CN1632700A - Azo/phthalocyanine composite single layer organic photoconductor and preparing method therefor - Google Patents
Azo/phthalocyanine composite single layer organic photoconductor and preparing method therefor Download PDFInfo
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- CN1632700A CN1632700A CN 200410084570 CN200410084570A CN1632700A CN 1632700 A CN1632700 A CN 1632700A CN 200410084570 CN200410084570 CN 200410084570 CN 200410084570 A CN200410084570 A CN 200410084570A CN 1632700 A CN1632700 A CN 1632700A
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- phthalocyanine
- azo
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- oxazolyl
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Abstract
This invention is a wide-frequency vibration and high light sensitive azo or phthalocyanine compound single layer organic photoelectricity conductor and its process method, which belongs to organic photoelectricity conductor technique field. The material mainly adopts charge carrier generation material and charge carrier transmission material and resin and conductive base material with certain proportion to form organic photoelectricity coating liquid and adopts the dipping and coating method. And the charge carrier generation material is the compound material of oxazolyl bisazo or metal phthalocyanine and the charge carrier transmission material adopts compounds of triaryl amine and hydrazone compound, and pyrazoline compound.
Description
Technical field
The invention belongs to the organic photoconductor technical field, be specifically related to azo/phthalocyanine composite single layer organic photoconductor of a kind of wideband response and better photosensitivity and preparation method thereof.
Background technology
Organic photoconductor is " heart " parts that can form the electric photographic imaging of photo-generated carrier and migration under the optical excitation.At present, the output of the annual organic photoconductor in the whole world has more than one hundred million, has produced huge economic benefit and social benefit.But also exist many problems to solve.
In order to obtain high luminous sensitivity and long-life organic photoconductor, it is compound that organic photo-generated carrier material that traditional photoconductor employing is single and organic charge carrier transferring material carry out stratiform, the double-decker organic photoconductor of composition function divergence type.Because repeatedly coating, complex manufacturing technology, control difficulty are big and cost is higher.If carrier generation materials and carrier mobility material are combined with each other, make the single-organic photoconductive body, not only technology simple, do not have the splitting problem, can reduce the generation of ozone, and the quantum efficiency and the photoconductive property that will significantly improve photoconductive material of combining closely between photoproduction material and transferring material.Therefore,, simplify production technology, improve the quality, reduce cost for the standardization of organic photoconductor product; Simultaneously, also in order to satisfy the needs that a drum is used more, overcome the incompatible limitation of photoconductor of present xerox and laser printing, be necessary to produce that a kind of (400nm～1000nm) has the single-organic photoconductive body of good wideband response and better photosensitivity near infrared wavelength region at visible light.
The most critical factor that influences the organic photoconductor performance is a carrier generation materials.And phthalocyanine and azo are the maximum carrier generation materials of present industrial use.Chinese invention patent (88100214.3 88100213.5) discloses first and has adopted the phthalocyanine compound to prepare the method for double-deck organic photoconductor, opened up the new way for preparing organic photoconductor with the compound new method of material blend, at visible region and near-infrared region whether good spectral response is not arranged but relate to such phthalocyanine blended complex as yet, and structure is the problem of the organic photoconductor of individual layer.Chinese invention patent (00131902.7) discloses a kind of phthalocyanine/phthalocyanine composite single layer organic photoconductor and preparation method, but phthalocyanine only has good spectral response in near-infrared region, so it is the laser printer of light source that this organic composite photoelectric conductor is only applicable to the near-infrared laser, also is difficult to satisfy the needs of wideband response.Chinese invention patent (97113319.0) adopts individual layer and the double-deck organic photoconductor of azo/phthalocyanine blended complex as charge carrier photoproduction material preparation, though it all has good spectral response at visible light near infrared range, the photosensitivity of single layer structure photoconductor is still well below double-deck photoconductor.
Summary of the invention
The purpose of this invention is to provide azo/phthalocyanine composite single layer photoconductor of a kind of wideband response and better photosensitivity and preparation method thereof.
