Charge transporting material and method of preparing charge transporting particulates used therein
First Claim
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1. 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);
space="preserve" listing-type="equation">--(--CO--A--CO--O--B--O--).sub.p --general formula (2);
space="preserve" listing-type="equation">--(--O--A--O--B--).sub.p --general formula (3);
space="preserve" listing-type="equation">--(--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 R1 to R4 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 C1-10 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R3 and R4 each independently represents an alkyl or aryl group;
R1 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R, and R2 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)2 ;
Y represents --COO--(CH2)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)2 ;
Y represents --COO--(CH2)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.
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Abstract
Disclosed are a charge transporting material useful as a material for organic electronic devices such as an electrophotographic photoreceptor, an organic EL device, and an organic solar cell and a process for the preparation of charge transporting fine particles. The charge transporting material comprises charge transporting fine particles formed with a charge transporting organic compound as an essential component, said charge transporting organic compound being selected from high molecular compounds and low molecular compounds, each having a positive hole transporting property or electron transporting property. The fine particles are granulated by emulsion dispersion, with a preferred average particle size of 0.01 to 50 μm, and particle size distribution of 1.0 to 2.0 in terms of the square root of the ratio of 90% average particle size to 10% average particle size of the total volume or total number of the fine particles. At least one portion of the surface of the fine particles may be covered with a second compound which may react with said charge transporting compound.
43 Citations
16 Claims
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1. 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);
space="preserve" listing-type="equation">--(--CO--A--CO--O--B--O--).sub.p --general formula (2);
space="preserve" listing-type="equation">--(--O--A--O--B--).sub.p --general formula (3);
space="preserve" listing-type="equation">--(--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 R1 to R4 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 C1-10 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R3 and R4 each independently represents an alkyl or aryl group;
R1 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R, and R2 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)2 ;
Y represents --COO--(CH2)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)2 ;
Y represents --COO--(CH2)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. - View Dependent Claims (2, 3, 4, 5, 15, 16)
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6. A charge transporting material comprising charge transporting fine particles formed with a charge transporting organic compound as an essential component,
wherein said charge transporting organic compound is at least one compound selected from a high-molecular compounds and low-molecular compounds, each having a positive hole transporting property or electron transporting property, wherein at least a portion of the surface of said charge transporting fine particles is covered with a second compound which may react with said charge transporting compound, and wherein said second compound which may react with said charge transporting compound is selected from the group consisting of silyl isocyanate compounds, polyvalent isocyanate compounds, silane coupling agents, and titanate coupling agents.
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7. A charge transporting material comprising charge transporting fine particles formed with a charge transporting organic compound as an essential component,
wherein said charge transporting organic compound is at least one compound selected from a high-molecular compounds and low-molecular compounds, each having a positive hole transporting property or electron transporting property, wherein at least a portion of the surface of said charge transporting fine particles is covered with a second compound which may react with said charge transporting compound, and wherein said second compound which may react with said charge transporting compound contains an amine based charge transporting compound.
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8. A process for the preparation of charge transporting fine particles, which comprises dissolving or dispersing a charge transporting compound and a second compound which may react with said 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 granulating to obtain charge transporting fine particles having at least a portion of the surface covered with a second compound which may react with said charge transporting compound
wherein said second compound which may react with said charge transporting compound is selected from the group consisting of silyl isocyanate compounds, polyvalent isocyanate compounds, silane coupling agents, and titanate coupling agents.
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11. 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):
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general formula (1);
space="preserve" listing-type="equation">--(--CO--A--CO--O--B--O--).sub.p --general formula (2);
space="preserve" listing-type="equation">--(--O--A--O--B--).sub.p --general formula (3);
space="preserve" listing-type="equation">--(--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 R1 to R4 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 C1-10 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R3 and R4 each independently represents an alkyl or aryl group;
R1 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group, R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2, C(CN)(CO2 R3), or C(CO2 R3)(CO2 R4), wherein R2 and R3 each independently represents an alkyl or aryl group;
R1 and R2 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)2 ;
Y represents --COO--(CH2)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)2 ;
Y represents --COO--(CH2)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.
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12. A process for the preparation of charge transporting fine particles, which comprises dissolving or dispersing a charge transporting compound and a second compound which may react with said 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 granulating to obtain charge transporting fine particles having at least a portion of the surface covered with a second compound which may react with said charge transporting compound,
wherein said second compound which may react with said charge transporting compound comprises an amine-based charge transporting compound.
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13. A process for the preparation of charge transporting fine particles according to claim to 12, wherein said charge transporting fine particles obtained by granulation are insoluble in said second medium.
Specification
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Current AssigneeFuji Xerox Company Limited (Xerox Holdings Corp.)
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Original AssigneeFuji Xerox Company Limited (Xerox Holdings Corp.)
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InventorsYamaguchi, Yasuhiro, Hoshizaki, Taketoshi, Iijima, Masakazu, Agata, Takeshi, Yamada, Wataru, Nukada, Katsumi
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Primary Examiner(s)KOPEC, MARK T
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Application NumberUS08/971,722Time in Patent Office694 DaysField of Search252/500, 524/81, 428/403, 428/405, 428/407US Class Current252/500CPC Class CodesC09K 11/06 containing organic luminesc...H10K 50/11 characterised by the electr...H10K 85/141 comprising aliphatic or ole...Y02E 10/549 Organic PV cellsY10T 428/2998 including synthetic resin o...
