Charge-transfer material and process for producing the same, electron-transfer agent, photoreceptor for electrophotography and organic electroluminescence element using said charge-transfer material

BACKGROUND OF THE INVENTION

[0002] 1. Field of Invention

[0003] The present invention relates to a technical field involving the use of electron-transfer materials, and more particularly, to a novel electron-transfer compound as well as to a process for producing such a compound. The present invention further relates to an electron-transfer agent containing such a compound, and also, to an electrophotographic photoreceptor and an organic electroluminescence element containing such an agent.

[0004] 2. Description of Related Art

[0005] Photocopiers, laser printers and other electrophotographic apparatuses are equipped with an electrophotographic photoreceptor. In the early days of development of photocopiers and laser printers, inorganic film was used in the photosensitive layer of the electrophotographic photoreceptors. Such inorganic film was formed of inorganic materials such as selenium, selenium-tellurium, selenium-arsenic and amorphous silicon.

[0006] As demand increases for inexpensive, environmentally less harmful electrophotographic photoreceptors, the photoreceptors incorporating organic film have become widely used and have replaced those with conventional photosensitive layers formed of inorganic film. The photosensitive layers formed of organic film are generally divided into two structurally different types: single-layered and multi-layered.

[0007] The single-layered photosensitive layer comprises a single layer of charge-transfer medium in which a charge-generation material has been dispersed. The single layer serves both to generate electrical charge and to transport charge. In comparison, the multi-layered photosensitive layer is formed as a multi-layered film comprising a charge-generation layer (CGL) and a charge-transfer layer (CTL) that are laminated on top of one another. The two layers have different functions with the charge-generation layer generating electrical charge and the charge-transfer layer transferring the generated charge.

[0008] While both types of the photosensitive layers are in use today, each requires a charge-transfer material with a high mobility in order to increase sensitivity.

[0009] The organic photosensitive layers are also divided into two different types, namely, positive charge photosensitive layers and negative charge photosensitive layers, based on the polarity they can be charged as well. Most of the known charge-transfer materials that have high mobility and are in practical use today are hole-drift type charge-transfer materials. Accordingly, the photoreceptors used in commercial electrophotographic products employ a negative charge photosensitive layer.

[0010] When these photosensitive layers are negatively charged by means of corona discharge phenomena, significant amounts of ozone are produced, causing many problems such as pollution of indoor environments and accelerated deterioration of the electrophotographic photoreceptor.

[0011] In order to avoid these problems occurring during the negative charging process, conventional electrophotographic apparatuses employ ozone filters or a special ozone-free charging technique. These approaches, however, bring about new problems, such as resulting in an undesirably large construction of the apparatus or complex electrophotography process. Further, none of these approaches has ever provided a practical solution.

[0012] As a result, the positive charge photoreceptors, which produce little ozone, are demanded in the marketplace as an effective countermeasure to the above-described problems, and to this end, a highly mobile electron-transfer material must be developed that can be used in the positive charge photosensitive layer.

[0013] Negative charge photoreceptors are better suited for use in color printers because of available toners. Also, by constructing the photosensitive layer as a single layer in a negative charge photoreceptor, the time required for the coating process, and thus the production cost, can be reduced. Constructing such a photosensitive layer, however, requires an electron-transfer material with even higher mobility, and no material has ever been found to have a sufficiently high electron mobility to provide such characteristics.

[0014] Therefore, a highly mobile electron-transfer material is as important in the negative charge photoreceptor as it is in the positive charge photoreceptor. Much effort has been made to find such material. The electron-transfer materials for use in the positive charge photoreceptor that are known to date include trinitrofluorenon (TNF), tetracyanoethylene, tetracyanoquinodimethane (TCNQ), quinone, diphenoquinone, naphthoquinone, anthraquinone, and derivatives thereof. Most of these electron-transfer materials, however, have a poor compatibility with binder resins so that it is difficult to uniformly disperse these materials in a photosensitive layer at a high concentration. Thus, the amount of the electron-transfer material contained in the photosensitive layer tends to be too small to provide sufficient electrical characteristics.

[0015] Unlike other electron-transfer materials, diphenoquinone compounds are known to have an exceptionally high compatibility with resins as well as a high electron mobility. On the other hand, diphenoquinone compounds tend to exhibit a strong color due to the long conjugated system within the molecule, and when used to form a photosensitive layer, diphenoquinone compounds absorb light that would otherwise reach the charge-generation material. As a result, the sensitivity of the photosensitive layer is decreased. Further, these compounds generate electrically stable radicals due to the symmetrical structure of their molecule skeletons. The radicals form electrical traps to hinder movement of electrons in a low electric field. Not only does this result in a reduced luminescence efficiency, and thus a reduced brightness of organic electroluminescence elements, but it also results in a high residual potential in the photosensitive layer of the photoreceptor.

[0016] One example of the electron-transfer material that has overcome the problem of reduced electron mobility in low electric fields is a compound described in Japanese Patent Laid-Open Publication No. Hei 9-34141, which has the structure shown by the following chemical formula 24:

[0017] The compound has a conjugated system involving three double bonds between an oxygen atom and a dicyanomethylene group within its molecular skeleton. Because of this relatively short conjugated system, the compound is capable of coloring only faintly and is thus less likely to absorb light.

[0018] Also, the dicyanomethylene group attached to one end of the quinone structure serves to keep the lives of the radicals produced during the movement of electrons short. As a result, the radicals are less likely to form traps even in a low electric field. However, movement of electrons is more restricted in this compound than in diphenoquinone compounds since its short conjugated system permits electrons to move within the molecule only over relatively short distances.

[0019] In practice, electrophotographic photoreceptors using the above compound are less than satisfactory when compared to the commercially available negative charge electrophotographic photoreceptors in terms of sensitivity and residual potential.

[0020] It is thus necessary for a practically useful electron-transfer material to meet two contradictory requirements: it must have a reduced ability to color and it must ensure a large degree of electron movement within the molecule. The former requirement is met by a short conjugated system in the chemical structure, whereas the latter is met by a long conjugated system provided by a larger molecular skeleton. A strong demand exists for a molecular structure that, aside from meeting these requirements, does not produce stable radicals.

SUMMARY OF THE INVENTION

[0021] The present invention has been devised to address the above-identified problems associated with the conventional art. It is thus an objective of the present invention to provide a novel useful electron-transfer material that can be dispersed in a photosensitive layer at a high concentration and has a high electron mobility. It is also an objective of the present invention to provide an electrophotographic photoreceptor with an improved sensitivity and residual potential, as well as to provide an organic electroluminescence element with a high luminescence efficiency.

[0022] In the search for a way to solve the above-described problems, the present inventors have found that a compound can be provided that has a novel molecular skeleton in which a quinone ring is connected via a double bond to a ring structure having an active methylene, as well as a production process of such a compound, a novel electron-transfer material, and an electrophotographic photoreceptor and an organic electroluminescence element containing such an electron-transfer material. The discovery ultimately led the present inventors to bring the present invention to completion.

[0023] Having been devised based on the above-described findings, the present invention provides a compound represented by the following general formula (1):

[0024] wherein R1 through R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (1′) that replaces the general formula (1) above:

[0025] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

BRIEF DESCRIPTION OF THE DRAWINGS

[0026]
FIG. 1 is an IR spectrum of a compound represented by the chemical formula (7).

[0027]
FIG. 2 is a 1H-NMR spectrum of the compound represented by the chemical formula (7).

[0028]
FIG. 3 is an IR spectrum of a compound represented by the chemical formula (8).

[0029]
FIG. 4 is a 1H-NMR spectrum of the compound represented by the chemical formula (8).

[0030]
FIG. 5 is an IR spectrum of a compound represented by the chemical formula (9).

[0031]
FIG. 6 is a 1H-NMR spectrum of the compound represented by the chemical formula (9).

[0032]
FIG. 7 is an IR spectrum of a compound represented by the chemical formula (10).

[0033]
FIG. 8 is a 1H-NMR spectrum of the compound represented by the chemical formula (10).

[0034]
FIG. 9 is an IR spectrum of a compound represented by the chemical formula (11).

[0035]
FIG. 10 is a 1H-NMR spectrum of the compound represented by the chemical formula (11).

[0036]
FIG. 11 is an IR spectrum of a compound represented by the chemical formula (12).

[0037]
FIG. 12 is a 1H-NMR spectrum of the compound represented by the chemical formula (12).

[0038]
FIG. 13 is an IR spectrum of a compound represented by the chemical formula (13).

[0039]
FIG. 14 is a 1H-NMR spectrum of the compound represented by the chemical formula (13).

[0040]
FIG. 15 is an IR spectrum of a compound represented by the chemical formula (14).

[0041]
FIG. 16 is a 1H-NMR spectrum of the compound represented by the chemical formula (14).

[0042]
FIG. 17 is an IR spectrum of a compound represented by the chemical formula (15).

[0043]
FIG. 18 is a 1H-NMR spectrum of the compound represented by the chemical formula (15).

[0044]
FIG. 19 is an IR spectrum of a compound represented by the chemical formula (16).

[0045]
FIG. 20 is a 1H-NMR spectrum of the compound represented by the chemical formula (16).

[0046]
FIG. 21 is a cross-sectional view showing one example of a multi-layered electrophotographic photoreceptor.

[0047]
FIG. 22 is a cross-sectional view showing one example of a single-layered electrophotographic photoreceptor.

[0048]
FIG. 23 is a cross-sectional view showing one example of an organic electroluminescence element.

[0049]
FIG. 24 is an IR spectrum of a compound represented by the chemical formula (29).

[0050]
FIG. 25 is a 1H-NMR spectrum of the compound represented by the chemical formula (29).

[0051]
FIG. 26 is an IR spectrum of a compound represented by the chemical formula (30).

[0052]
FIG. 27 is a 1H-NMR spectrum of the compound represented by the chemical formula (30).

[0053]
FIG. 28 is an IR spectrum of a compound represented by the chemical formula (31).

[0054]
FIG. 29 is a 1H-NMR spectrum of the compound represented by the chemical formula (31).

[0055]
FIG. 30 is an IR spectrum of a compound represented by the chemical formula (32).

[0056]
FIG. 31 is a 1H-NMR spectrum of the compound represented by the chemical formula (32).

[0057]
FIG. 32 is an IR spectrum of a compound represented by the chemical formula (33).

[0058]
FIG. 33 is a 1H-NMR spectrum of the compound represented by the chemical formula (33).

[0059]
FIG. 34 is an IR spectrum of a compound represented by the chemical formula (34).

[0060]
FIG. 35 is a 1H-NMR spectrum of the compound represented by the chemical formula (34).

[0061]
FIG. 36 is an IR spectrum of a compound represented by the chemical formula (35).

[0062]
FIG. 37 is a 1H-NMR spectrum of the compound represented by the chemical formula (35).

[0063]
FIG. 38 is an IR spectrum of a compound represented by the chemical formula (36).

[0064]
FIG. 39 is a 1H-NMR spectrum of the compound represented by the chemical formula (36).