The azo of wideband response provided by the invention and better photosensitivity/phthalocyanine composite single layer organic photoconductor mainly is made up of carrier generation materials, carrier transmission material, resin and conductive matrices, wherein:
(1) chemical structural formula of carrier generation materials Shi oxazolyl bisdiazo/metal phthalocyanine composite material ， oxazolyl bisdiazo and metal phthalocyanine is respectively:
Wherein, R
1, R
2Can be C
1～C
12Aliphatic group, C
1～C
12Alkoxy, halogen radical, hydroxyl, nitro, carboxylic acid group etc.; M can be copper, cobalt, nickel, aluminium, oxygen titanium or vanadyl etc.
(2) carrier transmission material is triaryl amine, hydrazone class, pyrazolines, triarylmethane class or tetraphenyl diphenyl amine compound.
(3) its composition weight share is counted:
Oxazolyl bisdiazo 1-5 part
Metal phthalocyanine 1-5 part
Carrier transmission material 80-300 part
Resin 100-300 part
Organic solvent 100-300 part
Adjuvant 0.1-0.5
The preparation method of the azo of above-mentioned wideband response and better photosensitivity/phthalocyanine composite single layer organic photoconductor is as follows:
(1) azo/phthalocyanine blended complex, resin and carrier transmission material are pressed the usage ratio dispersed with stirring in organic solvent, the solid content that makes solution is 10～50% (weight), promptly gets the organic photoconductive masking liquid;
(2) adopt dip coating that organic photoconductive solution is coated on the conductive matrices, its coating speed is 4.0～7.0mm/s, and coating fluid viscosity is at 300～500cp, and bake out temperature is 80～120 ℃, drying time is 3.5 hours, and dry organic photoconductive coat thickness is 15～45 μ m.
Characteristics of the present invention are that the introducing of: ① oxazolyl has improved disazo dissolubility Shi De oxazolyl bisdiazo and in common solvent such as tetrahydrofuran, toluene, methenyl choloride or dioxane etc. good dispersiveness arranged also, thereby have increased the composite effect between it and metal phthalocyanine and the carrier transmission material; 2. from electronic structure, the disazo conjugated degree height of oxazolyl, electron delocalization are strong, and both are easier to be compound for azo/phthalocyanine, and very high photoproduction efficient can be arranged in theory, thereby obtain higher photoconduction performance; 3. for obtain more can preferentially selecting on better photosensitivity Neng De oxazolyl bisdiazo/disazo acid amides aromatic ring of metal phthalocyanine composite photoelectric conductor ， oxazolyl electron-withdrawing power stronger-Cl or-NO
2Substituting group; 4. the quantity of photogenerated charge effect between You Yu oxazolyl bisdiazo/metal phthalocyanine compound and the cavity type carrier transmission material further strengthens, and promotes the right separation in light induced electron/hole, has improved the photosensitive property of photoconductor.
Sharp prepare the compound organic photoconductor of individual layer as carrier generation materials, can adopt solution dip-coating preparation technology, have that technology is simple, efficient is high, cost is low and alleviate characteristics such as environmental pollution with oxazolyl bisdiazo/metal phthalocyanine compound.The compound organic photoconductor of the individual layer of making has advantages such as wideband effect and better photosensitivity, and both can be used for the visible light is the Xerox of light source, and also can be used for the near-infrared laser is the laser printer of light source.
Description of drawings
The sem photograph of figure 1 Shi oxazolyl bisdiazo/TiOPc composite single layer optical conductor.
The uv-visible absorption spectroscopy of figure 2 Shi oxazolyl bisdiazo/TiOPc compounds.
Fig. 3 is based on the variation with optical source wavelength of Chun oxazolyl bisdiazo, pure TiOPc He the photosensitivity of the individual layer photoconductor of oxazolyl bisdiazo/TiOPc compound.
