JPS62267757A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS62267757A JPS62267757A JP11062186A JP11062186A JPS62267757A JP S62267757 A JPS62267757 A JP S62267757A JP 11062186 A JP11062186 A JP 11062186A JP 11062186 A JP11062186 A JP 11062186A JP S62267757 A JPS62267757 A JP S62267757A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- sensitive body
- sensitivity
- carboxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000049 pigment Substances 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 108091008695 photoreceptors Proteins 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 19
- 230000003595 spectral effect Effects 0.000 abstract description 5
- -1 cyano, carboxyl Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 3
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910001370 Se alloy Inorganic materials 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- YBKGVUWZCGXRIY-UHFFFAOYSA-N N,N-diethyl-4-methanehydrazonoylaniline Chemical class CCN(CC)C1=CC=C(C=NN)C=C1 YBKGVUWZCGXRIY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001596 poly (chlorostyrenes) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
- G03G5/0611—Squaric acid
Landscapes
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真プロセスにおいて使用される電子写真
用感光体に関する。更に詳しく言えば本発明は光導1t
N中にスクェアリリウム顔料を含有する電子写真用感光
体lc関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor used in an electrophotographic process. More specifically, the present invention is based on a light guide of 1 ton.
This invention relates to an electrophotographic photoreceptor lc containing a square lyllium pigment in nitrogen.
従来、電子写真用感光体として、無定形セレン、セレン
合金、硫化カドミウム、酸化亜鉛等の無機系感光材料や
ポリビニルカルバゾール・及びポリビニルカルバゾール
誘導体憂こ代表される有機系感光材料が広(知られてい
る。Conventionally, inorganic photosensitive materials such as amorphous selenium, selenium alloys, cadmium sulfide, and zinc oxide, as well as organic photosensitive materials such as polyvinyl carbazole and polyvinyl carbazole derivatives, have been widely used as electrophotographic photoreceptors. There is.
無定形セレン或いはセレン合金は電子写真用感光体とし
て極めて唆れた特性を有し、実用に供されていることは
周知の通りである。しかし。It is well known that amorphous selenium or selenium alloys have extremely attractive properties as photoreceptors for electrophotography and are used in practical applications. but.
その製造においては蒸着という煩雑な工程を経ねばなら
ず、父製造された蒸着膜は可撓性がないという欠点があ
る。酸化亜鉛を用いる場合ζこは、酸化亜鉛を樹脂中に
分散させた分散系感光材料として用いるが、このような
感光材料は機械的強度に難点があり、そのままでは反復
使用に耐え得ない。Its production requires a complicated step of vapor deposition, and the vapor-deposited film thus produced has the drawback of not being flexible. When zinc oxide is used, it is used as a dispersed photosensitive material in which zinc oxide is dispersed in a resin, but such photosensitive materials have a drawback in mechanical strength and cannot withstand repeated use as is.
肩磯元導電材料として広(知られているポリビニルカル
バゾールは透明性、皮膜形成性、可撓性などの点で優れ
ている利点があるものの、ポリビニルカルバゾール自身
は可視光域fこ感度を持たないためにそのままでは実用
に供することができず、従って種々の増感方法が考案さ
れてはいる。ところが色素増感剤を用いてポリビニルカ
ルバゾールを分光増感した場合には分光感度域は可視光
域にまで拡張されるものの、なお電子写真用感光体とし
て十分な感度は得られず光疲労が甚しいという欠点を持
つ。又、電子受容性化合物を用いて化学増感した場合1
こは電子写真用感光体として感度的には十分な感光体が
遵られ、一部のものは実用化されているがなお、機械的
強度、寿命等に問題点を残している。Kashiisomoto: Polyvinylcarbazole, which is widely known as a conductive material, has excellent advantages in terms of transparency, film-forming properties, and flexibility, but polyvinylcarbazole itself does not have sensitivity in the visible light range. Therefore, it cannot be put to practical use as it is, and therefore various sensitization methods have been devised.However, when polyvinylcarbazole is spectrally sensitized using a dye sensitizer, the spectral sensitivity range is within the visible light range. However, it still has the drawback of not being able to obtain sufficient sensitivity as a photoreceptor for electrophotography and suffers from severe photofatigue.Also, when chemically sensitized using an electron-accepting compound,
Although photoreceptors with sufficient sensitivity have been developed as photoreceptors for electrophotography, and some of them have been put into practical use, problems still remain in terms of mechanical strength, lifespan, and the like.