[0065]
FIG. 40 is an IR spectrum of a compound represented by the chemical formula (37).

[0066]
FIG. 41 is a 1H-NMR spectrum of the compound represented by the chemical formula (37).

[0067]
FIG. 42 is an IR spectrum of a compound represented by the chemical formula (38).

[0068]
FIG. 43 is a 1H-NMR spectrum of the compound represented by the chemical formula (38).

[0069]
FIG. 44 is an IR spectrum of a compound represented by the chemical formula (39).

[0070]
FIG. 45 is a 1H-NMR spectrum of the compound represented by the chemical formula (39).

[0071]
FIG. 46 is an IR spectrum of a compound represented by the chemical formula (40).

[0072]
FIG. 47 is a 1H-NMR spectrum of the compound represented by the chemical formula (40).

[0073]
FIG. 48 is an IR spectrum of a compound represented by the chemical formula (41).

[0074]
FIG. 49 is a 1H-NMR spectrum of the compound represented by the chemical formula (41).

[0075]
FIG. 50 is an IR spectrum of a compound represented by the chemical formula (42).

[0076]
FIG. 51 is a 1H-NMR spectrum of the compound represented by the chemical formula (42).

[0077]
FIG. 52 is an IR spectrum of a compound represented by the chemical formula (43).

[0078]
FIG. 53 is a 1H-NMR spectrum of the compound represented by the chemical formula (43).

[0079]
FIG. 54 is an IR spectrum of a compound represented by the chemical formula (45).

[0080]
FIG. 55 is a 1H-NMR spectrum of the compound represented by the chemical formula (45).

[0081]
FIG. 56 is an IR spectrum of a compound represented by the chemical formula (46).

[0082]
FIG. 57 is a 1H-NMR spectrum of the compound represented by the chemical formula (46).

[0083]
FIG. 58 is an IR spectrum of a compound represented by the chemical formula (47).

[0084]
FIG. 59 is a 1H-NMR spectrum of the compound represented by the chemical formula (47).

[0085]
FIG. 60 is an IR spectrum of a compound represented by the chemical formula (48).

[0086]
FIG. 61 is a 1H-NMR spectrum of the compound represented by the chemical formula (48).

[0087]
FIG. 62 is an IR spectrum of a compound represented by the chemical formula (49).

[0088]
FIG. 63 is a 1H-NMR spectrum of the compound represented by the chemical formula (49).

[0089]
FIG. 64 is an IR spectrum of a compound represented by the chemical formula (50).

[0090]
FIG. 65 is a 1H-NMR spectrum of the compound represented by the chemical formula (50).

[0091]
FIG. 66 is an IR spectrum of a compound represented by the chemical formula (51).

[0092]
FIG. 67 is a 1H-NMR spectrum of the compound represented by the chemical formula (51).

[0093]
FIG. 68 is an IR spectrum of a compound represented by the chemical formula (52).

[0094]
FIG. 69 is a 1H-NMR spectrum of the compound represented by the chemical formula (52).

[0095]
FIG. 70 is an IR spectrum of a compound represented by the chemical formula (53).

[0096]
FIG. 71 is a 1H-NMR spectrum of the compound represented by the chemical formula (53).

[0097]
FIG. 72 is an IR spectrum of a compound represented by the chemical formula (54).

[0098]
FIG. 73 is a 1H-NMR spectrum of the compound represented by the chemical formula (54).

[0099]
FIG. 74 is an IR spectrum of a compound represented by the chemical formula (55).

[0100]
FIG. 75 is a 1H-NMR spectrum of the compound represented by the chemical formula (55).

[0101]
FIG. 76 is an IR spectrum of a compound represented by the chemical formula (56).

[0102]
FIG. 77 is a 1H-NMR spectrum of the compound represented by the chemical formula (56).

[0103]
FIG. 78 is an IR spectrum of a compound represented by the chemical formula (57).

[0104]
FIG. 79 is a 1H-NMR spectrum of the compound represented by the chemical formula (57).

[0105]
FIG. 80 is an IR spectrum of a compound represented by the chemical formula (58).

[0106]
FIG. 81 is a 1H-NMR spectrum of the compound represented by the chemical formula (58).

[0107]
FIG. 82 is an IR spectrum of a compound represented by the chemical formula (59).

[0108]
FIG. 83 is a 1H-NMR spectrum of the compound represented by the chemical formula (59).

[0109]
FIG. 84 is an IR spectrum of a compound represented by the chemical formula (60).

[0110]
FIG. 85 is a 1H-NMR spectrum of the compound represented by the chemical formula (60).

[0111] Throughout the figures, the reference numeral 1 denotes an electroconductive substrate; the reference numeral 2 denotes a charge-generation layer; the reference numeral 3 denotes a charge-transfer layer; the reference numeral 4 denotes a photosensitive layer; the reference numerals 11 and 12 each denote an electrophotographic photoreceptor; the reference numeral 21 denotes an organic electroluminescence element; the reference numeral 22 denotes a first electrode; the reference numeral 25 denotes a luminescent layer; and the reference numeral 26 denotes a second electrode.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

[0112] The ring structure represented by W exhibits strong acidity and thus strong electron acceptability. Given this, the present inventors have designed a novel molecular skeleton in which the ring represented by W is connected via a double bond to a quinone ring, which is generally known to exhibit a strong electron acceptability. The dipole moment of this molecular skeleton must be large enough so that the generation of stable radicals, as in the case of diphenoquinone, is prevented.

[0113] The dipole moment of the molecular skeleton can readily be calculated by the molecular orbital method to be compared. Specifically, the molecular skeleton has a dipole moment (debye) of 0.001 or larger, preferably 0.01 or larger, and more preferably 0.1 or larger as determined by MOPAC/AM1 using the molecular skeleton bearing no substituents. In this manner, the resulting radicals have relatively short lives and are thus less likely to form electric traps. As a result, electron transfer can take place even in a low electric field, and the electron mobility is significantly enhanced in a strong electric field, as is the efficiency of electron movement.

[0114] The two interconnected ring structures, namely, the 6-membered ring and the ring represented by W, make the molecular skeleton of the above-described compound larger than that of the compound of the formula (24). This ensures a larger distance along which electrons can travel and thus facilitates movement of electrons within the molecule. As a result, the compound exhibits a high electron mobility.

[0115] In contrast to diphenoquinone compounds, asymmetric configuration of its conjugated system ensures the above compound's weak ability to exhibit color, so that it hardly absorbs light. Furthermore, the ring represented by W attached to one end of the quinone ring makes its molecular structure asymmetric. This facilitates the compatibility of the compound with resin, so that it can be dispersed in resin at a high concentration. These functions can readily be varied as desired by using different combinations of substituents. In this manner, it is possible to optimize the compatibility with resin or control the speed or the amount of electron movement.

[0116] In a preferred embodiment, the present invention provides a compound represented by the following general formula (2):

[0117] wherein R1 and R3 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (2′) that replaces the general formula (2) above:

[0118] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0119] Introduction of at least one alkyl group having 1 to 6 carbon atoms or at least one phenyl group into the substituents R1 and R3 can provide the molecular skeleton with the effect to push out electrons. In this manner, the polarization of the molecule, and thus the electron mobility within the molecule, is increased. The substituents that exhibit high compatibility with resin may be used in combination.

[0120] In a particularly preferred embodiment, the present invention provides a compound represented by the following general formula (3):

[0121] wherein X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (3′) that replaces the general formula (3) above:

[0122] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0123] Introduction of the bulky t-Bu group into the quinone ring can increase the compatibility with resin and provide the molecular skeleton with the effect to push out electrons. In this manner, the polarization of the molecule is increased and a compound with significantly increased electron mobility is obtained.

[0124] The present invention provides a compound represented by the following general formula (4):

[0125] wherein R1 through R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur.

[0126] By introducing a phenyl, thienyl, or furil group, each being an aromatic 6 π electron system, into the substituent R5 in the general formula (4) above, the molecular skeleton can be stabilized.

[0127] The present invention provides a compound represented by the following general formula (5):

[0128] wherein R1 through Rr are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur.

[0129] The present invention provides a compound represented by the following general formula (6):

[0130] wherein R1 through R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur.

[0131] The present invention provides a compound represented by the following general formula (44):

[0132] wherein R1 through R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur.

[0133] The present invention provides a compound represented by the following chemical formula (7):

[0134] The present invention provides a compound represented by the following chemical formula (8):

[0135] The present invention provides a compound represented by the following chemical formula (9):

[0136] The present invention provides a compound represented by the following chemical formula (10):

[0137] The present invention provides a compound represented by the following chemical formula (11):

[0138] The present invention provides a compound represented by the following chemical formula (12):

[0139] The present invention provides a compound represented by the following chemical formula (13):

[0140] The present invention provides a compound represented by the following chemical formula (14):

[0141] The present invention provides a compound represented by the following chemical formula (15):

[0142] The present invention provides a compound represented by the following chemical formula (16):

[0143] The present invention provides a compound represented by the following chemical formula (29):

[0144] The present invention provides a compound represented by the following chemical formula (30):

[0145] The present invention provides a compound represented by the following chemical formula (31):

[0146] The present invention provides a compound represented by the following chemical formula (32):

[0147] The present invention provides a compound represented by the following chemical formula (33):

[0148] The present invention provides a compound represented by the following chemical formula (34):

[0149] The present invention provides a compound represented by the following chemical formula (35):

[0150] The present invention provides a compound represented by the following chemical formula (36):

[0151] The present invention provides a compound represented by the following chemical formula (37):

[0152] The present invention provides a compound represented by the following chemical formula (38):

[0153] The present invention provides a compound represented by the following chemical formula (39):

[0154] The present invention provides a compound represented by the following chemical formula (40):

[0155] The present invention provides a compound represented by the following chemical formula (41):

[0156] The present invention provides a compound represented by the following chemical formula (42):

[0157] The present invention provides a compound represented by the following chemical formula (43):

[0158] The present invention provides a compound represented by the following chemical formula (45):

[0159] The present invention provides a compound represented by the following chemical formula (46):

[0160] The present invention provides a compound represented by the following chemical formula (47):

[0161] The present invention provides a compound represented by the following chemical formula (48):

[0162] The present invention provides a compound represented by the following chemical formula (49):

[0163] The present invention provides a compound represented by the following chemical formula (50):

[0164] The present invention provides a compound represented by the following chemical formula (51):

[0165] The present invention provides a compound represented by the following chemical formula (52):

[0166] The present invention provides a compound represented by the following chemical formula (53):

[0167] The present invention provides a compound represented by the following chemical formula (54):

[0168] The present invention provides a compound represented by the following chemical formula (55):

[0169] The present invention provides a compound represented by the following chemical formula (56):

[0170] The present invention provides a compound represented by the following chemical formula (57):

[0171] The present invention provides a compound represented by the following chemical formula (58):

[0172] The present invention provides a compound represented by the following chemical formula (59):

[0173] The present invention provides a compound represented by the following chemical formula (60):

[0174] In each of the chemical formulae (7) through (16), (29) through (43), and (45) through (60), t-Bu represents a tertiary butyl group ((CH3)3C—), n-Bu represents a straight-chained butyl group (CH3CH2CH2CH2—), Me represents a methyl group (CH3—), n-Pr represents a straight chained propyl group (CH3CH2CH2—), and i-Pr represents an isopropyl group ((CH3)2CH—).

