CN1453266A - Prepn and application of polyhydrazone as charge transfer material - Google Patents
Prepn and application of polyhydrazone as charge transfer material Download PDFInfo
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- CN1453266A CN1453266A CN 02118454 CN02118454A CN1453266A CN 1453266 A CN1453266 A CN 1453266A CN 02118454 CN02118454 CN 02118454 CN 02118454 A CN02118454 A CN 02118454A CN 1453266 A CN1453266 A CN 1453266A
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Abstract
Triphenylamine dialdehyde, trialdehyde and ethyl carbazolyl dialdehyde as material are made to react with diphenyl hydrazine, 1-naphthyl phenyl hydrazine, 2-naphthyl phenyl hydrazine and methyl phenyl hydrazine separately to obtain polyhydrazone charge transfer materials with hole transfer performance. This material has high smelting point and high stability, and is suitable for manufacturing organic photoconductive device with high stability and long service life. In addition, these compounds have triphenylamine and carbazole with excellent hole transferring performance as well as hole transferring dihydrazone and trihydrazone radical, so that they have high hole transferring performance and high mobility. The said characteristic is proved in the performance test of the photoelectronic devices.
Description
Technical field
The present invention relates to have the preparation method of the polyhydrazone charge transfer material of hole transport performance.
The invention still further relates to the application of above-mentioned materials.
Background technology
Organic photoelectrical material links together with xerography always, (U.S.Patent 2 from the '30s Carlson xerography, 221,776 (1940)) invention is to organic photoconductive material today flourish period, even if when the selenium photoconduction is risen in this world, the research of organic photoconductive material still is in active state on market.
Charge transfer material (hole or electronics) is a kind of as photoconductive material, is widely used in fields such as xerox, Laser Printing, nonlinear optics, electroluminescent, organic photoelectric pond.Compare with inorganic charge transfer material, that the organic charge transport material has is cheap, the Molecular Structure Design adjustment flexibly, can implement direct coating method fabricate devices, advantage (chemical Reviews such as preparation cost is low, environmental pollution is little and aftertreatment is easy, 1993, Vol.93, No.1).At present, in laser printer and xerographic printer core component photoconductor drum, the optical conductor more than 95% is made of organic materials.Wherein, hydrazone compounds is topmost a kind of in the charge transfer material used of present commercial organic light guide drum.Hydrazone compounds is a compounds that contains chromophoric group (C=N), and it generally is that diazotization, reduction and condensation three-step reaction by classics synthesizes.Simple and the high yield of its synthetic method makes this compounds become and is studied a more class organic light-guide material so far.
The charge transfer hydrazone class material that uses mostly is the lower single hydrazone class material of molecular weight greatly at present.The deficiency of these materials is, single hydrazone has only a charge transfer group, and transmission efficiency is not very desirable.In order to reach certain transmission efficiency, need to improve its concentration in polymers soln.Occur that organic low molecular is separated out easily like this, situation such as crystallization or reunion and influence the function (No.2, March/April 1996 for Journal ofImaging Science and Technology, Vol.40) of device; Simultaneously, material is embedded in a large amount of film-forming properties polymkeric substance, because the low molecule list hydrazone class material melting point low (is 95 degrees centigrade as DEH) of this class, the consistency of selected film-forming properties polymkeric substance and charge transfer material molecule is the problem of a key and effort when element manufacturing.In addition, it is improper to mate, and the existence of number of polymers will weaken the transmission performance of charge transfer material.On the other hand, to adopt function divergence type bilayer structure mostly be charge generation layer and charge transport layer to organic light guide drum.Charge transport layer is positioned at the outside surface of photoconductive device, directly contacts with paper, and this just need bear high-voltage charging and consequent ozone oxidation effect simultaneously, thereby charge transfer material is required harsh.The not high problem that also can influence the work-ing life of device of the wear resistance of organic low molecular, resistance to fatigue.
Summary of the invention
The fusing point that the objective of the invention is to overcome low molecule charge transfer material such as single hydrazone class is low, easily separates out, crystallization or problems such as reunion and charge transport ability relative deficiency, and proposes a kind of preparation method of polyhydrazone charge transfer material.
The preparation method of polyhydrazone charge transfer material provided by the invention, its key step is:
A) nitrosation reaction of amine: amine is dissolved in the excess ethanol solvent, and amine and alcoholic acid ratio are 1 (weight): 5-20 (volume), and it is best than being 1: 8-10.Under 15-30 ℃, optimum temps is following about 20 ℃, is stirred to its whole dissolvings.Keep solution temperature at 0-5 ℃ then, stir and slowly drip NaNO down
2The aqueous solution, the mol ratio of itself and amine is 1: 1, and concentration is 1 (weight): 20-40 (volume), and optimum concn is 1: 30.In this temperature range, continue to drip a certain amount of concentrated hydrochloric acid, NaNO afterwards
2With the ratio of concentrated hydrochloric acid be 1.5: 1-1: 1.5 (moles), best than being 1.1-1.React after 0.5-1.5 hour, filter and collect filter cake, be nitroso compound.
