Electrophotosensitive material

BACKGROUND OF THE INVENTION

The present invention relates to an electrophotosensitive material which is used for image forming apparatuses utilizing an electrophotography, such as electrostatic copying machine, laser beam printer, etc.

The electrophotography such as Carlson process includes a step of uniformly charging the surface of an electrophotosensitive material by a corona discharge; an exposure step of exposing the surface of the charged electrophotosensitive material to form an electrostatic latent image on the surface of the electrophotosensitive material; a developing step of bringing the formed electrostatic latent image into contact with a developer to visualize the electrostatic latent image due to a toner contained in the developer to form a toner image; a transferring step of transferring the toner image on a paper; a fixing step of fixing the transferred toner image; and a cleaning step of removing the toner remained on the photosensitive material.

As the electrophotosensitive material to be used for the above electrophotography, there have recently been suggested various organic photoconductors using an organic photoconductive compound having little toxicity in place of an inorganic photoconductive material (e.g. selenium, cadmium sulfide, etc.) whose handling is difficult because if it's toxicity. Such an organic photoconductor has an advantage such as good processability, easy manufacturing and great deal of freedom for design of performance.

As the organic photoconductor, a distributed function photosensitive layer containing an electric charge generating layer which generates an electric charge by light irradiation, and an electric charge transferring layer which transfer the generated electric charge is exclusively used.

A lot of studies about a binding resin which contains the above electric charge generating material and electron transferring material (consisting of hole transferring material and/or electron transferring material) and constitutes a photosensitive layer have been made so as to increase a mechanical strength (e.g. wear resistance, scratch resistance, etc.) of the photosensitive layer to prolong the life of the photoconductor. Particularly, polycarbonate resins (e.g. bisphenol A type, C type, Z type, fluorine-containing type, biphenyl copolymer type, etc.) have widely been utilized (Japanese Laid-Open Patent Publication Nos. 60-172045, 60-192950, 61-62039, 63-148263, 63-273064, 5-80548 and 5-88396).

In addition, it has also been known that the mechanical strength of the photosensitive layer is improved by increasing the molecular weight of the above polycarbonate resin (Japanese Laid-Open Patent Publication Nos. 5-113671 and 5-158249).

The mechanical strength of the photosensitive layer is improved by using the above-described polycarbonate resin as the binding resin, but the degree of the improvement is insufficient. In addition, the polycarbonate resin is inferior in compatibility with electric charge transferring material and despersion properties and, therefore, characteristics thereof can not be sufficiently utilized even if a material having excellent hole transferring characteristics is used. Accordingly, the sensitivity becomes inferior.

Furthermore, regarding a single-layer type photoconductor containing an electric charge transferring material and an electric charge generating material in a single layer, when using the polycarbonate resin as the binding resin in the photosensitive layer, the photosensitive layer is peeled off from a conductive substrate while using because the polycarbonate resin is inferior in adhesion to the conductive substrate such as aluminum, etc.

SUMMARY OF THE INVENTION

It is a main object of the present invention is to provide an electrophotosensitive material comprising a photosensitive layer in which a charge transferring material is uniformly dispersed in a binding resin, the electrophotosensitive material being superior in sensitivity.

It is another object of the present invention to provide an electrophotosensitive material provided with a photosensitive layer having a high mechanical strength such as wear resistance, etc. and being superior in adhesion to substrate.

The present inventors have studied intensively in order to accomplish the above objects. As a result, it has been found that, by using a specific electric charge transferring material, i.e. hole transferring material or electron transferring material, in combination with a specific polyester resin, the compatibility and dispersion properties of the electric charge transferring material to polyester resin are improved and, therefore, high electric charge transferring characteristics of the electric charge transferring material are fully exhibited, thereby improving the sensitivity of the photosensitive material.

The above specific polyester resin is superior in adhesion to conductive substrate and, therefore, the photosensitive layer is not likely to peel off from the conductive substrate while using the photosensitive material for a long period of time. Furthermore, the above polyester resin is also superior in mechanical strength such as wear resistance, etc. and, therefore, it becomes possible to prolong the life of the photosensitive material.

That is, the present invention provides an electrophotosensitive material comprising a conductive substrate and a photosensitive layer provided on the conductive substrate, the photosensitive layer comprising a binding resin of a polyester resin which is a substantially linear polymer obtained by using dihydroxy compounds represented by the following general formulas (1), (2) and (3), an electric charge generating material, and at least one of a hole transferring material selected from the group consisting of compounds represented by the following general formulas (HT1) to (HT13) and/or at least one of an electron transferring material selected from the group consisting of compounds represented by the following general formulas (ET1) to (ET14).

<Dihydroxy compounds>

General formula (1):

wherein R

1

is an alkylene group having 2 to 4 carbon atoms; and R

2

, R

3

, R

4

and R

5

are the same or different and indicate a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group or an aralkyl group

General formula (2):

wherein R

1

, R

2

, R

3

, R

4

and R

5

are as defined above; and n is an integer of not less than 2, preferably integer of 2 to 5

General formula (3):

wherein R

1

, R

2

, R

3

, R

4

and R

5

are as defined above; and R

6

and R

7

are the same or different and indicate an alkyl group having 1 to 10 carbon atoms

<Hole transferring material>

wherein R

8

, R

9

, R

10

, R

11

, R

12

and R

13

are the same or different and indicate a halogen atom, an alkyl group, an alkoxy group or an aryl group, and the alkyl group, alkoxy group and aryl group may have a substituent; and a, b, c, d, e and f are the same or different and indicate an integer of 0 to 5

wherein R

14

, R

15

, R

160

, R

17

and R

18

are the same or different and indicate a hologen atom, an alkyl group, an alkoxy group or an aryl group, and the alkyl group, alkoxy group and aryl group may have a substituent; and g, h, i, j and k are the same or different and indicate an integer of 0 to 5

wherein R

19

, R

20

, R

21

and R

22

are the same or different and indicate a halogen atom, an alkyl group, an alkoxy group or an aryl group, and the alkyl group, alkoxy group and aryl group may have a substituent; R

23

are the same or different and indicate a halogen atom, a cyano group, a nitro group, an alkyl group, an alkoxy group or an aryl group, and the alkyl group, alkoxy group and aryl group may have a substituent; m, n, o and p are the same or different and indicate an integer of 0 and 5; and q is an integer of 0 to 6

wherein R

24

, R

25

, R

26

and R

27

are the same or different and indicate a halogen atom, an alkyl group, an alkoxy group or an aryl group, and the alkyl group, alkoxy group and aryl group may have a substituent; and r, s, t and u are the same or different and indicate an integer of 0 to 5

wherein R

28

and R

29

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; and R

30

, R

31

, R

32

and R

33

are the same or different and indicate a hydrogen atom, an alkyl group or an aryl group

wherein R

34

, R

35

and R

36

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group

wherein R

37

, R

38

, R

39

and R

40

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group

wherein R

41

, R

42

, R

43

, R

44

and R

45

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group

wherein R

46

is a hydrogen atom or an alkyl group; and R

47

, R

48

and R

49

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group

wherein R

50

, R

51

and R

52

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group

wherein R

53

and R

54

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; and R

55

and R

56

are the same or different and indicate a hydrogen atom, an alkyl group or an aryl group

wherein R

57

R

58

, R

59

, R

60

, R

61

and R

62

are the same or different and indicate an alkyl group, an alkoxy group or an aryl group; α is an integer of 1 to 10; and v, w, x, y, z and A are the same or different and indicate 0 to 2

wherein R

63

, R

64

, R

65

and R

66

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; and Ar is a group (Ar1), (Ar2) or (Ar3) represented by the formulas:

[Electron transferring materials]

wherein R

67

, R

68

, R

69

and R

70

are the same or different and indicate a hydrogen atom, an alkyl group, an alkoxy group or an aryl group, and the alkyl group, alkoxy group and aryl group may have a substituent, provided that two of R

67

, R

68

, R

69

and R

70

are the same groups

wherein R

71

, R

72

, R

73

, R

74

and R

75

are the same or different and indicate a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group or a halogen atom

wherein R

76

is an alkyl group; R

77

is an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a halogen atom or a halogen-substituted alkyl group; and B is an integer of 0 to 5

wherein R

78

and R

79

are the same or different and indicate an alkyl group; C is an integer of 1 to 4; and D is an integer of 0 to 4

wherein R

80

is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, a halogen-substituted alkyl group or a halogen atom: E is an integer of 0 to 4; and F is an integer of 0 to 5

wherein G is an integer of 1 or 2

wherein R

81

is an alkyl group; and H is an integer of 1 to 4,

wherein R

82

and R

83

are the same or different and indicate a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyloxycarbonyl group, an alkoxy group, a hydroxyl group, a nitro group or a cyano group; and X indicates O, N—CN or C(CN)

2

wherein R

84

is a hydrogen atom, a halogen tom, an alkyl group or a phenyl group which may have a substituent; R

85

is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, a phenyl group which may have a substituent, an alkoxycarbonyl group, a N-alkylcarbamoyl group, a cyano group or a nitro group; and J is an integer of 1 to 3

wherein R

86

is an alkyl group which may have a substituent, a phenyl group which may have a substituent, a halogen atom, an alkoxycarbonyl group, a N-alkylcarbamoyl group, a cyano group or a nitro group; and K is an integer of 0 to 3

wherein R

87

and R

88

are the same or different and indicate a halogen atom, an alkyl group which may have a substituent, a cyano group, a nitro group or an alkoxycarbonyl group; and L and M indicate an integer of 0 to 3

wherein R

89

and R

90

are the same or different and indicate a phenyl group, a polycyclic aromatic group or a heterocyclic group, and these groups may have a substituent

wherein R

91

is an amino group, a dialkylamino group, an alkoxy group, an alkyl group or a phenyl group; and N is an integer of 1 to 2

wherein R

92

is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group or an aralkyl group

As the above binding resin, the polyester resin which is the substantially linear polymer obtained by using at least one of dihydroxy compounds represented by the general formula (1), (2) and (3) may be used in combination with a polycarbonate resin. Thereby, the compatibility is improved by the polycarbonate resin even if the polyester resin is used in combination with a material which is inferior in compatibility with polycarbonate resin.

Since the polyester resin in the present invention is superior in adhesion to conductive substrate, as described above, the above organic photosensitive layer using the polyester resin as the binding resin is suitable for using in the form of the single layer.

DETAILED EXPLANATION OF THE INVENTION

Examples of the alkylene group having 2 to 4 carbon atoms include ethylene group, propylene group, tetramethylene group.

Examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms, such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group or hexyl group. The above alkyl groups having 1 to 4 carbon atoms are alkyl groups having 1 to 6 carbon atoms excluding pentyl and hexyl groups. The alkyl groups having 1 to 10 carbon atoms are groups including octyl, nonyl and decyl groups, in addition to the above-described alkyl groups having 1 to 6 carbon atoms.

Examples of the aryl group include phenyl group, tolyl group, xylyl group, biphenylyl group, o-terphenyl group, naphthyl group, anthryl group or phenanthryl group.

Examples of the aralkyl group include aralkyl groups whose alkyl group moiety has 1 to 6 carbon atoms, such as benzyl group, phenethyl group, trityl group or benzhydryl group.

Examples of the alkoxy group include alkoxy groups having 1 to 6 carbon atoms, such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, t-butoxy group, pentyloxy group or hexyloxy group.

Examples of the halogen-substituted alkyl group include groups whose alkyl group moiety has 1 to 6 carbon atoms, such as chrolomethyl group, bromomethyl group, fluoromethyl group, iodomethyl group, 2-chloroethyl group, 1-fluoroethyl group, 3-chloropropyl group, 2-bromopropyl group, 1-chloropropyl group, 2-chloro-1-methylethyl group, 1-bromo-1-methylethyl group, 4-iodobutyl group, 3-fluorobutyl group, 3-chloro-2-methylpropyl group, 2-iodo-2-methylpropyl group, 1-fluoro-2-methylpropyl group, 2-chloro-1,1-dimethylethyl group, 2-bromo-1,1-dimethylethyl group, 5-bromopentyl group or 4-chlorohexyl group.

Examples of the polycyclic aromatic group include naphthyl group, phenanthryl group or anthryl group.

Examples of the heterocyclic group include thienyl group, pyrrolyl group, pyrrolidinyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, 2H-imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, pyranyl group, pyridyl group, piperidyl group, piperidino group, 3-morpholinyl group, morpholino group or thiazolyl group. In addition, it may also be a heterocylic group condenses with an aromatic ring.

Examples of the substituent which may be substituted on the above groups include halogen atom, amino group, hydroxyl group, optionally esterified carboxyl group, cyano group, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or alkenyl groups having 2 to 6 carbon atoms which may have an aryl group.

Next, examples of the hole transferring material will be described.

Examples of the benzidine derivative represented by the general formula (HT1) include the following compounds (HT1-1) to (HT1-11).

Examples of the phenylenediamine derivative represented by the general formula (HT2) include the following compounds (HT2-1) to (HT-2-6).

Examples of the naphthylenediamine derivative represented by the general formula (HT3) include the following compounds (HT3-1) to (HT3-5).

Examples of the phenythrenediamine derivative represented by the general formula (HT4) include the following compounds (HT4-1) to (HT4-3).

Examples of the butadiene derivative represented by the general formula (HT5) include the following compound (HT5-1).

Examples of the pyrene-hydrazone derivative represented by the general formula (HT6) include the following compound (HT6-1)

Examples of the acrolein derivative represented by the general formula (HT7) include the following compound (HT7-1).

Examples of the phenanthrenediamine derivative represented by the general formula (HT8) include the following compounds (HT8-1) to (HT8-2)

Examples of the carbazole-hydrazone derivative represented by the general formula (HT9) include the following compounds (HT9-1) and (HT9-2).

Examples of the quinoline-hydrazone derivative represented by the general formula (HT10) include the following compounds (HT10-1) and (HT10-2).

Examples of the stilbene derivative represented by the general formula (HT11) include the following compounds (HT11-1) and (HT11-2).

Examples of the compound represented by the general formula (HT12) include the following compounds (HT12-1) and (HT12-2).

Examples of the compound represented by the general formula (HT13) include the following compounds (HT13-1) to (HT13-3).

Next, examples of the electron transferring material will be described.

Examples of the diphenoquinone derivative represented by the general formula (ET1) include the following compounds (ET1-1) and (ET1-2).

Examples of the compound represented by the general formula (ET2) includes the following compounds (ET2-1) to (ET2-7).

Examples of the compound represented by the general formula (ET3) includes the following compounds (ET3-1) to (ET3-5).

Examples of the compound represented by the general formula (ET4) include the following compounds (ET4-1) and (ET4-2).

Examples of the compound represented by the general formula (ET5) includes the following compounds (ET5-1) and (ET5-2).

Examples of the compound represented by the general formula (ET6) includes the following compounds (ET6-1) and (ET6-2).

Examples of the compound represented by the general formula (ET7) includes the following compounds (ET7-1) and (ET7-2).

Examples of the compound represented by the general formula (ET8) includes the following compounds (ET8-1) to (ET8-3).

Examples of the compound represented by the general formula (ET9) include the following compound (ET9-1).

Examples of the compound resented by the general formula (ET10) include the following compound (ET10-1).

Examples of the compound represented by the general formula (ET11) include the following compound (ET11-1).

Examples of the compound represented by the general formula (ET12) include the following compound (ET12-1).

Examples of the compound represented by the general formula (ET13) include the following compound (ET13-1).

Examples of the compound represented by the general formula (ET14) include the following compound (ET14-1).

Next, the polyester resin to be used as the binding resin in the present invention will be explained.

The polyester resin in the present invention is a substantially linear polymer using the dihydroxy compound represented by the general formula (1), (2) or (3), as described above. That is, this polyester resin is a copolymer obtained by subjecting dicarboxylic acid or an ester-forming derivative thereof, at least one of the above dihydroxy compounds and other diol to polycondensation. The proportion of the above dihydroxy compound in the diol component is not less than 10 molar %, preferably not less than 30 molar %, more preferably not less than 50 molar %. When the proportion of the dihydroxy compound is lower than 10 molar %, the heat resistance is inferior and the molded article is liable to be deformed by heat. In addition, the dispersion properties and solubility to organic solvent of the colorant are liable to be deteriorated.

The polyester resin in the present invention has a limiting viscosity (measured in chloroform at 20° C.) of not less than 0.3 dl/g, preferably not less than 0.6 dl/g. When the limiting viscosity is less than 0.3 dl/g, mechanical characteristics (particularly, wear resistance, etc.) of the photosensitive material are deteriorated. On the other hand, when the limiting viscosity is more than 0.6 dl/g, the molded article having a sufficient mechanical characteristics can be obtained. However, it takes a longer time to dissolve the polyester resin in a solvent as the limiting viscosity becomes larger, and the viscosity of the solution is liable to increase. When the viscosity of the solution is too high, it becomes difficult to apply a coating solution for forming an organic photosensitive layer on a conductive substrate. Therefore, when the limiting viscosity increases two-fold or more, a problem on practical use arises. A polyester resin having an optimum limiting viscosity can be easily obtained by controlling melt polymerization conditions (e.g. molecular weight modifier, polymerization time, polymerization temperature, etc.) and conditions of the chain extending reaction of the postprocess).

The reason why the polyester resin is superior in compatibility and dispersion properties to the hole transferring material in the present invention is assumed that the solubility in solvent is improved by using the dihydroxy compound (1), (2) or (3) as the copolymerization component, without deteriorating the moldability of the polyester resin. In addition, the reason why the polyester resin is superior in adhesion to conductive substrate is considered that the ester bond moiety in the molecule of the polyester resin contributes to the adhesion to metal. Furthermore, the reason why the wear resistance of the photosensitive layer is improved is assumed that entanglement of polymer molecular chains is increased and the elasticity modulus is also increased by copolymerizing with the dihydroxy compound.

Examples of the dicarboxylic acid or ester-forming derivative thereof include aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,2-naphthalenedicarboxylic acid, 1,3-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 1,7-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2,2′-biphenyldicarboxylic acid, 3,3′-biphenyldicarboxylic acid, 4,4′-biphenyldicarboxylic acid, 9,9′-bis(4-carboxyphenylene)fluorene, etc.; aliphatic dicarboxylic acids such as maleic acid, adipic acid, sebacic acid, decamethylenedicarboxylic acid, etc.; and ester-forming derivatives thereof. These may be used alone or in combination thereof.

Examples of the fluorene dihydroxy compound represented by the above general formula (1) includes 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-propylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-dipropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-diisopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-n-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-di-n-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isobutylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-diisobutylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-(1-methylpropyl)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-bis(1-methylpropyl)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-diphenylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-benzylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-dibenzylphenyl]fluorene, 9,9-bis[4-(3-hydroxypropoxy)phenyl]fluorene, 9,9-bis[4-(4-hydroxybutoxy)phenyl]fluorene, etc. These may be used alone or in combination thereof. Among them, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene is preferred in view of optical characteristics and moldability.