Embodiment
Shang Shu oxazolyl bisdiazo/metal phthalocyanine blended complex, its preparation method is at normal temperatures with azo and two kinds of materials of phthalocyanine, after purified, the dried, with 0.1～9.9: 9.9～0.1 weight ratio solubilizer grinding and mixing 4～12 hours in sand mill or bowl mill, after grinding end, filter, drying makes azo/phthalocyanine blended complex.Used carrier transmission material is triaryl amine, hydrazone class, pyrazolines, triarylmethane class and tetraphenyl diphenyl amine compound.Used solvent, be tetrahydrofuran, dioxane, toluene, dimethylbenzene, butanone, cyclohexanone, methylene chloride, methenyl choloride, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, N, dinethylformamide or N,N-dimethylacetamide, or the mixed solvent of above-mentioned any two kinds of solvent compositions.Used resin is the multipolymer or the polyvinyl acetate resins of polycarbonate, polyvinyl butyral, polystyrene, polymethylmethacrylate, Polyvinylchloride, Vingon, polyacrylonitrile, vinylidene chloride-polyacrylonitrile.Used conductive matrices, be conduction sheet metal, ito glass or above scribble the polyester sheet of conducting medium, or drum type, banded conducting metal and electrical conductivity alloy.Adopt dip coating that this organic photoconductive solution is coated on the conductive matrices, its coating speed is 4.0～7.0mm/s, and coating fluid viscosity is at 300～500cp, and bake out temperature is 80～120 ℃, drying time is 3.5 hours, and dry organic photoconductive coat thickness is 15～45 μ m.
The present invention will be described in detail below in conjunction with embodiment.Unless stated otherwise, given photoconductive property data all obtain on the GDT-II light guide test instrument of test center of Zhejiang University development, and monochromatic light obtains with color filter, and intensity of illumination is 30 μ w.
Chemical structural formula is respectively:
De oxazolyl bisdiazo and TiOPc (wherein, R
1=OH, R
2=Cl M=TiO), mixes with the ratio of 1: 1 (by wt.), adds tetrahydrofuran and sand milling medium, and at room temperature sand milling is 6 hours, steams solvent ， De oxazolyl bisdiazo and TiOPc compound.Jiang oxazolyl bisdiazo/TiOPc compound, N, N '-diethyl-4-aminobenzaldehyde-1-phenyl-1 '-Alpha-Naphthyl hydrazone (α-naphthalene phenylhydrazone) and polycarbonate in dioxane, promptly get the organic photoconductive masking liquid with the ratio dispersed with stirring of 1: 75: 82 (weight ratio).Adopt dip coating above-mentioned masking liquid of coating on aluminium alloy drum base, its coating speed is 5.5mm/s, and coating fluid viscosity is at 450cp, and bake out temperature is 90 ℃, and drying time is 3.5 hours, and dry organic photoconductive coat thickness is 30 μ m.
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 2
Identical with embodiment 1, the ratio of Dan Shi oxazolyl bisdiazo/TiOPc compound, α-naphthalene phenylhydrazone and polycarbonate becomes 1: 70: 76 (weight ratio).
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 3
Identical with embodiment 1, the ratio of Dan Shi oxazolyl bisdiazo/TiOPc compound, α-naphthalene phenylhydrazone and polycarbonate becomes 1: 80: 80 (weight ratio).
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 4
Identical with embodiment 1, the ratio of Dan Shi oxazolyl bisdiazo/TiOPc compound, α-naphthalene phenylhydrazone and polycarbonate becomes 1: 68: 68 (weight ratio).
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 5
Identical with embodiment 1, the ratio of Dan Shi oxazolyl bisdiazo/TiOPc compound, α-naphthalene phenylhydrazone and polycarbonate becomes 1: 80: 90 (weight ratio).
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 6
Identical with embodiment 1, the ratio of Dan Shi oxazolyl bisdiazo/TiOPc compound, α-naphthalene phenylhydrazone and polycarbonate becomes 1: 60: 60 (weight ratio).
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 7
Identical with embodiment 1, the ratio of Dan Shi oxazolyl bisdiazo/TiOPc compound, α-naphthalene phenylhydrazone and polycarbonate becomes 1: 90: 100 (weight ratio).