B) nitroso compound is reduced into hydrazine: the nitro-compound that generates is put into there-necked flask, add excess ethanol solvent and quantitative zinc powder slightly.Wherein, the ratio of zinc powder and amine is 1-8: 1 (mole), best than being 4: 1, zinc powder is divided into 2-3 adding.Control reaction temperature 10-40 ℃, the best is 25-30 ℃, stirs a following Glacial acetic acid, and the ratio of itself and zinc powder is 2-1 (volume): 1 (weight).Back collection filtrate reacts completely.
C) hydrazine and aldehyde are condensed into hydrazone: aldehyde (molar ratio of itself and amine is 1-4: 1, best than being 2: 1) is dissolved in the alcohol solvent, obtains the saturated solution of aldehyde.Under 10-60 ℃, optimum temps is 20-40 ℃, is added drop-wise in the hydrazine solution.Reaction finishes the back and collects filter cake, obtains the synthetic hydrazone of wanting.
Aldehydes raw material involved in the present invention comprises: triphenylamine dialdehyde, three aldehyde, ethyl carbazole dialdehyde.
Solvent involved in the present invention comprises: polar solvent and non-polar solvent, and comprising acetone, methyl alcohol, ethanol etc. are generally non-polar solvent methyl alcohol, ethanol, and the most frequently used is ethanol.
Organic amine compound involved in the present invention comprises: N, N-diethylamide, N-methyl P-nethoxyaniline, N-ethyl P-nethoxyaniline, N-methyl are multiple to monomethylaniline etc. to monomethylaniline, N-ethyl.
Hydrazine class raw material involved in the present invention is: pentanoic, 1-naphthalene aniline, 2-naphthalene aniline or monomethylaniline.
Polyhydrazone charge transfer material provided by the invention is applied on photoconductor drum and the solar cell.
Description of drawings
Fig. 1 is the photoconductive property test curve of ethyl carbazole dialdehyde-2-naphthalene aniline hydrazone.
Embodiment
Embodiment 1: have at 500ml and add the 23.8g pentanoic in the there-necked flask of thermometer and dropping funnel, add 270ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 9g NaNO
2The aqueous solution that is made into.Afterwards, drip the 20ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.
Filter cake is joined the another there-necked flask, and add 35.6g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir and slowly drip the 60ml Glacial acetic acid down at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again triphenylamine dialdehyde 4.7g is dissolved in ethanol, is added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains triphenylamine dialdehyde pentanoic hydrazone.
Embodiment 2: have at 500ml and add 0.79gl-naphthalene aniline in the there-necked flask of thermometer and dropping funnel, add 50ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 0.25g NaNO
2The aqueous solution that is made into.Afterwards, drip the 0.56ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.
Filter cake is joined the another there-necked flask, and add 1.08g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir and slowly drip the 1.67ml Glacial acetic acid down at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again triphenylamine three aldehyde 0.1g are dissolved in ethanol, are added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains triphenylamine three aldehyde-1-naphthalene aniline hydrazone.
Embodiment 3: have at 500ml and add the 0.61g pentanoic in the there-necked flask of thermometer and dropping funnel, add 40ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 0.25g NaNO
2The aqueous solution that is made into.Afterwards, drip the 0.56ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.Filter cake is joined the another there-necked flask, and add 1.08g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir and slowly drip the 1.67ml Glacial acetic acid down at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again triphenylamine three aldehyde 0.1g are dissolved in ethanol, are added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains triphenylamine three aldehyde pentanoic hydrazones.
Embodiment 4: have at 500ml and add the 3.1g pentanoic in the there-necked flask of thermometer and dropping funnel, add 100ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 1.24g NaNO
2The aqueous solution that is made into.Afterwards, drip the 2.76ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.
Filter cake is joined the another there-necked flask, and add 5.38g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir and slowly drip the 8.3ml Glacial acetic acid down at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again ethyl carbazole dialdehyde 0.5g is dissolved in ethanol, is added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains ethyl carbazole dialdehyde pentanoic hydrazone.
Embodiment 5: have at 500ml and add 3.94g1-naphthalene aniline in the there-necked flask of thermometer and dropping funnel, add 100ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 0.7g NaNO
2The aqueous solution that is made into.Afterwards, drip the 1.6ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.