The cycloalkane dihydroxy compound represented by the above general formula (2) may be any one which is synthesized from cycloalkanone, and examples thereof include dihydroxy compounds to be derived from cyclohexanone, such as 1,-bis[4-(2-hydroxyethoxy)phenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-methylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-propylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dipropylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diisopropylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-n-butylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-di-n-butylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-isobutylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diisobutylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-(1-methylpropyl)phenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-bis(1-methylpropyl)phenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diphenylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3-benzylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dibenzylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)phenyl]-4-methylcyclohexane, 1,1-bis[4-(2-hydroxyethoxy)phenyl]-2,4,6-trimethylcyclohexane, 1,1-bis[4-(2-hydroxypropoxy)phenyl]cyclohexane, 1,1-bis[4-(2-hydroxybutoxy)phenyl]cyclohexane, etc.;

dihydroxy compounds to be derived from cyclopentanone, such as 1,1-bis[4-(2-hydroxyethoxy)phenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3-methylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3-propylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dipropylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diisopropylphenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3-n-butylphenyl]cyclopentane, etc.;

dihydroxy compounds to be derived from cycloheptanone, such as 1,1-bis[4(2-hydroxyethoxy)phenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3-methylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3-propylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dipropylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diisopropylphenyl]cycloheptane, 1,1-bis[4-(2-hydroxyethoxy)-3-n-butylphenyl]cycloheptane, etc.;

dihydroxy compounds to be derived from cyclooctanone, such as 1,1-bis[4-(2-hydroxyethoxy)phenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3-methylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3-propylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dipropylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-diisopropylphenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3-n-butylphenyl]cyclooctane, etc.; but are not limited in these compounds.

These cycloalkane dihydroxy compounds synthesized from cycloalkanone can be used alone or in combination thereof.

Among them, 1,1-bis[4-(2-hydroxyethoxy) phenyl]cyclohexane, 1,1-bis-[4-(2-hydroxyethoxy)-3-methylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]cyclohexane, 1,1-bis[4-(2-hydroxyethoxy) phenyl]cyclopentane, 1,1-bis[4-(2-hydroxyethoxy)-3-methylphenyl]cyclopentane, 1,1-bis [4-(2-hydroxyethoxy)-3,5-dimethylphenyl]cyclopentane, 1,1-bis [4-(2-hydroxyethoxy)phenyl]cyclooctane, 1,1-bis[4-(2-hydroxyethoxy)-3-methylphenyl ]cyclooctane and 1,1-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl ]cyclooctane are preferred in view of moldability.

The dihydroxy compound represented by the above general formula (3) may be any one which can be synthesized from alkanone, that is, dihydroxy compound represented by the general formula C

m

H

2m

O (m is an integer) which is derived from a straight-chain alkanone including a branched alkanone. Examples of the dihydroxy compound (3) include dihydroxy compounds to be derived from 4-methyl-2-pentanone, such as 2,2-bis[4-(2-hydroxyethoxy)phenyl]-4-methylpentane, 2,2-bis[4-(2-hydroxyethoxy)-3-methylphenyl ]-4-methylpentane, 2,2-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl ]-4-methylpentane, 2,2-bis [4-(2-hydroxyethoxy)-3-ethylphenyl]-4-methylpentane, 2,2-bis [4-(2-hydroxyethoxy)-3,5-diethylphenyl]-4-methylpentane, 2,2-bis[4-(2-hydroxyethoxy)-3-propylphenyl]-4-methylpentane, 2,2-bis[4-(2-hydroxyethoxy)-3,5-dipropylphenyl]-4-methylpentane, 2,2-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]-4methylpentane, 2,2-bis[4-(2-hydroxyethoxy)-3,5-diisopropylphenyl ]-4methylpentane, etc.;

dihydroxy compounds to be derived from 3-methyl-2-butanone, such as 2,2-bis[4-(2-hydroxyethoxy)phenyl]-3-methylbutane, 2,2-bis[4-(2-hydroxyethoxy)-3-methylphenyl]-3-methylbutane, 2,2-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-methylbutane, 2,2-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]-3-methylbutane, 2,2-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]-3-methylbutane, etc.;

dihydroxy compounds to be derived from 3-pentanone, such as 3,3-bis[4-(2-hydroxyethoxy)phenyl]pentane, 3,3-bis[4-(2-hydroxyethoxy)-3-methylphenyl ]pentane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-dimethyphenyl ]pentane, 3,3-bis[4-(2-hydroxyethoxy)-3-ethylphenyl ]pentane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl ]pentane, etc.;

dihydroxy compounds to be derived from 2,4-dimethyl-3-pentanone, such as 3,3-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentane, 3,3-bis[4-(2-hydroxyethoxy)-3-methylphenyl]-2,4-dimethylpentane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl ]-2,4-dimethylpentane, 3,3-bis[4-(2-hydroxyethoxy)-3-ethylphenyl ]-2,4-dimethylpentane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl ]-2,4-dimethylpentane, etc.;

dihydroxy compounds to be derived from 2,4-dimethyl-3-hexanone, such as 3,3-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3-methylphenyl]-2,4-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl ]-2,4-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3-ethylphenyl ]-2,4-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]-2,4-dimethylhexane, etc.;

dihydroxy compounds to be derived from 2,5-dimethyl-3-hexanone, such as 3,3-bis[4-(2-hydroxyethoxy)phenyl]-2,5-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3-methylphenyl]-2,5-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl ]-2,5-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3-ethylphenyl ]-2,5-dimethylhexane, 3,3-bis[4-(2-hydroxyethoxy)-3,5-diethylphenyl]-2,5-dimethylhexane, etc. These compounds can be used alone or in combination thereof.

As the other diol, there can be used in aliphatic glycols such as ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 1,5-pentanediol, 1,4-pentanediol, 1,3-pentanediol, etc.; diols having an aromatic ring at the main or side chain, such as 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1-phenylethane, etc; compounds having an aromatic ring and sulfur at the main chain, such as bis[4-(2-hydroxyethoxy)phenyl]sulfon, etc.: or other hydroxy compounds such as bis[4-(2-hydroxyethoxy)phenyl]-sulfon, tricyclodecanedimethylol, etc.

The polyester resin in the present invention can be produced by selecting a suitable method from known methods such as melt polymerization method (e.g. interesterification method and direct polymerization method), solution polymerization method and interfacial polymerization method. In that case, a conventional known method can also be used with respect to the reaction condition such as polymerization catalyst.

In order to produce the polyester resin in the present invention by the interesterfication method of the melt polymerization method, it is preferred that the proportion of at least one sort of the dihydroxy compound selected from the dihydroxy compounds of the general formulas (1), (2) and (3) is 10 to 95 molar % for the glycol component in the resin. When the proportion exceeds 95 molar %, there is a problem that the melt polymerization reaction does not proceed and the polymerization time becomes drastically long. Even then it is more than 95 molar %, the polyester resin can be easily produced by the solution polymerization method or interfacial polymerization method.

In the polyester resin (amorphous) produced by copolymerizing dicarboxylic acid or a derivative thereof with the above dihydroxy compound (1), (2) or (3), the weight-average molecular weight on the polystyrene basis of 100,000 (limiting viscosity in chloroform: 0.6 dl/g) is a critical value which can be easily obtained by a conventional known polymerization method.

In order to obtain a polymeric polyester resin having an limiting viscosity of not less than 0.6 dl/g, it is preferred to react with a diisocyanate after polymerizing by the above-described method. The molecular chain of the polyester can be extended to easily increase the limiting viscosity in chloroform to 0.6 dl/g or more by this post treatment, thereby improving mechanical characteristics such as wear resistance, etc.

All compounds having two isocyanate groups in the same molecule are included in the diisocyanate to be used in the present invention. More specifically, examples thereof include hexamethylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, methylene-4,4′-bisphenyl diisocyanate, xylylene diisocyanate, 3-isocyanatemethyl-3,5,5-trimethycyclohexyl isocyanate, etc. These may be used alone or in combination thereof. Among them, methylene-4,4′-bisphenyl diisocyanate is particularly preferred.

The amount of the diisocyanate to be reacted with the polyester polymer is normally within a range of 0.5- to 1.3-fold amount, preferably 0.8- to 1.1-fold amount, based on the mol numbers calculated on the basis of the number-average molecular weight. The terminal end of the polyester molecule is alcoholic OH, and the diisocyanate reacts with alcohol to form an urethane bond, thereby accomplishing the chain extending of the polyester. At this time, the amount of the urethane bond to be introduced into the polyester becomes not more than 1% (molar fraction) and, therefore, physical properties (e.g. refractive index, birefringence, glass transition point, transparency, etc.) of the whole resin are the same as those of the polyester resin before treatment.

In the above-described chain extending reaction, a suitable catalyst may be optionally used. Preferred examples of the catalyst include metal catalysts (e.g. tin octylate, dibutyltin dilaurate, lead naphthenate, etc.), diazobiscyclo[2,2,2]octane, tri-N-butylamine, etc. The amount of the catalyst to be added varies depending on the temperature of the chain extending reaction, and is normally not more than 0.01 mol, preferably not more than 0.001 mol, based on 1 mol of the diisocyanate.

The reaction proceeds by adding a suitable amount of the catalyst and diisocyanate to the above-described polyester at the molten state, followed by stirring under a dry nitrogen current.

The reaction temperature of the chain extending reaction varies depending on the condition. When the reaction is conducted in an organic solvent, the reaction temperature is preferably set at a temperature lower than a boiling point of a solvent. When using no organic solvent, it is preferably set at a temperature higher than a glass transition point of the polyester. Since the obtainable molecular weight and degree of coloring due to the side reaction are decided by the reaction temperature, the optimum reaction system and reaction temperature suitable for the system can be selected, taking the objective molecular weight and that of the polyester before reaction into consideration. For example, when using trichlorobenzene as the organic solvent, it becomes possible to conduct the reaction within a range of 130 to 150° C., and the coloring due to the side reaction is scarcely observed.

The molecular weight is drastically increased by the above-described chain extending reaction of the polyester and the limiting viscosity is increased. The final molecular weight varies depending on the molecular weight before the reaction, but the molecular weight of the chain-extended polyester can be increased to the objective value by changing the amount of the diisocyanate, in addition to the reaction temperature and reaction time. It is difficult to specify the reaction temperature and reaction time. However, the higher the temperature, or the longer the reaction time, the higher the resulting molecular weight is. In addition, when the amount of diisocyanate is the same amount or 1.1-fold amount of the mol numbers of polyester calculated from the number-average molecular weight, the effect of the chain extending is the highest.

The molecular weight of the polyester obtained by copolymerizing dicarboxylic acid or ester-forming derivative thereof with the dihydroxy compound (1), (2) or (3) is normally about 50,000 (limiting viscosity: 0.4 dl/g), and the maximum value thereof is about 100,000 (limiting viscosity: 0.6 dl/g). For example, a polymeric polyester having the limiting viscosity of 0.7 to 1.5 dl/g can be obtained by subjecting polyester having a molecular weight of about 50,000, which can be produced most easily, as the raw material to the chain extending reaction.

The molecular weight distributin of the chain-extended polyester is normally widened. The molecular weight distribution of the amorphous polyester obtained by copolymerizing the above-described special dihydroxy compound produced by the melt polymerization varies depending on various reaction conditions, but is normally about 2 (in ratio of weight-average molecular weight to number-average molecular weight). After the chain extending reaction, it normally become 4 or more. When it is not preferred that the molecular weight distribution exists, the molecular weight distribution can be optionally controlled using a molecular weight fractionation method which is normally known. As the molecular weight fractionation method, there can be used reprecipitation method due to poor solvent, method of passing through a column filled with gel to sift by the size of the molecule, method described in Analysis of Polymers, T. R. Crompton, Pergamon Press, etc.

In the present invention, a polycarbonate resin having a repeating unit represented by the following general formula (A) can be contained as the binding resin, in addition to the above polyester resin.

wherein R

Q

and R

R

are the same or different and indicate a hydrogen atom, an alkyl having 1 to 3 carbon atoms or an aryl gruop which may have a substituent, and R

Q

and R

R

may bond each other to form a ring; and R

S

, R

T

, R

U

, R

V

, R

W

, R

X

, R

Y

and R

Z

are the same or different and indicate a hydrogen atom, an alkyl having 1 to 3 carbon atoms, an aryl group which may have a substituent, or a halogen atom.

Such as polycarbonate resin may be a homopolymer using single monomers, or a copolymer using two or more sorts of monomers represented by the above repeating unit.

Examples of the polycarbonate resin represented by the general formula (A) will be descried hereinafter.

Regarding the blending proportion of the polycarbonate resin (A) to the polyester resin, the amount of the polycarbonate resin (A) is preferably 1 to 99 parts by weight, based on 100 parts by weight of the polyester resin.

The photosensitive material of the present invention can be applied to both cases where the photosensitive layer include single-layer and multi-layer types.

In order to obtain the single-layer type photosensitive material, a photosensitive layer containing an electric charge generating material, a hole transferring material, an electron transferring material and the above polyester resin as a binding resin may be formed on a conductive substrate by means such as application, etc.

In order to obtain the multi-layer type photosensitive material, an electric charge generating layer containing an electric charge generating material and a binding resin is firstly formed on a conductive substrate, and then an electric charge transferring layer containing any one of a hole transferring material and an electron transferring material and a binding resin may be formed on this electric charge generating layer, according to a negative charging type or a positive charging type. On the other hand, the electric charge generating layer may be formed after the electron transferring layer was formed on the conductive substrate. When the electric charge transferring layer contains the electron transferring material, the electric charge generating layer may contain the hole transferring material. On the other hand, when the electric charge transferring layer contains the hole transferring material, the electric charge generating layer may contain the electron transferring material.

Examples of the electric charge generating material include electric charge generating materials which have hitherto been known, such as material-free phthalocyanine, titanyl phthalocyanine, perylene pigments, bis-azo pigments, dithioketopyrrolopyrrole pigments, metal-free naphthalocyanine pigments, metal naphthalocyanine pigments, squaline pigments, tris-azo pigments, indigo pigments, azulenium pigments, cyanine pigments, etc. Various electric charge generating materials which have hitherto been known can be used in combination for the purpose of widening a sensitivity range of the electrophotosensitive material so as to present an absorption wavelength within a desired range.

When using any one of compounds represented by the formulas (HT1) to (HT13) as the hole transferring material, the compounds represented by the formulas (ET1) to (ET14) may be used as the electron transferring material to be used in combination with the hole transferring material, but other known electron transferring materials may also be used.

Examples of the known electron transferring material include diphenoquinone derivatives other than compounds represented by the general formula (ET1), malononitrile, thiopyran compounds, tetracyanoethylene, 2,4,8-trinitrothioxanthone, fluorenone compounds (e.g. 3,4,5,7-tetranitro-9-fluorenone), dinitrobenzene, dinitroanthracene, dinitroacridine, nitroanthraquinone, dinitroanthraquinone, succinic anhydride, maleic anhydride, dibromomaleic anhydride, etc.

When using any one of compounds represented by the formulas (ET1) to (ET14) as the electron transferring material, the compounds represented by the formulas (HT1) to (HT13) may be used as the hole transferring material to be used in combination with the electron transferring material, but other known electron transferring materials may also be used.

Examples of the known hole transferring material include nitrogen-containing cyclic compounds and condensed polycyclic compounds, for example, benzidine derivatives other than compound represented by the general formula (HT1); phenylenediamine derivatives other than compounds represented by the formula (HT2); styryl compounds such as 9-(4-diethylaminostyrl) anthracene, etc.; carbazole compounds such as polyvinyl carbazole, etc.; pyrazoline compounds such as 1-phenyl-3-(p-dimethylaminophenyl) pyrazoline, etc.; hydrazone compounds; triphenylamine compounds; indol compounds; oxazole compounds; isooxazole compounds; thiazole compounds; thiadiazole compounds; imidazole compounds; pyrazole compounds; triazole compounds, etc.

The above-described polyester resin to be used as the binding resin is preferably used as the binding resin for single-layer photosensitive material because of it's high adhesion to the conductive substrate. In case of the multi-layer photosensitive material, the wear resistance of the photosensitive layer is improved when using the polyester resin as the binding resin for surface layer. In that case, the polyester resin may be used for the layer of the substrate side, or other binding resin may also be used.

Examples of the other binding resin include above-described polycarbonate resin, styrene polymer, styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-acrylic acid copolymer, polyethylene, ethylene-vinyl acetate copolymer, chlorinated polyethylene, polyvinyl chloride, alkyd resin, polyvinyl butyral, polyamide, etc.

Additives such as deterioration inhibitors (e.g. sensitizers, antioxidants, ultraviolet absorbers, etc.) and plasticizers can be contained in the respective organic photosensitive layers of single-layer type and multi-layer type.

In order to improve the sensitivity of the electric charge generating layer, known sensitizers such as terphenyl, halonaphthoquinones, acenaphthylene, etc. may be used in combination with the electric charge generating material.

In the multi-layer photosensitive material, the electric charge generating material and binding resin, which constitute the electric charge generating layer, may be used in various proportions. It is preferred that the electric charge generating material is used in the amount of 5 to 1000 parts by weight, particularly 30 to 500 parts by weight, based on 100 parts by weight of the binding resin.

The hole transferring material or electron transferring material and binding resin, which constitute the electric charge transferring layer, can be used in various proportions within such a range as not to prevent the electron transfer and to prevent the crystallization. It is preferred that the hole transferring material is used in the amount of 10 to 500 parts by weight, particularly 25 to 200 parts by weight, based on 100 parts by weight of the binding resin, so as to easily transfer holes or electrons generated by light irradiation in the electric charge generating layer.

Furthermore, in the multi-layer type photosensitive layer, the electric charge generating layer is formed in the thickness of preferably about 0.01 to 10 μm, particularly about 0.01 to 5 μm, and the electric charge transferring layer is formed in the thickness of preferably about 2 to 100 μm, particularly about 5 to 50 μm.

In the single-layer type photosensitive material, it is preferred that the amount of the electric charge generating material is 0.1 to 50 parts by weight, particularly 0.5 to 30 parts by weight, based on 100 parts by weight of the binding resin. It is preferred that the amount of the hole transferring material is 20 to 500 parts by weight, particularly 30 to 200 parts by weight, based on 100 parts by weight of the binding resin. In addition, it is preferred that the single-layer type photosensitive layer is formed in the thickness of 5 to 100 μm, preferably about 10 to 50 μm.

A barrier layer may be formed, in such a range as not to inure the characteristics of the photosensitive material, between the conductive substrate and photosensitive layer in the single-layer type photosensitive material, or between the conductive substrate and electric charge generating layer or between the conductive substrate layer and electric charge transferring layer in the multi-layer type photosensitive material. Furthermore, a protective layer may be formed on the surface of the photosensitive layer.

As the conductive substrate on which the above respective layer are formed, various materials having a conductivity can be used, and examples thereof include metals such as aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, brass, etc.; plastic materials vapor-deposited or laminated with the above metal; glass materials coated with aluminum iodide, tin oxide, indium oxide, etc.

The conductive substrate may be made in the form of a sheet or a drum. The substrate itself may have a conductivity or only the surface of the substrate may have a conductivity. It is preferred that the conductive substrate has a sufficient mechanical strength when used.

When the above respective layers are formed by the application method, the above-described electric charge generating material, hole transferring material, electric charge transferring material and binding resin may be dispersed and mixed with a suitable solvent using roll mill, ball mill, atriter, paint shaker, ultrasonic dispersion device, etc., and the resulting solution may be applied using known means, followed by drying.

As the solvent, there can be used various organic solvents, and examples thereof include alcohols such as methanol, ethanol, isopropanol, butanol, etc.; aliphatic hydrocarbons such as n-hexane, octane, cyclohexane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.,; hydrocarbon halides such as dichloromethane, dichloroethane, carbon tetrachloride, chlorobenzene, etc.; ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, etc.; ketones such as acetone, methyl ethyl ketone, cyclohexanone, etc.; esters such as ethyl acetate, methyl acetate, etc.; dimethylformaldehyde, dimethylformamide, dimethyl sulfoxide, etc. These solvents may be used alone or in combination thereof.

In order to improve dispersion properties of the hole transferring material and electric charge generating material as well as a smoothness of the surface of the photosensitive layer, surfactants, leveling agents, etc. may be used.

EXAMPLES

The following Reference Examples, Examples and Comparative Examples further illustrate the present invention in detail.