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 8
Identical with embodiment 1, but R
1=OCH
3, R
2=C
5H
6
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 9
Identical with embodiment 1, but R
1=NO
2, R
2=CN.
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 10
Identical with embodiment 1, but R
1=COOH, R
2=NH
2
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 11
Identical with embodiment 1, but α-naphthalene phenylhydrazone becomes N, N '-diethyl-4-aminobenzaldehyde-1,1 '-diphenyl hydrazone (α-diphenyl hydrazone)
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Embodiment 12
Identical with embodiment 1, but α-naphthalene phenylhydrazone becomes α-naphthalene phenylhydrazone/trinitro-fluorenone (100/1, weight ratio) compound.
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Comparing embodiment 1
With chemical structural formula be:
De oxazolyl bisdiazo adds tetrahydrofuran and sand milling medium, and at room temperature sand milling is 4～8 hours, steams solvent ， De oxazolyl bisdiazo disperse particles.Jiang oxazolyl bisdiazo disperse particles, α-naphthalene phenylhydrazone, polycarbonate with the ratio dispersed with stirring of 1: 75: 82 (weight ratio) in dioxane, promptly get the organic photoconductive masking liquid.Adopt dip coating above-mentioned masking liquid of coating on aluminium alloy drum base, its coating speed is 5.5mm/s, and coating fluid viscosity is at 450cp, and bake out temperature is 90 ℃, and drying time is 3.5 hours, and dry organic photoconductive coat thickness is 30 μ m.
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
Comparing embodiment 2
With chemical structural formula be:
TiOPc add tetrahydrofuran and sand milling medium, at room temperature sand milling is 4～8 hours, steams solvent, the TiOPc disperse particles.With TiOPc disperse particles, α-naphthalene phenylhydrazone, polycarbonate with the ratio dispersed with stirring of 1: 75: 82 (weight ratio) in dioxane, promptly get the organic photoconductive masking liquid.Adopt dip coating above-mentioned masking liquid of coating on aluminium alloy drum base, its coating speed is 5.5mm/s, and coating fluid viscosity is at 450cp, and bake out temperature is 90 ℃, and drying time is 3.5 hours, and dry organic photoconductive coat thickness is 30 μ m.
The photoconductive data of the organic composite photoelectric conductor of this individual layer are as shown in table 1.
The photoconductive data of the organic composite photoelectric conductor of table 1 individual layer
Photosensitivity S
(luxs) -1Charging potential dark-decay rest potential
λ＝ λ＝ λ＝ λ＝ (V) (V/s) (V)
454nm 570nm 679nm 76nm
Embodiment 2 0.175 0.33 0.55 0.90 756 28 25
Embodiment 3 0.167 0.303 0.513 0.88 751 31 45
Embodiment 4 0.152 0.303 0.476 0.87 673 38 55
Embodiment 5 0.15 0.279 0.44 0.87 733 42 56
Embodiment 6 0.147 0.238 0.42 0.85 616 48 44
Embodiment 7 0.175 0.279 0.42 0.84 628 51 62
Embodiment 8 0.15 0.238 0.44 0.84 658 46 68
Embodiment 9 0.201 0.624 0.666 1.19 622 26 44
Embodiment 10 0.147 0.303 0.44 0.87 700 51 60
Embodiment 11 0.14 0.25 0.333 0.84 596 46 77
Embodiment 12 0.196 0.48 0.55 1.11 714 19 22
Relatively implement 0.126 0.225 0.15 0.11 647 40 63
Example 1
Relatively implement 0.12 0.20 0.33 0.833 752 44 34
Example 2
Claims (6)
1, the azo of a kind of wideband response and better photosensitivity/phthalocyanine composite single layer organic photoconductor is characterized in that mainly being made up of carrier generation materials, carrier transmission material, resin and conductive matrices, wherein:
(1) chemical structural formula of carrier generation materials Shi oxazolyl bisdiazo/metal phthalocyanine composite material ， oxazolyl bisdiazo and metal phthalocyanine is respectively:
Wherein, R
1, R
2Be C
1～C
12Aliphatic group, C
1～C
12Alkoxy, halogen radical, hydroxyl, nitro or carboxylic acid group; M is copper, cobalt, nickel, aluminium, oxygen titanium or vanadyl;
(2) carrier transmission material is triaryl amine, hydrazone class, pyrazolines, triarylmethane class or tetraphenyl diphenyl amine compound;
(3) it forms the weight share meter:
Oxazolyl bisdiazo 1-5 part
Metal phthalocyanine 1-5 part
Carrier transmission material 80-300 part
Resin 80-300 part
Organic solvent 80-300 part
Adjuvant 0.1-0.5 part
2, the azo of wideband response according to claim 1 and better photosensitivity/phthalocyanine composite single layer organic photoconductor, it is characterized in that said resin, is the multipolymer or the polyvinyl acetate resins of polycarbonate, polyvinyl butyral, polystyrene, polymethylmethacrylate, Polyvinylchloride, Vingon, polyacrylonitrile, vinylidene chloride-polyacrylonitrile.