[0175] The present invention provides a process for producing a compound represented by the following general formula (1):

[0176] wherein R1 to R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (1′) that replaces the general formula (1) above:

[0177] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring, the process involving the step of reacting in the presence of a base catalyst a benzoquinone compound represented by the following general formula (17):

[0178] wherein R1 to R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2, with a compound having an active methylene represented by the following general formula (18):

[0179] wherein the compound is a 4- to 8-membered ring; Y is oxygen or sulfur; and Z is a structure that has 2 or more atoms and forms a part of the ring. In this manner, the electron-transfer compound can be readily produced. A solvent which is inert against benzoquinone compound and the compound having an active methylene may be added along with the base catalyst to adjust the reaction rate.

[0180] The present invention provides a process for producing a compound represented by the following general formula (2):

[0181] wherein R1 and R3 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (2′) that replaces the general formula (2) above:

[0182] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring, the process involving the step of reacting in the presence of a base catalyst a benzoquinone compound represented by the following general formula (19):

[0183] wherein R1 and R3 are each independently selected from the group consisting of hydrogen, alkyl with 1 to 6 carbon atoms, and phenyl; and

[0184] X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2, with a compound having an active methylene represented by the following general formula (18):

[0185] wherein the compound is a 4- to 8-membered ring; Y is oxygen or sulfur; and Z is a structure having 2 or more atoms and forms a part of the ring.

[0186] The present invention provides a process for producing a compound represented by the following general formula (3):

[0187] wherein X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (3′) that replaces the general formula (3) above:

[0188] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring, the process involving the step of reacting in the presence of a base catalyst a benzoquinone compound represented by the following general formula (20):

[0189] wherein X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2, with a compound having an active methylene represented by the following general formula (18):

[0190] wherein the compound is a 4- to 8-membered ring; Y is oxygen or sulfur; and Z is a structure having 2 or more atoms and forms a part of the ring.

[0191] The present invention provides a process for producing a compound represented by the following general formula (4):

[0192] wherein R1 through R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur, the process involving the step of reacting in the presence of a base catalyst a benzoquinone compound represented by the following general formula (17):

[0193] wherein R1 through R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2, with a compound having an active methylene represented by the following general formula (21):

[0194] wherein R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and Y is oxygen or sulfur.

[0195] The present invention provides a process for producing a compound represented by the following general formula (5):

[0196] wherein R1 through R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur, the process involving the step of reacting in the presence of a base catalyst a benzoquinone compound represented by the following general formula (17):

[0197] wherein R1 through R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2, with a compound having an active methylene represented by the following general formula (22):

[0198] wherein R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and Y is oxygen or sulfir.

[0199] The present invention provides a process for producing a compound represented by the following general formula (6):

[0200] wherein R1 through R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur, the process involving the step of reacting in the presence of a base catalyst a benzoquinone compound represented by the following general formula (17):

[0201] wherein R1 through R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2, with a compound having an active methylene represented by the following general formula (23):

[0202] wherein R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur.

[0203] The present invention provides a process for producing a compound represented by the following general formula (44):

[0204] wherein R1 through R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfir, the process involving the step of reacting in the presence of a base catalyst a benzoquinone compound represented by the following general formula (17):

[0205] wherein R1 through R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2, with a compound having an active methylene represented by the following general formula (61):

[0206] wherein R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and Y is oxygen or sulfur.

[0207] The present invention provides a process for producing a compound in which the benzoquinone compound is reacted with the compound having an active methylene in the presence of the base catalyst and one or a mixture of two or more solvents selected from the group consisting of water, alcohol, and saturated aliphatic hydrocarbon solvent.

[0208] The present invention provides a process for producing a compound in which the benzoquinone compound is reacted with the compound having an active methylene in the presence of the base catalyst and a solvent that needs to be used in amounts of 50 ml or more to dissolve 1 g of the compound of the general formulae (1) through (6) and (44).

[0209] The present invention provides an electron-transfer agent comprising a resin containing as a charge-transfer material a compound represented by the following general formula (1):

[0210] wherein R1 through R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (1′) that replaces the general formula (1) above:

[0211] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0212] The present invention provides an electron-transfer agent comprising a resin containing as a charge-transfer material a compound represented by the following general formula (2):

[0213] wherein R1 and R3 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring having the structure shown in the following general formula (2′) that replaces the general formula (2) above:

[0214] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0215] The present invention provides an electron-transfer agent comprising a resin containing as a charge-transfer material a compound represented by the following general formula (3):

[0216] wherein X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (3′) that replaces the general formula (3) above:

[0217] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0218] The present invention provides an electrophotographic photoreceptor comprising an electroconductive substrate having at least a photosensitive layer disposed thereon, wherein the photosensitive layer contains as a charge-transfer material a compound represented by the following general formula (1):

[0219] wherein R1 through R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (1′) that replaces the general formula (1) above:

[0220] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0221] As described above, the use of the compound, which has a high electron mobility and high compatibility with resin, makes it possible to provide highly sensitive electrophotographic photoreceptors.

[0222] The present invention provides an electrophotographic photoreceptor comprising an electroconductive substrate having at least one photosensitive layer disposed thereon, wherein the photosensitive layer contains as a charge-transfer material a compound represented by the following general formula (2):

[0223] wherein R1 and R3 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (2′) that replaces the general formula (2) above:

[0224] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0225] As described above, the use of the compound, which has a high electron mobility and high compatibility with resin, makes it possible to provide electrophotographic photoreceptors with even higher sensitivity.

[0226] The present invention provides an electrophotographic photoreceptor comprising an electroconductive substrate having at least a photosensitive layer disposed thereon, wherein the photosensitive layer contains as a charge-transfer material a compound represented by the following general formula (3):

[0227] wherein X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (3′) that is to replace the general formula (3) above:

[0228] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0229] As described above, the use of the compound, which has a high electron mobility and high compatibility with resin, makes it possible to provide extremely sensitive electrophotographic photoreceptors.

[0230] The present invention provides an organic electroluminescence element including an organic film that can at least emit light and is disposed between a pair of electrodes, wherein the organic film contains a compound represented by the following general formula (1):

[0231] wherein R1 to R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (1′) that replaces the general formula (1) above:

[0232] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0233] The present invention provides an organic electroluminescence element including an organic film that can at least emit light and is arranged between a pair of electrodes, wherein the organic film contains a compound represented by the following general formula (2):

[0234] wherein R1 and R3 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (2′) that replaces the general formula (2) above:

[0235] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0236] The present invention provides an organic electroluminescence element including an organic film that can at least emit light and is arranged between a pair of electrodes, wherein the organic film contains a compound represented by the following general formula (3):

[0237] wherein X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (3′) that replaces the general formula (3) above:

[0238] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0239] The substituent represented by W in the general formulae (1) through (3) above does not include those represented by the following general formula (28):

[0240] wherein R′ is selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid.

[0241] As described above, not only does the compound of the present invention exhibit a high electron mobility, but it also makes it possible to design a proper molecular structure depending on functions required for the material for an electrophotographic photoreceptor or organic electroluminescence element that makes use of electron-transfer materials.

[0242] In cases where the substituents R1 through R6 in the above general formulae (1) through (6) and (44) are each selected from alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid, these substituents may be modified by other substituents. The modified substituents are also encompassed by the scope of the present invention. Among the substituents R1 through R6, R1 and R2 may link together to form a ring, as may R3 and R4.

[0243] The substituents R1 through R6 may be different from one another, or two or more of the substituents R1 through R6 may be identical to one another.

[0244] The substituent W, a 4- to 8-membered cyclic compound shown in the general formulae (1) through (3), may condense with other cyclic compounds and may form a fused ring. These fused rings are also encompassed by the scope of the present invention. The present invention further encompasses the case where the structure Z includes one or more of heteroatoms, the case where the structure Z consists only of carbon atoms, and the case where the structure Z is modified by a substituent.

[0245] Preferred embodiments of electron-transfer compounds, processes for producing the electron-transfer compounds, and electron-transfer agents of the present invention, as well as application examples thereof, will now be described in detail with reference to Tables A through AC mentioned below.

[0246] 1. Description of Compounds

[0247] An electron-transfer compound in accordance with the present invention has a novel molecular skeleton in which an active methylene group of a cyclic compound that bears the active methylene is attached to a quinone ring via a double bond. The structure of the compound is shown by the following general formula (1):

[0248] wherein R1 through Ra are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and W is a 4- to 8-membered ring and has the structure shown in the following general formula (1′) that replaces the general formula (1) above:

[0249] wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.

[0250] While specific examples of the electron-transfer compound are described below, they are not intended to limit the scope of the invention in any way. Tables A(1) through A(18) list structures of the compounds shown by the general formulae (101) through (314), each having six substituents, R1 through R6, whereas Tables A(19) through A(26) list structures of the compounds shown by the general formulae (315) through (423), each having five substituents, R1 through R5.

[0251] Table B is a list showing substituents S1 through S23, which can be independently used as the substituents R1 through R6, or R1 through R5, in the general formulae (101) through (423).

[0252] Tables C(1) through C(6) each show possible combinations of the six substituents R1 through R6 for the compounds of the general formulae (101) through (314), whereas Tables C(7) through C(11) each show possible combinations of the five substituents R1 through R5 for the compounds of the general formulae (315) through (423).

[0253] 2. Description of Production Process

[0254] A production process in accordance with the present invention involves reacting a benzoquinone compound with a compound having an active methylene in the presence of a base catalyst. The benzoquinone compound for use in the process of the present invention has the structure represented by the following general formula (17):

[0255] wherein R1 to R4 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2.

[0256] Preferably, R2 and R4 each are a hydrogen atom in the general formula (17), as shown by the following general formula (9):

100

[0257] wherein R1 and R3 are each independently selected from the group consisting of hydrogen, alkyl having 1 to 6 carbon atoms, and phenyl; and X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2.

[0258] Preferably, R1 and R3 in the general formula (19) each are a t-Bu group, as shown by the following general formula (20):

101

[0259] wherein X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2.

[0260] The compound having an active methylene for use in the process of the present invention has the structure represented by the following general formula (18):

102

[0261] wherein the compound is a 4- to 8-membered ring; Y is oxygen or sulfur; and Z is a structure that has 2 or more atoms and forms a part of the ring. Preferably, the compound having an active methylene of the general formula (18) is a compound represented by the following general formula (21):

103

[0262] wherein R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and Y is oxygen or sulfur.

[0263] It is also preferred that the compound having an active methylene of the general formula (18) be a compound represented by the following general formula (22):

104

[0264] wherein R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; and Y is oxygen or sulfur.

