SU1013897A1 - Electrophotographic material - Google Patents

Abstract

ELECTROPHOTOGRAPHIC MATERIAL, consisting of a conductive substrate and a polymer photosensitive composition containing an organic semiconductor made of poly Epoxypropylcarbazole and a sensitizer, differing from the fact that, in order to obtain a uniform sensitivity of the material in the range of 400-600 nm, it tetrafluoroborate pyrils of the general formula OSgND S .k. where R, R, i- N, OCH) Cs N, OCHs,, C-fcHs-, taken in an amount of 0.1-1.0 mole percent per poly-n-epoxypropylcarbazole unit .. oo 00 co

Description

The invention relates to the production of electrophotographic material and can be used in the field of the chemical-photographic industry, namely electrophotography. An electrophotographic material is known that consists of a conductive substrate and a polymer photosensitive composition containing an organic semiconductor poly-n-vinylcarbazole (PVC) and a 2,4,7-trinitrofluorone (TNF) sensitizer. The disadvantage of this material is that the layers of such a polymer the compositions are stiff and exhibit poor adhesion to the metal substrate. An electrophotographic material is also known, consisting of an electrically conductive substrate and an organic semiconductor layer of poly-epoxy propylcarbazole (PEPC) with a sensitizer, an organic dye (auramine, rhodamine, eosin, etc., 0.1-1.0 mol.%) or electron-withdrawing substance (chloranil, dinitrofluorenone, trinitrofluorenone, 1 ~ 100 mol.%). This material has properties and adhesion of semiconductors better than the composition based on C23 PVC. However, the known material has a photographic sensitivity in the visible region of the spectrum and the content of trinitrofluorenone 10 mol,% per PEPC link reaches a value of b-SW, and, therefore, does not meet all the requirements of modern recording and display equipment. Most closely related to the invention, the composition is an electrophotographic material H 3 consisting of an electrically conductive substrate and a photosensitive layer deposited on it containing PEPC and a triarylpyryl torus tetrafluoroborate sensitization of the general formula. The aim of the invention is to obtain a uniform photosensitivity of the material in the region of 400 600 nm. This goal is achieved by the fact that in an electrophotographic material consisting of an electrically conductive substrate and a photosensitive layer, the electrophotographic material as a sensitizer contains derivatives of tetrafluoroborate pyrillyl of the general formula where X R, R, RA H, ocHj, R3 H, OCH, OC5H5,. The proposed sensitizers (1) are not described in the literature, however, they were synthesized according to the general procedure for the preparation of styryl dyes by the interaction of 2,4-di (p-ethoxyphenyl) -b-methyl-pyri-tetrafluoroborate. poured benzaldehyde with acetic anhydride. The precipitate is filtered off, washed with ether, dried on. the air. The yield of tetraftrrborate 2,4-di- (p-ethoxyphenyl) -b- (l-methoxy-thyridine) -pyril or 8.1 g (75.5%) after recrystallization from acetic acid, yield 7.6 g (70.8% ). M.p. 224-225 "x-4450, 530 nm (in СН2Се2); Е„ „6, 4.4" 10 l / mol cm. Found,%: C 66.8; H 5.3. C3 (, Н29ВР404) Calculated,%: С 66.7; H 5.4. Example 2. The reaction with a wire is analogous to example 1, but instead of an andealdehyde, take 2.3 g of benzo dehyd. 7.2 g is obtained (66.6 %) tetra fluoroborate 2,4-di- (p-ethoxyphenyl) -styrylpyryl. After recrystallization from acetic acid, yield of 5.6 g (52.2%). mp. 248-250 ° C; Lts | x 450 them (c) -, 5x ao4 l / mol cm. Found,%: C 68.3; H 5.4; with dNgtVrts Lz Calculated,%: Qs 6: 8, 2; H 5, 5. Example of charger Reaction wire is similar Example 1, but instead of the Ivanic aldehyde, 3.3 g of y-ethoxybenzaldehyde are taken. 8 (72.2%) of 2,4-di- (p-ethoxyphenyl) -6- (p-ethoxystyryl) tetrafluoroborate are obtained. After recrystallization from acetic acid, yield 7 g (63, T: brl. 222-224 ° C; Lnp (v. 50, 535 nm (s); En, ax6., 3,3104, 3.8-10 10 l / mol cm. Found,%: C 67.1; H 5.5; .. Calculated,%: p. 67.1; H 5.6. antshozhichno example 1, but instead of an aldehyde take 3.65 g of faithful aldehyde. Get 8.8 g (77.5%) of 2,4-di- (P-ethoxyphenyl) -6- (m, p-dimethoxystyryl tetrafluorobrrate) ) -piril. After recrystallization from acetic acid, yield 7.85 (69.1%). M.p. 237-238 ° C; Dto1,455,545 named after (c); 5.7.10, 4.5 10 l / mol cm. Found:%: C 65.2; H 5.3. calculated,%: C 65.3; H 5.4. Example 5. The reaction wire is the same as in Example 1, but instead of anna aldehyde, 3.65 g of 2.4 dimethoxybenzaldehyde is taken. 2.4- (p-ethoxyphenyl) -6- (o, p-dimethoxystyryl) -pyryl are obtained .9.5 g (83.2%) of tetrafluoroborate. After recrystallization from acetic acid, yody: 8.4 g (74.1%). M.p. 187-189 ° C; Lto (445, 555 nm (in СН "СЮ"); E., 4 хY-, 2.0-104 l / mol. See Found,%: C 65.5; H 5.4; C, H3. Calculated ,: C, 65.3; H, 5.4. Example 6. The reaction is carried out analogously to example 1, but instead of anisic aldehyde, 4 g of ti -bayylbenzaldehyde is taken, 9.67 g (82.5%) of tetrafluoroborate 2,4-di are obtained - (p-ethoxyphenyl) -6- (p-phenyl styryl) -pyrily. After double crystallization from acetic acid, yield 8/23: g (70.2%). mp. 180-182 ° C .; Ltpah455, 510 nm (c; 6, 4.410 - l / mol sy. Found,%: C 71.4; H 5.2. CedIz of BP Oz Calculated,%: C 71.2; H 5.3. Example 7. The reaction is carried out as in example 1, but instead of anise aldehyde take 4.1 g 4-m toxi-1-naphthaldehyde. 8.4 g (71.3%) of 2,4-di- (p-ethoxyphenyl) -6- (4-methoxy-naphtholidene) -pyryl tetrafluoroborate are obtained: After recrystallization from acetic acid twice, the yield is 7.15 g (60.6%). So pl. 254255 C; L „ax460, 580 nm (in Сh ce); 6-3.9-Ut l / mol cm. Found: C: 69.0; H 5.3 Cz Ne BP404 Calculated: C 69.1; H 5.3: From the compounds obtained, electrophotographic material is prepared in the usual way. As control samples, photosensitive layers sensitized with tetrafluoroborate 2, 6-diphenyl-4- (n-anisyl) pyrite were examined. Watering of the photosensitive composition was carried out on aluminum substrates of mm size. Photosensitive compositions are watered from a mixture of toluene and acetonitrile (3: 1. By volume). At 18 C. The resulting layers are dried in the presence of saturated solvent vapors for 3 hours, and then dried for 6 hours at. The thickness of the photosensitive layer is 8-1 microns. Samples are charged to the corbator with a negative corona up to 225i25 V. Photosensitivity to the incandescent lamp and monochromatic light is determined from the half-decay of the potential. Photoelectric test results. The sensitivity of the PEPC layers sensitized by the proposed pyrile tetrafluoroborate derivatives is shown in the table below.