3, the azo of wideband response according to claim 1 and better photosensitivity/phthalocyanine composite single layer organic photoconductor, it is characterized in that said solvent, be tetrahydrofuran, dioxane, toluene, dimethylbenzene, butanone, cyclohexanone, methylene chloride, methenyl choloride, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, N, dinethylformamide, N, N-dimethyl acetamide a kind of, or the mixed solvent of above-mentioned any two kinds of solvent compositions.
4. the azo of wideband response according to claim 1 and better photosensitivity/phthalocyanine composite single layer organic photoconductor, it is characterized in that said conductive matrices, be conduction sheet metal, ito glass or above scribble the polyester sheet of conducting medium, or drum type, banded conducting metal or electrical conductivity alloy.
5, the preparation method of the azo of a kind of wideband response as claimed in claim 1 and better photosensitivity/phthalocyanine composite single layer organic photoconductor is characterized in that concrete steps are:
(1) azo/phthalocyanine blended complex, resin and carrier transmission material are pressed the usage ratio dispersed with stirring in organic solvent, the solid content of solution is 10～50% by weight, promptly gets the organic photoconductive masking liquid;
(2) adopt dip coating that organic photoconductive solution is coated on the conductive matrices, its coating speed is 4.0～7.0mm/s, and coating fluid viscosity is at 300～500cp, and bake out temperature is 80～120 ℃, drying time is 3.5 hours, and dry organic photoconductive coat thickness is 15～45 μ m.
6, the preparation method of the azo of wideband response according to claim 5 and better photosensitivity/phthalocyanine composite single layer organic photoconductor, it is characterized in that: said azo/phthalocyanine blended complex, its preparation method is at normal temperatures with azo and two kinds of materials of phthalocyanine, after purified, the dried, with 0.1～9.9: 9.9～0.1 weight ratio solubilizer grinding and mixing 4～12 hours in sand mill or bowl mill, after grinding end, filter, drying makes azo/phthalocyanine blended complex.
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| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10029988B2 (en) | 2013-03-15 | 2018-07-24 | Biomarin Pharmaceutical Inc. | HDAC inhibitors |
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| JPS5643643A (en) * | 1979-09-19 | 1981-04-22 | Hitachi Ltd | Composite type electrophotographic plate |
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| EP0743561B1 (en) * | 1995-05-17 | 2001-02-28 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
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| CN1056453C (en) * | 1997-06-05 | 2000-09-13 | 浙江大学 | Method for prepn. of broadband response organic photoelectric conductor |
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| TWI504686B (en) * | 2010-01-15 | 2015-10-21 | Fujifilm Corp | Pigment dispersion composition, colored curable composition, color filter for solid-state image sensor and method of producing the same, and solid-state image sensor |
| US9908899B2 (en) | 2011-02-28 | 2018-03-06 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
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| US10029988B2 (en) | 2013-03-15 | 2018-07-24 | Biomarin Pharmaceutical Inc. | HDAC inhibitors |
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