Reference Example 1

Dimethyl terephthalate (10.68 kg, 55 mol), 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (16.88 kg, 38.5 mol) and ethylene glycol (7.2 kg, 116 mol) were used as the raw material, and calcium acetate (15.99 g, 0.091 mol) was used as the catalyst. They were introduced in a reaction tank and the interesterification reaction was conducted by heating slowly from 190 to 230° C. with stirring according to a normal method. After drawing out a predetermined amount of ethanol from the system, germanium oxide (6.9 g, 0.066 mol) as the polymerization catalyst and trimethyl phosphate (14 g, 0.1 mol) as the agent for preventing coloring were introduced. Then, the heating tank was heated slowly to 280° C. and, at the same time, the pressure was reduced slowly to 1 Torr or less while drawing out ethylene glycol to be formed. This condition was maintained until the viscosity was increased and, after reaching a predetermined stirring torque (after about 2 hours), the reaction was terminated and the reaction product was extruded into water to obtain a pellet.

The limiting viscosity of this copolymer was 0.38 dl/g. The weight-average molecular weight determined by GPC was 55,000 and number-average molecular weight was 25,000. In addition, the glass transition temperature was 145° C.

The above polyester copolymer (30 g) was dissolved in trichlorobenzene to prepare a 40% (by weight) solution. Then, methylene-bis(4-phenylisocyanate) (0.337 g) whose mol numbers are 1.1 times as those of the polyester copolymer calculated by the number-average molecular weight, and diazobiscyclo[2,2,2]octane (0.175 mg) were added to the above solution, and the mixture was heated with stirring under a nitrogen gas current at 150° C. for 10 hours. The resulting reaction product was reprecipitated in methanol, and then washed with a large amount of methanol and distilled water to obtain a chain-extended polyester resin (1-1).

the limiting viscosity of this polyester resin was 0.76 dl/g. The weight-average molecular weight determined by GPC was 120,000 and number-average molecular weight was 38,000. The glass transition temperature was 145° C.

Reference Example 2

According to the same manner as that described in Reference Example 1 except for using 2,6-naphthalenedicarboxylic acid as the acid component and using ethylene glycol and bis[4-(2-hydroxyethoxy)phenyl]fluorene as the diol component, a chain-extended polyester resin (1-2) was obtained. The limiting viscosity of this polyester resin was 0.7 dl/g.

Reference Example 3

According to the same manner as that described in Reference Example 1 except for using succinic acid as the acid component and using ethylene glycol, bis[4-(2-hydroxyethoxy)phenyl]fluorene and 1,1-[4-(2-hydroxyethoxy)phenyl]cyclohexane as the diol component, a chain-extended polyester resin (1-3) was obtained. The limiting viscosity of this polyester resin was 0.8 dl/g.

Reference Example 4

Dimethyl terephthalate (10.68 kg, 55 mol), 1,1-bis[4-(2-hydroxyethoxy)phenyl]cyclohexane (13.71 kg, 38.5 mol) and ethylene glycol (7.2 kg, 116 mol) were used as the raw material and calcium acetate (15.99 g, 0.091 mol) was used as the catalyst. They were introduced in a reaction tank and the interesterification reaction was conducted by heating slowly from 190 to 230° C. with stirring according to a normal method. After drawing out a predetermined amount of ethanol from the system, germanium oxide (6.9 g, 0.066 mol) as the polymerization catalyst and trimethyl phosphate (14 g, 0.1 mol) as the agent for preventing coloring were introduced. Then, the heating tank was heated slowly to 280° C. and, at the same time, the pressure was reduced slowly to 1 Torr or less while drawing out ethylene glycol to be formed. This condition was maintained until the viscosity was increased and, after reaching a predetermined stirring torque (after about 2 hours), the reaction was terminated and the reaction product was extruded into water to obtain a pellet.

The limiting viscosity of this copolymer was 0/39 dl/g. The weight-average molecular weight determined by GPC was 55,000 and number-average molecular weight was 25,000. The glass transition temperature was 145° C.

The above polyester copolymer (30 g) was dissolved in trichlorobenzene to prepare a 40% (by weight) solution. Then, methylene-bis)4-phenylisocyanate) (0.337 g) whose mol numbers are 1.1 times as those of the polyester copolymer calculated by the number-average molecular weight, and diazobiscyclo[2,2,2]octane (0.175 mg) were added to the above solution, and the mixture was heated with stirring under a nitrogen gas current at 150° C. for 10 hours. The resulting reaction product was reprecipitated in methanol, and then washed with a large amount of methanol and distilled water to obtain a chain-extended polyester resin (2-1).

The limiting viscosity of this polyester resin was 0.76 dl/g. The weight-average molecular weight determined by GPC was 120,000 and number-average molecular weight was 38,000. The glass transition temperature was 115° C.

Reference Example 5

According to the same manner as that described in Reference Example 4 except for using 2,6-naphthalenedicarboxylic acid as the acid component and using ethylene glycol and 1,1-bis[4-(2-hydroxyethoxy)phenyl]cyclohexane as the diol component, a chain-extended polyester resin (2-2) was obtained. The limiting viscosity of this polyester resin was 0.8 dl/g.

Reference Example 6

According to the same manner as that described in Reference Example 4 except for using 2,6-naphthalenedicarboxylic acid as the acid component and using ethylene glycol and 1,1-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]cyclohexane as the diol component, a chain-extended polyester resin (2-3) was obtained. The limiting viscosity of this polyester resin was 0.8 dl/g.

Reference Example 7

Dimethyl terephthalate (10.68 kg, 55 mol), 2,2-bis[4-(2-hydroxyethoxy)phenyl]-4-methylpentane (13.60 kg, 38.5 mol) and ethylene glycol (7.2 kg, 116 mol) were used as the raw material and calcium acetate (15.99 g, 0.091 mol) was used as the catalyst. They were introduced in a reaction tank and the interesterification reaction was conducted by heating slowly from 190 to 230° C. with stirring according to a normal method. After drawing out a predetermined amount of ethanol from the system, germanium oxide (6.9 g, 0.066 mol) as the polymerization catalyst and trimethyl phosphate (14 g, 0.1 mol) as the agent for preventing coloring were introduced. Then, the heating tank was heated slowly to 280° C. and, at the same time, the pressure was reduced slowly to 1 Torr or less while drawing out ethylene glycol to be formed. This condition was maintained until the viscosity was increased and, after reaching a predetermined stirring torque (after about 2 hours), the reaction was terminated and the reaction product was extruded into water to obtain a pellet.

The limiting viscosity of this copolymer was 0.39 dl/g. The weight-average molecular weight determined by PGC was 55,000 and number-average molecular weight was 25,000. The glass transition temperature was 145° C.

The above polyester copolymer (30 g) was dissolved in trichlorobenzene to prepare a 40% (by weight) solution. Then, methylene-bis)4-phenylisocyanate) (0.337 g) whose mol numbers are 1.1 times as those of the polyester copolymer calculated by the number-average molecular weight, and diazobiscyclo[2,2,2]octane (0.175 mg) were added to the above solution, and the mixture was heated with stirring under a nitrogen gas current at 150° C.. for 10 hours. The resulting reaction product was reprecipitated in methanol, and then washed with a large amount of methanol and distilled water to obtain a chain-extended polyester resin (3-1).

The limiting viscosity of this polyester resin was 0.76 dl/g. The weight-average molecular weight determined by GPC was 120,000 and number-average molecular weight was 38,000. The glass transition temperature was 105° C.

Reference Example 8

According to the same manner as that described in Reference Example 7 except for using 2,6-naphthalenedicarboxylic acid as the acid component and using ethlene glycol and 2,2-bis[4-(2-hydroxyethoxy)-3-methylphenyl]-4-methylpentane as the diol component, a chain-extended polyester resin (3-2) was obtained. The limiting viscosity of this polyester resin was 0.8 dl/g.

Reference Example 9

According to the same manner as that described in Reference Example 7 except for using succinic acid as the acid component and using ethylene glycol and 2,2-bis[4-(2-hydroxyethoxy)phenyl]-4-methylpentane as the diol component, a chain-extended polyester resin (3-3) was obtained. The limiting viscosity of this polyester resin was 0.8 dl/g.

Examples 1 to 387

[Single-layer photosensitive material for digital light source (positive charging type)]

A metal-free phthalocyanine pigment represented by the following general formula (CGI) and a diphenoquinone compound represented by the following general formula (ETI-1) were used as the electric charge generating material and electron transferring material, respectively. In addition, the compound represented by any one of the above formulas (HT1) to (HT13) was used as the hole transferring material, respectively. Furthermore, any one of the polyester resins (1-1) to (1-3), (2-1) to (2-3) and (3-1) to (3-3) obtained in Reference Examples 1 to 9, or a mixture of this polyester resin and a polycarbonate resin was used as the binding resin. Furthermore, tetrahydrofuran was used as the solvent in which these components are dissolved.

The electric charge generating material and binding resin used were shown using the above compound number.

The amount of the respective materials to be blended is as follows:

Components

Amount (parts by weight)

Electric charge generating

5

material

Hole transferring material

50

Electron transferring material

30 (or 0)

Binding resin

90

Solvent

800

When the binding resin is the above mixture, the mixing proportion of the polyester resin to polycarbonate was 70 parts by weight: 20 parts by weight.

The above respective components were mixed and dispersed with a ball mill to prepare a coating solution for single-layer type photosensitive layer. Then, this coating solution was applied on an aluminum tube by a dip coating method, followed by hot-air drying at 100° C. for 60 minutes to obtain a single-layer type photosensitive material for digital light source, which has a single-layer type photosensitive layer of 15 to 20 μm in film thickness, respectively.

Comparative Example 1

According to the same manner as that described in Example 1 except for using the polycarbonate resin having a repeating unit of the above formula (A-4) alone as the binding resin, a single-layer photosensitive material was produced.

Comparative Example 2

According to the same manner as that described in Examples 1 except for using a compound represented by the following formula (HT14-1) as the hole transferring material, a single-layer photosensitive material was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the following test and their characteristics were evaluated.

<Evaluation of positive charging photosensitive material for digital light source>

Photosensitivity test

By using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of a photosensitive material obtained in the respective Examples and Comparative Examples to charge the surface at +700 V, respectively. Then, monochromatic light [wavelength: 780 nm (half-width: 20 nm), light intensity: 16 μW/cm

2

] from white light of a halogen lamp as an exposure light source through a band-pass filter was irradiated on the surface of the photosensitive material (irradiation time: 80 msec.). Furthermore, a surface potential at the time at which 330 msec. has passed since the beginning of exposure was measured as a potential after exposure V

L

(V).

Wear resistance test

A photosensitive material obtained in the respective Examples and Comparative Examples was fit with an imaging unit of a facsimile for normal paper (Model LDC-650, manufactured by Mita Industrial Co., Ltd.) and, after rotating 150,000 times without passing a paper through it, a change in thickness of a photosensitive layer before and after rotation was determined.

Adhesion test

The adhesion of the photosensitive layer was evaluated according to a checkers test described in JIS K5400 (Normal Testing Method of Paint). The adhesion (%) was determined by the following equation.

Adhesion (%)={Number of checkers which were not peeled off}/{Total numbers of checkers}×100

These test results are shown in Tables 1 to 18, together with the above-described compound No. of the binding resin and hole transferring material (HTM) used.

