CN101963767B - Method for preparing single-layer electropositive organic photoconductor drum - Google Patents
Method for preparing single-layer electropositive organic photoconductor drum Download PDFInfo
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- 239000002356 single layer Substances 0.000 title abstract 3
- 239000000463 material Substances 0.000 claims abstract description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011248 coating agent Substances 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000003618 dip coating Methods 0.000 claims abstract description 4
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 4
- 239000004417 polycarbonate Substances 0.000 claims abstract description 4
- 238000006482 condensation reaction Methods 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 3
- 238000005691 oxidative coupling reaction Methods 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 239000004411 aluminium Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000001819 mass spectrum Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000001228 spectrum Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- YACSIMLPPDISOJ-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-(3-methylphenyl)-n-phenylaniline Chemical class CC1=CC=CC(C=2C(=CC=C(NC=3C=CC=CC=3)C=2)C=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 YACSIMLPPDISOJ-UHFFFAOYSA-N 0.000 claims description 3
- GBQZGEGKNCBKLE-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N)C=C1 Chemical class FC1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N)C=C1 GBQZGEGKNCBKLE-UHFFFAOYSA-N 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 abstract description 17
- 239000000243 solution Substances 0.000 abstract 3
- QKZFBFSFZILINR-UHFFFAOYSA-N 3-methyl-N-[4-[4-(N-(3-methylphenyl)anilino)phenyl]phenyl]-N-phenylaniline Chemical compound CC=1C=C(C=CC1)N(C1=CC=C(C=C1)C1=CC=C(N(C2=CC=CC=C2)C2=CC(=CC=C2)C)C=C1)C1=CC=CC=C1.CC=1C=C(C=CC1)N(C1=CC=C(C=C1)C1=CC=C(N(C2=CC=CC=C2)C2=CC(=CC=C2)C)C=C1)C1=CC=CC=C1 QKZFBFSFZILINR-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 230000005525 hole transport Effects 0.000 abstract 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 1
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Abstract
The invention relates to a method for preparing a single-layer organic photoconductor drum. The method comprises the following steps of: (1) preparing an electronic transport material: performing hydroformylation on triphenylamine or 4-fluoro triphenylamine serving as an initiative material, performing condensation reaction on the initiative material and malononitrile, and performing oxidative coupling reaction on the initiative material and ferric chloride to obtain a target product, namely the electronic transport material; and (2) preparing a photoconductor drum: dissolving polycarbonate into tetrahydrofuran to obtain film forming agent solution, mixing X-type metal-free phthalocyanine, TPD-FCN, N-50 and the film forming agent solution, uniformly dispersing the mixed solution to prepare coating solution, forming a coated layer on the surface of an anode alumina substrate by a dip coating method, and drying the coated layer to obtain the single-layer organic photoconductor drum, wherein the X-type metal-free phthalocyanine is used as a charge generation material, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl -4,4'-diamine is used as a hole transport material, and the TPD-FCN is used as the electronic transport material.
Description
Technical field
The present invention relates to a kind of preparation method of organic light guide drum.
Background technology
Organic light guide drum is to apply the organic light-guide material layer and form [K.Y.Law on the aluminium base pipe of electric conductivity, Chemical Reviews, 93,449-486 (1993)], it can be described below based on the course of work of electrophotographic image forming principle: organic light guide drum in the dark is an insulator, can make its surface reach certain potentials (practicality requires the negative electricity or the positive electricity of 600-800V current potential) by corona charging or contact charging; When the light (as 780nm laser) with suitable wavelength shines, it is right that the light-guide material layer will produce the positive and negative charge of hole-electronics, and then the plus or minus charge transfer is arrived surperficial, neutralize the negative or positive on original surface, the electric charge of illumination part does not keep, and so just forms electrostatic latent image on the organic light guide drum surface; Through charged toner develop, transfer printing ink powder picture and text to paper, the hot pressing photographic fixing, finish printing interval one time.So go round and begin again, printer/duplicating machine carries out printing work continuously.
