Preparation method and application of TPD hole transport material with crystallization resistance

A technology of hole transport materials and anti-crystallization, which is applied in the preparation of organic compounds, preparation of amino compounds, chemical instruments and methods, etc., can solve the problems of loss of function, deterioration of device performance, etc., achieve excellent anti-crystallization, and solve the problem of device Performance deterioration or even loss of function, the effect of excellent hole transport ability

Inactive Publication Date: 2010-06-09
中船汉光科技股份有限公司
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0006] In order to overcome the shortcomings of the prior art, the present invention provides a preparation method and application of an anti-crystallization TPD hole transport material, which has excellent crystallization resistance while maintaining excellent hole transport ability, and can be well Solve the defect that the crystallization of TPD material in the organic photoconductive drum device will deteriorate the performance of the device or even lose its function

Method used

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  • Preparation method and application of TPD hole transport material with crystallization resistance
  • Preparation method and application of TPD hole transport material with crystallization resistance
  • Preparation method and application of TPD hole transport material with crystallization resistance

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Embodiment 1

[0018] Embodiment 1, the preparation method of the TPD hole transport material of the present invention is: in a mechanically stirred 500 ml three-necked bottle, put 21.7 grams (0.05 moles) of 2,2'-dimethyl-4,4'-di Toluene, 23.6 g (0.12 mol) 4,4'-dimethyldiphenylamine, 55 g (0.4 mol) potassium carbonate, 6.8 g (0.1 mol) copper powder (200-300 mesh) and 150 ml o-dichloro Benzene; under the protection of nitrogen, the mixture was heated to 180-185 ° C while stirring. After 24 hours, the reaction mixture was cooled to room temperature, 100 ml of water was added, the organic phase was separated, and then washed with 100 ml of water; the organic phase was washed with Dry magnesium sulfate over water, filter, remove o-dichlorobenzene by distillation under reduced pressure, pour into 200 ml of methanol, and stir vigorously to precipitate a precipitate; filter with suction to obtain a crude product of light yellow solid powder; dry the crude product in 100 ml of volume ratio 1:4 Recry...

Embodiment 2

[0021] Embodiment two, the TPD hole transport material of the present invention is used in the manufacture method of organic photoconductor drum is: in the ball mill tank of 500 milliliters, add 3 grams of Y-TiOPc, 2 grams of PVB, 250 milliliters of cyclohexanone and 200 milliliters of Reinforced glass beads (Φ2-3mm) were dispersed on a ball mill with a rotating speed of 180 rpm for 6 hours; the obtained CGM coating solution was coated on an aluminum drum base (diameter 24mm, length 240mm) by dip coating, 80 °C for half an hour to obtain a charge generation layer with a thickness of about 0.5 μm. Then, a solution formed by dissolving 10 grams of N-TPD-1 and 20 grams of PCZ-300 in 300 milliliters of tetrahydrofuran was coated on it, and dried at 100° C. for 1 hour after coating to obtain a charge (hole) transport with a thickness of about 15 μm. Floor.

[0022] The N-TPD-1 is replaced by N-TPD-2, N-TPD-3, m-TPD or TTPD.

[0023] The performance test and anti-crystallization i...

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Abstract

The invention relates to a preparation method and application of a TPD hole transport material with crystallization resistance. TPD compounds of the invention have the following structural formula, wherein N-TPD-1:R1=Me, and R2=4-Me; N-TPD-2:R1=H, and R2=H; and N-TPD-3:R1=H, and R2=3-Me. TPD molecules formed by using 2,2'-dimethylbenzidine segments with larger stereoscopic effect as an intermediate connecting structure can generate obvious molecular twist effect, and 2,2'-dimethyl-4,4'-diiodobiphenyl is selected to serve as a key material and reacts with a diarylamine material under the ullmann reaction condition to obtain the target product of the invention. The TPD hole transport material is used for an organic photoconductor (OPC) of a laser printer. The TPD hole transport material has excellent crystallization resistance when keeping excellent hole transporting capacity, and can well overcome the defect that when the TPD material is used in an organic photoconductor device, crystallization of the TPD material makes the performance of the device worsened even makes the functions of the device lost.

Description

technical field [0001] The invention relates to a preparation method and application of a crystallization-resistant TPD hole transport material, Background technique [0002] N, N, N', N'-tetraaryl biphenyl diamine compounds (TPD) are an important class of organic hole transport materials, and their excellent hole transport photophysical properties have been used in the field of optoelectronics. It has been recognized and widely used in electrophotography, electroluminescence and solar cells [S. Thayumanavan et al, Chemistry of Materials, 9, 3231 (1997)]. For example, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (m-TPD) as a typical hole Transmission materials have become commercial products for a wide range of applications. [0003] TPD compounds have always been used as functional materials for the charge transport layer of the organic photoconductive drum (OPC), the core device of laser printers and electrostatic copiers [P.M.Borsenberger, D.S.Weiss...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/50C07C209/10G03G5/06
Inventor 韩燕平刘双相席海涛
Owner 中船汉光科技股份有限公司
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