TABLE 1

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

1

1-1

—

HT1-1

128

2.3

100

2

1-1

—

HT1-2

128

2.0

100

3

1-1

—

HT1-3

130

2.8

100

4

1-1

—

HT1-4

134

2.5

100

5

1-1

—

HT1-5

131

2.4

100

6

1-1

—

HT1-6

130

3.0

100

7

1-1

—

HT1-7

130

2.7

100

8

1-1

—

HT1-8

133

2.1

100

9

1-1

—

HT1-9

131

2.5

100

10

1-1

—

HT1-10

129

2.9

100

11

1-1

—

HT1-11

132

2.5

100

12

1-1

—

HT2-1

151

1.4

100

13

1-1

—

HT2-2

148

1.9

100

14

1-1

—

HT2-3

141

1.6

100

15

1-1

—

HT2-4

155

2.0

100

16

1-1

—

HT2-5

150

1.8

100

17

1-1

—

HT2-6

140

2.2

100

18

1-1

—

HT3-1

143

1.5

100

19

1-1

—

HT3-2

143

2.0

100

20

1-1

—

HT3-3

147

1.9

100

21

1-1

—

HT3-4

152

2.2

100

22

1-1

—

HT3-5

145

1.6

100

23

1-1

—

HT4-1

148

2.1

100

24

1-1

—

HT4-2

150

1.8

100

25

1-1

—

HT4-3

150

2.1

100

26

1-1

—

HT5-1

158

2.5

100

27

1-1

—

HT6-1

160

2.7

100

28

1-1

—

HT7-1

159

3.0

100

TABLE 2

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

29

1-1

—

HT8-1

161

2.6

100

30

1-1

—

HT8-2

155

3.0

100

31

1-1

—

HT9-1

151

2.9

100

32

1-1

—

HT9-2

160

2.5

100

33

1-1

—

HT10-1

161

2.4

100

34

1-1

—

HT10-2

152

2.4

100

35

1-1

—

HT11-1

155

2.6

100

36

1-1

—

HT11-2

163

2.6

100

37

1-1

—

HT12-1

159

2.3

100

38

1-1

—

HT12-2

150

2.4

100

39

1-1

—

HT13-1

158

2.9

100

40

1-1

—

HT13-2

151

2.7

100

41

1-1

—

HT13-3

156

2.2

100

42

↓

↑

1-1

—

HT1-1

163

2.6

100

43

1-1

A-1

HT1-1

132

2.2

100

TABLE 3

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

44

1-2

—

HT1-1

130

2.9

100

45

1-2

—

HT1-2

129

2.5

100

46

1-2

—

HT1-3

128

2.2

100

47

1-2

—

HT1-4

130

2.0

100

48

1-2

—

HT1-5

129

2.4

100

49

1-2

—

HT1-6

132

2.4

100

50

1-2

—

HT1-7

130

3.0

100

51

1-2

—

HT1-8

129

2.6

100

52

1-2

—

HT1-9

128

2.9

100

53

1-2

—

HT1-10

131

2.3

100

54

1-2

—

HT1-11

130

2.8

100

55

1-2

—

HT2-1

143

1.8

100

56

1-2

—

HT2-2

149

1.4

100

57

1-2

—

HT2-3

150

1.6

100

58

1-2

—

HT2-4

155

2.0

100

59

1-2

—

HT2-5

146

1.4

100

60

1-2

—

HT2-6

152

1.9

100

61

1-2

—

HT3-1

145

1.5

100

62

1-2

—

HT3-2

143

1.5

100

63

1-2

—

HT3-3

147

1.9

100

64

1-2

—

HT3-4

154

2.1

100

65

1-2

—

HT3-5

150

1.7

100

66

1-2

—

HT4-1

146

2.0

100

67

1-2

—

HT4-2

149

2.1

100

68

1-2

—

HT4-3

141

1.9

100

69

1-2

—

HT5-1

154

2.5

100

70

1-2

—

HT6-1

160

2.4

100

71

1-2

—

HT7-1

165

2.1

100

TABLE 4

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

72

1-2

—

HT8-1

163

3.0

100

73

1-2

—

HT8-2

159

2.8

100

74

1-2

—

HT9-1

165

2.4

100

75

1-2

—

HT9-2

154

2.7

100

76

1-2

—

HT10-1

158

2.3

100

77

1-2

—

HT10-2

161

2.8

100

78

1-2

—

HT11-1

150

2.0

100

79

1-2

—

HT11-2

157

2.2

100

80

1-2

—

HT12-1

162

2.5

100

81

1-2

—

HT12-2

153

2.1

100

82

1-2

—

HT13-1

150

2.4

100

83

1-2

—

HT13-2

155

2.9

100

84

1-2

—

HT13-3

160

2.0

100

85

↓

↑

1-2

—

HT1-1

161

2.3

100

86

1-2

A-1

HT1-1

128

2.5

100

TABLE 5

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

87

1-3

—

HT1-1

132

2.4

100

88

1-3

—

HT1-2

131

2.3

100

89

1-3

—

HT1-3

129

2.0

100

90

1-3

—

HT1-4

132

2.7

100

91

1-3

—

HT1-5

128

2.9

100

92

1-3

—

HT1-6

130

2.8

100

93

1-3

—

HT1-7

127

2.1

100

94

1-3

—

HT1-8

129

2.6

100

95

1-3

—

HT1-9

130

2.6

100

96

1-3

—

HT1-10

132

2.2

100

97

1-3

—

HT1-11

131

3.0

100

98

1-3

—

HT2-1

155

1.8

100

99

1-3

—

HT2-2

149

2.2

100

100

1-3

—

HT2-3

140

1.5

100

101

1-3

—

HT2-4

155

2.1

100

102

1-3

—

HT2-5

147

1.4

100

103

1-3

—

HT2-6

154

2.0

100

104

1-3

—

HT3-1

141

1.7

100

105

1-3

—

HT3-2

152

2.2

100

106

1-3

—

HT3-3

147

1.5

100

107

1-3

—

HT3-4

153

1.6

100

108

1-3

—

HT3-5

143

1.6

100

109

1-3

—

HT4-1

150

2.0

100

110

1-3

—

HT4-2

148

1.9

100

111

1-3

—

HT4-3

146

1.6

100

112

1-3

—

HT5-1

159

2.9

100

113

1-3

—

HT6-1

151

2.5

100

114

1-3

—

HT7-1

163

2.5

100

TABLE 6

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

115

1-3

—

HT8-1

155

2.1

100

116

1-3

—

HT8-2

151

2.9

100

117

1-3

—

HT9-1

159

2.3

100

118

1-3

—

HT9-2

156

2.4

100

119

1-3

—

HT10-1

160

2.8

100

120

1-3

—

HT10-2

164

2.5

100

121

1-3

—

HT11-1

158

2.7

100

122

1-3

—

HT11-2

160

2.1

100

123

1-3

—

HT12-1

157

2.2

100

124

1-3

—

HT12-2

165

3.0

100

125

1-3

—

HT13-1

163

2.4

100

126

1-3

—

HT13-2

160

2.5

100

127

1-3

—

HT13-3

158

2.8

100

128

↓

↑

1-3

—

HT1-1

158

2.6

100

129

1-3

A-1

HT1-1

130

2.8

100

TABLE 7

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

130

2-1

—

HT1-1

129

2.0

100

131

2-1

—

HT1-2

128

2.2

100

132

2-1

—

HT1-3

131

1.8

100

133

2-1

—

HT1-4

130

1.7

100

134

2-1

—

HT1-5

132

1.5

100

135

2-1

—

HT1-6

121

1.9

100

136

2-1

—

HT1-7

130

1.6

100

137

2-1

—

HT1-8

128

2.0

100

138

2-1

—

HT1-9

129

1.5

100

139

2-1

—

HT1-10

128

2.1

100

140

2-1

—

HT1-11

130

1.8

100

141

2-1

—

HT2-1

152

1.7

100

142

2-1

—

HT2-2

155

1.6

100

143

2-1

—

HT2-3

141

1.4

100

144

2-1

—

HT2-4

146

1.0

100

145

2-1

—

HT2-5

150

1.7

100

146

2-1

—

HT2-6

140

1.4

100

147

2-1

—

HT3-1

151

1.0

100

148

2-1

—

HT3-2

148

1.2

100

149

2-1

—

HT3-3

153

1.6

100

150

2-1

—

HT3-4

149

1.4

100

151

2-1

—

HT3-5

142

1.3

100

152

2-1

—

HT4-1

150

1.1

100

153

2-1

—

HT4-2

147

1.4

100

154

2-1

—

HT4-3

154

1.5

100

155

2-1

—

HT5-1

154

1.7

100

156

2-1

—

HT6-1

151

1.5

100

157

2-1

—

HT7-1

155

2.0

100

TABLE 8

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

158

2-1

—

HT8-1

151

1.7

100

159

2-1

—

HT8-2

160

2.0

100

160

2-1

—

HT9-1

155

1.6

100

161

2-1

—

HT9-2

164

1.7

100

162

2-1

—

HT10-1

162

1.9

100

163

2-1

—

HT10-2

157

1.6

100

164

2-1

—

HT11-1

155

2.1

100

165

2-1

—

HT11-2

152

2.2

100

166

2-1

—

HT12-1

150

1.6

100

167

2-1

—

HT12-2

158

1.8

100

168

2-1

—

HT13-1

165

2.0

100

169

2-1

—

HT13-2

163

2.2

100

170

2-1

—

HT13-3

160

1.9

100

171

↓

↑

2-1

—

HT1-1

160

2.3

100

172

2-1

A-1

HT1-1

129

2.3

100

TABLE 9

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

173

2-2

—

HT1-1

129

1.7

100

174

2-2

—

HT1-2

131

1.9

100

175

2-2

—

HT1-3

130

1.5

100

176

2-2

—

HT1-4

129

2.1

100

177

2-2

—

HT1-5

128

1.7

100

178

2-2

—

HT1-6

131

1.7

100

179

2-2

—

HT1-7

131

1.8

100

180

2-2

—

HT1-8

129

2.2

100

181

2-2

—

HT1-9

130

1.6

100

182

2-2

—

HT1-10

132

2.0

100

183

2-2

—

HT1-11

129

1.8

100

184

2-2

—

HT2-1

150

1.1

100

185

2-2

—

HT2-2

149

1.6

100

186

2-2

—

HT2-3

154

1.5

100

187

2-2

—

HT2-4

142

1.8

100

188

2-2

—

HT2-5

152

1.9

100

189

2-2

—

HT2-6

154

1.2

100

190

2-2

—

HT3-1

143

1.7

100

191

2-2

—

HT3-2

151

1.1

100

192

2-2

—

HT3-3

148

1.0

100

193

2-2

—

HT3-4

147

1.6

100

194

2-2

—

HT3-5

143

1.3

100

195

2-2

—

HT4-1

150

1.4

100

196

2-2

—

HT4-2

146

1.0

100

197

2-2

—

HT4-3

141

1.7

100

198

2-2

—

HT5-1

160

1.6

100

199

2-2

—

HT6-1

163

1.9

100

200

2-2

—

HT7-1

154

2.0

100

TABLE 10

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

201

2-2

—

HT8-1

163

1.5

100

202

2-2

—

HT8-2

150

2.2

100

203

2-2

—

HT9-1

161

1.7

100

204

2-2

—

HT9-2

154

1.5

100

205

2-2

—

HT10-1

159

2.0

100

206

2-2

—

HT10-2

155

1.9

100

207

2-2

—

HT11-1

162

1.6

100

208

2-2

—

HT11-2

165

2.1

100

209

2-2

—

HT12-1

160

2.2

100

210

2-2

—

HT12-2

157

1.8

100

211

2-2

—

HT13-1

155

2.0

100

212

2-2

—

HT13-2

151

1.5

100

213

2-2

—

HT13-3

156

1.7

100

214

↓

↑

2-2

—

HT1-1

157

2.4

100

215

2-2

A-1

HT1-1

130

2.0

100

TABLE 11

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

216

2-3

—

HT1-1

128

2.3

100

217

2-3

—

HT1-2

133

2.0

100

218

2-3

—

HT1-3

130

2.1

100

219

2-3

—

HT1-4

131

1.7

100

220

2-3

—

HT1-5

129

1.9

100

221

2-3

—

HT1-6

130

2.2

100

222

2-3

—

HT1-7

127

1.8

100

223

2-3

—

HT1-8

131

2.1

100

224

2-3

—

HT1-9

128

1.6

100

225

2-3

—

HT1-10

128

1.8

100

226

2-3

—

HT1-11

129

2.0

100

227

2-3

—

HT2-1

147

1.0

100

228

2-3

—

HT2-2

140

1.3

100

229

2-3

—

HT2-3

154

1.8

100

230

2-3

—

HT2-4

150

1.0

100

231

2-3

—

HT2-5

142

1.5

100

232

2-3

—

HT2-6

143

1.7

100

233

2-3

—

HT3-1

150

1.2

100

234

2-3

—

HT3-2

153

1.0

100

235

2-3

—

HT3-3

149

1.1

100

236

2-3

—

HT3-4

142

1.6

100

237

2-3

—

HT3-5

143

1.5

100

238

2-3

—

HT4-1

152

1.0

100

239

2-3

—

HT4-2

148

1.2

100

240

2-3

—

HT4-3

151

1.6

100

241

2-3

—

HT5-1

163

1.8

100

242

2-3

—

HT6-1

165

2.0

100

243

2-3

—

HT7-1

159

2.1

100

TABLE 12

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

244

2-3

—

HT8-1

159

1.5

100

245

2-3

—

HT8-2

156

2.0

100

246

2-3

—

HT9-1

151

1.7

100

247

2-3

—

HT9-2

162

2.1

100

248

2-3

—

HT10-1

158

1.6

100

249

2-3

—

HT10-2

160

1.7

100

250

2-3

—

HT11-1

153

2.0

100

251

2-3

—

HT11-2

163

1.9

100

252

2-3

—

HT12-1

154

2.0

100

253

2-3

—

HT12-2

161

1.5

100

254

2-3

—

HT13-1

160

2.1

100

255

2-3

—

HT13-2

157

1.9

100

256

2-3

—

HT13-3

164

1.8

100

257

↓

↑

2-3

—

HT1-1

162

1.7

100

258

2-3

A-1

HT1-1

130

2.2

100

TABLE 13

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

259

3-1

—

HT1-1

120

2.5

100

260

3-1

—

HT1-2

118

2.1

100

261

3-1

—

HT1-3

121

2.6

100

262

3-1

—

HT1-4

119

2.3

100

263

3-1

—

HT1-5

122

2.5

100

264

3-1

—

HT1-6

121

2.2

100

265

3-1

—

HT1-7

123

2.4

100

266

3-1

—

HT1-8

119

2.9

100

267

3-1

—

HT1-9

120

2.8

100

268

3-1

—

HT1-10

120

2.0

100

269

3-1

—

HT1-11

123

2.7

100

270

3-1

—

HT2-1

140

1.8

100

271

3-1

—

HT2-2

145

1.6

100

272

3-1

—

HT2-3

139

1.4

100

273

3-1

—

HT2-4

130

1.8

100

274

3-1

—

HT2-5

135

2.1

100

275

3-1

—

HT2-6

144

1.4

100

276

3-1

—

HT3-1

132

2.2

100

277

3-1

—

HT3-2

141

1.7

100

278

3-1

—

HT3-3

133

1.5

100

279

3-1

—

HT3-4

140

1.9

100

280

3-1

—

HT3-5

138

2.0

100

281

3-1

—

HT4-1

142

2.2

100

282

3-1

—

HT4-2

139

1.6

100

283

3-1

—

HT4-3

131

2.0

100

284

3-1

—

HT5-1

141

2.5

100

285

3-1

—

HT6-1

152

2.4

100

286

3-1

—

HT7-1

150

2.4

100

TABLE 14

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

287

3-1

—

HT8-1

153

2.2

100

288

3-1

—

HT8-2

144

3.0

100

289

3-1

—

HT9-1

150

2.8

100

290

3-1

—

HT9-2

150

2.9

100

291

3-1

—

HT10-1

146

2.4

100

292

3-1

—

HT10-2

145

2.4

100

293

3-1

—

HT11-1

141

2.5

100

294

3-1

—

HT11-2

155

2.1

100

295

3-1

—

HT12-1

154

2.3

100

296

3-1

—

HT12-2

142

2.1

100

297

3-1

—

HT13-1

148

2.4

100

298

3-1

—

HT13-2

151

2.4

100

299

3-1

—

HT13-3

150

2.0

100

300

↓

↑

3-1

—

HT1-1

151

2.8

100

301

3-1

A-1

HT1-1

118

2.1

100

TABLE 15

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

302

3-2

—

HT1-1

121

2.6

100

303

3-2

—

HT1-2

120

2.5

100

304

3-2

—

HT1-3

120

3.0

100

305

3-2

—

HT1-4

118

2.2

100

306

3-2

—

HT1-5

119

2.2

100

307

3-2

—

HT1-6

120

2.5

100

308

3-2

—

HT1-7

122

2.9

100

309

3-2

—

HT1-8

122

2.6

100

310

3-2

—

HT1-9

121

2.1

100

311

3-2

—

HT1-10

120

2.3

100

312

3-2

—

HT1-11

121

2.4

100

313

3-2

—

HT2-1

138

1.4

100

314

3-2

—

HT2-2

135

1.8

100

315

3-2

—

HT2-3

135

1.5

100

316

3-2

—

HT2-4

144

1.5

100

317

3-2

—

HT2-5

140

2.1

100

318

3-2

—

HT2-6

142

1.8

100

319

3-2

—

HT3-1

135

2.0

100

320

3-2

—

HT3-2

136

2.1

100

321

3-2

—

HT3-3

130

1.6

100

222

3-2

—

HT3-4

141

1.7

100

323

3-2

—

HT3-5

132

1.9

100

324

3-2

—

HT4-1

142

1.5

100

325

3-2

—

HT4-2

140

1.9

100

326

3-2

—

HT4-3

139

1.5

100

327

3-2

—

HT5-1

142

2.0

100

328

3-2

—

HT6-1

151

2.4

100

329

3-2

—

HT7-1

151

2.3

100

TABLE 16

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

331

3-2

—

HT8-2

148

2.1

100

332

3-2

—

HT9-1

150

3.0

100

333

3-2

—

HT9-2

146

2.4

100

334

3-2

—

HT10-1

141

2.2

100

335

3-2

—

HT10-2

150

2.2

100

336

3-2

—

HT11-1

152

2.8

100

337

3-2

—

HT11-2

152

2.9

100

338

3-2

—

HT12-1

155

2.6

100

339

3-2

—

HT12-2

154

2.1

100

340

3-2

—

HT13-1

147

2.2

100

341

3-2

—

HT13-2

149

2.7

100

342

3-2

—

HT13-3

147

2.8

100

343

↓

↑

3-2

—

HT1-1

150

2.9

100

344

3-2

A-1

HT1-1

120

2.4

100

TABLE 17

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

345

3-2

—

HT1-1

118

2.9

100

346

3-2

—

HT1-2

117

2.3

100

347

3-2

—

HT1-3

120

2.3

100

348

3-2

—

HT1-4

123

2.4

100

349

3-2

—

HT1-5

119

2.5

100

350

3-2

—

HT1-6

119

3.0

100

351

3-2

—

HT1-7

121

2.8

100

352

3-2

—

HT-8

118

2.6

100

353

3-2

—

HT1-9

122

2.2

100

354

3-2

—

HT1-10

120

2.9

100

355

3-2

—

HT1-11

122

2.2

100

356

3-2

—

HT2-1

131

2.0

100

357

3-2

—

HT2-2

140

2.2

100

358

3-2

—

HT2-3

144

1.9

100

359

3-2

—

HT2-4

142

1.6

100

360

3-2

—

HT2-5

133

1.4

100

361

3-2

—

HT2-6

140

1.4

100

362

3-2

—

HT3-1

142

1.7

100

363

3-2

—

HT3-2

138

1.8

100

364

3-2

—

HT3-3

144

2.0

100

365

3-2

—

HT3-4

137

1.9

100

366

3-2

—

HT3-5

141

1.5

100

367

3-2

—

HT4-1

132

1.9

100

368

3-2

—

HT4-2

139

2.1

100

369

3-2

—

HT4-3

139

1.5

100

370

3-2

—

HT5-1

142

2.0

100

371

3-2

—

HT6-1

150

2.4

100

372

3-2

—

HT7-1

147

2.4

100

TABLE 18

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

244

3-3

—

HT8-1

151

3.0

100

374

3-3

—

HT8-2

149

2.1

100

375

3-3

—

HT9-1

140

2.4

100

376

3-3

—

HT9-2

150

2.0

100

377

3-3

—

HT10-1

150

2.9

100

378

3-3

—

HT10-2

141

2.6

100

379

3-3

—

HT11-1

143

2.3

100

380

3-3

—

HT11-2

155

2.7

100

381

3-3

—

HT12-1

146

2.2

100

382

3-3

—

HT12-2

153

2.5

100

383

3-3

—

HT13-1

148

2.1

100

384

3-3

—

HT13-2

154

2.5

100

385

3-3

—

HT13-3

152

2.4

100

386

↓

↑

3-3

—

HT1-1

149

2.1

100

387

3-3

A-1

HT1-1

120

2.4

100

Comp. Ex. 1

A-4

—

HT1-1

191

6.4

30

Comp. Ex. 2

1-1

—

HT14-1

239

2.6

100

In Tables 1 to 18, the photosensitive material having a mark (*) means that in which no electron transferring material is added.

Examples 388 to 759

[Single-layer photosensitive material for analog light source (positive charging type)]

According to the same manner as that described in Examples 1 to 387 except for using a bisazo pigment represented by the following formula (CG2) in place of the electric charge generating material (CG1) used in Examples 1 to 387, a single-layer photosensitive material for analog light source was produced, respectively.

Comparative Example 3

According to the same manner as that described in Example 388 except for using 90 parts by weight of the polycarbonate resin having a repeating unit of the above formula (A-4) as the binding resin, a single-layer photosensitive material was produced.

Comparative Example 4

According to the same manner as that described in Examples 388 except for using the compound represented by the above formula (HT14-1) as the hole transferring material, a single-layer photosensitive material was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the following tests and their characteristics were evaluated.

<Evaluation of positive charging photosensitive material for analog light source>

Photosensitivity test

By using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of a photosensitive material obtained in the respective Examples and Comparative Examples to charge the surface at +700 V, respectively. Then, white light (light intensity: 147 lux second) of a halogen lamp as an exposure light source was irradiated on the surface of the photosensitive material (irradiation time: 50 msec.). Furthermore, a surface potential at the time at which 330 msec. has passed since the beginning of exposure was measured as a potential after exposure V

L

(V).

Wear Resistance Test

A photosensitive material obtained in the respective Examples and Comparative Examples was fit with an electrostatic copying machine (Model DC-2556, manufactured by Mita Industrial Co., Ltd.) and, after rotating 150,000 times without passing a paper through it, a change in film thickness of a photosensitive layer before and after rotation was determined, respectively.

Adhesion test

It was measured according to the same manner as that described above.

These test results are shown in Tables 19 to 36, together with the above-described compound No. of the binding resin and the hole transferring material (HTM) used.

