４ 、Ｒ ５ 、Ｒ ８ 及びＲ ９ は置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。Ｒ ６ 及びＲ ７ は置換基を有してもよいアルキレン基又は置換基を有してもよいアリーレン基を示す。Ｒ ４ 、Ｒ ５ 、Ｒ ８ 及びＲ ９ とＲ ６ 及びＲ ７ はそれぞれ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よい有機残基を示す。）
【化４】
（式（４）中、Ｒ １０ 、Ｒ １１ 、Ｒ １２ 及びＲ １３ は置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。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よいアリーレン基を示す。Ａｒ １ 及びＡｒ ２ はそれぞれ同一であっても異なっていてもよい。ｍは０又は１を示す。）
【化５】
（式（５）中、Ａｒ ３ 及びＡｒ ４ は置換基を有してもよいアリール基を示す。Ａｒ ３ 及びＡｒ ４ はそれぞれ同一であっても異なっていてもよい。Ｒ １４ は置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。
但し、Ａｒ ３ 、Ａｒ ４ 及びＲ １４ のうちの少なくとも１つは下記一般式（６）で示される置換基を１つ以上有する。）
【化６】
（式（６）中、Ｒ １５ 及びＲ １６ は置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基、置換基を有してもよいアリール基又は水素原子を示す。Ｒ １５ 及びＲ １６ はそれぞれ同一であっても異なっていてもよい。Ａｒ ５ は置換基を有してもよいアリール基を示す。ｎ １ は０〜２の整数を示す。）
【化７】
（式（７）中、Ｒ １７ 及びＲ １８ は置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。Ｒ １７ 及びＲ １８ はそれぞれ同一であっても異なっていてもよい。Ａｒ ６ は置換基を有してもよいアリール基を示す。）
【化８】
（式（８）中、Ｒ １９ 及びＲ ２０ は置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基、置換基を有してもよいアリール基又は水素原子を示す。Ｒ １９ 及びＲ ２０ はそれぞれ同一であっても異なっていてもよい。Ａｒ ７ は置換基を有してもよ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、置換基を有してもよいアルキレン基、置換基を有してもよいアリーレン基、ＣＲ２１＝ＣＲ２２（Ｒ２１及びＲ２２は置換基を有してもよいアルキル基、置換基を有してもよいアリール基又は水素原子を示す。Ｒ２１及びＲ２２はそれぞれ同一であっても異なっていてもよい。）、Ｃ＝Ｏ、Ｓ＝Ｏ、ＳＯ２、酸素原子又は硫黄原子、或いは、これらを組み合わせた有機残基である請求項３又は４に記載の電子写真感光体。
【請求項６】 上記一般式（１）中のＺ又は一般式（３）中のＱが、下記一般式（９）又は（１０）で示される基である請求項３又は４に記載の電子写真感光体。
【化９】
（式（９）中、Ｘ１ 、Ｘ ２ 及びＸ３は置換基を有してもよいアルキレン基、（ＣＲ２３＝ＣＲ２４）ｍ１ （Ｒ ２３ 及びＲ ２４ は置換基を有してもよいアルキル基、置換基を有してもよいアリール基又は水素原子を示す。Ｒ ２３ 及びＲ ２４ はそれぞれ同一であっても異なっていてもよい。ｍ １ は１〜５の整数を示す。）、Ｃ＝Ｏ、Ｓ＝Ｏ、ＳＯ２、酸素原子又は硫黄原子を示す。Ａｒ８及びＡｒ９は置換基を有してもよいアリーレン基を示す。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。）
【化１０】
（式（１０）中、Ａｒ １０ は置換基を有してもよいアリーレン基を示す。Ｘ ４ 及びＸ ５ は（ＣＨ ２ ） ｇ （ｇは１〜１０の整数を示す。）、（ＣＨ＝ＣＲ ２５ ） ｈ （Ｒ ２５ は置換基を有してもよいアルキル基、置換基を有してもよいアリール基又は水素原子を示す。ｈは１〜５の整数を示す。）、Ｃ＝Ｏ又は酸素原子を示す。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７】 前記一般式（２）中のＲ１、Ｒ２及びＲ３が置換基を有してもよいアリール基である請求項４に記載の電子写真感光体。
【請求項８】 前記一般式（３）中のＲ４ 、Ｒ５ 、Ｒ８及びＲ９のうちの少なくとも２つが置換基を有してもよいアリール基であり、Ｒ ６及びＲ７が置換基を有してもよいアリーレン基である請求項４〜６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が置換基を有してもよいアリール基であり、Ｒ ６及びＲ７が置換基を有してもよいアリーレン基である請求項４〜６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（４）中のＲ１０及びＲ１１が置換基を有してもよいアリール基である請求項４に記載の電子写真感光体。
【請求項１１】 前記一般式（４）中のＲ１０〜Ｒ１３が置換基を有してもよいアリール基である請求項４に記載の電子写真感光体。
【請求項１２】 前記一般式（５）中のＲ１４が置換基を有してもよいアリール基である請求項４に記載の電子写真感光体。
【請求項１３】 前記一般式（６）中のＲ１６が置換基を有してもよいアリール基である請求項４に記載の電子写真感光体。
【請求項１４】 前記一般式（７）中のＲ１７及びＲ１８が置換基を有してもよいアリール基である請求項４に記載の電子写真感光体。
【請求項１５】 前記一般式（８）中のＲ２０が置換基を有してもよいアリール基である請求項４に記載の電子写真感光体。
【請求項１６】 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３〜１５のいずれかに記載の電子写真感光体。
【化１１】
（式（１１）中、Ｅは水素原子、ハロゲン原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、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、置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよ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、置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。Ｒ ２７ 及びＲ ２８ は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よいアリーレン基、置換基を有してもよいアルキレン基、−ＣＯＯ−、−Ｏ−、−ＯＯ−、−Ｓ−又は−ＣＯＮＲ２９−（Ｒ２９は水素原子、ハロゲン原子、置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。）を示す。ｆは０又は１を示す。）
【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（１２）で示される環状エーテル基である請求項３〜１６のいずれかに記載の電子写真感光体。
【化１２】
（式（１２）中、Ｒ３０及びＲ３１は水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。ｎは１〜１０の整数を示す。）
【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（１３）で示される脂環式エポキシ基である請求項３〜１７のいずれかに記載の電子写真感光体。
【化１３】
（式（１３）中、Ｒ３２及びＲ３３は水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアラルキル基又は置換基を有してもよいアリール基を示す。ｎは０〜１０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（１４）、（１５）、（１６）、（１７）、（１８）、（１９）及び（２０）のいずれかで示される基である請求項３〜１８のいずれかに記載の電子写真感光体。
【化１４】
【請求項２０】 前記連鎖重合性官能基を有する正孔輸送性化合物が同一分子内に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であって、その酸化電位が０．４〜１．２（Ｖ）である請求項１〜１９のいずれかに記載の電子写真感光体。
【請求項２１】 請求項１〜２０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、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、転写工程後の該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２２】 請求項１〜２５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像露光を行い該電子写真感光体上に静電潜像を形成する像露光手段、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有す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 photosensitive layer,Charge generation layeras well asThe charge transport layers are laminated in this order or in the reverse order.