[0265] It is also preferred that the compound having an active methylene of the general formula (18) be a compound represented by the following general formula (23):

105

[0266] wherein R5 and R6 are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkyl, aryl, heterocyclic ring, ester, alkoxy, aralkyl, allyl, amide, amino, acyl, alkenyl, alkynyl, carboxyl, carbonyl, and carboxylic acid; X is selected from the group consisting of oxygen, sulfur, and ═C(CN)2; and Y is oxygen or sulfur.

[0267] Examples of organic base catalysts that can serve as the base catalyst for use in the process of the present invention include primary amines, such as methylamine, ethylaamine, propylamine, and butylamine; secondary amines, such as dimethylamine, diethylamine, methylethylamine, dipropylamine, and dibutylamine; tertiary amines, such as trimethylamine, dimethylethylamine, methyldiethylamine, dimethylpropylamine, triethylamine, methylethylpropylamine, diethylpropylaamine, dipropylmethylamine, ethyldipropylamine, and tributylamine; cyclic amines, such as pyridine, 2,6-dimethylpyridine, quinoline, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4-diazabicyclo[2.2.2]octane; metal alkoxides, such as sodium methoxide, potassium methoxide, and butyl lithium; and metal amides, such as sodium amide and potassium amide.

[0268] Examples of inorganic base catalysts that can serve as the base catalyst for use in the present invention include basic gases such as ammonia, alkali metals such as sodium, potassium and lithium, metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, metal salts such as sodium carbonate and potassium carbonate. Among these bases, those having a base dissociation constant greater than that of pyridine are preferred since they can accelerate the reaction significantly. The base catalyst may be used as a mixture of two or more base catalysts.

[0269] The base catalyst may be used together with an inert solvent. Examples of the inert solvent include alcohols such as methanol, ethanol, 1-propanol, 2-propanol, butanol and ethylene glycol, saturated aliphatic hydrocarbons such as hexane, heptane, octane, cyclohexane and cycloheptane, aromatic hydrocarbons such as benzene, toluene and xylene, chloride-containing hydrocarbons such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethylether, diisopropylether, tetrahydrofuran (THF), dioxane and methoxyethanol, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, esters such as ethyl formate, propyl formate, methyl acetate, ethyl acetate, propyl acetate, butyl acetate and methyl propionate, and N-methylpyrrolidone. These inert solvents may be used independently or as a mixture of two or more solvents.

[0270] While the reaction may proceed at low temperatures depending on the type of the base catalyst used, it is preferably carried out at room temperature or above to reduce the reaction time. The reaction system may be heated or cooled depending on the conditions of the reaction. While it depends on the type of the materials used, the reaction may require stirring so that it can take place, or in some cases the reaction may proceed by simply allowing the mixture of the materials to stand still.

[0271] 3. Description of Electron-Transfer Agent

[0272] An electron-transfer agent of the present invention comprises a resin and the electron-transfer compound. Examples of the resin for use in the electron-transfer agent include polycarbonate resin, styrene resin, acrylic resin, styrene-acrylic resin, ethylene-vinyl acetate resin, polypropylene resin, vinyl chloride resin, chlorinated polyether, vinyl chloride-vinyl acetate resin, polyester resin, nylon resin, vinyl acetate resin, furan resin, nitrile resin, alkyd resin, polyacetal resin, polymethylpentene resin, polyamide resin, polyurethane resin, epoxy resin, polyarylate resin, diarylate resin, polysulfone resin, polyethersulfone resin, polyarylsulfone resin, silicone resin, ketone resin, polyvinylbutyral resin, polyether resin, phenol resin, EVA (ethylene-vinyl acetate copolymer) resin, ACS (acrylonitrile-chlorinated polyethylene-styrene)resin, ABS (acrylonitrile-butadiere-styrene) resin, polyimide resin and epoxyarylate.

[0273] These resins may be used independently, as a copolymer of these resins or as a mixture of two or more resins.

[0274] Preferably, the resins with different molecular weights may be mixed together in order to enhance the hardness and wear-resistance.

[0275] The electron-transfer agent of the present invention contains the resin and the compound of the general formula (1), and the compound is dispersed in the resin.

[0276] When the preferred compound of the general formula (2) is used, it enhances the electron mobility, whereas when the particularly preferred compound of the general formula (3) is used, it enhances the electron mobility and the compatibility with the resin. In addition, these electron-transfer agents may be used as high-performance materials in various applications, including electrophotographic photoreceptors, electroconductive agents, charge-controlling agents, EL elements, photoelectric conversion elements, sensitizing agents for photochemical reactions, and high electroconductivity materials using charge-transfer complexes.

[0277] 4. Description of Application Examples

[0278] a. Description of Electrophotographic Photoreceptor

[0279] An electrophotographic photoreceptor of the present invention includes an electroconductive substrate and a photosensitive layer disposed thereon. The photosensitive layer contains the electron-transfer compound as a charge-transfer material.

[0280] An exemplary electrophotographic photoreceptor of the present invention is denoted by reference numeral 11 in FIG. 21 and by reference numeral 12 in FIG. 22. The electrophotographic photoreceptor 11 is of a multi-layered type, whereas the electrophotographic photoreceptor 12 is of a single-layered type. The electrophotographic photoreceptors 11 and 12 each show one embodiment in which organic film containing the compound of the present invention is used in a photosensitive layer.

[0281] Referring to FIG. 21, the electrophotographic photoreceptor 11 includes a cylindrical electroconductive substrate 1. A charge-generation layer 2 and a charge-transfer layer 3 are disposed on the electroconductive substrate 1 in this order. The charge-generation layer 2 and the charge-transfer layer 3 together form a photosensitive layer 4.

[0282] The charge-generation layer 2 as shown in FIG. 21 includes at least a charge-generation material and may be formed by depositing the charge-generation material, by making use of a binder resin, on the electroconductive substrate 1 as a foundation.

[0283] Although the charge-generation layer 2 may be formed by using various methods, including conventional methods, it is preferably formed by dispersing or dissolving, along with the binder resin, the charge-generation material into a proper solvent so as to make a coating solution, coating the electroconductive substrate 1, which serves as a foundation, with the coating solution, and then drying the coating. Alternatively, the charge-generation layer 2 may be formed by vacuum-depositing the charge-generation material on the substrate.

[0284] The charge-transfer layer 3 includes at least a charge-transfer material, which will be described later, and may be formed by, for example, depositing the charge-transfer material, by making use of a binder resin, on the charge-generation layer 2 as the foundation for the charge-transfer layer 3. Although the charge-transfer layer 3 may be formed by using various methods, including conventional methods, it is typically formed by dispersing or dissolving, along with the binder resin, the charge-transfer material into a proper solvent so as to make a coating solution, coating the charge-generation layer 2, which serves as a foundation, with the coating solution, and then drying the coating.

[0285] Referring now to FIG. 22, one example of the single-layered electrophotographic photoreceptor is denoted by reference numeral 12. With the same numerals assigned to the same components as those in the electrophotographic photoreceptor 11 of the first example, the electrophotographic photoreceptor 12 includes a single-layered photosensitive layer 4 formed on the electroconductive substrate 1. The photosensitive layer 4 contains the charge-generation material and the charge-transfer material.

[0286] Although the photosensitive layer 4 may be formed by using various methods, including conventional methods, it is preferably formed by dispersing or dissolving, along with the binder resin, the charge-generation material into a proper solvent and then dissolving the charge-transfer material so as to make a coating solution, coating the electroconductive substrate 1, which serves as a foundation, with the coating solution, and then drying the coating. The charge-generation material and the charge-transfer material will be described later.

[0287] The electroconductive substrate 1 for use in the present invention may be formed of various electroconductive materials and may be of any material and shape. For example, it may be a metal article of a metal or an alloy of metals, including aluminum, magnesium, brass, stainless steel, nickel, chromium, titanium, gold, silver, copper, tin, platinum, molybdenum and indium; it may be a plastic plate or film with an electroconductive material, such as the aforementioned metal or carbon, vapor-deposited or plated thereon to impart conductivity; or it may be an electroconductive glass plate coated with tin oxide, indium oxide, aluminum iodide or copper iodide.

[0288] Cylindrical aluminum tubes are commonly used, and may or may not be surface-treated by aluminum-anodizing. A resin layer may be deposited on the surface of the aluminum tube, or on the anodized aluminum layer in the case of the surface-treated tube.

[0289] The resin layer is provided for the purposes of enhancing adhesion, serving as a barrier to prevent electric current from flowing from the substrate, and covering surface defects of the substrate. Various types of resin can be used in the resin layer, including polyethylene resin, acrylic resin, epoxy resin, polycarbonate resin, polyurethane resin, vinyl chloride resin, vinyl acetate resin, polyvinylbutyral resin, polyamide resin and nylon resin.

[0290] The resin layer may be formed solely of a single resin, or it may be formed of a mixture of two or more resins or in conjunction with the aluminum-anodizing treatment. Further, metal compounds, metal oxides, carbon, silica, resin powder and other materials may be dispersed in the resin layer. In addition, various pigments, electron acceptors and electron donors may be added in order to improve characteristics of the resin layer.

[0291] Examples of the charge-generation material for use in the present invention include selenium, selenium-tellurium, selenium-arsenic, amorphous silicon, phthalocyanine pigments, monoazo pigments, trisazo pigments, polyazo pigments, indigo pigments, toluidine pigments, pyrazoline pigments, perylene pigments, quinacridone pigments and pyrylium salts. Among these, disazo pigments and phthalocyanine pigments are particularly preferred in order to obtain a high sensitivity because they are highly compatible with the compound of the present invention.

[0292] Of the phthalocyanine pigments, particularly preferred are oxytitanium phthalocyanine, copper phthalocyanine, metal-free phthalocyanine, hydroxygallium phthalocyanine, and diol adducts of oxytitanium phthalocyanine, each of which shows high absorption at longer wavelengths. These charge-generation materials may be used independently or as a mixture of two or more materials in order to obtain optimum wavelengths at which the photosensitivity peaks or has increased sensitivity.

[0293] Examples of the binder resins that can be used to form the photosensitive layer 4 include polycarbonate resin, styrene resin, acrylic resin, styrene-acrylic resin, ethylene-vinyl acetate resin, polypropylene resin, vinyl chloride resin, chlorinated polyether, vinyl chloride-vinyl acetate resin, polyester resin, nylon resin, vinyl acetate resin, furan resin, nitrile resin, alkyd resin, polyacetal resin, polymethylpentene resin, polyamide resin, polyurethane resin, epoxy resin, polyarylate resin, diarylate resin, polysulfone resin, polyethersulfone resin, polyarylsulfone resin, silicone resin, ketone resin, polyvinylbutyral resin, polyether resin, phenol resin, EVA (ethylene-vinyl acetate copolymer) resin, ACS (acrylonitrile-chlorinated polyethylene-styrene)resin, ABS (acrylonitrile-butadiene-styrene) resin, polyimide resin and epoxy arylate.

[0294] These resins may be used independently or as a mixture or a copolymer of two or more resins. Preferably, the resins with different molecular weights may be mixed together in order to enhance the hardness and wear-resistance. The binder resin can be used in each of the charge-generation layer 2 and the charge-transfer layer 3 in the multi-layered photoreceptor shown in FIG. 21.