TABLE 19

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

388

1-1

—

HT1-1

195

1.7

100

389

1-1

—

HT1-2

180

1.5

100

390

1-1

—

HT1-3

177

2.0

100

391

1-1

—

HT1-4

181

1.6

100

392

1-1

—

HT1-5

181

1.6

100

393

1-1

—

HT1-6

180

1.7

100

394

1-1

—

HT1-7

179

1.2

100

395

1-1

—

HT1-8

180

1.0

100

396

1-1

—

HT1-9

180

1.8

100

397

1-1

—

HT1-10

181

2.0

100

398

1-1

—

HT1-11

178

1.3

100

399

1-1

—

HT2-1

195

1.0

100

400

1-1

—

HT2-2

209

0.8

100

401

1-1

—

HT2-3

194

0.8

100

402

1-1

—

HT2-4

198

0.7

100

403

1-1

—

HT2-5

202

0.9

100

404

1-1

—

HT2-6

193

1.1

100

405

1-1

—

HT3-1

206

1.2

100

406

1-1

—

HT3-2

195

0.6

100

407

1-1

—

HT3-3

210

0.7

100

408

1-1

—

HT3-4

194

0.7

100

409

1-1

—

HT3-5

200

0.9

100

410

1-1

—

HT4-1

207

1.2

100

411

1-1

—

HT4-2

192

1.1

100

412

1-1

—

HT4-3

192

1.0

100

413

1-1

—

HT5-1

203

1.4

100

414

1-1

—

HT6-1

208

1.3

100

415

1-1

—

HT7-1

218

1.9

100

TABLE 20

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

416

1-1

—

HT8-1

204

1.3

100

417

1-1

—

HT8-2

216

1.7

100

418

1-1

—

HT9-1

203

1.9

100

419

1-1

—

HT9-2

215

1.6

100

420

1-1

—

HT10-1

211

1.6

100

421

1-1

—

HT10-2

211

2.0

100

422

1-1

—

HT11-1

200

1.4

100

423

1-1

—

HT11-2

219

1.9

100

424

1-1

—

HT12-1

204

1.2

100

425

1-1

—

HT12-2

218

1.8

100

426

1-1

—

HT13-1

214

1.5

100

427

1-1

—

HT13-2

212

1.1

100

428

1-1

—

HT13-3

207

1.0

100

429

↓

↑

1-1

—

HT1-1

192

1.3

100

430

1-1

A-1

HT1-1

180

1.8

100

TABLE 21

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

431

1-2

—

HT1-1

203

1.3

100

432

1-2

—

HT1-2

178

1.7

100

433

1-2

—

HT1-3

185

1.7

100

434

1-2

—

HT1-4

182

2.0

100

435

1-2

—

HT1-5

182

1.2

100

436

1-2

—

HT1-6

179

1.6

100

437

1-2

—

HT1-7

178

1.9

100

438

1-2

—

HT1-8

183

1.8

100

439

1-2

—

HT1-9

177

1.5

100

440

1-2

—

HT1-10

181

1.3

100

441

1-2

—

HT1-11

180

1.0

100

442

1-2

—

HT2-1

200

0.8

100

443

1-2

—

HT2-2

200

1.2

100

444

1-2

—

HT2-3

206

0.6

100

445

1-2

—

HT2-4

203

1.1

100

446

1-2

—

HT2-5

199

1.0

100

447

1-2

—

HT2-6

210

0.7

100

448

1-2

—

HT3-1

208

0.9

100

449

1-2

—

HT3-2

201

0.9

100

450

1-2

—

HT3-3

202

0.9

100

451

1-2

—

HT3-4

194

1.2

100

452

1-2

—

HT3-5

192

0.6

100

453

1-2

—

HT4-1

195

0.7

100

454

1-2

—

HT4-2

199

0.9

100

455

1-2

—

HT4-3

195

0.8

100

456

1-2

—

HT5-1

207

1.8

100

457

1-2

—

HT6-1

215

1.6

100

458

1-2

—

HT7-1

212

1.6

100

TABLE 22

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

459

1-2

—

HT8-1

217

1.9

100

460

1-2

—

HT8-2

208

2.0

100

461

1-2

—

HT9-1

215

1.3

100

462

1-2

—

HT9-2

205

1.2

100

463

1-2

—

HT10-1

210

1.3

100

464

1-2

—

HT10-2

210

1.4

100

465

1-2

—

HT11-1

214

1.4

100

466

1-2

—

HT11-2

206

1.0

100

467

1-2

—

HT12-1

217

1.5

100

468

1-2

—

HT12-2

200

2.0

100

469

1-2

—

HT13-1

205

1.7

100

470

1-2

—

HT13-2

203

1.4

100

471

1-2

—

HT13-3

219

1.1

100

472

↓

↑

1-2

—

HT1-1

197

1.1

100

473

1-2

A-1

HT1-1

179

1.6

100

TABLE 23

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

474

1-3

—

HT1-1

197

1.8

100

475

1-3

—

HT1-2

183

1.5

100

476

1-3

—

HT1-3

180

2.0

100

477

1-3

—

HT1-4

178

1.1

100

478

1-3

—

HT1-5

184

1.8

100

479

1-3

—

HT1-6

180

1.9

100

480

1-3

—

HT1-7

182

1.2

100

481

1-3

—

HT1-8

177

1.3

100

482

1-3

—

HT1-9

179

1.6

100

483

1-3

—

HT1-10

179

1.4

100

484

1-3

—

HT1-11

182

1.0

100

485

1-3

—

HT2-1

193

1.2

100

486

1-3

—

HT2-2

209

0.6

100

487

1-3

—

HT2-3

211

0.8

100

488

1-3

—

HT2-4

215

0.8

100

489

1-3

—

HT2-5

193

0.7

100

490

1-3

—

HT2-6

208

1.0

100

491

1-3

—

HT3-1

208

0.9

100

492

1-3

—

HT3-2

200

1.1

100

493

1-3

—

HT3-3

190

1.2

100

494

1-3

—

HT3-4

191

0.9

100

495

1-3

—

HT3-5

204

0.8

100

496

1-3

—

HT4-1

207

1.0

100

497

1-3

—

HT4-2

192

0.8

100

498

1-3

—

HT4-3

200

0.6

100

499

1-3

—

HT5-1

204

1.8

100

500

1-3

—

HT6-1

212

1.0

100

501

1-3

—

HT7-1

210

1.2

100

TABLE 24

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

502

1-3

—

HT8-1

210

1.8

100

503

1-3

—

HT8-2

215

1.2

100

504

1-3

—

HT9-1

214

1.6

100

505

1-3

—

HT9-2

217

1.0

100

506

1-3

—

HT10-1

208

1.4

100

507

1-3

—

HT10-2

215

1.9

100

508

1-3

—

HT11-1

209

1.1

100

509

1-3

—

HT11-2

210

1.5

100

510

1-3

—

HT12-1

210

1.6

100

511

1-3

—

HT12-2

218

1.6

100

512

1-3

—

HT13-1

212

1.1

100

513

1-3

—

HT13-2

207

1.8

100

514

1-3

—

HT13-3

206

1.4

100

515

↓

↑

1-3

—

HT1-1

195

1.5

100

516

1-3

A-1

HT1-1

180

1.2

100

TABLE 25

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

517

2-1

—

HT1-1

200

0.8

100

518

2-1

—

HT1-2

180

0.7

100

519

2-1

—

HT1-3

178

1.4

100

520

2-1

—

HT1-4

179

0.8

100

521

2-1

—

HT1-5

182

1.0

100

522

2-1

—

HT1-6

181

0.9

100

523

2-1

—

HT1-7

181

1.2

100

524

2-1

—

HT1-8

179

1.2

100

525

2-1

—

HT1-9

182

0.9

100

526

2-1

—

HT1-10

183

0.7

100

527

2-1

—

HT1-11

180

1.3

100

528

2-1

—

HT2-1

198

0.8

100

529

2-1

—

HT2-2

204

0.7

100

530

2-1

—

HT2-3

218

0.6

100

531

2-1

—

MT2-4

195

0.4

100

532

2-1

—

HT2-5

218

0.6

100

533

2-1

—

HT2-6

200

0.7

100

534

2-1

—

HT3-1

200

0.5

100

535

2-1

—

HT3-2

198

0.5

100

536

2-1

—

HT3-3

212

0.5

100

537

2-1

—

HT3-4

209

0.8

100

538

2-1

—

HT3-5

206

0.7

100

539

2-1

—

HT4-1

193

0.4

100

540

2-1

—

HT4-2

197

0.6

100

541

2-1

—

HT4-3

216

0.6

100

542

2-1

—

HT5-1

216

0.9

100

543

2-1

—

HT6-1

215

0.8

100

544

2-1

—

HT7-1

218

0.9

100

TABLE 26

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

545

2-1

—

HT8-1

192

0.9

100

546

2-1

—

HT8-2

205

1.3

100

547

2-1

—

HT9-1

203

0.7

100

548

2-1

—

HT9-2

208

1.2

100

549

2-1

—

HT10-1

216

0.8

100

550

2-1

—

HT10-2

210

1.4

100

551

2-1

—

HT11-1

212

1.0

100

552

2-1

—

HT11-2

215

1.0

100

553

2-1

—

HT12-1

208

0.9

100

554

2-1

—

HT12-2

208

0.9

100

555

2-1

—

HT13-1

217

0.8

100

556

2-1

—

HT13-2

214

1.3

100

557

2-1

—

HT13-3

209

1.1

100

558

2-1

—

HT1-1

193

0.5

100

559

2-1

A-1

HT1-1

179

0.7

100

TABLE 27

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

560

2-2

—

HT1-1

179

0.7

100

561

2-2

—

HT1-2

176

1.1

100

562

2-2

—

HT1-3

181

1.2

100

563

2-2

—

HT1-4

180

1.4

100

564

2-2

—

HT1-5

178

0.8

100

565

2-2

—

HT1-6

181

0.7

100

566

2-2

—

HT1-7

177

1.3

100

567

2-2

—

HT1-8

177

1.2

100

568

2-2

—

HT1-9

182

0.9

100

569

2-2

—

HT1-10

179

0.9

100

570

2-2

—

HT1-11

180

1.0

100

571

2-2

—

HT2-1

193

0.7

100

572

2-2

—

HT2-2

208

0.8

100

573

2-2

—

HT2-3

200

0.5

100

574

2-2

—

HT2-4

197

0.6

100

575

2-2

—

HT2-5

202

0.6

100

576

2-2

—

HT2-6

202

0.6

100

577

2-2

—

HT3-1

196

0.7

100

578

2-2

—

HT3-2

200

0.5

100

579

2-2

—

HT3-3

195

0.4

100

580

2-2

—

HT3-4

197

0.8

100

581

2-2

—

HT3-5

206

0.6

100

582

2-2

—

HT4-1

197

0.8

100

583

2-2

—

HT4-2

197

0.7

100

584

2-2

—

HT4-3

190

0.7

100

585

2-2

—

HT5-1

218

0.7

100

586

2-2

—

HT6-1

218

0.9

100

587

2-2

—

HT7-1

203

1.0

100

TABLE 28

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

588

2-2

—

HT8-1

204

1.3

100

589

2-2

—

HT8-1

208

0.9

100

590

2-2

—

HT9-1

210

1.1

100

591

2-2

—

HT9-2

216

1.0

100

592

2-2

—

HT10-1

207

1.0

100

593

2-2

—

HT10-2

200

1.0

100

594

2-2

—

HT11-1

219

1.2

100

595

2-2

—

HT11-2

216

1.3

100

596

2-2

—

HT12-1

220

0.9

100

597

2-2

—

HT12-2

213

0.8

100

598

2-2

—

HT13-1

217

0.8

100

599

2-2

—

HT13-2

205

0.7

100

600

2-2

—

HT13-3

204

1.4

100

601

↓

↑

2-2

—

HT1-1

200

0.6

100

602

2-2

A-1

HT1-1

182

0.7

100

TABLE 29

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

603

2-3

—

HT1-1

198

0.6

100

604

2-3

—

HT1-2

177

1.4

100

605

2-3

—

HT1-3

180

0.7

100

606

2-3

—

HT1-4

179

0.9

100

607

2-3

—

HT1-5

177

1.3

100

608

2-3

—

HT1-6

180

0.7

100

609

2-3

—

HT1-7

180

1.4

100

610

2-3

—

HT1-8

182

0.9

100

611

2-3

—

HT1-9

178

0.9

100

612

2-3

—

HT1-10

179

1.0

100

613

2-3

—

HT1-11

183

0.8

100

614

2-3

—

HT2-1

208

0.7

100

615

2-3

—

HT2-2

195

0.8

100

616

2-3

—

HT2-3

192

0.5

100

617

2-3

—

HT2-4

200

0.5

100

618

2-3

—

HT2-5

200

0.4

100

619

2-3

—

HT2-6

210

0.6

100

620

2-3

—

HT3-1

206

0.6

100

621

2-3

—

HT3-2

191

0.6

100

622

2-3

—

HT3-3

198

0.7

100

623

2-3

—

HT3-4

200

0.5

100

624

2-3

—

HT3-5

207

0.8

100

625

2-3

—

HT4-1

204

0.4

100

626

2-3

—

HT4-2

210

0.8

100

627

2-3

—

HT4-3

199

0.5

100

628

2-3

—

HT5-1

212

1.3

100

629

2-3

—

HT6-1

200

1.0

100

630

2-3

—

HT7-1

200

1.0

100

TABLE 30

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

631

2-3

—

HT8-1

203

0.7

100

632

2-3

—

HT8-2

216

1.3

100

633

2-3

—

HT9-1

220

1.0

100

634

2-3

—

HT9-2

219

0.9

100

635

2-3

—

HT10-1

216

0.9

100

636

2-3

—

HT10-2

200

1.2

100

637

2-3

—

HT11-1

210

0.8

100

638

2-3

—

HT11-2

215

1.2

100

639

2-3

—

HT12-1

207

1.0

100

640

2-3

—

HT12-2

207

1.4

100

641

2-3

—

HT13-1

218

0.9

100

642

2-3

—

HT13-2

204

1.3

100

643

2-3

—

HT13-3

208

1.0

100

644

↓

↑

2-3

—

HT1-1

201

0.9

100

645

2-3

A-1

HT1-1

179

1.2

100

TABLE 31

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

646

3-1

—

HT1-1

195

1.9

100

647

3-1

—

HT1-2

170

1.0

100

648

3-1

—

HT1-3

170

1.7

100

649

3-1

—

HT1-4

168

1.4

100

650

3-1

—

HT1-5

170

1.4

100

651

3-1

—

HT1-6

167

1.8

100

652

3-1

—

HT1-7

169

1.5

100

653

3-1

—

HT1-8

173

1.0

100

654

3-1

—

HT1-9

172

1.6

100

655

3-1

—

HT1-10

170

1.2

100

656

3-1

—

HT1-11

171

1.2

100

657

3-1

—

HT2-1

176

1.2

100

658

3-1

—

HT2-2

179

0.7

100

659

3-1

—

HT2-3

179

1.9

100

660

3-1

—

HT2-4

180

1.1

100

661

3-1

—

HT2-5

184

0.8

100

662

3-1

—

HT2-6

175

0.7

100

663

3-1

—

HT3-1

176

1.0

100

664

3-1

—

HT3-2

184

0.6

100

665

3-1

—

HT3-3

180

1.2

100

666

3-1

—

HT3-4

185

0.8

100

667

3-1

—

HT3-5

180

1.1

100

668

3-1

—

HT4-1

183

1.0

100

669

3-1

—

HT4-2

181

1.0

100

670

3-1

—

HT4-3

179

0.9

100

671

3-1

—

HT5-1

193

1.5

100

672

3-1

—

HT6-1

181

1.4

100

673

3-1

—

HT7-1

189

1.4

100

TABLE 32

Adhe-

Binding resin

VL

Wear

sion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

674

3-1

—

HT8-1

194

1.0

100

675

3-1

—

HT8-2

190

1.1

100

676

3-1

—

HT9-1

181

1.6

100

677

3-1

—

HT9-2

181

1.9

100

678

3-1

—

HT10-1

192

1.4

100

679

3-1

—

HT10-2

185

1.0

100

680

3-1

—

HT11-1

193

1.3

100

681

3-1

—

HT11-2

186

1.3

100

682

3-1

—

HT12-1

180

1.4

100

683

3-1

—

HT12-2

185

1.8

100

684

3-1

—

HT13-1

188

1.5

100

685

3-1

—

HT13-2

182

2.0

100

686

3-1

—

HT13-3

195

1.2

100

687‡

3-1

—

HT1-1

188

1.3

100

688

3-1

A-1

HT1-1

170

1.8

100

TABLE 33

Adhe-

Binding resin

VL

Wear

sion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

689

3-2

—

HT1-1

185

1.1

100

690

3-2

—

HT1-2

170

1.0

100

691

3-2

—

HT1-3

170

1.9

100

692

3-2

—

HT1-4

171

1.1

100

693

3-2

—

HT1-5

173

1.8

100

694

3-2

—

HT1-6

173

1.7

100

695

3-2

—

HT1-7

170

1.5

100

696

3-2

—

HT1-8

169

1.2

100

697

3-2

—

HT1-9

168

1.6

100

698

3-2

—

HT1-10

170

1.6

100

699

3-2

—

HT1-11

170

1.3

100

700

3-2

—

HT2-1

175

0.7

100

701

3-2

—

HT2-2

185

0.7

100

702

3-2

—

HT2-3

181

0.6

100

703

3-2

—

HT2-4

182

1.0

100

704

3-2

—

HT2-5

175

1.1

100

705

3-2

—

HT2-6

177

0.9

100

706

3-2

—

HT3-1

177

1.2

100

707

3-2

—

HT3-2

180

0.8

100

708

3-2

—

HT3-3

180

0.7

100

709

3-2

—

HT3-4

183

0.8

100

710

3-2

—

HT3-5

176

1.0

100

711

3-2

—

HT4-1

179

1.0

100

712

3-2

—

HT4-2

185

1.2

100

713

3-2

—

HT4-3

178

0.9

100

714

3-2

—

HT5-1

180

1.8

100

715

3-2

—

HT6-1

180

2.0

100

716

3-2

—

HT7-1

190

1.1

100

TABLE 34

Adhe-

Binding resin

VL

Wear

sion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

717

3-2

—

HT8-1

196

1.5

100

718

3-2

—

HT8-2

184

0.9

100

719

3-2

—

HT9-1

182

0.8

100

720

3-2

—

HT9-2

184

1.2

100

721

3-2

—

HT10-1

195

0.7

100

722

3-2

—

HT10-2

189

1.0

100

723

3-2

—

HT11-1

191

1.0

100

724

3-2

—

HT11-2

180

1.3

100

725

3-2

—

HT12-1

188

0.9

100

726

3-2

—

HT12-2

188

1.3

100

727

3-2

—

HT13-1

193

0.7

100

728

3-2

—

HT13-2

184

1.1

100

729

3-2

—

HT13-3

185

1.4

000

730‡

3-2

—

HT1-1

190

1.2

100

731

3-2

A-1

HT1-1

168

1.3

100

TABLE 35

Adhe-

Binding resin

VL

Wear

sion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

717

3-3

—

HT1-1

168

2.0

100

718

3-3

—

HT1-2

166

1.4

100

719

3-3

—

HT1-3

170

2.0

100

720

3-3

—

HT1-4

170

1.7

100

721

3-3

—

HT1-5

168

1.5

100

722

3-3

—

HT1-6

167

1.5

100

723

3-3

—

HT1-7

173

1.6

100

724

3-3

—

HT1-8

172

1.5

100

725

3-3

—

HT1-9

171

1.0

100

726

3-3

—

HT1-10

169

1.8

100

727

3-3

—

HT1-11

169

1.8

100

728

3-3

—

HT2-1

175

1.2

100

729

3-3

—

HT2-2

180

1.1

100

730

3-3

—

HT2-3

180

1.1

100

731

3-3

—

HT2-4

177

0.8

100

732

3-3

—

HT2-5

181

0.7

100

733

3-3

—

HT2-6

178

0.7

100

734

3-3

—

HT3-1

184

1.0

100

735

3-3

—

HT3-2

184

0.6

100

736

3-3

—

HT3-3

176

1.2

100

737

3-3

—

HT3-4

181

0.9

100

738

3-3

—

HT3-5

179

0.6

100

739

3-3

—

HT4-1

180

0.7

100

740

3-3

—

HT4-2

182

1.0

100

741

3-3

—

HT4-3

182

1.2

100

742

3-3

—

HT5-1

180

1.8

100

743

3-3

—

HT6-1

181

1.8

100

744

3-3

—

HT7-1

190

1.5

100

TABLE 36

Adhe-

Binding resin

VL

Wear

sion

Ex.

Main

Blend

HTM

(V)

(μm)

(%)

745

3-3

—

HT8-1

182

1.2

100

746

3-3

—

HT8-2

185

1.4

100

747

3-3

—

HT9-1

185

2.0

100

748

3-3

—

HT9-2

190

1.3

100

749

3-3

—

HT10-1

193

1.3

100

750

3-3

—

HT10-2

188

1.4

100

751

3-3

—

HT11-1

184

1.9

100

752

3-3

—

HT11-2

190

1.0

100

753

3-3

—

HT12-1

192

1.1

100

754

3-3

—

HT12-2

188

1.4

100

755

3-3

—

HT13-1

195

1.9

100

756

3-3

—

HT13-2

193

1.7

100

757

3-3

—

HT13-3

190

1.7

000

758‡

3-3

—

HT1-1

185

1.6

100

759

3-3

A-1

HT1-1

172

1.9

100

Comp. Ex. 3

A-4

—

HT1-1

242

5.5

30

Comp. Ex. 4

1-1

—

HT14-1

305

1.4

100

In Tables 19 to 36, the photosensitive material having a mark (*) means that in which no electron transferring material is added.

Examples 760 to 795

Multi-layer photosensitive material for digital light source (negative charging type)

2 Parts by weight of the pigment represented by the above formula (CG1) as the electric charge generating material and 1 part by weight of a polyvinyl butyral as the binding resin were mixed and dispersed, together with 120 parts by weight of dichloromethane as the solvent, by using a ball mill to prepare a coating solution for electric charge generating layer. Then, this coating solution was applied on an aluminum tube by a dip coating method, followed by hot-air drying at 100° C. for 60 minutes to give an electric charge generating layer having a thickness of 0.5 μm.

Then, 80 parts by weight of the hole transferring material represented by the above formula (HT1), (HT2) or (HT3) and 90 parts by weight of any one of polyester resins (1—1) to (1-3), (2-1) to (2-3) and (3-1) to (3—3) obtained in Reference Examples 1 to 9 or a mixture of this polyester resin and a polycarbonate resin as the binding resin were mixed and dispersed, together with 800 parts by weight of tetrahydrofuran, by using a ball mill to prepare a coating solution for electric charge transferring layer. Then, this coating solution was applied on the above electric charge generating layer by a dip coating method, followed by hot-air drying at 100° C. for 60 minutes to form an electric charge transferring layer having a thickness of 15 μm., thereby producing a negative charging type multi-layer photosensitive material for digital light source, respectively.

When using a mixture of the polyester resin and polycarbonate resin as the binding resin, 70 parts by weight of the polyester resin and 20 parts by weight of the polycarbonate resin were used in combination.

Comparative Example 5

According to the same manner as that described in Example 760 except for using 90 parts by weight of the polycarbonate resin having a repeating unit of the above formula (A-4) as the binding resin of the electric charge transferring material, a negative charging type multi-layer photosensitive material for digital light source was produced.

Comparative Example 6

According to the same manner as that described in Examples 760 except for using the compound represented by the above formula (HT14-1) as the hole transferring material, a negative charging type multi-layer photosensitive material for digital light source was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the following tests and their characteristics were evaluated.

Evaluation of negative charging photosensitive material for digital light source

Photosensitivity test

By using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of a photosensitive material obtained in the respective Examples and Comparative Examples to charge the surface at −700 V, respectively. Then, monochromatic light [wavelength: 780 nm (half-width: 20 nm), light intensity: 16 μW/cm

2

] from white light of a halogen lamp as an exposure light source through a band-pass filter was irradiated on the surface of the photosensitive material (irradiation time: 80 msec.). Furthermore, a surface potential at the time at which 330 msec. has passed since the beginning of exposure was measured as a potential after exposure V

L

(V).

Wear resistance test

A photosensitive material obtained in the respective Examples and Comparative Examples was fit with an imaging unit of an electrostatic laser printer (Model LP-2080, manufactured by Mita Industrial Co., Ltd.) and, after rotating 150,000 times without passing a paper through it, a change in thickness of a photosensitive layer before and after rotation was determined, respectively.

These test results are shown in Tables 37 to 38, together with the above-described compound No. of the binding resin and hole transferring material used.

