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EP0102745A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Triarylmethane compounds, their preparation and use as photoconductive systems

Assignee: 3M Co
•
Filing: 1983-07-28
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Granted: —
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Expires: 2003-07-28
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Abstract

Abstract Compounds which are useful as sensitisers of photoconductors, having the general formula: in which: like symbols represent identical substituents, at least 4 of R 1 to R 9 represent hydrogen atoms and the remaining R 1 to R 9 pairs of groups independently represent: (i) hydrogen, an alkyl group having from 1 to 18 carbon atoms, a substituted alkyl group or an aryl or substituted aryl group, (ii) a halogen atom, a cyano group, a carboxy or alkoxycarbonyl group, a hydroxy group, an alkoxy group, a nitro group or a sulphonic acid group, providing that not more than two such groups (ii) are present in each ring, (iii) an acylamino group, a secondary acylamino group, or a tertiary amino group, in which the pendant substituent groups on the nitrogen atom are alkyl, aryl or aralkyl, providing not more than two sush groups (iii) may be present in each benzocarbazole ring, and (iv) any two groups R 1 to R 9 on adjacent carbon atoms in a ring may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, R 10 represents an alkyl or substituted alkyl group, an aralkyl group, or an aryl or substituted aryl group, Ar represents a heteroaromatic nucleus eontaining 5 or 6 members in the ring at least one of which is O, N or S, or an aromatic ring of the formula: in which: R 11 to R 16 independently represent a hydrogen or halogen atom, an alkyl or substituted alkyl, an aryl or substituted aryl, hydroxy, alkoxy or aryloxy group, one of R" to R 15 may additionally represent an aldehyde or acetyl group or a dialkylamino group, up to two of R" to R 15 may additionally represent a cyano, carboxy, alkoxy carbonyl, sulphonic acid or nitro group, and any two adjacent R" to R 15 groups may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, and X represents an anion.

Inventors

  • 👤 David Edgar Brown
  • 👤 Kenneth Reynolds

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-26 19:50
CPC Classifications
C; C09; C09B; C09B11/00; C09B11/04; C09B11/26; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0622; G03G5/0644; G03G5/0661

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 322 words
A compound of the general formula: in which: like symbols represent identical substituents, at least 4 of R 1 to R 9 represent hydrogen atoms and the remaining R 1 to R 9 pairs of groups independently represent: (i) hydrogen, an alkyl group having from 1 to 18 carbon atoms, a substituted alkyl group or an aryl or substituted aryl group, (ii) a halogen atom, a cyano group, a carboxy or alkoxycarbonyl group, a hydroxy group, an alkoxy group, a nitro group or a sulphonic. acid group, providing that not more than two such groups (ii) are present in each ring, (iii) an acylamino group, a secondary acylamino group, or a tertiary amino group, in which the pendant substituent groups on the nitrogen atom are alkyl, aryl or aralkyl, providing not more than two such groups (iii) may be present in each benzocarbazole ring, and (iv) any two groups R1 to R 9 on adjacent carbon atoms in a ring may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, R 10 represents an alkyl or substituted alkyl group, an aralkyl group, or an aryl or substituted aryl group, Ar represents a heteroaromatic nucleus containing 5 or 6 members in the ring at least one of which is 0, N or S, or an aromatic ring of the formula: in which: R 11 to R 15 independently represent a hydrogen or halogen atom, an alkyl or substituted alkyl, an aryl or substituted aryl, hydroxy, alkoxy or aryloxy group, one of R 11 to R 15 may additionally represent an aldehyde or acetyl group or a dialkylamino group, up to two of R 11 to R 15 may additionally represent a cyano, carboxy, alkoxy carbonyl, sulphonic acid or nitro group, and any two adjacent R 11 to R 15 groups may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, and X represents an anion.
Claim 2
Dependent Claim 322 words
A compound of the general formula: in which: like symbols represent identical substituents, at least 4 of R 1 to R 9 represent hydrogen atoms and the remaining R 1 to R 9 pairs of groups independently represent: (i) hydrogen, an alkyl group having from 1 to 18 carbon atoms, a substituted alkyl group or an aryl or substituted aryl group, (ii) a halogen atom, a cyano group, a carboxy or alkoxycarbonyl group, a hydroxy group, an alkoxy group, a nitro group or a sulphonic. acid group, providing that not more than two such groups (ii) are present in each ring, (iii) an acylamino group, a secondary acylamino group, or a tertiary amino group, in which the pendant substituent groups on the nitrogen atom are alkyl, aryl or aralkyl, providing not more than two such groups (iii) may be present in each benzocarbazole ring, and (iv) any two groups R1 to R 9 on adjacent carbon atoms in a ring may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, R 10 represents an alkyl or substituted alkyl group, an aralkyl group, or an aryl or substituted aryl group, Ar represents a heteroaromatic nucleus containing 5 or 6 members in the ring at least one of which is 0, N or S, or an aromatic ring of the formula: in which: R 11 to R 15 independently represent a hydrogen or halogen atom, an alkyl or substituted alkyl, an aryl or substituted aryl, hydroxy, alkoxy or aryloxy group, one of R 11 to R 15 may additionally represent an aldehyde or acetyl group or a dialkylamino group, up to two of R 11 to R 15 may additionally represent a cyano, carboxy, alkoxy carbonyl, sulphonic acid or nitro group, and any two adjacent R 11 to R 15 groups may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, and X represents an anion.
Claim 3
Dependent Claim 17 words
A compound as claimed in Claim 1, characterised in that X represents chloride, bromide or trifluoromethane sulphonate.
Claim 4
Dependent Claim 15 words
A compound as claimed in Claim 1, characterised in that X represents tetrafluoroborate or perchlorate.
Claim 5
Dependent Claim 23 words
A compound as claimed in any one of Claims 1 to 3, characterised in that R 1 to R 9 are each hydrogen.
Claim 6
Dependent Claim 15 words
A compound as claimed in any preceding claim, characterised in that R 10 is ethyl.
Claim 7
Dependent Claim 22 words
A compound as claimed in any preceding claim, characterised in that at least three of R 11 to R 15 are hydrogen.
Claim 8
Dependent Claim 19 words
A compound as claimed in any preceding claim, characterised in that R 13 is dialkylamino, alkoxy or N0 2.
Claim 9
Dependent Claim 63 words
A method of preparing a dye as claimed in Claim 1, characterised in that bis(benzo[a]carbazol-5-yl)aryl methane is converted to the desired compound in accordance with the reaction scheme: in which R 1 to R 10 and Ar are as defined in Claim 1, by oxidation utilising lead tetraacetate in the presence of acetic acid and/or trifluoroacetic acid or by photolysis in chloroform solution.
Claim 10
Dependent Claim 55 words
A photosensitive element comprising a support, the surface of which is electrically conducting or is made electrically conductive by the provision of a conductive layer, the electrically conductive surface having coated thereon a photosensitive layer comprising a photoconductive material and as a sensitiser a compound as claimed in any one of Claims 1 to 7.
Claim 11
Dependent Claim 32 words
A photosensitive element as claimed in Claim 9, characterised in that said compound is present in an effective sensitising amount in the range of 0.01 to 10% by weight of photosensitive layer.
Claim 12
Dependent Claim 21 words
A photosensitive element as claimed in Claim 9 or Claim 10, characterised in that the photosensitive layer comprises a bis(benzo[a]carbazol-5-yl)aryl methane.
Claim 13
Dependent Claim 18 words
A photosensitive element as claimed in Claim 11, characterised in that the photosensitive layer comprises a bis(benzo[a]carbazol-5-yl)phenyl methane.

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