電荷発生層と電荷輸送層を有する積層型の感光体が従来
のものに比べ優れた電気特性を有することが報告されて
いる。これらの感光体に用いられる1!荷発生材料とし
ては、ビスアゾ類、トリスアゾ類、フタロシアニン類、
ビリリウム類、スクェアリリウム類等が知られており、
可視領域から近赤外領域まで感度を有するものとしては
フタロシアニン類、トリスアゾ類、スクェアリリウム類
が報告されている。It has been reported that a laminated photoreceptor having a charge generation layer and a charge transport layer has electrical properties superior to those of conventional photoreceptors. 1 used for these photoreceptors! Materials that generate chemicals include bisazos, trisazos, phthalocyanines,
Viryliums, squarelilliums, etc. are known.
Phthalocyanines, trisazos, and squareyliums have been reported to have sensitivity from the visible region to the near-infrared region.
シカシながら、フタロシアニン類は分光感度が長波長に
片寄り赤色再現性ζこ劣るという欠点を有し、トリスア
ゾ類は優れた電気特性と充分な感度を有するζこいたっ
ていない。However, phthalocyanines have the drawbacks of spectral sensitivity biased towards long wavelengths and poor red color reproducibility, while trisazos have excellent electrical properties and sufficient sensitivity.
また特開昭49−105536号等に示されるスクエア
+31Jウム化合物は比較的高い感度を有するものの帯
電性、暗減衰等(こ欠点を有し、高い感度と低い暗減垂
を両立するには至っていない。In addition, although the square +31J umium compound shown in JP-A-49-105536 has relatively high sensitivity, it has drawbacks such as chargeability and dark decay, and it is difficult to achieve both high sensitivity and low dark decay. not present.
本発明の目的は前述の欠点を解消し、可視域から近赤外
領域にわたって分光感度を有し、高感度で優れた電気特
性を有する電子写真感光体を提供することをこある。SUMMARY OF THE INVENTION An object of the present invention is to eliminate the above-mentioned drawbacks, and to provide an electrophotographic photoreceptor having spectral sensitivity from the visible region to the near-infrared region, high sensitivity, and excellent electrical properties.
〔問題点を解決するための手段及び作用〕本発明の目的
は下記一般式(1)で示される非対称スクェアリリウム
化合物を感光材料とする電子写真感光体により達成する
ことができる。[Means and effects for solving the problems] The objects of the present invention can be achieved by an electrophotographic photoreceptor using an asymmetric square lylium compound represented by the following general formula (1) as a photosensitive material.
〇−
〇−
一般式(1)中、Arlはフェニル基、または炭素&2
1〜6の直鎖状アルキル基、水酸基、炭素数1〜4のア
ルコ午シ基、ハロゲン原子、ニトロ基、シアノ基、カル
ボ中シル基、炭素数1〜4のアルコキシカルボニル基、
もしくはトリフルオロメチル基で、4換されているフェ
ニル基を表わし、Ar2及びAr3は互(こ凹−ではな
(、それぞれフェニレン基、または水酸基、メチルシ5
、カルボキシル基、ハロゲン原子、トリフルオロメチル
基から選択される少な(とも1つの置換基で置換されて
いるフェニレン基を表わす。〇- 〇- In general formula (1), Arl is a phenyl group, or carbon &2
1 to 6 linear alkyl groups, hydroxyl groups, alkoxycarbonyl groups having 1 to 4 carbon atoms, halogen atoms, nitro groups, cyano groups, carboxyl groups, alkoxycarbonyl groups having 1 to 4 carbon atoms,
or a trifluoromethyl group, representing a phenyl group substituted with 4;
, a carboxyl group, a halogen atom, and a trifluoromethyl group (both represent a phenylene group substituted with one substituent).
前記一般式(1)で表わされたスクエアIJ IJウム
化合物の具体例を以下に構造式で示す。式中、Meはメ
チル基を表わす。Specific examples of the square IJ compound represented by the general formula (1) are shown below in terms of structural formulas. In the formula, Me represents a methyl group.
一般式(I)で示されるスクェアリリウム顔料は多層構
造を有する成子写真用感光体に使用することができる。The square aryllium pigment represented by the general formula (I) can be used in a Seiko photographic photoreceptor having a multilayer structure.