The charge generation layer,Charge generating materialWhen,Hole-transporting compound having a chain-growth functional groupThingsBy heat or ultraviolet raysRupolymerizationorIs a bridgeByCuringLetTateWhenincluding
An electrophotographic photosensitive member characterized by this.
2. The hole-transporting compound having a chain-growth functional group,In the same molecule2Has one or more chain-growth functional groupsIt is a hole transporting compoundThe electrophotographic photosensitive member according to claim 1.
3. The hole-transporting compound having a chain-growth functional group has the following general formula (1).Compounds indicated byThe electrophotographic photosensitive member according to claim 1 or 2.
[Chemical 1]
(formula(1)Among them, A indicates a hole transporting group...P1And P2Indicates a chain-growth functional group..P1 as well asP2IsRespectivelySameThereAlso differentBeMay be good..Z indicates an organic residue which may have a substituent.Su.Y indicates a hydrogen atom..a, b and d indicate an integer of 0 or 1 or more...However, when a = 0, b + d is an integer of 3 or more.And, B or d is 0, then a is an integer greater than or equal to 2.And, In other cases a + b + d is an integer of 3 or moreIs.Also, when a is 2 or moreIsP1Are the sameThereAlso differentBeMoyoI.When d is 2 or moreIsP2Are the sameThereAlso differentBeMoyoI.When b is 2 or moreIsZ is the sameThereAlso differentBeMay be good..)
4. BeforeGeneral formula (1)A insideof,P1 Binding site withAnd the binding site with ZRespectivelyThe hole-transporting compound replaced with a hydrogen atom,The following general formula (2), (3), (4), (5), (6) and (7)Indicated byThe compound, the condensed ring hydrocarbon or the condensed complex ring (provided that the compound represented by the following general formula (7), the condensed ring hydrocarbon and the condensed complex ring have one or more substituents represented by the following general formula (8). )Claim3The electrophotographic photosensitive member according to.
[Chemical 2]
(formula(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,R 1 , R 2 And R 3 OfAt least 2Indicates an aryl group..R1, R2And R3May be the same or different..)
[Chemical 3]
(In equation (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. R 6 And R 7 Indicates an alkylene group which may have a substituent or an arylene group which may have a substituent. R 4 , R 5 , R 8 And R 9 And R 6 And R 7 May be the same or different. Q indicates an organic residue which may have a substituent. )
[Chemical 4]
(In equation (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. 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. Ar 1 And Ar 2 May be the same or different. m represents 0 or 1. )
[Chemical 5]
(In equation (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 one or more substituents represented by the following general formula (6). )
[Chemical 6]
(In equation (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. R 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. )
[Chemical 7]
(In equation (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. 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 equation (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. R 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, CR.21= CR22(R21And R22Indicates an alkyl group that may have a substituent, an aryl group that may have a substituent, or a hydrogen atom.Su.R21And R22IsRespectivelySameThereAlso differentBeMay be good..), C = O, S = O, SO2, Oxygen atom or sulfur sourceChild orYes,theseCombinationSetOrganic residuesIsClaim3 or 4The electrophotographic photosensitive member according to.
Claim6] The above general formula (1)During ~Z or general formula (3)During ~Q is the following general formula (9)Or (10)Indicated byIs the basisClaim3 or 4The electrophotographic photosensitive member according to.