[0295] Examples of the solvent for use in the coating solution include alcohols such as methanol, ethanol, 1-propanol, 2-propanol and butanol, saturated aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane and cycloheptane, aromatic hydrocarbons such as toluene and xylene, chloride-containing hydrocarbons such as dichloromethane, dichloroethane, chloroform, and chlorobenzene, ethers such as dimethylether, diethylether, tetrahydrofuran (THF) and methoxyethanol, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, esters such as ethyl formate, propyl formate, methyl acetate, ethyl acetate, propyl acetate, butyl acetate and methyl propionate, N,N-dimethylformamide and dimethylsulfoxide. These solvents may be used independently or as a mixture of two or more solvents.

[0296] In the electrophotographic photoreceptor of the present invention, the photosensitive layer 4 contains as a charge-transfer material the compound of the general formula (1). The compound is preferable since it has a high electron mobility, has reduced ability to exhibit colors and can be dispersed in the photosensitive layer at a high concentration. When the preferred compound of the general formula (2) is used, it enhances the electron mobility, whereas when the particularly preferred compound of the general formula (3) is used, it also enhances the compatibility with the resin.

[0297] Other charge-transfer materials may also be added to the electrophotographic photoreceptor of the present invention. In such a case, the sensitivity is increased and the residual potential is decreased, with the result that characteristics of the electrophotographic photoreceptor of the present invention are improved.

[0298] An electroconductive high molecular compound as a charge-transfer material may be added to the electrophotographic photoreceptor for the purpose of improving the characteristics of the photoreceptor. Examples of the electroconductive polymer include polyvinylcarbazole, halogenated polyvinylcarbazole, polyvinylpyrene, polyvinylindoloquinoxaline, polyvinylbenzothiophene, polyvinylanthracene, polyvinylacridine, polyvinylpyrazoline, polyacetylene, polythiophene, polypyrrole, polyphenylene, polyphenylene vinylene, polyisothianaphtene, polyaniline, polydiacetylene, polyheptadiene, polypyridinediyl, polyquinoline, polyphenylenesulfide, polyferrocenylene, polyperinaphthylene, and polyphthalocyanine.

[0299] Low molecular compounds may also be used for this purpose, including trinitrofluorenon, tetracyanoethylene, tetracyanoquinodimethane, quinone, diphenoquinone, naphthoquinone, anthraquinone and derivatives thereof, polycyclic aromatic compounds such as anthracene, pyrene and phenanthrene, nitrogen-containing heterocyclic compounds such as indole, carbazole and imidazole, fluorenone, fluorene, oxadiazole, oxazole, pyrazoline, hydrazone, triphenylmethane, triphenylamine, enamine, stilbene and butadiene compounds.

[0300] Also used are polymeric solid electrolytes obtained by doping polymers, such as polyethyleneoxide, polypropyleneoxide, polyacrylonitrile, poly methacrylic acid, with metal ions such as Li ions. Further, an organic electron-transfer complex may also be used that consists of an electron donor compound and an electron acceptor compound as represented by tetrathiafulvalene-tetracyanoquinodimethane. These compounds may be added independently or as a mixture of two or more compounds to obtain desired photosensitive characteristics.

[0301] In order to improve photosensitive characteristics, durability or mechanical properties of the photoreceptor of the present invention, antioxidants, UV-absorbing agents, radical scavengers, softeners, hardeners or cross-linking agents may be added to the coating solution for producing the photoreceptor of the present invention, provided that these agents do not affect the characteristics of the electrophotographic photoreceptor.

[0302] The finished appearance of the photoreceptor and the life of the coating solution are improved by further adding dispersion stabilizers, anti-settling agents, anti-flooding agents, leveling agents, anti-foaming agents, thickeners and flatting agents.

[0303] In addition, a surface-protection layer may be provided on the photosensitive layer 4. The surface-protection layer may be organic film formed of epoxy resin, melamine resin, polyvinylformal resin, polycarbonate resin, fluororesin, polyurethane resin or silicone resin, or it may be film formed of siloxane structure resulting from hydrolysis of silane coupling agents. In this manner, the durability of the photoreceptor is enhanced. The surface-protection layer may serve to improve functions other than the durability.

[0304] b. Description of Organic Electroluminescence Elements

[0305] An organic electroluminescence element of the present invention includes a pair of electrodes and a layer disposed between the electrodes, and containing at least one luminescent substance. The electroluminescence element contains the compound represented by the general formula (1) as a compound to impart the electron mobility.

[0306] An organic electroluminescence element is an element in which a single layer or multiple layers of organic film (luminescent layer) are disposed between a pair of electrodes.

[0307] Referring to FIG. 23, an exemplary organic electroluminescence element is denoted by reference numeral 21. The organic electroluminescence element 21 includes a glass substrate 23, a first electrode (ITO electrode) 22 formed of indium-tin oxide (ITO) and deposited on one surface of the glass substrate 23, a luminescent layer 25 closely arranged on one surface of the first electrode 22, and a second electrode 26 closely arranged on a surface of the luminescent layer 25 that is opposite the first electrode 22.

[0308] The luminescent layer 25 contains a luminescent material and may further contain a hole-transfer material for transporting holes injected from the anode (the first electrode 22) to the luminescent material or an electron-transfer material for transporting electrons moving from the cathode (the second electrode 26) to the luminescent material. The luminescent material may have the ability to move holes or electrons.

[0309] When the luminescent layer has a multi-layered structure, the organic electroluminescence element may include a luminescent layer, an electron-transfer layer, and a hole-transfer layer that are laminated on top of one another between the pair of electrodes.

[0310] The order of laminating the layers can be changed depending on the purpose of the element.

[0311] Examples of the luminescent material include anthracene, naphthalene, phenanthlene, pyrene, tetracene, coronene, chrysene, fluoresceine, perylene, phthaloperylene, naphthaloperylene, perynone, phthaloperynone, naphthaloperynone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldadine, bis-benzoxazoline, bis-styrile, pyrazine, cyclopentadiene, metal complexes of quinoline, metal complexes of aminoquinoline, metal complexes of benzoquinoline, imine, diphenylethylene, vinylanthracene, diaminocarbazole, triphenylamine, benzidine-type triphenylamine, styrileamine-type triphenylamine, diamine-type triphenylaminepyran, thiopyran, polymethine, merocyanine, imidazole-chelated oxynoid compounds, metal complexes of porphyrin, phthalocyanine complexes, rare earth metal complexes, quinacridone, rubrene, and fluorescent dyes for use in dye laser and in brightening.

[0312] Examples of the hole-transfer material include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyaryl alkanes, stilbene, butadiene, amine, diamine, triphenylamine, indole, carbazole, triphenylmethane, enamine and their derivatives, and polyvinyl carbazole, polysilane and polymeric materials such as electroconductive polymers.

[0313] Aside from the electron-transfer compounds of the present invention, examples of the electron-transfer material include quinolinol complexes, fluorenon, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthraquinodimethane, anthrone, and derivatives thereof.

[0314] Examples of the electroconductive material for use in the anode include carbon, aluminum, brass, stainless steel, chromium, titanium, copper, tin, molybdenum, indium, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and alloys thereof, metal oxides for use in ITO substrate and NESA substrate, such as tin oxide, indium oxide, aluminum iodide and copper iodide, and organic electroconductive resins, such as polythiophene and polypyrrole.

[0315] Examples of the electroconductive material for use in the cathode include, but are not limited to, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum and alloys thereof. Typical examples of the alloy include, but are not limited to, magnesium/silver, magnesium/indium, and lithium/aluminum.

[0316] The ratio of the alloy is controlled by the temperature, atmosphere, and degree of vacuum of the evaporation source so that a proper ratio is selected. When necessary, each of the anode and the cathode may be formed as a layered structure consisting of two or more layers.

5. EXAMPLES

[0317] Production examples of the compounds in accordance with the present invention and examples of the electron-transfer agents will now be described in detail, as will the electrophotographic photoreceptors and the organic electroluminescence elements as application examples.

[0318] First, examples of one production process of the compound represented by the general formula (1) is described.

Production Example 1

[0319] A mixture of 0.44 g (2 mmols) of 2,6-di-tert-butylbenzoquinone, which served as a benzoquinone compound, 0.23 g (2 mmols) of a pyrazolone compound having an active methylene, and 2 mL pyridine, which served as a base catalyst, was stirred at room temperature to allow the reaction to proceed. The reaction mixture was concentrated and was purified through silica gel column chromatography (developing solvent=hexane:ethyl acetate=10:1) to obtain 2,6-di-tert-butyl-4-(1,3-dimethyl-5-oxo-4-pyrazolilidene)-2,5-cyclohexadiene-1-one, the compound represented by the formula (7), at a yield of 36%. This reaction is shown by the following chemical equation (25):

106

Production Example 2

[0320] The experiment was carried out in the same manner as in Example 1, except that the base catalyst, pyridine, was replaced by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0321] The product was obtained at a yield of 35%.

Production Example 3

[0322] The experiment was carried out in the same manner as in Example 1, except that the base catalyst, pyridine, was replaced by trimethylamine. The product was obtained at a yield of 32%.

Production Example 4

[0323] The experiment was carried out in the same manner as in Example 1, except that the base catalyst, pyridine, was replaced by 2,6-dimethylpyridine. The product was obtained at a yield of 35%.

Production Example 5

[0324] The experiment was carried out in the same manner as in Example 1, except that the base catalyst, pyridine, was replaced by tributylamine. The product was obtained at a yield of 30%.

Production Example 6

[0325] The experiment was carried out in the same manner as in Example 1, except that 20 ml ethanol was added as an inert solvent and the base catalyst, pyridine, was replaced by sodium hydroxide. The product was obtained at a yield of 30%.

Production Examples 7 through 15

[0326] Different compounds were used as a compound having an active methylene group. The reaction temperature, reaction time, and yield are shown in Table D(1) for each compound. The structure formula and the name of the compound are shown in Tables D(2) and D(3) for each of the compounds of the formulae (8) through (16) obtained in respective Production Examples.

[0327] The melting point and the results of the elemental analysis are shown in Table E for each of the compounds of the formulae (7) through (16) obtained in Production Example 1 and respective Production Examples 7 through 15.

[0328] The IR and NMR charts are shown in FIGS. 1 through 20 for each of the compounds of the formulae (7) through (16) obtained in Production Example 1 and in Production Examples 7 through 15.

[0329] For IR spectrography, samples were prepared by using the potassium bromide (KBr)-pellet method. For NMR spectrography, deuterated chloroform was used as the sample solvent, and measurements were taken at a frequency of 60 MHz. The horizontal and the vertical axes of the NMR chart indicate chemical shifts and the intensity, respectively.

Comparative Production Example

[0330] The experiment was carried out in the same manner as in Example 1, except that the basic solvent, triethylamine, was not used. The reaction did not take place and no product was obtained.