すなわち1ttr発生層及び’4M輸送層から成る二層
構造の感光層を含む電子写真用感光体1こおいて、スク
エアIJ リウム顔料を含有した電荷発生層ならびに公
知のi!電荷輸送層もうけることにより高感度でかつ帯
電性、暗減衰等の電気特性の改善された感光体を得るこ
とができる。That is, in an electrophotographic photoreceptor 1 including a photosensitive layer with a two-layer structure consisting of a 1ttr generation layer and a 4M transport layer, a charge generation layer containing a square IJium pigment and a known i! By providing a charge transport layer, it is possible to obtain a photoreceptor with high sensitivity and improved electrical properties such as chargeability and dark decay.
電荷輸送層としては、N−メチル−N−フェニルヒドラ
ジノ−3−メチリデン−9−エチルカルバゾール、p−
ジエチルアミノベンズアルデヒド−N、N’−ジフェニ
ルヒドラゾン、p−ジエチルアミノベンズアルデヒド−
N−α−ナフデルーN−フェニルヒドラゾン等のヒドラ
ゾン類、1−フェニル−3−(p−ジエチルアミノスチ
リル)−5−(p−ジエチルアミノフェニル)ピラゾリ
ン、1−〔キノリル(2) ) −3−(p−ジエチル
アミノスチリル)−5−(p−ジエチルアミノフェニル
)ピラゾリン等のピラゾリン類、2− (p−ジエチル
アミノスチリル)−6−ジニチルアsノベンズオキプゾ
ール等のオキサゾール系化合物、ビス(4−ジエチルア
ミノ−2−メチルフェニル)−フェニルメタン等のトリ
アリールメタン系化合物、 N、N’−ジフェニル−N
、N’−ビス−(3−メチルフェニル)−(1,1’−
ビフェニル〕−4,4’−ジアミン等のジアミン系化合
物をバインダー樹脂中に含有したもの、あるいはポIJ
−N−ビニルカルバゾール、ポリビニルアントラセン等
の光導1u性ポリマーが用いられる。As the charge transport layer, N-methyl-N-phenylhydrazino-3-methylidene-9-ethylcarbazole, p-
Diethylaminobenzaldehyde-N,N'-diphenylhydrazone, p-diethylaminobenzaldehyde-
Hydrazones such as N-α-nafdel-N-phenylhydrazone, 1-phenyl-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[quinolyl(2))-3-(p Pyrazolines such as -diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, oxazole compounds such as 2-(p-diethylaminostyryl)-6-dinithylaminobenzoquipzole, bis(4-diethylamino-2 -methylphenyl)-triarylmethane compounds such as phenylmethane, N,N'-diphenyl-N
, N'-bis-(3-methylphenyl)-(1,1'-
Biphenyl]-4,4'-diamine and other diamine-based compounds contained in the binder resin, or poly-IJ
-N-vinylcarbazole, polyvinylanthracene, and other light-guiding 1u polymers are used.
本発明の二層構造の電子写真用感光体の荷電について説
明すると、第1図及び第2図に示すようζこ導電性支持
体1上にスクェアリリウム顔料を含有した電荷発生層2
と電荷輸送物質を含有した1!荷輸送層3との積層体よ
り成る感光層4を設ける。電荷発生層2と電荷輪送層3
の積層順位は任意である。To explain the charging of the electrophotographic photoreceptor having a two-layer structure according to the present invention, as shown in FIGS.
and 1 containing a charge transport substance! A photosensitive layer 4 made of a laminate with a cargo transport layer 3 is provided. Charge generation layer 2 and charge transport layer 3
The stacking order of is arbitrary.
電荷発生層はスクェアリリウム顔料単独で用いても良い
が、バインダー樹脂と併用して形成することもできる。The charge generation layer may be formed by using the square lyllium pigment alone, but it can also be formed by using it in combination with a binder resin.
顔料のバインダー樹脂に対する比率はto:1il1%
〜90重量%、好ましくは10重量%〜50重量係であ
る。The ratio of pigment to binder resin is to:1il1%
90% by weight, preferably 10% to 50% by weight.
バインダー樹脂を併用せずにスクェアリリウム顔料単独
で電荷発生層を形成する方法としては溶剤2布及び真空
蒸着法がある。Methods for forming a charge generation layer using a square aryllium pigment alone without using a binder resin include a solvent 2 cloth method and a vacuum evaporation method.