[Chemical 9]
(formula(9)Medium, X1 , X 2 as well asX3Is an alkylene group which may have a substituent, (CR23= CR24) M1 (R 23 And R 24 Indicates an alkyl group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. R 23 And R 24 May be the same or different. m 1 Indicates an integer of 1-5. ), C = O, S = O, SO2, Indicates an oxygen atom or a sulfur atomSu.Ar8And Ar9Indicates an arylene group which may have a substituent...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..)
[Chemical 10]
(In equation (10), Ar 10 Indicates an arylene group which may have a substituent. X 4 And X 5 Is (CH 2 ) g (G indicates an integer of 1 to 10.), (CH = CR 25 ) h (R 25 Indicates an alkyl group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. h represents an integer of 1-5. ), C = O or an oxygen atom. u, v and w represent integers from 0 to 10. However, u, v and w cannot be 0 at the same time. )
Claim7] BeforeGeneral formula (2)During ~R1, R2And R3Claims that is an aryl group which may have a substituent.4The electrophotographic photosensitive member according to.
Claim8] BeforeGeneral formula (3)During ~R4 ,R5 ,R8And R9OfofAt least two are aryl groups that may have substituents., R 6And R7Claims that is an arylene group which may have a substituent.4-6The electrophotographic photosensitive member according to any one of.
Claim9] BeforeGeneral formula (3)During ~R4 ,R5 ,R8And R9Is an aryl group that may have a substituent, R 6And R7Claims that is an arylene group which may have a substituent.4-6The electrophotographic photosensitive member according to any one of.
1.0] BeforeGeneral formula (4)During ~R10And R11Claims that is an aryl group which may have a substituent.4The electrophotographic photosensitive member according to.
1.1] BeforeGeneral formula (4)During ~R10~ R13Claims that is an aryl group which may have a substituent.4The electrophotographic photosensitive member according to.
1.2] BeforeGeneral formula (5)During ~R14Claims that is an aryl group which may have a substituent.4The electrophotographic photosensitive member according to.
1.3] BeforeGeneral formula (6)During ~R16Claims that is an aryl group which may have a substituent.4The electrophotographic photosensitive member according to.
1.4] BeforeGeneral formula (7)During ~R17And R18Claims that is an aryl group which may have a substituent.4The electrophotographic photosensitive member according to.
Claim15] BeforeGeneral formula (8)During ~R20Claims that is an aryl group which may have a substituent.4The electrophotographic photosensitive member according to.
Claim16] SaidChain polymerizableSensualGroup P1 as well asP2Claim that one or both are unsaturated polymerizable functional groups represented by the following general formula (11).3~15The electrophotographic photosensitive member according to any one of.
[Chemical 11]
(formula(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.Su. R 27 And R 28 IsMay be the same or different from each other.. )ShowSu.W may have a substituentIaLeeLenMay have groups and substituentsIaLucilene group, -COO-, -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. )Show..f indicates 0 or 1..)
Claim17] SaidChain polymerizableSensualGroup P1 as well asP2Claim that one or both are cyclic ether groups represented by the following general formula (12).3~16The electrophotographic photosensitive member according to any one of.
[Chemical 12]
(formula(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 is 1-10Indicates an integer..)
Claim18] SaidChain polymerizableSensualGroup P1 as well asP2Claim that one or both are alicyclic epoxy groups represented by the following general formula (13).3~17The electrophotographic photosensitive member according to any one of.
[Chemical 13]
(formula(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 is0 to 010Indicates an integer..)
Claim19] SaidChain polymerizableSensualGroup P1 as well asP2One or both are the following general formula (14), (15), (16), (17), (18), (19) andIn any of (20)In the group shownA claim3~18The electrophotographic photosensitive member according to any one of.
[Chemical 14]
2.0] The hole-transporting compound having the chain-growth functional groupIn the same molecule2Hole-transporting compound with one or more chain-growth functional groupsAnd thatClaims 1 to which the oxidation potential is 0.4 to 1.2 (V).19The electrophotographic photosensitive member according to any one of.
2.1] Claims 1 and 20The electrophotographic photosensitive member according to any one ofWhen, Charging means for charging the electrophotographic photosensitive member, The electricityChild photophotoreceptorElectrostatic latent image formed onDevelopment means for developing with toner, and,After the transfer processThe electrographSelected from the group consisting of cleaning means to collect the toner remaining on the photoconductorRuat least1With one meansToA process cartridge that is integrally supported and can be attached to and detached from the main body of the electrophotographic apparatus.
2.2The electrophotographic photosensitive member according to any one of claims 1 to 25, a charging means for charging the electrophotographic photosensitive member, and charging.TheFor electrophotographic photosensitive membershandPerform image exposureOn the electrophotographic photosensitive memberImage exposure means for forming an electrostatic latent image, The electricityChild photophotoreceptorElectrostatic latent image formed onDevelopment means for developing with toner, and, The electrophotographic photosensitive memberThe toner image aboveOn the transfer materialAn electrophotographic apparatus comprising a transfer means for transfer.
【００１１】
【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、
該感光層が、電荷発生層及び電荷輸送層をこの順に又は逆順に積層した構成であり、
該電荷発生層が、電荷発生材料と、連鎖重合性官能基を有する正孔輸送性化合物を熱又は紫外線による重合又は架橋によって硬化させたものとを含む
ことを特徴とする電子写真感光体、該電子写真感光体を有するプロセスカートリッジ及び電子写真装置が提供される。
0011
[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.