[0331] Next, examples of the manner by which the electron mobility of the electron-transfer agent of the present invention was measured are described in conjunction with comparative examples.

Example 1

[0332] 5 g of oxytitanium phthalocyanine was dry-milled together with 50 ml of glass beads for 100 hours on a paint shaker. 50 mL of n-propanol and 5 g of polyvinylbutyral were then added, and the mixture was wet-milled for 1 hour. 100 mL of methyl ethyl ketone solvent was then added to the milled product, and the product was dispersed into the solvent for 10 hours. The resulting dispersion solution was applied to an aluminum-laminated PET film with a bar-coater and was dried to form a 0.5 μm-thick charge-generation layer.

[0333] Next, a coating solution was prepared consisting of 8 parts by weight of the compound of the formula (7), 10 parts by weight of polycarbonate and 100 parts by weight of tetrahydrofuran (THF). The coating solution was applied with a bar-coater and was then dried at 80° C. for 1 hour to form a 10 μm-thick charge-transfer layer. Gold was vapor-deposited onto the charge-transfer layer to a thickness of 0.04 μm (40 nm) as an opposed electrode. The electron mobility was measured by applying an electric field to the film and irradiating the film with a laser pulse.

Examples 2 through 10

[0334] The electron mobility was measured in the same manner as in Example 1 above, except that the compound represented by the formula (7) was replaced by the compound represented by the formula (8) through (16).

Comparative Example 1

[0335] The electron mobility was measured in the same manner as in Example 1 above, except that the compound represented by the formula (7) was replaced by the compound represented by the formula (24).

[0336] Results

[0337] The electron mobilities measured at an electric field of 30×105V/cm are shown in Table F.

[0338] As can be seen from Table F, the electron mobility was 1×10−8 (cm2 V·sec) or higher in each of Examples 1 through 10 and was in each case higher than the electron mobility obtained in Comparative Example 1 (1×10−9 (cm2/V·sec)).

[0339] While application examples of the present invention are described below with reference to comparative examples, they are not intended to limit the scope of the invention in any way.

Examples of Organic Electroluminescence Elements

Application Example 1

[0340] The compound represented by the formula (7) and tris(8-hydroxyquinolinol) aluminum complex were dissolved in chloroform at a ratio of 3:1. The solution was applied by spin-coating to a cleaned glass plate having an ITO electrode to form a 0.07 μm-thick luminescent layer. A 10:1 alloy of magnesium and silver was vapor-deposited onto the luminescent layer to form a 0.2 μm-thick electrode and thus obtain an organic electroluminescence element as shown in FIG. 23.

Application Examples 2 through 10

[0341] In each Application Example, an organic electroluminescence element was obtained by replacing the compound of the chemical formula (7) of Application Example 1 with each of the compounds of the chemical formulae (8) through (16). The amount of luminescence that each of the organic electroluminescence elements obtained in Application Examples 1 through 10 emitted when applied a direct current at 5V was shown in Table G.

[0342] As can be seen from Table G, the amount of luminescence was 60(cd/m2) or larger and was sufficiently high in each of Application Examples 1 through 10.

Examples of Electrophotographic Photoreceptors for use in Photocopiers

Application Example 11

[0343] 10 parts by weight of polycarbonate as a binder resin and 80 parts by weight of THF as a solvent were mixed with 1 part by weight of a dis-azo pigment as a charge-generation material shown by the following chemical formula (26):

107

[0344] The mixture was kneaded for dispersal for 10 hours in a sand mill. As charge-transfer materials, 9 parts by weight of a triphenyldiamine compound shown by the following chemical formula (27):

108

[0345] and 2 parts by weight of the compound shown by the formula (7) were dissolved in the mixture to form a coating solution. An aluminum drum as an electroconductive substrate 1 was dipped in this coating solution to apply coating. The drum was then dried at 80° C. for 1 hour to form a 20 μm-thick photosensitive layer 4 that served both to generate charge and to transport charge. In this manner, a single-layered electrophotographic photoreceptor 12 was prepared.

Application Examples 12 through 20

[0346] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 11 with each of the compounds of the chemical formulae (8) through (16).

Comparative Example 2

[0347] A single-layered electrophotographic photoreceptor was prepared in the same manner as in Example 11, except that the compound represented by the formula (7) was replaced by the compound represented by the formula (24).

Examples of Electrophotographic Photoreceptors for use in Printers

Application Example 21

[0348] 5 g of oxytitanium phthalocyanine was dry-milled together with 50 ml of glass beads for 100 hours on a paint shaker. 50 mL of n-propanol and 5 g of polyvinylbutyral were then added and the mixture was wet-milled for 1 hour. 100 mL of methyl ethyl ketone solvent was then added to the milled product, and the product was dispersed into the solvent for 10 hours. An aluminum drum as the electroconductive substrate 1 was dipped in the resulting dispersion solution to apply coating. The coating was then dried to form a 0.2 μm-thick charge-generation layer 2.

[0349] Next, a coating solution was prepared consisting of 8 parts by weight of the compound of the formula (7), 10 parts by weight of polycarbonate and 100 parts by weight of tetrahydrofuran (THF). The drum with the charge-generation layer 2 formed thereon was dipped in the coating solution to apply coating. The coating was then dried at 80° C. for 1 hour to form a 20 μm-thick charge-transfer layer 3. In this manner, a multi-layered electrophotographic photoreceptor was obtained.

Application Examples 22 through 30

[0350] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 21 with each of the compounds of the chemical formulae (8) through (16).

Comparative Example 3

[0351] A multi-layered electrophotographic photoreceptor was prepared in the same manner as in Application Example 21 above, except that the compound represented by the formula (7) was replaced by the compound represented by the formula (24).

[0352] Application Example 31

[0353] A mixture of 1 part by weight of oxytitanium phthalocyanine as a charge-generation material, 10 parts by weight of polycarbonate as a binder resin, and 80 parts by weight of THF as a solvent was kneaded for dispersal for 10 hours in a sand mill. As charge-transfer materials, 9 parts by weight of triphenyldiamine compound shown by the formula (26) and 2 parts by weight of the compound shown by the formula (7) were dissolved in the mixture to form a coating solution. An aluminum drum as an electroconductive substrate 1 was dipped in this coating solution to apply coating. The drum was then dried at 80° C. for 1 hour to form a 20 μm-thick photosensitive layer 4 that served both to generate charge and to transport charge. In this manner, a single-layered electrophotographic photoreceptor was manufactured.

Application Examples 32 through 40

[0354] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 31 with each of the compounds of the chemical formulae (8) through (16).

Comparative Example 4

[0355] A single-layered electrophotographic photoreceptor was prepared in the same manner as in Example 31, except that the compound represented by the formula (7) was replaced by the compound represented by the formula (24)

Application Example 41

[0356] A mixture of 1 part by weight of oxytitanium phthalocyanine as a charge-generation material, 10 parts by weight of polycarbonate as a binder resin, and 80 parts by weight of THF as a solvent was kneaded for dispersal for 10 hours in a sand mill. As charge-transfer materials, 1 part by weight of triphenyldiamine compound shown by the formula (26) and 9 parts by weight of the compound shown by the formula (7) were dissolved in the mixture to form a coating solution. An aluminum drum as an electroconductive substrate 1 was dipped in this coating solution to apply coating. The drum was then dried at 80° C. for 1 hour to form a 20 μm-thick photosensitive layer 4 that served both to generate charge and to transport charge. In this manner, a single-layered electrophotographic photosensitive layer was obtained.

Application Examples 42 through 50

[0357] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 41 with each of the compounds of the formulae (8) through (16).

Comparative Example 5

[0358] A single-layered electrophotographic photoreceptor was prepared in the same manner as in Application Example 41, except that the compound represented by the formula (7) was replaced by the compound represented by the formula (24).

[0359] Conditions for Measurement

[0360] A corona discharger was adjusted to generate a corona discharge current of 17 μA. The electrophotographic photoreceptors prepared in Application Examples 11 through 40 and Comparative Examples 2 through 4 were positively charged by the corona discharge in a dark environment and each photoreceptor was measured for the charged electric potential. The photoreceptors were then exposed to white light, and the exposure E/50 (lux·sec) at which the surface potential of each electrophotographic photoreceptor decreased by half, from 700V down to 350V, was measured. This half decay exposure reflects the sensitivity of the electrophotographic photoreceptor: the smaller the half decay exposure, the higher the sensitivity.

[0361] Results

[0362] The results of the measurement for Application Examples 11 through 20 and Comparative Example 2 are as shown in Table H below.

[0363] The results for Application Examples 11 through 20 and Comparative Example 2 were obtained for positively charged, single-layered photoreceptors for use in photocopiers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (7) through (16), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24). Also, the chargeability of the photoreceptor is enhanced.

[0364] The results of the measurement for Application Examples 21 through 30 and Comparative Example 3 are as shown in Table 1.

[0365] The results for Application Examples 21 through 30 and Comparative Example 3 were obtained for positively charged, multi-layered photoreceptors for use in printers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (7) through (16), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0366] The results of the measurement for Application Examples 31 through 40 and Comparative Example 4 are as shown in Table J.

[0367] The results for Application Examples 31 through 40 and Comparative Example 4 were obtained for positively charged, single-layered photoreceptors for use in printers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (7) through (16), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0368] Next, a corona discharger was adjusted to generate a corona discharge current of 17 μA. The electrophotographic photoreceptors prepared in Application Examples 41 through 50 and Comparative Example 5 were negatively charged by the corona discharge in a dark environment and each photoreceptor was measured for the charged electric potential. The photoreceptors were then exposed to white light, and the exposure E/50 (lux·sec) at which the absolute value of the surface potential of each electrophotographic photoreceptor decreased by half, from −700V up to −350V, was measured. The results are shown in Table K. The half decay exposure reflects the sensitivity of the electrophotographic photoreceptor: the smaller the half decay exposure, the higher the sensitivity.

[0369] The results for Application Examples 41 through 50 and Comparative Example 5 were obtained for negatively charged, single-layered photoreceptors for use in printers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (7) through (16), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0370] While a description has been given of examples of electrophotographic photoreceptors in which the organic film is used as the photosensitive layer, these examples are illustrative rather than restrictive and do not limit the scope of the invention in any way. For example, the present invention also encompasses within its scope an electrophotographic photoreceptor in which the above-described organic film is used as a foundation layer disposed between the photosensitive layer and the electroconductive substrate. Although organic film for use as the foundation layer needs to have a proper conductivity, the organic film containing the compound represented by the general formula (1) has a high electron mobility and is thus suitable for this purpose so that a highly sensitive electrophotographic photoreceptor can be obtained through the use of such organic film.

[0371] Alternatively, the organic film may be used as a protection layer formed over the photosensitive layer. To summarize, the present invention encompasses within its scope any electrophotographic photoreceptor incorporating organic film that contains the compound represented by the general formula (1).

