US 5,965,063 A · Charge transporting material and method of preparing charge transporting particulates used therein

A charge transporting material comprising charge transporting fine particles formed with a charge transporting organic compound as an essential component,

wherein said charge transporting compound is a high-molecular compound represented by any one of the following general formulas (1) to (6):
general formula (1):
--(--CO--A--CO--O--B--O--).sub.p --
general formula (2):
--(--O--A--O--B--).sub.p --
general formula (3):
--(--CO--A--CONH--B--NH--).sub.p --
general formula (4):
##STR77## general formula (5):
##STR78## general formula (6):
##STR79## wherein A and B each represents a monovalent or divalent aliphatic hydrocarbon or aromatic hydrocarbon group which may be substituted and at the same time, at least one of A and B is a group represented by any one of the general formulas (7) to (15) and p represents an integer of 5 to 5000;
general formula (7):
##STR80## general formula (8):
##STR81## wherein R.sub.1 to R.sub.4 described in the formulas (7) and (8) each independently represents a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, a halogen atom, or a substituted or unsubstituted aryl group;
X represents a substituted or unsubstituted divalent aryl group;
k and l each independently represents an integer selected from 0 or 1;
and T represents a divalent C.sub.1-10 alkyl group, allyl group, alkylcarbonyl group, allylcarbonyl group, alkylamino group, allylamino group, a hydroxyalkyl group, or hydroxyallyl group which may be branched;
general formula (9):
##STR82## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.3 and R.sub.4 each independently represents an alkyl or aryl group;
R.sub.1 represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m represents an integer of from 0 to 2;
general formula (10):
##STR83## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group;
R.sub.1 and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (11):
##STR84## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group;
R.sub.1 and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (12):
##STR85## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group;
R.sub.1 and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (13):
##STR86## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group;
R, and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (14):
##STR87## wherein X represents an oxygen atom or C(CN).sub.2 ;
Y represents --COO--(CH.sub.2).sub.n or ##STR88## wherein n represents an integer from 1 to 6;
Z represents an alkyl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m represents an integer of from 0 to 2;
general formula (15):
##STR89## wherein X represents an oxygen atom or C(CN).sub.2 ;
Y represents --COO--(CH.sub.2).sub.n or, wherein n represents an integer from 1 to 6;
Z represents an alkyl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2.

44 more elements

A process for the preparation of charge transporting fine particles, which comprises dissolving or dispersing a charge transporting compound in a first medium which can dissolve or disperse said compound therein, dissolving or dispersing the resultant solution or dispersion in a second medium different from said first medium, and removing said first medium and/or second medium, thereby carrying out granulation, wherein said charge transporting compound is a high-molecular compound represented by any one of the following general formulas (1) to (6):

general formula (1):
--(--CO--A--CO--O--B--O--).sub.p --
general formula (2):
--(--O--A--O--B--).sub.p --
general formula (3):
--(--CO--A--CONH--B--NH--).sub.p --
general formula (4):
##STR90## general formula (5):
##STR91## general formula (6):
##STR92## wherein A and B each represents a monovalent or divalent aliphatic hydrocarbon or aromatic hydrocarbon group which may be substituted and at the same time, at least one of A and B is a group represented by any one of the general formulas (7) to (15) and p represents an integer of 5 to 5000;
general formula (7):
##STR93## general formula (8):
##STR94## wherein R.sub.1 to R.sub.4 described in the formulas (7) and (8) each independently represents a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, a halogen atom, or a substituted or unsubstituted aryl group;
X represents a substituted or unsubstituted divalent aryl group;
k and l each independently represents an integer selected from 0 or 1;
and T represents a divalent C.sub.1-10 alkyl group, allyl group, alkylcarbonyl group, allylcarbonyl group, alkylamino group, allylamino group, a hydroxyalkyl group, or hydroxyallyl group which may be branched;
general formula (9):
##STR95## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.3 and R.sub.4 each independently represents an alkyl or aryl group;
R.sub.1 represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m represents an integer of from 0 to 2;
general formula (10):
##STR96## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group, R.sub.1 and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (11):
##STR97## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group;
R.sub.1 and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (12):
##STR98## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group;
R.sub.1 and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (13):
##STR99## wherein X represents an oxygen atom, C(CN).sub.2, C(CN)(CO.sub.2 R.sub.3), or C(CO.sub.2 R.sub.3)(CO.sub.2 R.sub.4), wherein R.sub.2 and R.sub.3 each independently represents an alkyl or aryl group;
R.sub.1 and R.sub.2 each independently represents an alkyl group, an aryl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2;
general formula (14):
##STR100## wherein X represents an oxygen atom or C(CN).sub.2 ;
Y represents --COO--(CH.sub.2).sub.n or ##STR101## wherein n represents an integer from 1 to 6;
Z represents an alkyl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m represents an integer of from 0 to 2;
general formula (15):
##STR102## wherein X represents an oxygen atom or C(CN).sub.2 ;
Y represents --COO--(CH.sub.2).sub.n or, wherein n represents an integer from 1 to 6;
Z represents an alkyl group, a halogen atom, a nitro group, an acyl group, or a cyano group;
and m and l each independently represents an integer of from 0 to 2.

42 more elements

Charge transporting material and method of preparing charge transporting particulates used therein

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Charge transporting material and method of preparing charge transporting particulates used therein

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Abstract

Claims16