The photosensitive layer has a charge generation layer and a charge transport layer is formed by laminating in this order or in reverse order,
The charge generating layer comprises a charge generating material, by that the polymerization or to heat or ultraviolet hole-transporting compound that having a chain polymerizable functional group and those cured by crosslinking
An electrophotographic photosensitive member, characterized in that, the process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member is provided.
上記で説明したような本発明に係わる連鎖重合性官能基の中でも、下記の一般式（１１）、（１２）及び（１３）で示されるものが好ましい。 Among the chain-growth functional groups according to the present invention as described above, those represented by the following general formulas (11) , (12) and (13) are preferable.
式（１１）中、Ｅは水素原子、フッ素、塩素、臭素等のハロゲン原子、置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等のアルキル基、置換基を有してもよいベンジル基、フェネチル基、ナフチルメチル基、フルフリル基、チエニル基等のアラルキル基、置換基を有してもよいフェニル基、ナフチル基、アンスリル基、ピレニル基、チオフェニル基、フリル基等のアリール基、ＣＮ基、ニトロ基、メトキシ基、エトキシ基、プロポキシ基等のアルコキシ基、−ＣＯＯＲ２６又は−ＣＯＮＲ２７Ｒ２８を示す。 In the formula (11) , E has a hydrogen atom, a halogen atom such as fluorine, chlorine and bromine, an alkyl group such as a methyl group, an ethyl group, a propyl group and a butyl group which may have a substituent, and a substituent. Aralkyl groups such as benzyl group, phenethyl group, naphthylmethyl group, flufuryl group and thienyl group, which may have a substituent, phenyl group which may have a substituent, naphthyl group, anthryl group, pyrenyl group, thiophenyl group, frill group and the like. Shows an alkoxy group such as an aryl group, a CN group, a nitro group, a methoxy group, an ethoxy group or a propoxy group, -COOR 26 or -CONR 27 R 28 .
Ｗは置換基を有してもよいフェニレン基、ナフチレン基、アントラセニレン基等のアリーレン基、置換基を有してもよいメチレン基、エチレン基、ブチレン基等のアルキレン基、−ＣＯＯ−、−Ｏ−、−ＯＯ−、−Ｓ−又は−ＣＯＮＲ２９ を示す。 W is a substituent having also good awe Eniren group, a naphthylene group, an arylene group such as anthracenylene group, an optionally substituted methylene group, an ethylene group, A alkylene group such as butylene group, -COO- , -O -, - OO -, - shows the S- or -CONR 29.
ここでＲ２６ 、Ｒ ２７ 、Ｒ ２８ 及びＲ２９は水素原子、フッ素、塩素、臭素等のハロゲン原子、置換基を有してもよいメチル基、エチル基、プロピル基等のアルキル基、置換基を有してもよいベンジル基、フェネチル基等のアラルキル基及び置換基を有してもよいフェニル基、ナフチル基、アンスリル基等のアリール基を示す。Ｒ２８とＲ２９は互いに同一であっても異なっていてもよい。また、ｆは０又は１を示す。 Here, R 26 , R 27 , R 28 and R 29 are hydrogen atoms, halogen atoms such as fluorine, chlorine and bromine, alkyl groups such as methyl group, ethyl group and propyl group which may have substituents and substituents. a benzyl group which may have a phenyl group which may have an aralkyl group and a substituted group such as a phenethyl group, a naphthyl group, shows the aryl group such as anthryl group. R 28 and R 29 may be the being the same or different. Further, f indicates 0 or 1.
式（１２）中、Ｒ３０及びＲ３１は水素原子、置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等のアルキル基、置換基を有してもよいベンジル基、フェネチル基等のアラルキル基又は置換基を有してもよいフェニル基、ナフチル基等のアリール基を示す。ｎは１〜１０の整数を示す。 In the formula (12) , R 30 and R 31 are a hydrogen atom, an alkyl group such as a methyl group which may have a substituent, an ethyl group, a propyl group and a butyl group, and a benzyl group which may have a substituent. aralkyl or phenyl group which may have a substituent such as a phenethyl group, shows the aryl group such as phenyl or naphthyl. n represents an integer of 1 to 10.
式（１３）中、Ｒ３２及びＲ３３は水素原子、置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等のアルキル基、置換基を有してもよいベンジル基、フェネチル基等のアラルキル基又は置換基を有してもよいフェニル基、ナフチル基等のアリール基を示す。ｎは０又は１〜１０の整数を示す。 In the formula (13) , R 32 and R 33 are a hydrogen atom, an alkyl group such as a methyl group which may have a substituent, an ethyl group, a propyl group and a butyl group, and a benzyl group which may have a substituent. aralkyl or phenyl group which may have a substituent such as a phenethyl group, shows the aryl group such as phenyl or naphthyl. n represents an integer of 0 or 1 to 10.