tetrafluorbo () at

Table continuation

Table continuation

Table continuation

Also

1.0

2,4-Di- (P-ethoxyphenyl) -6- (h-phenylstyrene) pyrillium tetrafluoroborate

1.0

Also

15.0

15.0

11.0

7.8

43.0

14.0

2,4-di- (p-ethoxy phenyl) -6- (4-methoxy-naphtholidene) -pyrillium tetrafluoroborate

1.0

Also

0.1

2,6-Diphenyl-4- (h-aniline hyperylium

tetrafluoroborate

Table continuation

1.0 .. 7.0

Also

The above tests allow us to conclude that the proposed materials have a higher electrophotographic sensitivity compared to materials based on PEPK sensitized with a 2,6-diphenyl-4- (p-anisyl) pyril-ayloborate. .

On the basis of the results of the Testing Research Institute, it was established that the material for the continuation of the table

540

0.93

0.63 560 580

0.51,600

0.28

7/18

6.0 400 420

7.94

10.78 440

12.43 460

11.22 480 500

9.60

6.23 5.21 4.46 3.24 2.49

new PEPC sensitized with the proposed pyrillum salts, unlike the material based on PEPC sensitized with tetrafluoroborate 2,6-diphenyl-4- (p-anisyl) -pyril, has a uniform sensitivity in the 400.-600 nm range and can be used for write information on. modern microfilm equipment.

Claims (1)

ELECTROPHOTOGRAPHIC MATERIAL, consisting of a conductive substrate and a polymer photosensitive composition containing an organic semiconductor of poly-Nepoxypropylcarbazole and a sensitizer, distinguished by the fact that, in order to obtain uniform sensitivity of the material in the region of 400-600 nm, sensitizer it contains derivatives of tetrafluoroborates. pyrilium of the general formula. where R, R ₁ , R ₂ = n, DOS ₃ ; R ₃ = H, OCH ₃ , OS ₄ H ₅ , C, _L H5-, taken in an amount of 0.1-1.0 molar percent, calculated on the link of poly-I-epoxypropylcarbazole., Sae ζ © 10'13897