[0372] While cases have been described in which a benzoquinone compound is reacted with a compound incorporating an active methylene in the presence of a base catalyst alone, the present invention also encompasses other cases. According to the present invention, the yield of the desired product can be increased by carrying out the reaction using, along with the base catalyst, a solvent that can hardly dissolve the desired product. As used herein, the term “desired product” refers to any of the compounds represented by the general formulae (1) through (6) and (44).

[0373] When the reaction is carried out by using the base catalyst alone, a side reaction takes place by which the compound having an active methylene further adds to the desired product that has resulted from the reaction of the benzoquinone compound with the compound having an active methylene. As a result, by-products are produced.

[0374] When the benzoquinone compound reacts with the active methylene using a solvent that can hardly dissolve the desired product (inert solvent), along with the base catalyst, the resulting desired product is removed from the reaction system by crystallizing it with the help of the solvent that can hardly dissolve the desired product.

[0375] As a result, the further addition of the compound having an active methylene to the desired product can be prevented.

[0376] It is believed that by allowing the reaction to proceed in the solvent that can hardly dissolve the desired product, the side reaction can be suppressed so that the yield of the desired product is increased.

[0377] Preferably, the solvent is an alcohol solvent, such as methanol, ethanol and butanol, a saturated aliphatic hydrocarbon, such as heptane and hexane, or water. These solvents may be used independently or as a mixture of two or more solvents. Of these, water, methanol, ethanol, and butanol are particularly preferred because of their cost performance and low solubility against the desired product.

[0378] The solvent for use with the base catalyst (inert solvent) is not limited to alcohols, saturated aliphatic hydrocarbons or water. The solvent may be any solvent that requires 50 ml or more to dissolve Ig of the desired product and may be used independently or as a mixture of two or more solvents.

[0379] Other examples of the production process of the compound of the present invention will now be described in detail.

Production Example 16

[0380] A mixture of 0.44 g (2 mmols) of 2,6-di-tert-butylbenzoquinone, which served as a benzoquinone compound, 0.35 g (2 mmols) of methylphenylpyrazolone, which served as a compound having an active methylene, 0.5 mL pyridine, which served as a base catalyst, and 4 mL water was allowed to undergo reaction for 5 hours at 45° C. while being stirred. Subsequently, the reaction mixture was added to 4 mL water and the mixture was filtrated. The resulting crystals were washed with 8 mL methanol and were then recrystallized with a mixture of chloroform and methanol. As a result, 0.63 g of 2,6-di-tert-butyl-4-(3-methyl-1-phenyl-5-oxo-4-pyrazolidene)-25-cyclohexadiene-1-one was obtained. The yield of the product was 84%.

Production Example 17

[0381] The process was carried out in the same manner as in Production Example 16, except that 1 ml pyridine and 2 ml water were used. The product was obtained at a yield of 65%.

Production Example 18

[0382] The process was carried out in the same manner as in Production Example 16, except that 1 ml pyridine and 4 ml water were used. The product was obtained at a yield of 75%.

Production Example 19

[0383] The process was carried out in the same manner as in Production Example 16, except that methanol was used in place of water. The product was produced at a yield of 62%.

Production Example 20

[0384] The process was carried out in the same manner as in Production Example 16, except that hexane was used in place of water. The product was produced at a yield of 51%.

Production Example 21

[0385] The process was carried out in the same manner as in Production Example 16, except that 2 ml chloroform was used in place of water. The product was produced at a yield of 34%.

Production Example 22

[0386] The process was carried out in the same manner as in Production Example 16, except that 2 ml toluene was used in place of water. The product was produced at a yield of 35%.

[0387] The comparisons between each of Production Examples 16 through 20 and Production Example 7 indicate that while each process can produce the same compound represented by the formula (8), higher yields of 84%, 65%, 75%, 62%, and 51% were achieved in Production Examples 16, 17, 18, 19, and 20, respectively, as compared to the 32% yield in Production Example 7. In comparison, the yields obtained in Production Examples 21 and 22 with the use of chloroform and toluene were comparable to that of Production Example 7, with no apparent increase in the yield.

Production Examples 23 through 37

[0388] Different compounds were used as a compound having an active methylene group. The reaction temperature, reaction time, and yield are shown in Tables L(1) and L(2) for each compound. The structure formula and the name of the compound are shown in Tables M(1) through M(3) for each of the compounds of the formulae (29) through (43) obtained in respective Production Examples.

[0389] The melting point and the results of the elemental analysis are shown in Table N for each of the compounds of the formulae (29) through (43) obtained in Production Examples 23 through 37.

[0390] The IR and NMR charts are shown in FIGS. 24 through 53 for each of the compounds of the formulae (29) through (43) obtained in Production Examples 23 through 37.

[0391] Next, the examples of measuring the electron mobility of the electron transfer agent of the present invention are described in conjunction with comparative examples.

Examples 11 through 25

[0392] The electron mobility was measured in the same manner as in Example 1 above, except that the compound represented by the formula (7) was replaced by the compound represented by the formulae (29) through (43).

[0393] Results

[0394] The electron mobilities measured at an electric field of 3.0×105V/cm are shown in Table O.

[0395] As can be seen from Table O, the electron mobility was 1×10−8 (cm2 V·sec) or higher in each of Examples 11 through 25 and was in each case higher than the electron mobility obtained in Comparative Example 1 (1×10−9 (cm2/V·sec)).

Examples of Electrophotographic Photoreceptors for use in Printers

Application Examples 51 through 65

[0396] In each Application Example, an organic electroluminescence element was obtained by replacing the compound of the chemical formula (7) of Application Example 1 with each of the compounds of the chemical formulae (29) through (43). The amount of luminescence that each of the organic electroluminescence elements obtained, in Application Examples 51 through 65 emitted when applied a direct current at 5V, is shown in Table P.

[0397] As can be seen from Table P, the amount of luminescence was 60(cd/m2) or larger and was sufficiently high in each of Application Examples 51 through 65. Examples of Electrophotographic Photoreceptors for use in Photocopiers

Application Examples 66 through 80

[0398] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 11 with each of the compounds of the chemical formulae (29) through (43).

Examples of Electrophotographic Photoreceptors for use in Printers

Application Examples 81 through 95

[0399] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 21 with each of the compounds of the chemical formulae (29) through (43).

Application Examples 96 through 110

[0400] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 31 with each of the compounds of the chemical formulae (29) through (43).

Application Examples 111 through 125

[0401] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 41 with each of the compounds of the formulae (29) through (43).

[0402] Conditions for Measurement

[0403] A corona discharger was adjusted to generate a corona discharge current of 17 μA. The electrophotographic photoreceptors prepared in Application Examples 66 through 110 were positively charged by the corona discharge in a dark environment and each photoreceptor was measured for the charged electric potential. The photoreceptors were then exposed to white light, and the exposure E/50 (lux·sec) at which the surface potential of each electrophotographic photoreceptor decreased by half, from 700V down to 350V, was measured. This half decay exposure reflects the sensitivity of the electrophotographic photoreceptor.

[0404] Results

[0405] The results of the measurement for Application Examples 66 through 80 are shown in Table Q below together with the results of Comparative Example 2.

[0406] The results for Application Examples 66 through 80 and Comparative Example 2 were obtained for positively charged, single-layered photoreceptors for use in photocopiers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (29) through (43), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24). Also, the chargeability of the photoreceptor is enhanced.

[0407] The results of the measurement for Application Examples 81 through 95 are shown in Table R below together with the results of Comparative Example 3.

[0408] The results for Application Examples 81 through 95 and Comparative Example 3 were obtained for positively charged, multi-layered photoreceptors for use in printers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (29) through (43), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0409] The results of the measurement for Application Examples 96 through 110 are shown in Table S below together with the results of Comparative Example 4.

[0410] The results for Application Examples 96 through 110 and Comparative Example 4 were obtained for positively charged, single-layered photoreceptors for use in printers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (29) through (43), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0411] Next, a corona discharger was adjusted to generate a corona discharge current of 17 μA. The electrophotographic photoreceptors prepared in Application Examples 111 through 125 were negatively charged by the corona discharge in a dark environment and each photoreceptor was measured for the charged electric potential. The photoreceptors were then exposed to white light, and the exposure E/50 (lux·sec) at which the absolute value of the surface potential of each electrophotographic photoreceptor decreased by half, from −700V up to −350V, was measured. The results are shown in Table T. The half decay exposure reflects the sensitivity of the electrophotographic photoreceptor.

[0412] The results for Application Examples 111 through 125 and Comparative Example 5 were obtained for negatively charged, single-layered photoreceptors for use in printers. The comparisons between each Application Example and Comparative Example suggest that through the use of the electron-transfer materials of the chemical formulae (29) through (43), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0413] Other examples of the production process of the compound of the present invention will now be described in detail.

Production Example 38

[0414] A mixture of 0.88 g (4 mmols) of 2,6-di-tert-butylbenzoquinone, which served as a benzoquinone compound, 0.75 g (4 mmols) of 3-methyl-1-p-tolyl-5-pyrazolone, which served as a cyclic compound having an active methylene, and 4 mL pyridine, which served as a base catalyst, was allowed to undergo reaction for 20 hours at 25° C. while being stirred. Subsequently, the reaction mixture was concentrated and was purified through column chromatography (hexane:ethyl acetate=10:1). As a result, 0.83 g of the compound shown by the chemical formula (45) is obtained as the desired product (yield=53%).

Production Examples 39 through 53

[0415] Different compounds were used as a compound having an active methylene group. The reaction temperature, reaction time, and yield are shown in Tables U(1) and U(2) for each compound. The structure formula and the name of the compound are shown in Tables V(1) through V(3) for each of the compounds of the formulae (45) through (60) obtained in respective Production Examples.

[0416] The melting point and the results of the elemental analysis are shown in Table W for each of the compounds of the formulae (45) through (60) obtained in Production Examples 38 through 53.

[0417] The IR and NMR spectra are shown in FIGS. 54 through 85 for each of the compounds of the formulae (45) through (60) obtained in Production Examples 38 through 53.

Examples 26 through 41

[0418] The electron mobility was measured in the same manner as in Example 1 above, except that the compound represented by the formula (7) was replaced by the compound represented by the formulae (45) through (60).

[0419] Results

[0420] The electron mobilities measured at an electric field of 3.0×105V/cm are shown in Table X.

[0421] As can be seen from Table X, the electron mobility was 1×10−8 (cm2V·sec) or higher in each of Examples 26 through 41 and was in each case higher than the electron mobility obtained in Comparative Example 1.

Production Examples of Organic Electroluminescence Elements

Application Examples 126 through 141

[0422] Each of the organic electroluminescence elements of Application Examples 126 through 141 was obtained by replacing the compound of the chemical formula (7) of Application Example 1 with each of the compounds of the chemical formulae (45) through (60). The amount of luminescence that each of the organic electroluminescence elements obtained, in Application Examples 126 through 141 emitted when applied a direct current at 5V, is shown in Table Y.

[0423] As can be seen from Table Y, the amount of luminescence was 60(cd/m2) or higher and was sufficiently high in each of Application Examples 126 through 141. Production Examples of Electrophotographic Photoreceptors for use in Photocopiers

Application Examples 142 through 157

[0424] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) with each of the compounds of the chemical formulae (45) through (60). Production Examples of Electrophotographic Photoreceptors for use in Printers

Application Examples 158 through 173

[0425] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 21 with each of the compounds of the chemical formulae (45) through (60).