なお、上記一般式（１２）及び一般式（１３）のＲ３０ 、Ｒ ３１ 、Ｒ ３２ 及びＲ３３が有してもよい置換基としては、フッ素、塩素、臭素、ヨウ素等のハロゲン原子又はメチル基、エチル基、プロピル基、ブチル基等のアルキル基又はメトキシ基、エトキシ基、プロポキシ基等のアルコキシ基又はフェノキシ基、ナフトキシ基等のアリールオキシ基又はベンジル基、フェネチル基、ナフチルメチル基、フルフリル基、チエニル基等のアラルキル基又はフェニル基、ナフチル基、アンスリル基、ピレニル基等のアリール基等が挙げられる。 The substituents that R 30 , R 31 , R 32 and R 33 of the general formula (12) and the general formula (13) may have include halogen atoms such as fluorine, chlorine, bromine and iodine or methyl. Alkyl group such as group, ethyl group, propyl group, butyl group or methoxy group, ethoxy group, propoxy group or other alkoxy group or phenoxy group, naphthoxy group or other aryloxy group or benzyl group, phenethyl group, naphthylmethyl group, furfuryl Examples thereof include an aralkyl group such as a group and a thienyl group or an aryl group such as a phenyl group, a naphthyl group, an anthryl group and a pyrenyl group.
また、上記一般式（１１）、（１２）及び（１３）の中でも、更に特に好ましい連鎖重合性官能基としては、下記一般式（１４）、（１５）、（１６）、（１７）、（１８）、（１９）及び（２０）で示される基が挙げられる。 Further, among the above general formulas (11) , (12) and (13), more particularly preferable chain-growth functional groups include the following general formulas (14) , (15), (16), (17) and (17). Examples include the groups represented by 18), (19) and (20).
式（１）中、Ｐ１及びＰ２は連鎖重合性官能基を示す。Ｐ１とＰ２はそれぞれ同一であっても異なっていてもよい。Ｚは置換基を有してもよい有機残基を示す。Ｙは水素原子を示す。ａ、ｂ及びｄは、０又は１以上の整数を示す。但し、ａ＝０の場合はｂ＋ｄは３以上の整数であり、ｂ又はｄが０の場合はａは２以上の整数であり、その他の場合はａ＋ｂ＋ｄは３以上の整数である。また、ａが２以上の場合はＰ１は同一であっても異なっていてもよい。ｄが２以上の場合はＰ２は同一であっても異なっていてもよい。またｂが２以上の場合はＺは同一であっても異なっていてもよい。 Wherein (1), P 1 and P 2 shows the chain polymerizable functional group. P 1 and P 2 may each be the same or different. Z is shows the good organic residue may have a substituent. Y represents a hydrogen atom. a, b and d represent an integer of 0 or 1 or more. However, when a = 0, b + d is an integer of 3 or more, when b or d is 0, a is an integer of 2 or more, and in other cases, a + b + d is an integer of 3 or more. In addition, if a is 2 or more P 1 is but it may also have be the same or different. If d is 2 or more P 2 is but it may also have be the same or different. In the case b is 2 or more Z may or may not be the same.
式（２）中、Ｒ１、Ｒ２及びＲ３は置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等の炭素数１以上１０以下のアルキル基、置換基を有してもよいベンジル基、フェネチル基、ナフチルメチル基、フルフリル基、チエニル基等のアラルキル基又は置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基を示す。 In the formula (2) , R 1 , R 2 and R 3 have an alkyl group having 1 or more and 10 or less carbon atoms, such as a methyl group, an ethyl group, a propyl group and a butyl group, which may have a substituent, and a substituent. A phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a thiophenyl group, which may have an aralkyl group or a substituent such as a benzyl group, a phenethyl group, a naphthylmethyl group, a flufuryl group, a thienyl group, etc. It shows an aryl group such as a frill group, a pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group and a dibenzothiophenyl group.
但し、Ｒ１、Ｒ２及びＲ３のうち少なくとも２つはアリール基を示し、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。更に、その中でもＲ１、Ｒ２及びＲ３のすべてがアリール基であるものが特に好ましい。また、上記一般式（２）のＲ１又はＲ２又はＲ３のうち任意の２つはそれぞれ直接もしくは結合基を介して結合してもよい。その結合基としては、メチレン基、エチレン基、プロピレン基等のアルキレン基、酸素、硫黄原子等のヘテロ原子、ＣＨ＝ＣＨ基等が挙げられる。 However, at least two of R 1, R 2 and R 3 represents an aryl group, R 1, R 2 and R 3 may each be the same or different. Further, among them, those in which all of R 1 , R 2 and R 3 are aryl groups are particularly preferable. Also, but it may also be bonded via any two direct or linking groups each of R 1 or R 2 or R 3 in the general formula (2). Examples of the bonding group include an alkylene group such as a methylene group, an ethylene group and a propylene group, a hetero atom such as an oxygen and a sulfur atom, and a CH = CH group.