電荷発生層の膜厚は0.1〜3μ好ましくは0.2〜1
μである。The thickness of the charge generation layer is 0.1 to 3 μm, preferably 0.2 to 1 μm.
μ.
バインダー中に分散させる際Iこは顔料を粉砕して用い
るが、粉砕方法は5PEX MILL、ボールミル、R
ED ogvIt (商品名)などにより公知方法を用
いることができる。When dispersing in the binder, the pigment is ground and used, but the grinding method is 5PEX MILL, ball mill, R
A known method such as ED ogvIt (trade name) can be used.
電荷発生層のバインダーとしては、それ自身が光導電性
を有していても光導電性を有していなくても良い。光導
電性を有するバインダーとシテハポリビニルカルバゾー
ル、ポリビニルカルバゾール誘導体、ポリビニルナフタ
レン、ポリビニルアントラセン、ポリビニルピレン等の
光導′iヒ性ポリマー、又はその他の′JL衛輸送能を
有する有機マ) IJラックス料などがある。The binder of the charge generation layer may or may not itself have photoconductivity. A photoconductive binder and a photoconductive polymer such as polyvinylcarbazole, polyvinylcarbazole derivatives, polyvinylnaphthalene, polyvinylanthracene, polyvinylpyrene, or other organic polymers having photoconductive transport ability, IJ lux agent, etc. be.
又、バインダーとして光導taを有さない公知の絶縁性
樹脂をも使用することができる。公知絶縁性樹脂として
は、ポリスチレン、ポリエステル、ポリビニルトリエン
、ポリビニルアニソール、ポリクロロスチレン、ポリビ
ニルブチラール、ポリビニルアセテート、ポリビニ′ル
ブチルメタクリレート、コポリスチレン−ブタジェン、
ポリサルホン、コポリスチレン−メチルメタクリレート
、ポリカーボネートなどが使用できる。Furthermore, a known insulating resin without light guide ta can also be used as the binder. Known insulating resins include polystyrene, polyester, polyvinyltriene, polyvinylanisole, polychlorostyrene, polyvinyl butyral, polyvinyl acetate, polyvinylbutyl methacrylate, copolystyrene-butadiene,
Polysulfone, copolystyrene-methyl methacrylate, polycarbonate, etc. can be used.
この際、得られる感光体の4械的強度を更に改善する目
的で一般の高分子材料と同様(こ可塑剤を用いることが
できる。可塑剤としては、例えば塩素化パラフィン、塩
素化ビフェニル、ホスフェート系可塑剤、フタレート系
可塑剤などを用いることができ、バインダーに対してO
〜10%重量添加され感光体の感度や電気特性の低下を
伴うことな(その機械的強度を更に改善することが67
Eである。At this time, in order to further improve the mechanical strength of the resulting photoreceptor, plasticizers can be used in the same way as general polymer materials. Examples of plasticizers include chlorinated paraffin, chlorinated biphenyl, and phosphate. type plasticizers, phthalate type plasticizers, etc. can be used, and O
~10% by weight is added without deteriorating the sensitivity or electrical properties of the photoreceptor (it is possible to further improve its mechanical strength).
It is E.
感光層4上に保護層あるいは感光層4と導電性支持体1
の間に中間層を入れてもよい。保護層としては、余積酸
化物を樹脂中に分散したもの、電子受容性化合物を樹脂
中に添加したものがある。中間層としては、酸化アルミ
ニウムなどの金属酸化物あるいはアクリル樹脂、フェノ
ール樹脂、ポリエステル樹脂、ポリウレタンなどがある
。A protective layer or a photosensitive layer 4 and a conductive support 1 are provided on the photosensitive layer 4.
An intermediate layer may be placed in between. The protective layer may be one in which a residual oxide is dispersed in a resin, or one in which an electron-accepting compound is added to a resin. Examples of the intermediate layer include metal oxides such as aluminum oxide, acrylic resins, phenolic resins, polyester resins, polyurethanes, and the like.
スクェアリリウム顔料を分散させたバインダーは導電性
支持体上に塗布される。塗布方法としては浸漬法、スプ
レー法、バーコーター法、アプリケータ法等の方法があ
るが、いずれの方法によっても良好な感光層を形成させ
ることができる。A binder in which square aryllium pigment is dispersed is applied onto a conductive support. Coating methods include a dipping method, a spray method, a bar coater method, and an applicator method, and a good photosensitive layer can be formed by any of these methods.