Filter cake is joined the another there-necked flask, and add 3.3g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir down and slow Dropwise 5 .0ml Glacial acetic acid at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again ethyl carbazole dialdehyde 0.3g is dissolved in ethanol, is added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains ethyl carbazole dialdehyde-1-naphthalene aniline hydrazone.
Embodiment 6: have at 500ml and add 3.94g2-naphthalene aniline in the there-necked flask of thermometer and dropping funnel, add 100ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 0.7g NaNO
2The aqueous solution that is made into.Afterwards, drip the 1.6ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.
Filter cake is joined the another there-necked flask, and add 3.3g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir down and slow Dropwise 5 .0ml Glacial acetic acid at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again ethyl carbazole dialdehyde 0.3g is dissolved in ethanol, is added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains ethyl carbazole dialdehyde-2-naphthalene aniline hydrazone.
Embodiment 7: have at 500ml and add the 0.39g monomethylaniline in the there-necked flask of thermometer and dropping funnel, add 40ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 0.25g NaNO
2The aqueous solution that is made into.Afterwards, drip the 0.56ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.
Filter cake is joined the another there-necked flask, and add 1.08g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir and slowly drip the 1.67ml Glacial acetic acid down at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again triphenylamine three aldehyde 0.1g are dissolved in ethanol, are added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains triphenylamine three aldehyde monomethylaniline hydrazones.
Embodiment 8: have at 500ml and add 0.79g2-naphthalene aniline in the there-necked flask of thermometer and dropping funnel, add 50ml ethanol, stirring at room is to its whole dissolvings.Place there-necked flask ice bath to be cooled to 0-5 ℃ then, under stirring condition, slowly drip 0.25g NaNO
2The aqueous solution that is made into.Afterwards, drip the 0.56ml concentrated hydrochloric acid.Continued stirring reaction 1 hour, and filtered and collect filter cake.
Filter cake is joined the another there-necked flask, and add 1.08g zinc powder (dividing secondary to add) and a certain amount of ethanol.Stir and slowly drip the 1.67ml Glacial acetic acid down at 20-25 ℃.Drip off the back and continue reaction 1 hour.Filter out filtrate, and transfer in the there-necked flask of original use.Again triphenylamine three aldehyde 0.1g are dissolved in ethanol, are added drop-wise in the hydrazine solution, reaction is 2 hours about 30 ℃.Reaction finishes after-filtration and collects filter cake, obtains triphenylamine three aldehyde-2-naphthalene aniline hydrazone.
The polyhydrazone charge transfer material stability excellence of the present invention's preparation is suitable for the application such as devices such as organic photoconductor electroluminescence (organic light guide drum) and organic solar batteries.
Fig. 1 that the present invention provides is to be the photoconductive property test curve of example with ethyl carbazole dialdehyde-2-naphthalene aniline hydrazone, and the photoconduction test is carried out on ETA8200 type electrostatic analyzer, and light source is 24V, and the 5W incandescent light is by the visible light of colour filter intercepting 780nm.Photoconductor surface fills negative electricity, and the charger charging voltage is-5.5KV.V in the table
0Be that surface-charged receives voltage, V
rBe the residual voltage behind the exposure 10s, R
dBe dark-decay speed, the intensity I of light source is 51ux, E
1/2(=T
1/2* be that surface voltage decays to the required energy of a half, wherein T I)
1/2Surface voltage decays to the required time of a half when being illumination.
Table 1 that the present invention provides and table 2 have been enumerated the characteristic of the polyhydrazone charge transfer material that several the present invention of utilization prepare.
Table 1: second-order transition temperature and fusing point
Material glass transition temperature (Tg) fusing point (Tm)
75 ℃ 242 ℃ of triphenylamine three aldehyde pentanoic hydrazones
Triphenylamine three aldehyde-152 ℃ of * of 1-naphthalene aniline hydrazone
Triphenylamine three aldehyde-155 ℃ of * of 2-naphthalene aniline hydrazone
90 ℃ 256 ℃ of triphenylamine three aldehyde monomethylaniline hydrazones
85 ℃ 142 ℃ of ethyl carbazole dialdehyde pentanoic hydrazones
Ethyl carbazole dialdehyde-95 ℃ of * of 1-naphthalene aniline hydrazone
Ethyl carbazole dialdehyde-120 ℃ of * of 2-naphthalene aniline hydrazone
80 ℃ 231 ℃ of ethyl carbazole dialdehyde monomethylaniline hydrazones wherein
*Material is an amorphous structure, no fusing point.