TABLE 37

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

760

1-1

—

HT1-1

−86

2.4

761

1-1

—

HT2-1

−88

2.4

762

1-1

—

HT3-1

−85

2.2

763

1-1

A-1

HT1-1

−90

2.5

764

1-2

—

HT1-1

−94

2.5

765

1-2

—

HT2-1

−92

2.3

766

1-2

—

HT3-1

−90

2.5

767

1-2

A-1

HT1-1

−97

2.6

768

1-3

—

HT1-1

−88

2.1

769

1-3

—

HT2-1

−85

2.2

770

1-3

—

HT3-1

−86

2.4

771

1-3

A-1

HT1-1

−85

2.5

772

2-1

—

HT1-1

−90

1.1

773

2-1

—

HT2-1

−84

1.4

774

2-1

—

HT3-1

−85

1.5

775

2-1

A-1

HT1-1

−86

1.5

776

2-2

—

HT1-1

−85

1.3

777

2-2

—

HT2-1

−90

1.6

778

2-2

—

HT3-1

−85

1.3

779

2-2

A-1

HT1-1

−86

1.4

780

2-3

—

HT1-1

−86

1.3

781

2-3

—

HT2-1

−84

1.6

782

2-3

—

HT3-1

−90

1.5

783

2-3

A-1

HT1-1

−90

1.8

784

3-1

—

HT1-1

−66

2.4

785

3-1

—

HT2-1

−60

2.3

786

3-1

—

HT3-1

−70

2.6

787

3-1

A-1

HT1-1

−71

2.2

TABLE 38

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

788

3-2

—

HT1-1

−66

2.7

789

3-2

—

HT2-1

−71

2.4

790

3-2

—

HT3-1

−70

2.3

791

3-2

A-1

HT1-1

−61

2.7

792

3-3

—

HT1-1

−64

2.3

793

3-3

—

HT2-1

−69

2.5

794

3-3

—

HT3-1

−74

2.6

795

3-3

A-1

HT1-1

−71

2.5

Comp. Ex. 5

A-4

—

HT1-1

−121

6.0

Comp. Ex. 6

1-1

—

HT14-1

−193

2.5

Examples 796 to 831

Multi-layer photosensitive material for digital light source (positive charging type)

80 Parts by weight of the compound represented by the above formulas (HT1), (HT2) or (HT3) as the hole transferring material and 90 parts by weight of any one of polyester resins (1—1) to (1-3), (2-1) to (2-3) and (3-1) to (3—3) obtained in Reference Examples 1 to 9 or a mixture of this polyester resin and polycarbonate resin as the binding resin were mixed and dispersed, together with 800 parts by weight of tetrahydrofuran as the solvent, by using a ball mill to prepare a coating solution for electric charge transferring layer. Then, this coating solution was applied on an aluminum tube by a dip coating method, followed by hot-air drying at 100° C. for 60 minutes to give an electric charge transferring layer having a thickness of 15 μm.

Then, 2 parts by weight of the pigment represented by the above formula (CG1) as the electric charge generating material and 1 parts by weight of the polyester resin represented by the above general formula (1—1) as the binding resin were mixed and dispersed, together with 120 parts by weight of tetrahydrofuran, by using a ball mill to prepare a coating solution for electric charge generating layer. Then, this coating solution was applied on the above electric charge transferring layer by a dip coating method, followed by hot-air drying at 90° C. for 60 minutes to form an electric charge generating layer having a thickness of 10 μm, thereby producing a positive charging type multi-layer photosensitive material for digital light source, respectively.

When using a mixture of the polyester resin and polycarbonate resin as the binding resin, 0.7 parts by weight of the polyester resin and 0.3 parts by weight of the polycarbonate resin were used in combination.

Comparative Example 7

According to the same manner as that described in Example 796 except for using 90 parts by weight of the polycarbonate resin having a repeating unit of the above formula (A-4) as the binding resin of the electric charge transferring material, a positive charging type multi-layer photosensitive material for digital light source was produced.

Comparative Example 8

According to the same manner as that described in Examples 796 except for using the compound represented by the above formula (HT14-1) as the hole transferring material, a positive charging type multi-layer photosensitive material for digital light source was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the photosensitivity test and wear resistance test according to the above evaluation method of the positive charging type photosensitive material for digital light source.

The test results are shown in Tables 39 and 40, together with the above-described compound No. of the binding resin and the hole transferring material (HTM) used.

TABLE 39

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

796

1-1

—

HT1-1

126

2.6

797

1-1

—

HT2-1

130

2.5

798

1-1

—

HT3-1

130

2.5

799

1-1

A-1

HT1-1

125

2.6

800

1-2

—

HT1-1

128

2.3

801

1-2

—

HT2-1

136

2.3

802

1-2

—

HT3-1

131

2.3

803

1-2

A-1

HT1-1

130

3.0

804

1-3

—

HT1-1

121

2.1

805

1-3

—

HT2-1

128

2.4

806

1-3

—

HT3-1

124

2.2

807

1-3

A-1

HT1-1

125

2.5

808

2-1

—

HT1-1

132

1.4

809

2-1

—

HT2-1

130

1.6

810

2-1

—

HT3-1

129

1.7

811

2-1

A-1

HT1-1

128

1.6

812

2-2

—

HT1-1

132

1.5

813

2-2

—

HT2-1

130

1.9

814

2-2

—

HT3-1

130

2.0

815

2-2

A-1

HT1-1

126

1.7

816

2-3

—

HT1-1

125

1.4

817

2-3

—

HT2-1

124

1.7

818

2-3

—

HT3-1

126

1.6

819

2-3

A-1

HT1-1

130

1.9

820

3-1

—

HT1-1

104

2.4

821

3-1

—

HT2-1

109

1.9

822

3-1

—

HT3-1

108

2.3

823

3-1

A-1

HT1-1

100

2.3

TABLE 40

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

824

3-2

—

HT1-1

114

2.2

825

3-2

—

HT2-1

111

2.4

826

3-2

—

HT3-1

109

2.6

827

3-2

A-1

HT1-1

110

3.0

828

3-3

—

HT1-1

109

2.4

829

3-3

—

HT2-1

108

2.9

830

3-3

—

HT3-1

114

2.9

831

3-3

A-1

HT1-1

112

2.4

Comp. Ex. 7

A-4

—

HT1-1

160

6.6

Comp. Ex. 8

1-1

—

HT14-1

211

2.5

Examples 832 to 867

Multi-layer photosensitive material for analog light source (negative charging type)

According to the same manner as that described in Examples 760 to 795 except for using 2 parts by weight of the pigment represented by the above formula (CG2) as the electric charge generating material, a negative charging type multi-layer photosensitive material for analog light source was obtained, respectively.

Comparative Example 9

According to the same manner as that described in Example 832 except for using 90 parts by weight of the polycarbonate resin having a repeating unit of the above formula (A-4_ as the binding resin of the electric charge transferring material, a negative charging type multi-layer photosensitive material for analog light source was produced.

Comparative Example 10

According to the same manner as that described in Examples 832 except for using the compound represented by the above formula (HT14-1) as the hole transferring material, a negative charging type multi-layer photosensitive material for analog light source was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the following tests and their characteristics were evaluated.

Evaluation of negative charging photosensitive material for analog light source

Photosensitivity test

by using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of a photosensitive material obtained in the respective Examples and Comparative Examples to charge the surface at −700 V, respectively. Then, white light (light intensity: 147 lux second) from a halogen lamp as an exposure light source was irradiated on the surface of the photosensitive material (irradiation time: 50 msec.). Furthermore, a surface potential at the time at which 330 msec. has passed since the beginning of exposure was measured as a potential after exposure V

L

(V).

Wear resistance test

A photosensitive material obtained in the respective Examples and Comparative Examples was fit with an electrostatic copying machine modified for negative charging specification (Model DC-2556, manufactured by Mita Industrial Co., Ltd.) and, after rotating 150,000 times without passing a paper through it, a change in thickness of a photosensitive layer before and after rotation was determined, respectively.

These test results are shown in Tables 41 and 42, together with the above-described compound No. of the binding resin and the hole transferring material (HTM) used.

TABLE 41

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

832

1-1

—

HT1-1

−94

1.9

833

1-1

—

HT2-1

−99

2.4

834

1-1

—

HT3-1

−101

2.2

835

1-1

A-1

HT1-1

−93

1.5

836

1-2

—

HT1-1

−100

1.7

837

1-2

—

HT2-1

−106

1.9

838

1-2

—

HT3-1

−98

2.0

839

1-2

A-1

HT1-1

−96

1.9

840

1-3

—

HT1-1

−93

2.1

841

1-3

—

HT2-1

−92

2.4

842

1-3

—

HT3-1

−99

2.2

843

1-3

A-1

HT1-1

−94

1.9

844

2-1

—

HT1-1

−96

1.2

845

2-1

—

HT2-1

−101

1.2

846

2-1

—

HT3-1

−100

1.1

847

2-1

A-1

HT1-1

−95

1.1

848

2-2

—

HT1-1

−93

1.6

849

2-2

—

HT2-1

−96

1.0

850

2-2

—

HT3-1

−92

1.3

851

2-2

A-1

HT1-1

−91

1.5

852

2-3

—

HT1-1

−90

1.6

853

2-3

—

HT2-1

−89

1.5

854

2-3

—

HT3-1

−91

1.4

855

2-3

A-1

HT1-1

−90

1.7

856

3-1

—

HT1-1

−89

1.9

857

3-1

—

HT2-1

−88

2.2

858

3-1

—

HT3-1

−86

2.6

859

3-1

A-1

HT1-1

−84

2.4

TABLE 42

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

860

3-2

—

HT1-1

−81

2.2

861

3-2

—

HT2-1

−86

2.4

862

3-2

—

HT3-1

−89

2.2

863

3-2

A-1

HT1-1

−83

2.1

864

3-3

—

HT1-1

−85

2.4

865

3-3

—

HT2-1

−90

2.3

866

3-3

—

HT3-1

−86

2.2

867

3-3

A-1

HT1-1

−86

2.1

Comp. Ex. 9

A-4

—

HT1-1

−139

5.6

Comp. Ex. 10

1-1

—

HT14-1

−172

2.0

Examples 868 to 903

Multi-layer photosensitive material for analog light source (positive charging type)

According to the same manner as that described in Examples 796 to 831 except for using 2 parts by weight of the pigment represented by the above formula (CG2) as the electric charge generating material, a positive charging type multi-layer photosensitive material for analog light source was obtained, respectively.

Comparative Example 11

According to the same manner as that described in Example 868 except for using 90 parts by weight of the polycarbonate resin having a repeating unit of the above formula (A-4) as the binding resin of the electric charge transferring material, a positive-charging type multi-layer photosensitive material for analog light source was produced.

Comparative Example 12

According to the same manner as that described in Examples 868 except for using the compound represented by the above formula (HT14-1) as the hole transferring material, a positive-charging type multi-layer photosensitive material for analog light source was produced.

The resulting electrophotosensitive materials of the respective Examples and comparative Examples were subjected to the photosensitivity test and wear resistance test according to the above evaluation method of the positive charging type photosensitive material for analog light source.

The test results are shown in Tables 43 and 44, together with the above-described compound No. of the binding resin and the hole transferring material (HTM) used.

TABLE 43

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

868

1-1

—

HT1-1

131

2.1

869

1-1

—

HT2-1

138

2.0

870

1-1

—

HT3-1

142

1.9

871

1-1

A-1

HT1-1

140

2.2

872

1-2

—

HT1-1

120

2.1

873

1-2

—

HT2-1

129

2.2

874

1-2

—

HT3-1

126

2.2

875

1-2

A-1

HT1-1

124

2.5

876

1-3

—

HT1-1

126

2.4

877

1-3

—

HT2-1

121

2.3

878

1-3

—

HT3-1

127

2.2

879

1-3

A-1

HT1-1

124

2.2

880

2-1

—

HT1-1

123

1.4

881

2-1

—

HT2-1

129

1.4

882

2-1

—

HT3-1

126

1.3

883

2-1

A-1

HT1-1

123

1.2

884

2-2

—

HT1-1

128

1.4

885

2-2

—

HT2-1

126

1.4

886

2-2

—

HT3-1

122

1.4

887

2-2

A-1

HT1-1

130

1.5

888

2-3

—

HT1-1

121

1.6

889

2-3

—

HT2-1

120

1.5

890

2-3

—

HT3-1

129

1.9

891

2-3

A-1

HT1-1

120

1.5

892

3-1

—

HT1-1

111

2.2

893

3-1

—

HT2-1

106

2.2

894

3-1

—

HT3-1

114

2.4

895

3-1

A-1

HT1-1

108

2.4

TABLE 44

Binding resin

VL

Wear

Ex.

Main

Blend

HTM

(V)

(μm)

896

3-2

—

HT1-1

110

2.1

897

3-2

—

HT2-1

111

2.6

898

3-2

—

HT3-1

105

2.4

899

3-2

A-1

HT1-1

108

2.3

900

3-3

—

HT1-1

108

2.3

901

3-3

—

HT2-1

107

2.4

902

3-3

—

HT3-1

106

2.2

903

3-3

A-1

HT1-1

105

2.3

Comp.

A-4

—

HT1-1

180

5.9

Ex. 11

Comp.

1-1

—

HT14-1

224

2.7

Ex. 12

Examples 904 to 1182

Single-layer photosensitive material for digital light source (positive charging type)

The metal-free phthalocyanine pigment represented by the above general formula (CG1) and benzidine derivative represented by the above general formula (HT1-1) were used as the electric charge generating material and hole transferring material, respectively. In addition, the compound represented by any one of the above formulas (ET1) to (ET14) was used as the electron transferring material, respectively.

Furthermore, any one of the polyester resins (1—1) to (1-3), (2-1) to (2-3) and (3-1) to (3—3) obtained in Reference Examples 1 to 9, or a mixture of this polyester resin and a polycarbonate resin was used as the binding resin.

Furthermore, tetrahydrofuran was used as the solvent in which these components are dissolved.

The electron transferring material (ETM) and binding resin used were shown using the above compound number.

The amount of the respective materials to be blended is as follows:

Amount

Components

(parts by weight)

Electric charge generating material

5

Electron transferring material

30

Hole transferring material

50

Binding resin

90

Solvent

800

When the binding resin is the above mixture, the mixing proportion of the polyester resin to polycarbonate was 70 parts by weight: 20 parts by weight.

The above respective components were mixed and dispersed for 50 hours with a ball mill to prepare a coating solution for single-layer type photosensitive layer. Then, this coating solution was applied on an aluminum tube by a dip coating method, followed by hot-air drying at 100° C. for 60 minutes to give a single-layer type photosensitive material for digital light source, which has a single-layer type photosensitive layer of 15 to 20 μm in thickness, respectively.

Comparative Example 13

According to the same manner as that described in Example 1 except for using a compound represented by the following formula (ET15-1) as the electron transferring material, a singly-layer photosensitive material was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the photosensitivity test, wear resistance test and adhesion test according to the same manner as that described in Examples 1 to 387, and their characteristics were evaluated.

These test results are shown in Tables 45 to 53, together with the above-described compound No. of the binding resin and electron transferring material (ETM) used.

In Tables 45 to 53, the results of Examples 1, 44, 87, 130, 173, 216, 259, 302 and 345 as well as Comparative Example 1 are also shown.