父、導電性支持体としては、金属や導電処理を施した紙
、導電層を有する高分子フィルムやガラスなどが使用で
きる。As the conductive support, metal, paper treated with conductivity, a polymer film having a conductive layer, glass, etc. can be used.
本発明の電子写真用感光体は、複写機のみならず半導体
レーザープリンターなどに広く用いることができる。The electrophotographic photoreceptor of the present invention can be widely used not only in copying machines but also in semiconductor laser printers and the like.
次に本発明を実施例1こより説明する。Next, the present invention will be explained from Example 1.
実施例1
具体例の構造式&1の化合物を1重量部−こポリエステ
ル樹脂(デュポン製、アトへツシブ49000) 1重
+&部、テトラヒドロ7ラン10重量部を加え、ボール
ミルで4時間粉砕、混合した分散液を、バーコーターを
用いてアルミニウムを蒸着したポリエステルフィルム〔
東し製、メタルミー(登録商標)〕上に塗布し、70℃
で5時間乾燥させ、膜厚1μの電荷発生層を作成した。Example 1 1 part by weight of the compound of structural formula &1 of the specific example, 1 part by weight of polyester resin (manufactured by DuPont, Atohetsusib 49000), and 10 parts by weight of tetrahydro 7 run were added, and the mixture was ground and mixed in a ball mill for 4 hours. The dispersion was coated with aluminum using a bar coater to form a polyester film [
Made by Toshi, coated on Metal Me (registered trademark) and heated at 70°C.
The mixture was dried for 5 hours to form a charge generation layer with a thickness of 1 μm.
この電荷発生層上に、N、N’−ジフェニル−N、N′
−ビス−(3−メチルフェニル)−(1,1’−ビフェ
ニル)−4,4’−ジアミン1重量部、ポリカーボネー
ト樹脂〔奇人製、パンライト(登録商標)〕11重量部
テトラヒドロフラン10重量部からなる均一@液をアプ
リケーターを用いて塗布し、70’Qで16時間乾燥さ
せて厚さ22μの電荷輸送層を形成し、感光体を作成し
た。On this charge generation layer, N,N'-diphenyl-N,N'
-Bis-(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine 1 part by weight, polycarbonate resin [manufactured by Kijin, Panlite (registered trademark)] 11 parts by weight Tetrahydrofuran 10 parts by weight A uniform @ solution was applied using an applicator and dried at 70'Q for 16 hours to form a charge transport layer with a thickness of 22 μm, thereby producing a photoreceptor.
次に静電複写紙試験装置(川口電機製、エレクトロスタ
ティック・ペーパー・アナライザー5P−428)を用
いて、−6KVのコロナ放電を施して負帯電させた後、
2秒間暗所放置し、続いてタングステンランプを用い、
表面の照度が10ルツクスになるよう昏こ感光層に光照
射を施し、その表面電位が暗所数It後の表面電位VD
の172になる露光量E1/2を求めた。その結果は初
期帯’dt電位V0=−1010’/ 、 2秒間暗所
放置後の電位vDpp: −950v %E 1/2
= 2.9ルツクス・秒、残留電位RP=OVであった
。Next, using an electrostatic copying paper testing device (manufactured by Kawaguchi Electric, Electrostatic Paper Analyzer 5P-428), a -6KV corona discharge was applied to negatively charge the paper, and then the paper was negatively charged.
Leave it in the dark for 2 seconds, then use a tungsten lamp,
The dark photosensitive layer is irradiated with light so that the surface illuminance is 10 lux, and the surface potential after the number of dark places is VD.
The exposure amount E1/2, which is 172, was determined. The results are: initial band 'dt potential V0 = -1010'/, potential after being left in the dark for 2 seconds vDpp: -950v %E 1/2
= 2.9 lux·sec, residual potential RP=OV.
また、長波長の光に対して極めてすぐれた感度を有する
ことを明らかにするため以下の測定を行なった。上記の
感光体を暗所でコロナ放電を行い帯電させた後、モノク
ロメータ−を用いて800 nm lこ分光した1μW
/−の単色光を感光体tこ照射した。そしてその表面電
位が172になるまでの時間を測り、露光量を求めた。In addition, the following measurements were performed to demonstrate that the material has extremely high sensitivity to long wavelength light. After charging the above photoconductor by performing corona discharge in a dark place, it was separated into 800 nm and 1 μW using a monochromator.