式（３）中、Ｒ４、Ｒ５、Ｒ８及びＲ９は置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等の炭素数１以上１０以下のアルキル基、置換基を有してもよいベンジル基、フェネチル基、ナフチルメチル基、フルフリル基、チエニル基等のアラルキル基又は置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基を示す。Ｒ４、Ｒ５、Ｒ８及びＲ９はそれぞれ同一であっても異なっていてもよい。Ｒ６及びＲ７は置換基を有してもよいメチレン基、エチレン基、プロピレン基等の炭素数１以上１０以下のアルキレン基、又は置換基を有してもよいアリーレン基（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、ベンゾチオフェン、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個の水素を取り除いたアリーレン基。）を示す。Ｒ６とＲ７はそれぞれ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よい有機残基を示す。 In formula (3) , R 4 , R 5 , R 8 and R 9 may have substituents, such as methyl group, ethyl group, propyl group, butyl group and other alkyl groups having 1 to 10 carbon atoms , and substitutions. A phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, which may have an aralkyl group or a substituent such as a benzyl group, a phenethyl group, a naphthylmethyl group, a flufuryl group, a thienyl group, which may have a group, thiophenyl group, a furyl group, a pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, shows the aryl group such as a dibenzothiophenyl group. R 4 , R 5 , R 8 and R 9 may be the same or different, respectively. R 6 and R 7 may have a substituent, an alkylene group having 1 to 10 carbon atoms such as a methylene group, an ethylene group, and a propylene group, or an arylene group (benzene, naphthalene, etc.) which may have a substituent. anthracene, to indicate phenanthrene, pyrene, benzothiophene, pyridine, quinoline, benzoquinoline, carbazole, phenothiazine, benzofuran, benzothiophene, dibenzofuran, arylene groups were removed two hydrogen than dibenzothiophene or the like.) the. R 6 and R 7 may be the same or different, respectively. Q indicates an organic residue which may have a substituent.
更に、その中でも上記一般式（３）中のＲ４、Ｒ５、Ｒ８及びＲ９のうち２つ以上が置換基を有してもよいアリール基であり、Ｒ６及びＲ７が置換基を有してもよいアリーレン基である場合が好ましく、更にＲ４、Ｒ５、Ｒ８及びＲ９が４つとも全て置換基を有してもよいアリール基である場合が特に好ましい。また、上記一般式（３）のＲ４又はＲ５又はＲ６のうち任意の２つあるいはＲ７又はＲ８又はＲ９のうち任意の２つはそれぞれ直接もしくは結合基を介して結合してもよい。その結合基としては、メチレン基、エチレン基、プロピレン基等のアルキレン基、酸素、硫黄原子等のヘテロ原子、ＣＨ＝ＣＨ基等が挙げられる。 Further, among them, two or more of R 4 , R 5 , R 8 and R 9 in the above general formula (3) are aryl groups which may have a substituent, and R 6 and R 7 are substituents. It is preferable that it is an arylene group which may have a substituent, and further, it is particularly preferable that all four of R 4 , R 5 , R 8 and R 9 are aryl groups which may have a substituent. Also, attached via an R 4 or R 5 or any two or any two direct or linking groups each of R 7 or R 8 or R 9 of R 6 in the general formula (3) also not good. Examples of the bonding group include an alkylene group such as a methylene group, an ethylene group and a propylene group, a hetero atom such as an oxygen and a sulfur atom, and a CH = CH group.
式（４）中、Ｒ １０ 、Ｒ １１ 、Ｒ １２ 及びＲ１３は置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等の炭素数１以上１０以下のアルキル基、置換基を有してもよいベンジル基、フェネチル基、ナフチルメチル基、フルフリル基、チエニル基等のアラルキル基又は置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基を示す。Ｒ１０ 、Ｒ １１ 、Ｒ １２ 及びＲ１３はそれぞれ同一であっても異なっていてもよい。 In the formula (4), R 10 , R 11 , R 12 and R 13 are substituted with an alkyl group having 1 or more and 10 or less carbon atoms such as a methyl group, an ethyl group, a propyl group and a butyl group which may have a substituent. A phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, which may have an aralkyl group or a substituent such as a benzyl group, a phenethyl group, a naphthylmethyl group, a flufuryl group, a thienyl group, which may have a group, thiophenyl group, a furyl group, a pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, shows the aryl group such as a dibenzothiophenyl group. R 10 , R 11 , R 12 and R 13 may be the same or different, respectively.
Ａｒ１は置換基を有してもよいアリーレン基（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、ベンゾチオフェン、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個の水素を取り除いたアリーレン基。）を示す。ｍは０又は１を示す。Ａｒ２はｍ＝０の場合、置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基を示す。ｍ＝１の場合は上記Ａｒ１と同様なアリーレン基を示す。尚、ｍ＝１の場合は、Ａｒ１とＡｒ２はそれぞれ同一であっても異なっていてもよい。 Ar 1 is more than an arylene group which may have a substituent (benzene, naphthalene, anthracene, phenanthrene, pyrene, benzothiophene, pyridine, quinoline, benzoquinoline, carbazole, phenothiazine, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene and the like 2). arylene group was removed pieces of hydrogen.) shows the. m represents 0 or 1. When m = 0, Ar 2 may have a substituent, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a thiophenyl group, a furyl group, a pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, shows the aryl group such as a dibenzothiophenyl group. When m = 1, an arylene group similar to that of Ar 1 is shown. When m = 1, Ar 1 and Ar 2 may be the same or different.
