# US 4,394,428 A · Photoconductive composition and elements comprising two different compounds having a dioxaborin nucleas on a derivative thereof

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- Number: US 4,394,428 A
- Document ID: US4394428A
- Status: Granted
- Kind: A
- Application number: 06/305,257
- Filed: 1981-09-24
- Granted: 1983-07-19
- Earliest claimed: 1981-09-24
- Assignees: Eastman Kodak Company
- Inventors: James A. Van Allan; Jerome H. Perlstein; George A. Reynolds; Thomas E. Goliber
- Web page: https://patentgrep.com/patent/US4394428A

## CPC

- G03G 5/064: {containing three hetero atoms}
- G03G 5/062: {containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen}
- G03G 5/067: {containing hetero rings}
- Y10S 430/10: Donor-acceptor complex photoconductor
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Photoconductive compositions having improved quantum efficiency are disclosed. The compositions comprise: (a) an electron donating photoconductor; and sensitizing amounts of (b) a first electron acceptor selected from cyanine and styryl methine dyes having a 1,3,2-dioxaborin nucleus and (c) a second electron acceptor selected from methine-free compounds having a nucleus selected from the group consisting of 1,3,2-dioxaborin; 1,3,2-oxazoborin and 1,3,2-diazoborins.

## Claims

### Claim 1

A photoconductive element comprising a support and a layer of a photoconductor composition comprising:
(a) an electron donating photoconductor; and sensitizing amounts of
(b) a first electron acceptor selected from cyanine and styryl methine dyes having a 1,3,2-dioxaborin nucleus and
(c) a second electron acceptor selected from methine-free compounds having a nucleus selected from the group consisting of 1,3,2-dioxaborin; 1,3,2-oxazoborin and 1,3,2-diazoborins.

### Claim 2

A photoconductive element comprising a support and a photoconductor composition comprising:
(a) an electron donor comprising a triarylamine component and sensitizing amounts of
(b) a first electron acceptor having a structure selected from the group consisting of: ##STR50## wherein: R.sub.1 and R.sub.2 each independently represents hydrogen, alkyl, aryl or taken together with the carbon atom to which they are attached form a fused mono- or polynuclear carbocyclic group having 6 to 10 carbon atoms or a fused heterocyclic group selected from pyran-4-one, thiopyran-4-one, thiophene and furane;
A.sub.1 represents substituted aminoaryl, alkylamino, julolylidine or aryl;
A.sub.2 represents a nitrogen-containing heterocyclic nucleus;
(c) a second electron acceptor selected from the group consisting of: ##STR51## wherein: R.sub.3, R.sub.4 and R.sub.5 each independently represents hydrogen, hydroxy, alkyl, aryl, furyl, alkoxy, thienyl or trihaloalkyl, or
R.sub.3 and R.sub.4 or R.sub.4 and R.sub.5, taken together with the carbon atoms to which they are attached represent fused thiopyran, or a mono- or polynuclear carbocyclic group having 6 to 10 carbon atoms;
R.sub.7 represents the atoms necessary to form a member selected from the group consisting of pyran, thiopyran and benzopyran;
Y.sub.1 and Y.sub.2 represent fluoro or
Y.sub.1 and Y.sub.2 taken together with B form a 1,3,2-dioxaborin nucleus;
Z represents O, and ##STR52## wherein R.sub.6 represents aryl or R.sub.6 together with ##STR53## represents a fused benzothiazolene nucleus.

### Claim 3 (depends on 2)

An element as in claim 2 wherein
R.sub.1 and R.sub.2 each independently represents hydrogen, phenyl, furyl, thienyl, trifluoromethyl, or taken together with the carbon atoms to which they are attached form a fused nucleus selected from the group consisting of naphthyl, pyranone, benzothiazole, tropylium, thiopyrylium and flavylium;
A.sub.1 represents a nucleus selected from the group consisting of julolidine, phenyl, phenylmethoxycarbonylamino, methoxyphenyl, dimethylaminophenyl, diethylaminophenyl and dimethylamino;
A.sub.2 represents a nucleus selected from the group consisting of benzoazole and benzothiazole;
R.sub.3, R.sub.4 and R.sub.5 each independently represents methyl, methoxy, phenyl, hydroxyphenyl, ethylphenyl, methylphenyl, nitrophenyl, dimethylaminophenyl, cyanophenyl, methoxyphenyl, furyl, thienyl or trifluoromethyl; or
R.sub.3 and R.sub.4 or R.sub.4 and R.sub.5, taken together with the carbon atom to which they are attached, form a fused substituent selected from the group consisting of phenyl, naphthyl and hydroxy naphthyl;
Y.sub.1 and Y.sub.2 represent fluro or taken together form a dioxaborin nucleus.

### Claim 4

A photoconductive element comprising a support and a photoconductor composition comprising:
(a) tri-p-tolylamine as the electron donor and a sensitizing amount of
(b) as a first electron acceptor a dye selected from the group of dyes disclosed in Table II herein, and
(c) as a second electron acceptor a compound selected from the group consisting of (1,3-diphenyl-1,3-propanedioato-0,0')difluoroboron and (1-trifluoromethyl-3-phenyl-1,3-propanedioato-0,0')difluoroboron.

### Claim 5

A method of enhancing the quantum efficiency of electron donating photoconductive compositions comprising the step of adding a sensitizing amount of an electron accepting sensitizer characterized in that the sensitizer is a combination of
(a) a first electron acceptor selected from cyanine and styryl methine dyes having a 1,3,2-dioxaborin nucleus and
(b) a second electron acceptor selected from methine-free compounds having a nucleus selected from the group consisting of 1,3,2-dioxaborin; 1,3,2-oxazoborin and 1,3,2-diazoborins.