Table 2: photoconductive property
The sensitivity of material charging voltage rest potential dark-decay speed
(V) (V) (V/sec) (luxsec) triphenylamine three aldehyde diphenylamines hydrazone-665-30 60 1.0253 triphenylamines three aldehyde-1-naphthalene aniline hydrazone-849-35 70 0.4210 triphenylamines three aldehyde-2-naphthalene aniline hydrazone-513-39 70 0.3941 triphenylamines three aldehyde methylaniline hydrazone-750-39 88 1.1839 ethyl carbazole dialdehyde diphenylamines hydrazone-783-193 89 5.8125 ethyl carbazole dialdehydes-1-naphthalene aniline hydrazone-691-87 85 0.8917 ethyl carbazole dialdehydes-2-naphthalene aniline hydrazone-707-15 140 0.3452 ethyl carbazole dialdehyde methylaniline hydrazone-1000 * * **Bad light
Claims (7)
1, each method of a kind of system of polyhydrazone charge transfer material, its key step is:
A) nitrosation reaction of amine: amine is dissolved in the excess ethanol solvent, and amine and alcoholic acid ratio are 1 (weight): 5-20 (volume), under 15-30 ℃, are stirred to its whole dissolvings; Keep solution temperature at 0-5 ℃ then, stir and slowly drip NaNO down
2The aqueous solution, the mol ratio of itself and amine is 1: 1, concentration is 1 (weight): 20-40 (volume), continues to drip a certain amount of concentrated hydrochloric acid, NaNO afterwards in this temperature range
2With the ratio of concentrated hydrochloric acid be 1.5: 1-1: 1.5 (moles), react after 0.5-1.5 hour, filter to collect filter cake, be nitroso compound;
B) nitroso compound is reduced into hydrazine: the nitro-compound that generates is put into there-necked flask, add excess ethanol solvent and quantitative zinc powder slightly; Wherein, the ratio of zinc powder and amine is 1-8: 1 (mole), and control reaction temperature 10-40 ℃, stir a following Glacial acetic acid, the ratio of itself and zinc powder is 2-1 (volume): 1 (weight); Back collection filtrate reacts completely;
C) hydrazine and aldehyde are condensed into hydrazone: aldehyde is dissolved in the alcohol solvent, and the molar ratio of aldehyde and amine is 1-4: 1, obtain the saturated solution of aldehyde; Under 10-60 ℃, be added drop-wise in the hydrazine solution; React and collect filter cake after 0.5-8 hour, obtain the synthetic hydrazone of wanting;
Aldehydes raw material described in the above-mentioned steps is: triphenylamine dialdehyde, three aldehyde or ethyl carbazole dialdehyde;
Described hydrazine class raw material is: pentanoic, 1-naphthalene aniline, 2-naphthalene aniline or monomethylaniline;
Described solvent is: acetone, methyl alcohol or ethanol;
Described organic amine compound is: N, N-diethylamide, N-methyl P-nethoxyaniline, N-ethyl P-nethoxyaniline, N-methyl to monomethylaniline or N-ethyl to monomethylaniline.
2, the method for claim 1 is characterized in that, amine and alcoholic acid ratio are 1 in the step (a): 8-10; Solvent temperature is 20 ℃, NaNO
2With the concentration of amine be 1: 30; NaNO
2With the ratio of concentrated hydrochloric acid be 1.1-1: 1.
3, the method for claim 1 is characterized in that, the ratio of zinc powder and amine is 4: 1 (mole) in the step (b); Temperature of reaction is 25-30 ℃.
4, the method for claim 1 is characterized in that, the mol ratio of aldehyde and amine is 2: 1 in the step (c); Dropping temperature is 20-40 ℃.
5, the method for claim 1 is characterized in that, zinc powder adds for dividing 2-3 time in the step (b).
6, the method for claim 1 is characterized in that, the condensation reaction time of hydrazine and aldehyde is 1-2 hour in the step (c).
7, make the application of polyhydrazone charge transfer material on photoconductor drum and solar cell of each by claim 1.
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| CN 02118454 CN1453266A (en) | 2002-04-24 | 2002-04-24 | Prepn and application of polyhydrazone as charge transfer material |
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| CN 02118454 CN1453266A (en) | 2002-04-24 | 2002-04-24 | Prepn and application of polyhydrazone as charge transfer material |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015528836A (en) * | 2012-07-04 | 2015-10-01 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Organic dyes containing hydrazone moieties and their use in dye-sensitized solar cells |
| CN105272879A (en) * | 2014-06-27 | 2016-01-27 | 京瓷办公信息系统株式会社 | Hydrazone derivative of triphenylamine and electrophotographic photosensitive member |
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2002
- 2002-04-24 CN CN 02118454 patent/CN1453266A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015528836A (en) * | 2012-07-04 | 2015-10-01 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Organic dyes containing hydrazone moieties and their use in dye-sensitized solar cells |
| CN105272879A (en) * | 2014-06-27 | 2016-01-27 | 京瓷办公信息系统株式会社 | Hydrazone derivative of triphenylamine and electrophotographic photosensitive member |
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