The electricity conversion that it is found that organic photoconductor is very low, is difficult to reach the practicability requirement.Studies show that, organic photoelectrical material is different from inorganic semiconductor material, it can not have good quantity of photogenerated charge simultaneously and produce ability and charge transport ability, and it is unisexuality on charge transfer, promptly it can not be side by side can transmission electronic again can transporting holes.These factors cause the organic photoconductor molecule to be subjected to the electron-hole pair that optical excitation produces can not separated effectively and transmission, thereby recombine into the neutral molecule inactivation easily, so its overall charge carrier photoproduction efficient low (showing as the electricity conversion of poor efficiency).In order to address this problem, later people are born the charge generation function and the charge transfer functional separation of organic photoconductor respectively by different organic photoelectrical materials., the electricity conversion that makes organic photoconductor like this reaches degree of being practical but increasing substantially, develop thus that by charge generation layer (CGL) and charge transport layer (CTL) double-decker be the function divergence type organic photoconductor [P.M.Borsenberger of main type, D.S.Weiss, OrganicPhotoreceptors for Xerography, Marcel Dekker, New York, 1998].In the organic light guide drum preparation of practicality; in order to take into account the needs of other performance (as electric charge hold facility, adhesiveness between layers, wearing quality etc.); usually also will add other coating, so general utility functions divergence type organic light guide drum should be the sandwich construction of two-layer above coating.
In principle, photoconductor drum takes negative charging or positive charging modes can realize the electrophotographic image forming purpose.The function divergence type organic light guide drum that generally adopts has the general tactic pattern of aluminium base-charge generation layer-hole transmission layer (for electronegativity OPC) or aluminium base-charge generation layer-electron transfer layer (for electropositivity OPC) at present.(dissolubility, with film-forming resin compatibility) is good more than electron transport material (ETM) because functional (transfer rate) and the practicality of hole mobile material (HTM), the design of HTM molecule is synthetic in addition also has more means and approach than ETM molecule, therefore in the past few decades, the charge transport materials of a large amount of development and application is HTM[Y.Shirota, Journal of Materials Chemistry, 10,1-25 (2000); P.Strohriegl et al., Advanced Materials, 14,1439-1452 (2002)], electronegative in the market sandwich construction OPC accounts for the absolute status more than 90%.Also be because the extensive availability of hole mobile material, people are once when development electropositivity OPC, be not to use ETM according to Al base-CGL-ETL tactic pattern, prepare electropositive sandwich construction OPC[US Patents 5733696,7115346B2 and 7491989B2 but utilize electronegativity function divergence type OPC material to reverse mode (promptly becoming Al base-HTL-CGL structural order) fully] by Al base-CGL-HTL structural order by coating cleverly.
In the manufacturing process of sandwich construction OPC, each functional layer need be applied on the aluminium drum base one by one by step-by-step process and (will be coated with at least 2 times); Thickness of each layer and uniformity requirement are very high, otherwise will have a strong impact on the performance of photoconductor drum.Generally speaking, the preparation of sandwich construction OPC exist that operation is long, process conditions are complicated, difficult, relatively low, the improved place of the more high needs of total cost of production efficiency of high finished product rate control.Exist possible ozone (charging process generations) to pollute when in addition, using negative charge organic optical drum and to the problems such as development instability of bi-component toner (present main toner type).
Summary of the invention:
In order to overcome the shortcoming of prior art, the invention provides a kind of preparation method of individual layer electropositivity organic light guide drum, its technology is simple, the efficient height, cost is low.
The present invention includes the following step: (1), preparation electron transport material-TPD-FCN or TPD-CN: with triphenylamine or 4-fluorine triphenylamine is initiation material, after its hydroformylation, by with the condensation reaction of third dicyan, with the ferric trichloride oxidative coupling reaction, can obtain target product electron transport material-TPD-FCN or TPD-CN; (2), preparation photoconductor drum: use polycarbonate (PCZ-300) to be dissolved in tetrahydrofuran (THF) and obtain film forming agent solution, with X-type metal-free phthalocyanine is charge generating material, with N, N '-two (3-tolyl)-N, N '-diphenyl-1,1 '-biphenyl-4,4 '-diamines (trade name N-50) is a hole mobile material, is electron transport material with TPD-FCN (or TPD-CN); Step is: 1. X-type metal-free phthalocyanine, TPD-FCN or TPD-CN, N-50 and film forming agent solution are mixed in the ratio of mass ratio 1: 2-10: 5-15: 100-250; 2. mixed liquor is uniformly dispersed with ultrasound wave or bowl mill, makes coating fluid; 3. in the dip-coating mode, form coat, promptly obtain the individual layer organic light guide drum after the oven dry at the anodised aluminium primary surface.