更に、その中でも上記一般式（４）中のＲ１０及びＲ１１が置換基を有してもよいアリール基である場合が好ましく、Ｒ１０ 、Ｒ １１ 、Ｒ １２ 及びＲ１３が４つとも全て置換基を有してもよいアリール基である場合が特に好ましい。また、上記一般式（４）のＲ１０とＲ１１又はＲ１２とＲ１３又はＡｒ１とＡｒ２は、それぞれ直接もしくは結合基を介して結合してもよい。その結合基としては、メチレン基、エチレン基、プロピレン基等のアルキレン基、酸素、硫黄原子等のヘテロ原子、ＣＨ＝ＣＨ基等が挙げられる。 Furthermore, it is preferred if R 10 and R 11 are an aryl group which may have a substituent in the general formula (4) Among them, R 10, R 11, R 12 and R 13 are all even four It is particularly preferable that the aryl group may have a substituent. Also, R 10 and R 11 or R 12 and R 13 or Ar 1 and Ar 2 in the general formula (4) is but it may also be bonded directly or through a linking group, respectively. Examples of the bonding group include an alkylene group such as a methylene group, an ethylene group and a propylene group, a hetero atom such as an oxygen and a sulfur atom, and a CH = CH group.
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）で示される置換基を１つ以上有する。 In the formula (5), at least one of Ar 3, Ar 4 and R 14 has a substituent represented by the following general formula (6) one or more.
上記一般式（５）及び（６）中、Ａｒ３、Ａｒ４及びＡｒ５は、置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基を示す。Ｒ１４、Ｒ１５及びＲ１６は置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等の炭素数１以上１０以下のアルキル基、置換基を有してもよいベンジル基、フェネチル基、ナフチルメチル基、フルフリル基、チエニル基等のアラルキル基、置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基又は水素原子を示す（但し、Ｒ１４が水素原子である場合は除く。）。なお、Ａｒ３及びＡｒ４とＲ１５及びＲ１６はそれぞれ同一であっても異なっていてもよい。 In the above general formulas (5) and (6), Ar 3 , Ar 4 and Ar 5 are phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, thiophenyl group and frill group which may have a substituent. , a pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, shows the aryl group such as a dibenzothiophenyl group. R 14 , R 15 and R 16 may have an alkyl group having 1 or more and 10 or less carbon atoms such as a methyl group, an ethyl group, a propyl group and a butyl group, which may have a substituent, and a benzyl group which may have a substituent. , Fenetyl group, naphthylmethyl group, furfuryl group, aralkyl group such as thienyl group, phenyl group which may have a substituent, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, thiophenyl group, frill group, pyridyl group, Indicates an aryl group or a hydrogen atom such as a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group or a dibenzothiophenyl group (however, when R 14 is a hydrogen atom). Excludes . ). It should be noted that Ar 3 and Ar 4 and R 15 and R 16 may be the same or different, respectively.
更に、その中でもＲ１４及びＲ１６がアリール基である場合が特に好ましい。また、Ｒ１４又はＡｒ３又はＡｒ４のうち任意の２つ、又はＡｒ５及びＲ１６はそれぞれ直接もしくは結合基を介して結合してもよい。その結合基としては、メチレン基、エチレン基、プロピレン基等のアルキレン基、酸素、硫黄原子等のヘテロ原子、ＣＨ＝ＣＨ基等が挙げられる。ｎ１は０〜２の整数を示す。 Further, among them, it is particularly preferable that R 14 and R 16 are aryl groups. Also, two of any of R 14, or Ar 3 or Ar 4, or Ar 5 and R 16 but it may also be bonded directly or through a linking group, respectively. Examples of the bonding group include an alkylene group such as a methylene group, an ethylene group and a propylene group, a hetero atom such as an oxygen and a sulfur atom, and a CH = CH group. n 1 represents an integer from 0 to 2.
但し、上記一般式（７）、縮合環炭化水素及び縮合複合環は、下記一般式（８）で示される置換基を１つ以上有する。 However, the general formula (7), condensed hydrocarbons and condensed composite ring has a substituent represented by the following general formula (8) one or more.
上記一般式（７）及び（８）中、Ａｒ６及びＡｒ７は置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基を示す。Ｒ１７、Ｒ１８、Ｒ１９及びＲ２０は置換基を有してもよいメチル基、エチル基、プロピル基、ブチル基等の炭素数１以上１０以下のアルキル基、置換基を有してもよいベンジル基、フェネチル基、ナフチルメチル基、フルフリル基、チエニル基等のアラルキル基、置換基を有してもよいフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、チオフェニル基、フリル基、ピリジル基、キノリル基、ベンゾキノリル基、カルバゾリル基、フェノチアジニル基、ベンゾフリル基、ベンゾチオフェニル基、ジベンゾフリル基、ジベンゾチオフェニル基等のアリール基又は水素原子を示す（但しＲ１７及びＲ１８が水素原子である場合は除く。）。なお、Ｒ１７とＲ１８及びＲ１９とＲ２０はそれぞれ同一であっても異なっていてもよい。 In the above general formulas (7) and (8), Ar 6 and Ar 7 may have a substituent, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a thiophenyl group, a furyl group, a pyridyl group, quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, shows the aryl group such as a dibenzothiophenyl group. R 17 , R 18 , R 19 and R 20 may have a substituent. Even if they have an alkyl group having 1 or more and 10 or less carbon atoms such as a methyl group, an ethyl group, a propyl group and a butyl group, and a substituent. Good benzyl group, phenethyl group, naphthylmethyl group, fulfuryl group, aralkyl group such as thienyl group, phenyl group which may have a substituent, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, thiophenyl group, frill group, Indicates an aryl group or a hydrogen atom such as a pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, a dibenzothiophenyl group (however, R 17 and R 18 are hydrogens). Except when it is an atom . ). R 17 and R 18 and R 19 and R 20 may be the same or different, respectively.