TABLE 45

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

1

1-1

—

ET1-1

128

2.3

100

904

1-1

—

ET1-2

132

2.1

100

905

1-1

—

ET2-1

114

2.3

100

908

1-1

—

ET2-2

110

2.9

100

907

1-1

—

ET2-3

120

2.9

100

908

1-1

—

ET2-4

108

2.7

100

909

1-1

—

ET2-5

111

2.6

100

910

1-1

—

ET2-6

110

2.1

100

911

1-1

—

ET2-7

112

2.4

100

912

1-1

—

ET3-1

109

3.0

100

913

1-1

—

ET3-2

105

2.6

100

914

1-1

—

ET3-3

100

2.0

100

915

1-1

—

ET3-4

106

2.2

100

916

1-1

—

ET3-5

105

2.0

100

917

1-1

—

ET4-1

111

2.5

100

918

1-1

—

ET4-2

103

2.3

100

919

1-1

—

ET5-1

101

2.8

100

920

1-1

—

ET5-2

100

3.2

100

921

1-1

—

ET6-1

106

2.5

100

922

1-1

—

ET6-2

114

3.1

100

923

1-1

—

ET7-1

120

2.7

100

924

1-1

—

ET7-2

121

2.2

100

925

1-1

—

ET8-1

133

2.2

100

926

1-1

—

ET8-2

135

3.1

100

927

1-1

—

ET8-3

131

2.9

100

928

1-1

—

ET9-1

130

2.1

100

929

1-1

—

ET10-1

129

2.7

100

930

1-1

—

ET11-1

136

2.7

100

931

1-1

—

ET12-1

136

2.5

100

932

1-1

—

ET13-1

129

3.1

100

933

1-1

—

ET14-1

130

3.0

100

934

1-1

A-1

ET3-4

106

2.8

100

TABLE 46

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

44

1-2

—

ET1-1

130

2.9

100

935

1-2

—

ET1-2

136

3.0

100

936

1-2

—

ET2-1

111

2.3

100

937

1-2

—

ET2-2

120

2.6

100

938

1-2

—

ET2-3

108

3.1

100

939

1-2

—

ET2-4

106

2.1

100

940

1-2

—

ET2-5

105

2.4

100

941

1-2

—

ET2-6

112

2.4

100

942

1-2

—

ET2-7

113

2.4

100

943

1-2

—

ET3-1

114

2.7

100

944

1-2

—

ET3-2

104

2.5

100

945

1-2

—

ET3-3

118

2.8

100

946

1-2

—

ET3-4

110

2.8

100

947

1-2

—

ET3-5

106

3.1

100

948

1-2

—

ET4-1

104

3.3

100

949

1-2

—

ET4-2

103

2.3

100

950

1-2

—

ET5-1

102

3.1

100

951

1-2

—

ET5-2

116

3.0

100

952

1-2

—

ET6-1

117

2.0

100

953

1-2

—

ET6-2

112

2.7

100

954

1-2

—

ET7-1

120

2.7

100

955

1-2

—

ET7-2

121

2.9

100

956

1-2

—

ET8-1

130

3.1

100

957

1-2

—

ET8-2

134

3.2

100

958

1-2

—

ET8-3

136

2.8

100

959

1-2

—

ET9-1

130

2.4

100

960

1-2

—

ET10-1

133

3.2

100

961

1-2

—

ET11-1

132

2.9

100

962

1-2

—

ET12-1

132

2.4

100

963

1-2

—

ET13-1

136

2.4

100

964

1-2

—

ET14-1

130

3.0

100

965

1-2

A-1

ET3-4

110

3.1

100

TABLE 47

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

87

1-3

—

ET1-1

132

2.4

100

966

1-3

—

ET1-2

139

2.8

100

967

1-3

—

ET2-1

114

2.3

100

968

1-3

—

ET2-2

109

2.6

100

969

1-3

—

ET2-3

113

3.1

100

970

1-3

—

ET2-4

112

3.3

100

971

1-3

—

ET2-5

118

2.1

100

972

1-3

—

ET2-6

110

3.0

100

973

1-3

—

ET2-7

111

2.5

100

974

1-3

—

ET3-1

104

2.5

100

975

1-3

—

ET3-2

106

2.7

100

976

1-3

—

ET3-3

108

2.5

100

977

1-3

—

ET3-4

110

2.7

100

978

1-3

—

ET3-5

111

2.2

100

979

1-3

—

ET4-1

114

3.0

100

980

1-3

—

ET4-2

113

2.8

100

981

1-3

—

ET5-1

120

3.3

100

982

1-3

—

ET5-2

109

2.7

100

983

1-3

—

ET6-1

111

2.3

100

984

I-3

—

ET6-2

119

2.3

100

985

1-3

—

ET7-1

121

3.1

100

986

1-3

—

ET7-2

120

2.1

100

987

1-3

—

ET8-1

139

2.0

100

988

1-3

—

ET8-2

140

2.9

100

989

1-3

—

ET8-3

131

2.4

100

990

1-3

—

ET9-1

132

2.4

100

991

1-3

—

ET10-1

130

3.2

100

992

1-3

—

ET11-1

129

2.5

100

993

1-3

—

ET12-1

114

2.8

100

994

1-3

—

ET13-1

113

2.1

100

995

1-3

—

ET14-1

122

2.6

100

996

1-3

A-1

ET3-4

110

2.6

100

TABLE 48

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

130

2-1

—

ET1-1

129

2.0

100

997

2-1

—

ET1-2

139

1.4

100

998

2-1

—

ET2-1

114

1.8

100

999

2-1

—

ET2-2

105

1.6

100

1000

2-1

—

ET2-3

110

1.2

100

1001

2-1

—

ET2-4

106

2.1

100

1002

2-1

—

ET2-5

101

1.5

100

1003

2-1

—

ET2-6

106

1.6

100

1004

2-1

—

ET2-7

111

2.2

100

1005

2-1

—

ET3-1

110

1.5

100

1006

2-1

—

ET3-2

114

1.3

100

1007

2-1

—

ET3-3

100

2.0

100

1008

2-1

—

ET3-4

104

1.5

100

1009

2-1

—

ET3-5

102

1.9

100

1010

2-1

—

ET4-1

101

1.3

100

1011

2-1

—

ET4-2

108

1.2

100

1012

2-1

—

ET5-1

119

1.9

100

1013

2-1

—

ET5-2

120

2.0

100

1014

2-1

—

ET6-1

109

1.3

100

1015

2-1

—

ET6-2

111

1.6

100

1016

2-1

—

ET7-1

119

1.6

100

1017

2-1

—

ET7-2

121

1.7

100

1018

2-1

—

ET8-1

136

1.4

100

1019

2-1

—

ET8-2

140

1.7

100

1020

2-1

—

ET8-3

139

2.1

100

1021

2-1

—

ET9-1

132

1.9

100

1022

2-1

—

ET10-1

133

1.9

100

1023

2-1

—

ET11-1

140

2.2

100

1024

2-1

—

ET12-1

138

1.3

100

1025

2-1

—

ET13-1

141

2.0

100

1026

2-1

—

ET14-1

136

2.0

100

1027

2-1

A-1

ET3-4

111

1.8

100

TABLE 49

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

173

2-2

—

ET1-1

129

1.7

100

1028

2-2

—

ET1-2

140

1.3

100

1029

2-2

—

ET2-1

114

1.8

100

1030

2-2

—

ET2-2

106

1.8

100

1031

2-2

—

ET2-3

109

1.8

100

1032

2-2

—

ET2-4

111

1.4

100

1033

2-2

—

ET2-5

119

2.0

100

1034

2-2

—

ET2-6

114

1.5

100

1035

2-2

—

ET2-7

116

2.1

100

1036

2-2

—

ET3-1

119

1.2

100

1037

2-2

—

ET3-2

120

1.7

100

1038

2-2

—

ET3-3

116

1.9

100

1039

2-2

—

ET3-4

117

1.4

100

1040

2-2

—

ET3-5

109

1.6

100

1041

2-2

—

ET4-1

112

2.0

100

1042

2-2

—

ET4-2

116

1.2

100

1043

2-2

—

ET5-1

115

1.7

100

1044

2-2

—

ET5-2

113

1.7

100

1045

2-2

—

ET6-1

120

1.5

100

1046

2-2

—

ET6-2

119

2.0

100

1047

2-2

—

ET7-1

109

1.5

100

1048

2-2

—

ET7-2

111

1.9

100

1049

2-2

—

ET8-1

130

1.8

100

1050

2-2

—

ET8-2

139

1.5

100

1051

2-2

—

ET8-3

134

1.5

100

1052

2-2

—

ET9-1

140

1.5

100

1053

2-2

—

ET10-1

141

1.6

100

1054

2-2

—

ET11-1

136

1.3

100

1055

2-2

—

ET12-1

136

1.3

100

1056

2-2

—

ET13-1

135

1.7

100

1057

2-2

—

ET14-1

130

1.7

100

1058

2-2

A-1

ET3-4

120

1.7

100

TABLE 50

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

216

2-3

—

ET1-1

128

2.3

100

1059

2-3

—

ET1-2

134

1.4

100

1060

2-3

—

ET2-1

111

1.7

100

1061

2-3

—

ET2-2

109

1.6

100

1062

2-3

—

ET2-3

114

1.7

100

1063

2-3

—

ET2-4

112

1.7

100

1064

2-3

—

ET2-5

107

1.7

100

1065

2-3

—

ET2-6

109

1.3

100

1066

2-3

—

ET2-7

111

1.6

100

1067

2-3

—

ET3-1

114

1.6

100

1068

2-3

—

ET3-2

113

1.5

100

1069

2-3

—

ET3-3

113

1.8

100

1070

2-3

—

ET3-4

112

1.2

100

1071

2-3

—

ET3-5

109

1.9

100

1072

2-3

—

ET4-1

110

2.0

100

1073

2-3

—

ET4-2

108

2.2

100

1074

2-3

—

ET5-1

118

1.4

100

1075

2-3

—

ET5-2

117

2.0

100

1076

2-3

—

ET6-1

110

1.5

100

1077

2-3

—

ET6-2

111

1.5

100

1078

2-3

—

ET7-1

121

1.8

100

1079

2-3

—

ET7-2

120

1.2

100

1080

2-3

—

ET8-1

141

1.8

100

1081

2-3

—

ET8-2

142

2.1

100

1082

2-3

—

ET8-3

138

1.3

100

1083

2-3

—

ET9-1

137

1.3

100

1084

2-3

—

ET10-1

130

2.0

100

1085

2-3

—

ET11-1

129

1.5

100

1086

2-3

—

ET12-1

136

2.0

100

1087

2-3

—

ET13-1

135

1.2

100

1088

2-3

—

ET14-1

140

1.5

100

1089

2-3

A-1

ET3-4

120

1.8

100

TABLE 51

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

259

3-1

—

ET1-1

120

2.0

100

1090

3-1

—

ET1-2

126

2.1

100

1091

3-1

—

ET2-1

98

2.3

100

1092

3-1

—

ET2-2

100

2.2

100

1093

3-1

—

ET2-3

101

2.2

100

1094

3-1

—

ET2-4

94

2.2

100

1095

3-1

—

ET2-5

95

2.2

100

1096

3-1

—

ET2-6

108

3.1

100

1097

3-1

—

ET2-7

101

3.2

100

1098

3-1

—

ET3-1

102

2.8

100

1099

3-1

—

ET3-2

99

2.8

100

1100

3-1

—

ET3-3

94

2.7

100

1101

3-1

—

ET3-4

104

2.9

100

1102

3-1

—

ET3-5

103

3.2

100

1103

3-1

—

ET4-1

102

2.9

100

1104

3-1

—

ET4-2

100

2.1

100

1105

3-1

—

ET5-1

104

2.3

100

1106

3-1

—

ET5-2

103

3.2

100

1107

3-1

—

ET6-1

110

3.3

100

1108

3-1

—

ET6-2

111

2.7

100

1109

3-1

—

ET7-1

114

2.9

100

1110

3-1

—

ET7-2

112

3.0

100

1111

3-1

—

ET8-1

125

2.8

100

1112

3-1

—

ET8-2

130

2.1

100

1113

3-1

—

ET8-3

131

2.3

100

1114

3-1

—

ET9-1

130

2.3

100

1115

3-1

—

ET10-1

125

2.4

100

1116

3-1

—

ET11-1

126

2.8

100

1117

3-1

—

ET12-1

127

2.4

100

1118

3-1

—

ET13-1

136

2.4

100

1119

3-1

—

ET14-1

141

3.0

100

1120

3-1

A-1

ET3-4

110

3.1

100

TABLE 52

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

302

3-2

—

ET1-1

121

2.6

100

1121

3-2

—

ET1-2

128

2.3

100

1122

3-2

—

ET2-1

104

2.4

100

1123

3-2

—

ET2-2

110

2.8

100

1124

3-2

—

ET2-3

101

3.1

100

1125

3-2

—

ET2-4

100

2.6

100

1126

3-2

—

ET2-5

96

2.7

100

1127

3-2

—

ET2-6

92

3.1

100

1128

3-2

—

ET2-7

101

3.3

100

1129

3-2

—

ET3-1

106

3.2

100

1130

3-2

—

ET3-2

103

2.9

100

1131

3-2

—

ET3-3

94

2.8

100

1132

3-2

—

ET3-4

98

3.3

100

1133

3-2

—

ET3-5

101

2.7

100

1134

3-2

—

ET4-1

102

2.0

100

1135

3-2

—

ET4-2

104

2.0

100

1136

3-2

—

ET5-1

100

2.8

100

1137

3-2

—

ET5-2

110

2.9

100

1138

3-2

—

ET6-1

111

3.1

100

1139

3-2

—

ET6-2

114

3.1

100

1140

3-2

—

ET7-1

119

2.8

100

1141

3-2

—

ET7-2

120

2.4

100

1142

3-2

—

ET8-1

131

2.1

100

1143

3-2

—

ET8-2

132

2.5

100

1144

3-2

—

ET8-3

133

2.6

100

1145

3-2

—

ET9-1

134

3.1

100

1146

3-2

—

ET10-1

129

2.9

100

1147

3-2

—

ET11-1

132

2.8

100

1148

3-2

—

ET12-1

136

3.3

100

1149

3-2

—

ET13-1

132

2.6

100

1150

3-2

—

ET14-1

133

2.6

100

1151

3-2

A-1

ET3-4

109

2.6

100

TABLE 53

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

345

3-3

—

ET1-1

118

2.9

100

1152

3-3

—

ET1-2

121

2.6

100

1153

3-3

—

ET2-1

108

2.1

100

1154

3-3

—

ET2-2

104

2.8

100

1155

3-3

—

ET2-3

107

2.0

100

1156

3-3

—

ET2-4

107

2.8

100

1157

3-3

—

ET2-5

100

2.3

100

1158

3-3

—

ET2-6

99

2.7

100

1159

3-3

—

ET2-7

101

3.0

100

1160

3-3

—

ET3-1

92

3.0

100

1161

3-3

—

ET3-2

94

3.3

100

1162

3-3

—

ET3-3

93

2.6

100

1163

3-3

—

ET3-4

97

2.6

100

1164

3-3

—

ET3-5

99

2.1

100

1165

3-3

—

ET4-1

100

2.3

100

1166

3-3

—

ET4-2

109

2.9

100

1167

3-3

—

ET5-1

107

3.2

100

1168

3-3

—

ET5-2

104

2.4

100

1169

3-3

—

ET6-1

110

2.4

100

1170

3-3

—

ET6-2

118

2.5

100

1171

3-3

—

ET7-1

120

2.5

100

1172

3-3

—

ET7-2

116

2.5

100

1173

3-3

—

ET8-1

129

2.2

100

1174

3-3

—

ET8-2

127

2.2

100

1175

3-3

—

ET8-3

126

2.8

100

1176

3-3

—

ET9-1

129

3.1

100

1177

3-3

—

ET10-1

130

2.7

100

1178

3-3

—

ET11-1

128

2.4

100

1179

3-3

—

ET12-1

132

2.3

100

1180

3-3

—

ET13-1

133

2.8

100

1181

3-3

—

ET14-1

140

2.2

100

1182

3-3

A-1

ET3-4

100

3.1

100

Comp.

A-4

—

ET1-1

190

5.5

100

Ex. 1

Comp.

1-1

—

ET15-1

221

2.6

100

Ex. 13

Examples 1183 to 1461

[Single-layer photosensitive material for analog light source (positive charging type]

According to the same manner as that described in Examples 904 to 1182 except for using the bisazo pigment represented by the above formula (CG2) in place of the electric charge generating material (CG1) used in Examples 904 to 1182, a single-layer photosensitive material for analog light source was produced, respectively.

Comparative Example 14

According to the same manner as that described in Example 388 except for using the compound represented by the above formula (ET15-1) as the electron transferring material, a single-layer photosensitive material was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the photosensitivity test, wear resistance test and adhesion test according to the same manner as that described in Examples 388 to 759, and their characteristics were evaluated.

These test results are shown in Tables 54 to 62, together with the above-described compound No. of the binding resin and hole transferring material (ETM) used.

In Tables 54 to 62, the results of Examples 388, 431, 474, 517, 560, 603, 646, 689 and 717 as well as Comparative Example 3 are also shown.