The characterization data of described TPD-FCN or TPD-CN is: N, N '-two [p-(1,1-dicyano vinyl) phenyl]-N, N '-two (p-fluorophenyl)-1,1 '-biphenyl-4,4 '-diamines (TPD-FCN): red solid powder, 228 ℃ of fusing points; Hydrogen spectrum (DMSO-d
6, 400MHz) δ 8.23 (s, 2H), 7.84 (d, 4H, J=8.9Hz), 7.74 (d, 4H, J=8.4Hz), 7.39-7.27 (m, 12H), 6.90 (d, 4H, J=8.9Hz); Mass spectrum (EI): m/z676 (M
+, 100%); Ultimate analysis [C
44H
26F
2N
6]: theoretical value C, 78.09; H, 3.87; N, 12.42; F, 5.61. measured value C, 77.69; H, 3.88; N, 12.35; F, 5.56; N, N '-two [p-(1,1-dicyano vinyl) phenyl]-N, N '-diphenyl-1,1 '-biphenyl-4,4 '-diamines (TPD-CN): orange solids powder, 227 ℃ of fusing points; Hydrogen spectrum (CDCl
3, 400MHz) δ 7.76 (d, 4H, J=8.8Hz), 7.57 (d, 4H, J=8.2Hz), 7.53 (s, 2H), 7.41 (t, 4H, J=7.7Hz), 7.30-7.20 (m, 10H), 7.01 (d, 4H, J=8.9Hz); Mass spectrum (EI): m/z 640 (M
+, 100%); Ultimate analysis [C
44H
28N
6]: theoretical value C, 82.48; H, 4.40; N, 13.12. measured value C, 82.05; H, 4.41; N, 13.03.
Described step (2) the 3. bake out temperature in step is 60-90 ℃, and drying time is 1-3 hour; The thickness of coat is 5-20 μ m.
Technology of the present invention is simple, the efficient height, and cost is low.
Embodiment
Embodiment 1: polycarbonate (PCZ-300) is dissolved in THF, and to make mass percentage concentration be 10% film forming agent solution; Get the PCZ-300 solution of 200 grams 10%, add 6 gram X-type metal-free phthalocyanines, be uniformly dispersed with bowl mill; Other gets the PCZ-300 solution of 300 grams 10%, adds 12 gram TPD-FCN and 32 gram N-50, stirring and dissolving; Two parts solution is merged, stir, obtain coating fluid; Adopt the dip-coating mode, coating fluid be applied to the aluminium base surface of Φ 24 * L250mm, dry after 1.5 hours, promptly obtain photoconductive layer thickness and be 15-20 μ m's but layer organic light guide drum.The photoelectric properties parameter sees Table 1.
Embodiment 2: except that replacing the TPD-FCN with electron transport material TPD-CN, all steps are identical with embodiment 1.The photoelectric properties parameter sees Table 1.
Comparative Examples 1: except that not using electron transport material TPD-FCN or TPD-CN, all steps are identical with embodiment 1.The photoelectric properties parameter sees Table 1.
The individual layer electropositivity organic light guide drum photoelectric properties parameter list that table 1. the present invention relates to
The present invention is specified by above instantiation.It is pointed out that in spirit of the present invention and the scope stated, can make many variations and modification.Therefore, above-mentioned specific embodiment is not to be used to limit the present invention.
Claims (3)
1. the preparation method of an individual layer electropositivity organic light guide drum, it is characterized in that: comprise the following steps: (1), preparation electron transport material-TPD-FCN or TPD-CN: with triphenylamine or 4-fluorine triphenylamine is initiation material, after its hydroformylation, by with the condensation reaction of third dicyan, with the ferric trichloride oxidative coupling reaction, can obtain target product electron transport material-TPD-FCN or TPD-CN; (2), preparation photoconductor drum: use polycarbonate to be dissolved in tetrahydrofuran and obtain film forming agent solution, with X-type metal-free phthalocyanine is charge generating material, with N, N '-two (3-tolyl)-N, N '-diphenyl-1,1 '-biphenyl-4,4 '-diamines are hole mobile material, are electron transport material with TPD-FCN or TPD-CN; Step is: 1. with X-type metal-free phthalocyanine, TPD-FCN or TPD-CN, N, and N '-two (3-tolyl)-N, N '-diphenyl-1,1 '-biphenyl-4,4 '-diamines and film forming agent solution mix in the ratio of mass ratio 1: 2-10: 5-15: 100-250; 2. mixed liquor is uniformly dispersed with ultrasound wave or bowl mill, makes coating fluid; 3. in the dip-coating mode, form coat, promptly obtain the individual layer organic light guide drum after the oven dry at the anodised aluminium primary surface.