その中でも、Ｒ２０がアリール基である場合が好ましく、更に正孔輸送性基が一般式（７）で、かつＲ１７とＲ１８がアリール基である場合が特に好ましい。また、Ｒ１７又はＲ１８又はＡｒ６のうち任意の２つ、又はＡｒ７及びＲ２０はそれぞれ直接もしくは結合基を介して結合してもよい。その結合基としては、メチレン基、エチレン基、プロピレン基等のアルキレン基、酸素、硫黄原子等のヘテロ原子、ＣＨ＝ＣＨ基等が挙げられる。ｎ２は０〜２の整数を示す。 Among them, it is preferable that R 20 is an aryl group, and it is particularly preferable that the hole transporting group is the general formula (7) and R 17 and R 18 are aryl groups. Also, two of any of R 17 or R 18, or Ar 6, or Ar 7 and R 20 but it may also be bonded directly or through a linking group, respectively. Examples of the bonding group include an alkylene group such as a methylene group, an ethylene group and a propylene group, a hetero atom such as an oxygen and a sulfur atom, and a CH = CH group. n 2 represents an integer from 0 to 2.
また、上記一般式（１）中のＺ又は上記一般式（３）中のＱは、置換基を有してもよいアルキレン基、置換基を有してもよいアリーレン基、ＣＲ２１＝ＣＲ２２（Ｒ２１及びＲ２２はアルキル基、アリール基又は水素原子を示す。Ｒ２１及びＲ２２はそれぞれ同一であっても異なっていてもよい。）、Ｃ＝Ｏ、Ｓ＝Ｏ、ＳＯ２、酸素原子又は硫黄原子、或いは、これらの組み合わせた有機残基を示す。その中でも下記一般式（９）で示されるものが好ましく、下記一般式（１０）で示されるものが特に好ましい。 Further, Z in the general formula (1) or Q in the general formula (3) is an alkylene group which may have a substituent, an arylene group which may have a substituent, and CR 21 = CR 22. (R 21 and R 22 is an alkyl group, shows the aryl group or a hydrogen atom. R 21 and R 22 may each be the same or different.), C = O, S = O, SO 2, oxygen atom or sulfur atom, walk is an organic residue obtained by these combinations. Among them, the one represented by the following general formula (9) is preferable, and the one represented by the following general formula (10) is particularly preferable.
上記一般式（９）中、Ｘ１ 、Ｘ ２ 及びＸ３は置換基を有してもよいメチレン基、エチレン基、プロピレン基等の炭素数１以上２０以下のアルキレン、（ＣＲ２３＝ＣＲ２４）ｍ１ （Ｒ ２３ 及びＲ ２４ は置換基を有してもよいアルキル基、置換基を有してもよいアリール基又は水素原子を示す。Ｒ ２３ 及びＲ ２４ はそれぞれ同一であっても異なっていてもよい。ｍ １ は１〜５の整数を示す。）、Ｃ＝Ｏ、Ｓ＝Ｏ、ＳＯ２、酸素原子又は硫黄原子を示す。Ａｒ８及びＡｒ９は置換基を有してもよいアリーレン基（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、ベンゾチオフェン、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アリーレン基。）を示す。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 , X 2 and X 3 are alkylene groups having 1 or more and 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). ) M 1 (R 23 and R 24 indicate an alkyl group which may have a substituent, an aryl group which may have a substituent or a hydrogen atom. R 23 and R 24 are the same or different, respectively. good .m 1 even though is an integer of 1 to 5.), shows the C = O, S = O, SO 2, oxygen atom or sulfur atom. Ar 8 and Ar 9 may have substituents (benzene, naphthalene, anthracene, phenanthrene, pyrene, benzothiophene, pyridine, quinoline, benzoquinoline, carbazole, phenothiazine, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene arylene groups were removed two hydrogen atoms from equal.) shows a. p , q, r, s and t represent integers from 0 to 10. However then, p, q, r, it is not the name s and t are 0 at the same time.
上記一般式（１０）中、Ｘ４及びＸ５は（ＣＨ２）ｇ （ｇは１〜１０の整数を示す。）、（ＣＨ＝ＣＲ２５）ｈ （Ｒ ２５ は置換基を有してもよいアルキル基、置換基を有してもよいアリール基又は水素原子を示す。ｈは１〜５の整数を示す。）、Ｃ＝Ｏ、又は酸素原子を示す。Ａｒ１０は置換基を有してもよいアリーレン基（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、ベンゾチオフェン、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アリーレン基。）を示す。ｕ、ｖ及びｗは０〜１０の整数を示す。特に、０〜５の整数の時が好ましい。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 are (CH 2 ) g (g represents an integer of 1 to 10) , (CH = CR 25 ) h (R 25 may have a substituent). alkyl group, .h indicating an aryl group or a hydrogen atom may have a substituent is an integer of 1 to 5.), shows the C = O, or oxygen atom. Ar 10 is more than an arylene group which may have a substituent (benzene, naphthalene, anthracene, phenanthrene, pyrene, benzothiophene, pyridine, quinoline, benzoquinoline, carbazole, phenothiazine, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene and the like 2). It shows an arylene group from which one hydrogen atom has been removed . ). u , v and w represent integers from 0 to 10. In particular, it preferred when the integer 0-5. However, u, v and w it is not name a 0 at the same time.
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