TABLE 54

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

388

1-1

—

ET1-1

195

1.7

100

1183

1-1

—

ET1-2

191

1.9

100

1184

1-1

—

ET2-1

180

1.1

100

1185

1-1

—

ET2-2

179

1.5

100

1186

1-1

—

ET2-3

176

1.2

100

1187

1-1

—

ET2-4

182

1.3

100

1188

1-1

—

ET2-5

184

2.4

100

1189

1-1

—

ET2-6

181

2.4

100

1190

1-1

—

ET2-7

176

2.1

100

1191

1-1

—

ET3-1

173

1.8

100

1192

1-1

—

ET3-2

174

1.8

100

1193

1-1

—

ET3-3

173

1.7

100

1194

1-1

—

ET3-4

170

1.3

100

1195

1-1

—

ET3-5

178

1.1

100

1196

1-1

—

ET4-1

181

2.1

100

1197

1-1

—

ET4-2

179

2.3

100

1198

1-1

—

ET5-1

184

1.9

100

1199

1-1

—

ET5-2

182

1.8

100

1200

1-1

—

ET6-1

188

1.7

100

1201

1-1

—

ET6-2

191

2.1

100

1202

1-1

—

ET7-1

198

1.6

100

1203

1-1

—

ET7-2

199

1.6

100

1204

1-1

—

ET8-1

201

2.3

100

1205

1-1

—

ET8-2

202

1.5

100

1206

1-1

—

ET8-3

206

1.3

100

1207

1-1

—

ET9-1

210

1.2

100

1208

1-1

—

ET10-1

210

1.1

100

1209

1-1

—

ET11-1

200

2.3

100

1210

1-1

—

ET12-1

204

1.3

100

1211

1-1

—

ET13-1

202

1.9

100

1212

1-1

—

ET14-1

200

2.2

100

1213

1-1

A-1

ET3-4

176

1.8

100

TABLE 55

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

431

1-2

—

ET1-1

203

1.3

100

1214

1-2

—

ET1-2

200

1.9

100

1215

1-2

—

ET2-1

184

2.1

100

1216

1-2

—

ET2-2

186

2.3

100

1217

1-2

—

ET2-3

185

1.8

100

1218

1-2

—

ET2-4

182

2.4

100

1219

1-2

—

ET2-5

187

1.9

100

1220

1-2

—

ET2-6

184

2.1

100

1221

1-2

—

ET2-7

188

1.7

100

1222

1-2

—

ET3-1

180

1.1

100

1223

1-2

—

ET3-2

177

1.5

100

1224

1-2

—

ET3-3

172

2.3

100

1225

1-2

—

ET3-4

178

2.0

100

1226

1-2

—

ET3-5

181

2.1

100

1227

1-2

—

ET4-1

184

1.3

100

1228

1-2

—

ET4-2

183

1.4

100

1229

1-2

—

ET5-1

182

1.2

100

1230

1-2

—

ET5-2

181

2.1

100

1231

1-2

—

ET6-1

184

1.8

100

1232

1-2

—

ET6-2

186

1.7

100

1233

1-2

—

ET7-1

189

1.6

100

1234

1-2

—

ET7-2

191

1.3

100

1235

1-2

—

ET8-1

194

1.5

100

1236

1-2

—

ET8-2

192

2.1

100

1237

1-2

—

ET8-3

193

1.3

100

1238

1-2

—

ET9-1

198

2.3

100

1239

1-2

—

ET10-1

200

1.3

100

1240

1-2

—

ET11-1

201

1.8

100

1241

1-2

—

ET12-1

203

1.2

100

1242

1-2

—

ET13-1

200

2.1

100

1243

1-2

—

ET14-1

199

2.1

100

1244

1-2

A-1

ET3-4

184

1.9

100

TABLE 56

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

474

1-3

—

ET1-1

197

1.8

100

1245

1-3

—

ET1-2

194

1.7

100

1246

1-3

—

ET2-1

181

1.3

100

1247

1-3

—

ET2-2

186

1.1

100

1248

1-3

—

ET2-3

185

2.2

100

1249

1-3

—

ET2-4

180

1.8

100

1250

1-3

—

ET2-5

190

1.9

100

1251

1-3

—

ET2-6

182

1.8

100

1252

1-3

—

ET2-7

179

2.1

100

1253

1-3

—

ET3-1

176

2.3

100

1254

1-3

—

ET3-2

172

1.9

100

1255

1-3

—

ET3-3

178

1.2

100

1256

1-3

—

ET3-4

177

1.9

100

1257

1-3

—

ET3-5

171

2.1

100

1258

1-3

—

ET4-1

181

1.8

100

1259

1-3

—

ET4-2

183

1.7

100

1260

1-3

—

ET5-1

86

2.3

100

1261

1-3

—

ET5-2

185

2.1

100

1262

1-3

—

ET6-1

179

1.9

100

1263

1-3

—

ET6-2

182

1.8

100

1264

1-3

—

ET7-1

190

1.7

100

1265

1-3

—

ET7-2

186

1.7

100

1266

1-3

—

ET8-1

185

2.1

100

1267

1-3

—

ET8-2

186

2.3

100

1268

1-3

—

ET8-3

190

2.1

100

1269

1-3

—

ET9-1

186

2.0

100

1270

1-3

—

ET10-1

192

1.3

100

1271

1-3

—

ET11-1

191

2.0

100

1272

1-3

—

ET12-1

194

1.8

100

1273

1-3

—

ET13-1

193

1.9

100

1274

1-3

—

ET14-1

191

2.1

100

1275

1-3

A-1

ET3-4

184

1.0

100

TABLE 57

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

517

2-1

—

ET1-1

200

0.8

100

1276

2-1

—

ET1-2

196

0.9

100

1277

2-1

—

ET2-1

184

0.9

100

1278

2-1

—

ET2-2

183

1.0

100

1279

2-1

—

ET2-3

186

1.2

100

1280

2-1

—

ET2-4

190

1.3

100

1281

2-1

—

ET2-5

182

0.9

100

1282

2-1

—

ET2-6

191

0.8

100

1283

2-1

—

ET2-7

185

0.6

100

1284

2-1

—

ET3-1

176

1.2

100

1285

2-1

—

ET3-2

180

1.3

100

1286

2-1

—

ET3-3

184

1.1

100

1287

2-1

—

ET3-4

184

0.9

100

1288

2-1

—

ET3-5

179

0.8

100

1289

2-1

—

ET4-1

181

0.6

100

1290

2-1

—

ET4-2

184

0.6

100

1291

2-1

—

ET5-1

180

1.2

100

1292

2-1

—

ET5-2

180

1.2

100

1293

2-1

—

ET6-1

186

1.3

100

1294

2-1

—

ET6-2

187

0.9

100

1295

2-1

—

ET7-1

189

1.2

100

1296

2-1

—

ET7-2

193

0.9

100

1297

2-1

—

ET8-1

186

1.3

100

1298

2-1

—

ET8-2

184

0.9

100

1299

2-1

—

ET8-3

189

1.1

100

1300

2-1

—

ET9-1

192

1.2

100

1301

2-1

—

ET10-1

194

0.8

100

1302

2-1

—

ET11-1

194

0.9

100

1303

2-1

—

ET12-1

188

0.9

100

1304

2-1

—

ET13-1

192

1.1

100

1305

2-1

—

ET14-1

190

1.1

100

1306

2-1

A-1

ET3-4

180

1.3

100

TABLE 58

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

560

2-2

—

ET1-1

192

0.9

100

1307

2-2

—

ET1-2

190

1.2

100

1308

2-2

—

ET2-1

179

1.3

100

1309

2-2

—

ET2-2

186

1.1

100

1310

2-2

—

ET2-3

185

0.9

100

1311

2-2

—

ET2-4

178

1.0

100

1312

2-2

—

ET2-5

182

1.2

100

1313

2-2

—

ET2-6

180

1.1

100

1314

2-2

—

ET2-7

180

0.9

100

1315

2-2

—

ET3-1

171

0.8

100

1316

2-2

—

ET3-2

176

0.6

100

1317

2-2

—

ET3-3

175

1.2

100

1318

2-2

—

ET3-4

173

0.9

100

1319

2-2

—

ET3-5

176

1.3

100

1320

2-2

—

ET4-1

184

1.4

100

1321

2-2

—

ET4-2

182

0.8

100

1322

2-2

—

ET5-1

181

1.2

100

1323

2-2

—

ET5-2

192

1.3

100

1324

2-2

—

ET6-1

190

0.9

100

1325

2-2

—

ET6-2

186

1.3

100

1326

2-2

—

ET7-1

192

0.9

100

1327

2-2

—

ET7-2

194

1.0

100

1328

2-2

—

ET8-1

193

1.0

100

1329

2-2

—

ET8-2

186

1.3

100

1330

2-2

—

ET8-3

192

1.1

100

1331

2-2

—

ET9-1

191

0.8

100

1332

2-2

—

ET10-1

190

0.7

100

1333

2-2

—

ET11-1

196

0.6

100

1334

2-2

—

ET12-1

186

0.8

100

1335

2-2

—

ET13-1

199

1.2

100

1336

2-2

—

ET14-1

204

1.1

100

1337

2-2

A-1

ET3-4

177

1.1

100

TABLE 59

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

603

2-3

—

ET1-1

198

0.6

100

1338

2-3

—

ET1-2

199

0.9

100

1339

2-3

—

ET2-1

181

1.3

100

1340

2-3

—

ET2-2

182

1.2

100

1341

2-3

—

ET2-3

186

1.1

100

1342

2-3

—

ET2-4

183

1.0

100

1343

2-3

—

ET2-5

181

0.9

100

1344

2-3

—

ET2-6

177

0.7

100

1345

2-3

—

ET2-7

184

1.2

100

1346

2-3

—

ET3-1

176

1.4

100

1347

2-3

—

ET3-2

177

0.9

100

1348

2-3

—

ET3-3

174

1.2

100

1349

2-3

—

ET3-4

179

1.3

100

1350

2-3

—

ET3-5

181

0.9

100

1351

2-3

—

ET4-1

183

0.8

100

1352

2-3

—

ET4-2

182

1.3

100

1353

2-3

—

ET5-1

186

1.2

100

1354

2-3

—

ET5-2

184

0.9

100

1355

2-3

—

ET6-1

184

1.1

100

1356

2-3

—

ET6-2

182

0.9

100

1357

2-3

—

ET7-1

187

0.8

100

1358

2-3

—

ET7-2

189

0.8

100

1359

2-3

—

ET8-1

192

1.3

100

1360

2-3

—

ET8-2

190

1.2

100

1361

2-3

—

ET8-3

194

1.4

100

1362

2-3

—

ET9-1

193

1.2

100

1363

2-3

—

ET10-1

191

1.1

100

1364

2-3

—

ET11-1

196

0.8

100

1365

2-3

—

ET12-1

194

0.9

100

1366

2-3

—

ET13-1

190

1.2

100

1367

2-3

—

ET14-1

194

1.1

100

1368

2-3

A-1

ET3-4

182

1.3

100

TABLE 60

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

646

3-1

—

ET1-1

195

1.9

100

1369

3-1

—

ET1-2

190

1.3

100

1370

3-1

—

ET2-1

184

0.9

100

1371

3-1

—

ET2-2

179

0.8

100

1372

3-1

—

ET2-3

176

1.3

100

1373

3-1

—

ET2-4

173

1.2

100

1374

3-1

—

ET2-5

176

1.2

100

1375

3-1

—

ET2-6

175

1.0

100

1376

3-1

—

ET2-7

181

1.0

100

1377

3-1

—

ET3-1

176

1.0

100

1378

3-1

—

ET3-2

175

1.0

100

1379

3-1

—

ET3-3

179

1.0

100

1380

3-1

—

ET3-4

180

0.9

100

1381

3-1

—

ET3-5

172

0.8

100

1382

3-1

—

ET4-1

184

1.2

100

1383

3-1

—

ET4-2

183

1.3

100

1384

3-1

—

ET5-1

188

1.3

100

1385

3-1

—

ET5-2

181

0.9

100

1386

3-1

—

ET6-1

186

0.7

100

1387

3-1

—

ET6-2

185

0.8

100

1388

3-1

—

ET7-1

184

0.6

100

1389

3-1

—

ET7-2

186

1.4

100

1390

3-1

—

ET8-1

191

0.6

100

1391

3-1

—

ET8-2

190

1.0

100

1392

3-1

—

ET8-3

186

1.0

100

1393

3-1

—

ET9-1

193

0.9

100

1394

3-1

—

ET10-1

192

0.8

100

1395

3-1

—

ET11-1

191

1.2

100

1396

3-1

—

ET12-1

189

0.9

100

1397

3-1

—

ET13-1

201

1.2

100

1398

3-1

—

ET14-1

204

1.3

100

1399

3-1

A-1

ET3-4

186

1.1

100

TABLE 61

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

689

3-2

—

ET1-1

185

1.1

100

1400

3-2

—

ET1-2

186

1.0

100

1401

3-2

—

ET2-1

174

1.0

100

1402

3-2

—

ET2-2

175

2.1

100

1403

3-2

—

ET2-3

176

2.3

100

1404

3-2

—

ET2-4

179

2.3

100

1405

3-2

—

ET2-5

182

1.5

100

1406

3-2

—

ET2-6

180

1.5

100

1407

3-2

—

ET2-7

176

1.9

100

1408

3-2

—

ET3-1

171

2.1

100

1409

3-2

—

ET3-2

170

1.9

100

1410

3-2

—

ET3-3

170

1.7

100

1411

3-2

—

ET3-4

174

1.6

100

1412

3-2

—

ET3-5

170

1.7

100

1413

3-2

—

ET4-1

176

1.8

100

1414

3-2

—

ET4-2

175

1.9

100

1415

3-2

—

ET5-1

177

2.0

100

1416

3-2

—

ET5-2

180

2.3

100

1417

3-2

—

ET6-1

181

2.4

100

1418

3-2

—

ET6-2

183

2.1

100

1419

3-2

—

ET7-1

184

1.8

100

1420

3-2

—

ET7-2

180

1.2

100

1421

3-2

—

ET8-1

185

1.3

100

1422

3-2

—

ET8-2

191

1.0

100

1423

3-2

—

ET8-3

190

1.1

100

1424

3-2

—

ET9-1

186

1.0

100

1425

3-2

—

ET10-1

189

2.1

100

1426

3-2

—

ET11-1

191

2.3

100

1427

3-2

—

ET12-1

185

0.9

100

1428

3-2

—

ET13-1

186

1.2

100

1429

3-2

—

ET14-1

180

1.2

100

1430

3-2

A-1

ET3-4

172

1.1

100

TABLE 62

Binding resin

VL

Wear

Adhesion

Ex.

Main

Blend

ETM

(V)

(μm)

(%)

717

3-3

—

ET1-1

196

1.5

100

1431

3-3

—

ET1-2

199

1.1

100

1432

3-3

—

ET2-1

181

2.0

100

1433

3-3

—

ET2-2

184

2.0

100

1434

3-3

—

ET2-3

188

2.0

100

1435

3-3

—

ET2-4

179

2.0

100

1436

3-3

—

ET2-5

184

2.3

100

1437

3-3

—

ET2-6

183

1.8

100

1438

3-3

—

ET2-7

187

1.7

100

1439

3-3

—

ET3-1

179

1.6

100

1440

3-3

—

ET3-2

176

1.5

100

1441

3-3

—

ET3-3

177

1.9

100

1442

3-3

—

ET3-4

174

2.1

100

1443

3-3

—

ET3-5

178

2.2

100

1444

3-3

—

ET4-1

181

2.1

100

1445

3-3

—

ET4-2

180

2.3

100

1446

3-3

—

ET5-1

176

1.9

100

1447

3-3

—

ET5-2

175

1.9

100

1448

3-3

—

ET6-1

179

1.8

100

1449

3-3

—

ET6-2

180

1.7

100

1450

3-3

—

ET7-1

184

2.1

100

1451

3-3

—

ET7-2

185

2.4

100

1452

3-3

—

ET8-1

183

1.9

100

1453

3-3

—

ET8-2

184

1.8

100

1454

3-3

—

ET8-3

182

1.7

100

1455

3-3

—

ET9-1

184

1.6

100

1456

3-3

—

ET10-1

185

1.5

100

1457

3-3

—

ET11-1

191

1.3

100

1458

3-3

—

ET12-1

174

1.8

100

1459

3-3

—

ET13-1

180

1.9

100

1460

3-3

—

ET14-1

184

2.1

100

1461

3-3

—

ET3-4

179

2.2

100

Comp.

A-4

—

ET1-1

242

5.5

30

Ex. 3

Comp

1-1

—

ET15-1

222

1.9

100

Ex. 14

Examples 1462 to 1506

[Multi-layer photosensitive material for digital light source (positive charging type)]

2 Parts by weight of the pigment represented by the above formula (CG1) as the electric charge generating material and 1 part by weight of a polyvinyl butyral as the binding resin were mixed and dispersed, together with 120 parts by weight of dichloromethane as the solvent, using a ball mill to prepare a coating solution for electric charge generating layer. Then, this coating solution was applied on an aluminum tube by a dip coating method, followed by hot-air drying at 100° C. for 60 minutes to give an electric charge generating layer having a thickness of 0.5 μm.

Then, 80 parts by weight of the hole transferring material represented by the above formulas (ET1), (ET2), (ET3) or (ET5) and 90 parts by weight of any one of polyester resins (1—1) to (1-3), (2-1) to (2-3) and (3-1) to (3—3) obtained in Reference Examples 1 to 9 or a mixture of this polyester resin and polycarbonate resin as the binding resin were mixed and dispersed, together with 800 parts by weight of tetrahydrofuran, by using a ball mill to prepare a coating solution for electric charge transferring layer. Then, this coating solution was applied on the above electric charge generating layer by a dip coating method, followed by hot-air drying at 100° C. for 60 minutes to form an electric charge transferring material having a thickness of 15 μm, thereby producing a positive charging type multi-layer photosensitive material for digital light source, respectively.

When using a mixture of the polyester resin and polycarbonate resin as the binding resin, 70 parts by weight of the polyester resin and 20 parts by weight of the polycarbonate resin were used in combination.

Comparative Example 15

According to the same manner as that described in Examples 1462 except for using 90 parts by weight of the polycarbonate resin having a repeating unit of the above formula (A-4) as the binding resin of the electric chare transferring material, a positive charging type multi-layer photosensitive material for digital light source was produced.

Comparative Example 16

According to the same manner as that described in Examples 1462 except for using the compound represented by the above formula (ET15-1) as the electron transferring material, a positive charging type multi-layer photosensitive material for digital light source was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the photosensitivity test and wear resistance test according to the above evaluation test of the positive charging photosensitive material for digital light source.

The test results are shown in Tables 63 and 64, together with the above-described compound No. of the binding resin and electron transferring material used.

TABLE 63

Binding resin

VL

Wear

Ex.

Main

Blend

ETM

(V)

(μm)

1462

1-1

—

ET1-1

164

2.7

1463

1-1

—

ET2-1

160

2.6

1464

1-1

—

ET3-4

158

2.1

1465

1-1

—

ET5-l

160

2.4

1466

1-1

A-1

ET1-1

163

2.4

1467

1-2

—

ET1-1

182

2.8

1468

1-2

—

ET2-1

174

2.5

1469

1-2

—

ET3-4

172

2.4

1470

1-2

—

ET5-1

173

2.3

1471

1-2

A-1

ET1-1

169

2.2

1472

1-3

—

ET1-1

180

2.6

1473

1-3

—

ET2-1

174

2.7

1474

1-3

—

ET3-4

172

2.8

1475

1-3

—

ET5-1

169

3.0

1476

1-3

A-1

ET1-1

174

3.0

1477

2-1

—

ET1-1

167

1.4

1478

2-1

—

ET2-1

170

1.8

1479

2-1

—

ET3-4

174

1.7

l480

2-1

—

ET5-1

172

1.6

1481

2-1

A-1

ET1-1

179

1.5

1482

2-2

—

ET1-1

172

1.3

1483

2-2

—

ET2-1

170

1.2

1484

2-2

—

ET3-4

169

1.4

1485

2-2

—

ET5-1

173

1.6

1486

2-2

A-1

ET1-1

170

1.8

TABLE 64

Binding resin

VL

Wear

Ex.

Main

Blend

ETM

(V)

(μm)

1487

2-3

—

ET1-1

163

2.0

1488

2-3

—

ET2-1

160

1.9

1489

2-3

—

ET3-4

169

2.1

1490

2-3

—

ET5-1

172

2.0

1491

2-3

A-1

ET1-1

170

1.9

1492

3-1

—

ET1-1

159

3.0

1493

3-1

—

ET2-1

160

3.2

1494

3-1

—

ET3-4

162

2.6

1495

3-1

—

ET5-1

155

2.5

1496

3-1

A-1

ET1-1

146

2.8

1497

3-2

—

ET1-1

151

2.7

1498

3-2

—

ET2-1

150

2.6

1499

3-2

—

ET3-4

154

2.5

1500

3-2

—

ET5-1

152

2.8

1501

3-2

A-1

ET1-1

153

2.6

1502

3-3

—

ET1-1

160

2.7

1503

3-3

—

ET2-1

154

2.5

1504

3-3

—

ET3-4

152

2.3

1505

3-3

—

ET5-1

157

2.4

1506

3-3

A-1

ET1-1

156

2.4

Comp. Ex. 15

A-4

—

ET1-1

212

5.7

Comp. Ex. 16

1-1

—

ET15-1

244

2.4

Examples 1507 to 1551

[Multi-layer photosensitive material for analog light source (positive charging type)]

According to the same manner as that described in Examples 1462 to 1506 except for using 2 parts by weight of the pigment represented by the above formula (CG2) as the electric charge generating material, a positive charging type multi-layer photosensitive material for analog light source was obtained, respectively.

Comparative Example17

According to the same manner as that described in Example 1507 except for using 90 parts by weight of the polycarbonate resin having a repeating unit of the above formula (A-4) as the binding resin of the electric charge transferring material, a positive charging type multi-layer photosensitive material for analog light source was produced.

Comparative Example 18

According to the same manner as that described in Example 1507 except for using the compound represented by the above formula (ET15-1) as the electron transferring material, a positive charging type multi-layer photosensitive material for analog light source was produced.

The resulting electrophotosensitive materials of the respective Examples and Comparative Examples were subjected to the photosensitivity test and wear resistance test according to the above evaluation test of the positive charging photosensitive material for analog light source.

The test results are shown in Tables 65 and 66, together with the above-described compound No. of the binding resin and electron transferring material used.

TABLE 65

Binding resin

VL

Wear

Ex.

Main

Blend

ETM

(V)

(μm)

1507

1-1

—

ET1-1

186

2.0

1508

1-1

—

ET2-1

175

1.9

1509

1-1

—

ET3-4

177

2.2

1510

1-1

—

ET5-1

172

2.4

1511

1-1

A-1

ET1-1

188

2.1

1512

1-2

—

ET1-1

180

2.4

1513

1-2

—

ET2-1

169

2.3

1514

1-2

—

ET3-4

172

2.3

1515

1-2

—

ET5-1

175

2.3

1516

1-2

A-1

ET1-1

185

2.1

1517

1-3

—

ET1-1

181

1.9

1518

1-3

—

ET2-1

166

2.0

1519

1-3

—

ET3-4

172

1.8

1520

1-3

—

ET5-1

174

1.9

1521

1-3

A-1

ET1-1

188

1.9

1522

2-1

—

ET1-1

190

1.6

1523

2-1

—

ET2-1

175

1.8

1524

2-1

—

ET3-4

173

1.7

1525

2-1

—

ET5-1

175

1.5

1526

2-1

A-1

ET1-1

183

1.4

1527

2-2

—

ET1-1

183

1.5

1528

2-2

—

ET2-1

179

1.3

1529

2-2

—

ET3-4

170

1.7

1530

2-2

—

ET5-1

174

1.9

1531

2-2

A-1

ET1-1

183

1.6

TABLE 66

Binding resin

VL

Wear

Ex.

Main

Blend

ETM

(V)

(μm)

1532

2-3

—

ET1-1

190

1.3

1533

2-3

—

ET2-1

174

1.2

1534

2-3

—

ET3-4

177

1.8

1535

2-3

—

ET5-1

180

1.7

1536

2-3

A-1

ET1-1

188

1.2

1537

3-1

—

ET1-1

178

2.0

1538

3-1

—

ET2-1

166

1.8

1539

3-1

—

ET3-4

165

1.7

1540

3-1

—

ET5-1

170

1.5

1541

3-1

A-1

ET1-1

177

2.1

1542

3-2

—

ET1-1

175

2.0

1543

3-2

—

ET2-1

170

1.9

1544

3-2

—

ET3-4

166

1.8

1545

3-2

—

ET5-1

165

1.7

1546

3-2

A-1

ET1-1

175

1.9

1547

3-3

—

ET1-1

171

2.4

1548

3-3

—

ET2-1

170

2.3

1549

3-3

—

ET3-4

163

2.1

1550

3-3

—

ET5-1

164

2.0

1551

3-3

A-1

ET1-1

174

2.2

Ccmp. Ex. 17

A-4

—

ET1-1

230

6.1

Comp. Ex. 18

1-1

—

ET15-1

290

2.4

Number	Date	Country	Kind
7-092776	Apr 1995	JP
7-092777	Apr 1995	JP

Number	Name	Date
3615406	Merrill	Oct 1971
3647431	Rossi	Mar 1972
3658520	Brantly et al.	Apr 1972
3703371	Merrill	Nov 1972
3703372	Merrill	Nov 1972
3865789	Wyhof	Feb 1975
3865869	Kuehn et al.	Feb 1975
4769304	Kondo et al.	Sep 1988
4772526	Kan et al.	Sep 1988
4996124	Buettner et al.	Feb 1991
5436100	Shimada et al.	Jul 1995
5521044	Muto et al.	May 1996
5578405	Ikegami et al.	Nov 1996
5616441	Kawaguchi et al.	Apr 1997
5830615	Miyamoto et al.	Nov 1998

Number	Date	Country
2048135	Apr 1971	DE
3215646	Nov 1982	DE
0011980	Jun 1980	EP
0 506 387	Sep 1992	EP
0552740	Jul 1993	EP
0 574 154	Dec 1993	EP
2022016	Jul 1970	FR
2126764	Oct 1972	FR
60-192950	Oct 1985	JP
61-62039	Mar 1986	JP
63-148263	Jun 1988	JP
1-273064	Oct 1989	JP
5-80548	Apr 1993	JP
5-88396	Apr 1993	JP
5-113671	May 1993	JP
5-173341	Jul 1993	JP
5-232722	Sep 1993	JP
6-51550	Feb 1994	JP
60-172045	Sep 1995	JP
5-158249	Jun 1996	JP

Electrophotosensitive material

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Priority Claims (2)

Parent Case Info

US Referenced Citations (15)

Foreign Referenced Citations (20)

Non-Patent Literature Citations (9)