2. the preparation method of individual layer electropositivity organic light guide drum according to claim 1, it is characterized in that: the characterization data of described TPD-FCN or TPD-CN is: N, [p-(1 for N '-two, 1-dicyano vinyl) phenyl]-N, N '-two (p-fluorophenyl)-1,1 '-biphenyl-4,4 '-diamines (TPD-FCN): red solid powder, 228 ℃ of fusing points; Hydrogen spectrum (DMSO-d
6, 400MHz) δ 8.23 (s, 2H), 7.84 (d, 4H, J=8.9Hz), 7.74 (d, 4H, J=8.4Hz), 7.39-7.27 (m, 12H), 6.90 (d, 4H, J=8.9Hz); Mass spectrum (EI): m/z676 (M
+, 100%); Ultimate analysis [C
44H
26F
2N
6]: theoretical value C, 78.09; H, 3.87; N, 12.42; F, 5.61. measured value C, 77.69; H, 3.88; N, 12.35; F, 5.56; N, N '-two [p-(1,1-dicyano vinyl) phenyl]-N, N '-diphenyl-1,1 '-biphenyl-4,4 '-diamines (TPD-CN): orange solids powder, 227 ℃ of fusing points; Hydrogen spectrum (CDCl
3, 400MHz) δ 7.76 (d, 4H, J=8.8Hz), 7.57 (d, 4H, J=8.2Hz), 7.53 (s, 2H), 7.41 (t, 4H, J=7.7Hz), 7.30-7.20 (m, 10H), 7.01 (d, 4H, J=8.9Hz); Mass spectrum (EI): m/z 640 (M
+, 100%); Ultimate analysis [C
44H
28N
6]: theoretical value C, 82.48; H, 4.40; N, 13.12. measured value C, 82.05; H, 4.41; N, 13.03.
3. the preparation method of individual layer electropositivity organic light guide drum according to claim 1 is characterized in that: described step (2) the 3. bake out temperature in step is 60-90 ℃, and drying time is 1-3 hour; The thickness of coat is 5-20 μ m.
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| CN107357145B (en) * | 2017-08-24 | 2020-12-18 | 中船重工汉光科技股份有限公司 | Electronegative single-layer organic photoconductor drum and preparation method thereof |
| CN113238463B (en) * | 2021-04-29 | 2022-11-11 | 广东乐普泰新材料科技有限公司 | Preparation method of single-layer electronegative organic photosensitive drum |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1144343A (en) * | 1995-05-11 | 1997-03-05 | 中国科学院化学研究所 | Organic light guide drum for laser printer and its manufacturing method |
| CN1400508A (en) * | 2001-08-08 | 2003-03-05 | 中国科学院化学研究所 | Production method of single-layer organic photocon |
| CN1911897A (en) * | 2006-08-23 | 2007-02-14 | 邯郸光导重工高技术有限公司 | Method of synthesizing TPD kind photoelectric material |
| CN1912750A (en) * | 2006-08-23 | 2007-02-14 | 邯郸光导重工高技术有限公司 | Preparation method of positive charge organic optical drum |
| CN101723838A (en) * | 2009-11-26 | 2010-06-09 | 国营汉光机械厂 | Preparation method and application of TPD hole transport material with crystallization resistance |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08113726A (en) * | 1994-10-17 | 1996-05-07 | Hitachi Ltd | Oxomolybdenum phthalocyanine compound and electrophotographic receptor produced by using the compound |
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- 2010-09-03 CN CN2010102716836A patent/CN101963767B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1144343A (en) * | 1995-05-11 | 1997-03-05 | 中国科学院化学研究所 | Organic light guide drum for laser printer and its manufacturing method |
| CN1400508A (en) * | 2001-08-08 | 2003-03-05 | 中国科学院化学研究所 | Production method of single-layer organic photocon |
| CN1911897A (en) * | 2006-08-23 | 2007-02-14 | 邯郸光导重工高技术有限公司 | Method of synthesizing TPD kind photoelectric material |
| CN1912750A (en) * | 2006-08-23 | 2007-02-14 | 邯郸光导重工高技术有限公司 | Preparation method of positive charge organic optical drum |
| CN101723838A (en) * | 2009-11-26 | 2010-06-09 | 国营汉光机械厂 | Preparation method and application of TPD hole transport material with crystallization resistance |
Non-Patent Citations (1)
| Title |
|---|
| Xingbo Cao.etc.Undoped, red organic light-emitting diodes based on a N,N,N’,N’-tetraphenylbenzidine (TPD) derivative as red emitter witha triphenylamine derivative as hole-transporting layer.《Dyes and Pigments》.2010,第84卷(第2期),203-207. * |
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