/- monochromatic light was irradiated onto the photoreceptor. Then, the time until the surface potential reached 172 was measured, and the exposure amount was determined.
その結果14.5 erg/−であった。The result was 14.5 erg/-.
実施例2〜10
実施例11こおいて41のスクェアリリウム顔料の力)
わりに表1に示すように&2.3.4.5.6.11.
12.17.19〔それぞれ実施例2〜10〕のスクェ
アリリウム顔料を用いたこと以外は実施例1と同様にし
て感光体を作成し評価した結果を表1に示す。Examples 2 to 10 (Power of square lylium pigment in Example 11 and 41)
Instead, as shown in Table 1, &2.3.4.5.6.11.
12.17.19 Photoreceptors were prepared and evaluated in the same manner as in Example 1, except that the square aryllium pigments of Examples 2 to 10 were used, and the results are shown in Table 1.
表1
〔発明の効果〕
本発明は可視域から近赤外領域にわたって分光感度を有
し、高感度で優れた電気特性を有するスクェアリリウム
化合物を含有する感光層を有する電子写真感光体を提供
したものであり、帯電性、暗減衰等の電気的特性に優れ
、複写機のみならず、半導体レーザープリンターなどに
広く用いることができる。Table 1 [Effects of the Invention] The present invention provides an electrophotographic photoreceptor having a photosensitive layer containing a square aryllium compound that has spectral sensitivity from the visible region to the near-infrared region and has high sensitivity and excellent electrical properties. It has excellent electrical properties such as chargeability and dark decay, and can be widely used not only in copying machines but also in semiconductor laser printers and the like.
第1図及び第2図は、本発明の電子写真感光体例の断面
図である。
図中符号:
1・・・導電性支持体;2・・・電荷発生層;3・・・
電荷輸送層;4・・・感光層。
第1図
第 2 図1 and 2 are cross-sectional views of examples of the electrophotographic photoreceptor of the present invention. Symbols in the figure: 1... Conductive support; 2... Charge generation layer; 3...
Charge transport layer; 4... Photosensitive layer. Figure 1 Figure 2
Claims (1)
直鎖状アルキル基、水酸基、炭素数1〜4のアルコキシ
基、ハロゲン原子、ニトロ基、シアノ基、カルボキシル
基、炭素数1〜4のアルコキシカルボニル基もしくはト
リフルオロメチル基で置換されているフェニル基を表わ
し、Ar_2及びAr_3は互に同一ではなく、それぞ
れフェニレン基、または水酸基、メチル基、カルボキシ
ル基、ハロゲン原子、トリフルオロメチル基から選択さ
れる少なくとも1つの置換基で置換されているフェニレ
ン基を表わす。〕 で示されるスクエアリリウム顔料を含有する感光層を有
することを特徴とする電子写真感光体。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, Ar_1 is a phenyl group, a linear alkyl group having 1 to 6 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms] , represents a phenyl group substituted with a halogen atom, a nitro group, a cyano group, a carboxyl group, an alkoxycarbonyl group having 1 to 4 carbon atoms, or a trifluoromethyl group, and Ar_2 and Ar_3 are not the same and each represents a phenylene group. , or a phenylene group substituted with at least one substituent selected from a hydroxyl group, a methyl group, a carboxyl group, a halogen atom, and a trifluoromethyl group. ] An electrophotographic photoreceptor characterized by having a photosensitive layer containing a squarerium pigment represented by the following.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11062186A JPS62267757A (en) | 1986-05-16 | 1986-05-16 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11062186A JPS62267757A (en) | 1986-05-16 | 1986-05-16 | Electrophotographic sensitive body |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62267757A true JPS62267757A (en) | 1987-11-20 |
JPH0513511B2 JPH0513511B2 (en) | 1993-02-22 |
Family
ID=14540431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11062186A Granted JPS62267757A (en) | 1986-05-16 | 1986-05-16 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62267757A (en) |
-
1986
- 1986-05-16 JP JP11062186A patent/JPS62267757A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPH0513511B2 (en) | 1993-02-22 |
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