Application Examples 174 through 189

[0426] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 31 with each of the compounds of the chemical formulae (45) through (60).

Application Examples 190 through 205

[0427] In each Application Example, an electrophotographic photoreceptor was obtained by replacing the compound of the chemical formula (7) of Application Example 41 with each of the compounds of the formulae (45) through (60).

[0428] Conditions for Measurement

[0429] A corona discharger was adjusted to generate a corona discharge current of 17 μA. The electrophotographic photoreceptors prepared in Application Examples 142 through 157, 158 through 173, and 174 through 189 were each positively charged by the corona discharge in a dark environment and each photoreceptor was measured for the charged electric potential. The photoreceptors were then exposed to white light, and the exposure E/50 (lux·sec) at which the surface potential of each electrophotographic photoreceptor decreased by half, from 700V down to 350V, was measured. This half decay exposure reflects the sensitivity of the electrophotographic photoreceptor.

[0430] Results

[0431] The results of the measurement for Application Examples 142 through 157 and the results for Comparative Example 2 are as shown in Table Z.

[0432] The results for Application Examples 142 through 157 and Comparative Example 2 were obtained for positively charged, single-layered photoreceptors for use in photocopiers. The comparisons between each of Application Examples 142 through 157 and Comparative Example 2 suggest that through the use of the electron-transfer materials of the chemical formulae (45) through (60), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24). Also, the chargeability of the photoreceptor is enhanced.

[0433] The results of the measurement for Application Examples 158 through 173 and Application Example 3 are as shown in Table AA below.

[0434] The results for Application Examples 158 through 173 and Comparative Example 3 were obtained for positively charged, multi-layered photoreceptors for use in printers. The comparisons between each of Application Examples 158 through 173 and Comparative Example 3 suggest that through the use of the electron-transfer materials of the chemical formulae (45) through (60), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0435] The results of the measurement for Application Examples 174 through 189 and Comparative Example 4 are as shown in Table AB below.

[0436] The results for Application Examples 174 through 189 and Comparative Example 4 were obtained for positively charged, single-layered photoreceptors for use in printers. The comparisons between each of Application Examples 174 through 189 and Comparative Example 4 suggest that through the use of the electron-transfer materials of the chemical formulae (45) through (60), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0437] Next, a corona discharger was adjusted to generate a corona discharge current of 17 μA. The electrophotographic photoreceptors prepared in Application Examples 190 through 205 were each negatively charged by the corona discharge in a dark environment and each photoreceptor was measured for the charged electric potential. The photoreceptors were then exposed to white light, and the exposure E/50 (lux sec) at which the absolute value of the surface potential of each electrophotographic photoreceptor decreased by half, from −700V up to −350V, was measured. The results are shown in Table AC. The half decay exposure reflects the sensitivity of the electrophotographic photoreceptor.

[0438] The results for Application Examples 190 through 205 and Comparative Example 5 were obtained for negatively charged, single-layered photoreceptors for use in printers. The comparisons between each of Application Examples 190 through 205 and Comparative Example 5 suggest that through the use of the electron-transfer materials of the chemical formulae (45) through (60), a photoreceptor can be obtained that has a higher sensitivity than the photoreceptor using the compound of the formula (24).

[0439] As set forth, the electron-transfer compounds of the present invention have a structure in which two ring structures, a quinone ring and a ring structure incorporating an active methylene group, are connected with each other via a double bond and therefore have a large molecular skeleton that permits a large distance for electron movement within the molecule. Accordingly, the compounds of the present invention show a high electron mobility to allow electrons to move freely within the molecule and thus are capable of coloring only faintly, which helps reduce the light absorption. Asymmetrical molecular structure of the compounds of the present invention contributes to their high compatibility with resins.

[0440] The present invention also provides a simple process for producing the electron-transfer compounds that makes use of a base catalyst. Also, an efficient electron-transfer agent can be obtained by mixing the electron-transfer compound with a proper resin. Further, a highly sensitive photosensitive layer can be obtained by using the electron-transfer compound in electrophotographic photoreceptors.

[0441] The high compatibility of the electron-transfer compound with binder resins makes it possible to disperse the compound in the photosensitive layer uniformly and abundantly. In this regard, the incident light is not prevented from passing through to the charge-generation material because of the ability of the electron-transfer compound to color only faintly. As a result, a highly sensitive electrophotographic photoreceptor is obtained. Such an electrophotographic photoreceptor can be used to serve both as the positive charge type and as the negative charge type.

[0442] Moreover, the electron-transfer compounds of the present invention can be used as an electron-transfer material for use in organic electroluminescence elements. The present invention permits selection of substituents that can provide the characteristics required of the electron-transfer compound for serving as a particular high-performance material and permits designing a desired molecular structure for the electron-transfer compound.

1TABLE A1A list of general formulas (substituents R1˜R6)No.General formula101

109

102

110

103

111

104

112

105

113

106

114

107

115

108

116

109

117

110

118

111

119

112

120

113

121

114

122

[0443]

2

TABLE A2

A list of general formulas (substituents R1˜R6)

No.
General formula

115

123

116

124

117

125

118

126

119

127

120

128

121

129

122

130

123

131

124

132

125

133

126

134

127

135

128

136

[0444]

3

TABLE A3

A list of general formulas (substituents R1˜R6)

No.
General formula

129

137

130

138

131

139

132

140

133

141

134

142

135

143

136

144

137

145

138

146

139

147

140

148

141

149

142

150

[0445]

4

TABLE A4

A list of general formulas (substituents R1˜R6)

No.
General formula

143

151

144

152

145

153

146

154

147

155

148

156

149

157

150

158

151

159

152

160

153

161

154

162

155

163

156

164

[0446]

5

TABLE A5

A list of general formulas (substituents R1˜R6)

No.
General formula

157

165

158

166

159

167

160

168

161

169

162

170

163

171

164

172

165

173

166

174

167

175

168

176

169

177

170

178

[0447]

6

TABLE A6

A list of general formulas (substituents R1˜R6)

No.
General formula

171

179

172

180

173

181

174

182

175

183

176

184

177

185

178

186

179

187

180

188

181

189

182

190

183

191

184

192

[0448]

7

TABLE A7

A list of general formulas (substituents R1˜R6)

No.
General formula

185

193

186

194

187

195

188

196

189

197

190

198

191

199

192

200

193

201

194

202

195

203

196

204

197

205

198

206

[0449]

8

TABLE A8

A list of general formulas (substituent R1˜R6)

No.
General formula

199

207

200

208

201

209

202

210

203

211

204

212

205

213

206

214

207

215

208

216

209

217

210

218

211

219

212

220

[0450]

9

TABLE A9

A list of general formulas (substituents R1˜R6)

No.
General formula

213

221

214

222

215

223

216

224

217

225

218

226

219

227

220

228

221

229

222

230

223

231

224

232

225

233

226

234

[0451]

10

TABLE A10

A list of general formulas (substituents R1˜R6)

No.
General formula

227

235

228

236

229

237

230

238

231

239

232

240

233

241

234

242

235

243

236

244

237

245

238

246

239

247

240

248

[0452]

11

TABLE A11

A list of general formulas (substituents R1˜R6)

No.
General formula

241

249

242

250

243

251

244

252

245

253

246

254

247

255

248

256

249

257

250

258

251

259

252

260

253

261

254

262

[0453]

12

TABLE A12

A list of general formulas (substituents R1˜R6)

No.
General formula

255

263

256

264

257

265

258

266

259

267

260

268

261

269

262

270

263

271

264

272

265

273

266

274

267

275

268

276

[0454]

13

TABLE A13

A list of general formulas (substituents R1˜R6)

No.
General formula

269

277

270

278

271

279

272

280

273

281

274

282

275

283

276

284

277

285

278

286

279

287

280

288

281

289

282

290

[0455]

14

TABLE A14

A list of general formulas (substituents R1˜R6)

No.
General formula

283

291

284

292

285

293

286

294

287

295

288

296

289

297

290

298

291

299

292

300

293

301

294

302

[0456]

15

TABLE A15

A list of general formulas (substituents R1˜R6)

No.
General formula

295

303

296

304

297

305

298

306

299

307

300

308

[0457]

16

TABLE A16

A list of general formulas (substituents R1˜R6)

No.
General formula

301

309

302

310

303

311

304

312

305

313

306

314

[0458]

17

TABLE A17

A list of general formulas (substituents R1˜R6)

No.
General formula

307

315

308

316

309

317

310

318

311

319

312

320

[0459]

18

TABLE A18

A list of general formulas (substituents R1˜R6)

No.
General formula

313

321

314

322

[0460]

19

TABLE A19

A list of general formulas (substituents R1˜R5)

No.
General formula

315

323

316

324

317

325

318

326

319

327

320

328

321

329

322

330

323

331

324

332

325

333

326

334

327

335

328

336

[0461]

20

TABLE A20

A list of general formulas (substituents R1˜R5)

No.
General formula

329

337

330

338

331

339

332

340

333

341

334

342

335

343

336

344

337

345

338

346

339

347

340

348

341

349

342

350

[0462]

21

TABLE A21

A list of general formulas (substituents R1˜R5)

No.
General formula

343

351

344

352

345

353

346

354

347

355

348

356

349

357

350

358

351

359

352

360

353

361

354

362

355

363

356

364

[0463]

22

TABLE A22

A list of general formulas (substituents R1˜R5)

No.
General formula

357

365

358

366

359

367

360

368

361

369

362

370

363

371

364

372

365

373

366

374

367

375

368

376

369

377

370

378

[0464]

23

TABLE A23

A list of general formulas (substituents R1˜R5)

No.
General formula

371

379

372

380

373

381

374

382

375

383

376

384

378

385

379

386

380

387

381

388

382

389

383

390

384

391

385

392

[0465]

24

TABLE A24

A list of general formulas (substituents R1˜R5)

No.
General formula

386

393

387

394

388

395

389

396

390

397

391

398

392

399

393

400

394

401

395

402

396

403

397

404

398

405

399

406

[0466]

25

TABLE A25

A list of general formulas (substituents R1˜R5)

No.
General formula

400

407

401

408

402

409

403

410

404

411

405

412

406

413

407

414

408

415

409

416

410

417

411

418

412

419

413

420

[0467]

26

TABLE A26

A list of general formulas (substituents R1˜R5)

No.
General formula

414

421

415

422

416

423

417

424

418

425

419

426

420

427

421

428

422

429

423

430

[0468]

27

TABLE B

A list of substituents

Substituent's

No.
substituent

S1
—H

S2
—CH3

S3
-t-Bu

S4
—OCH3

S5
—CF3

S6
—NO2

S7
—CO2CH3

S8
—CH═CH—CH═CH2

S9
—C2H5

S10
—Cl

S11

431

S12

432

S13

433

S14

434

S15

435

S16

436

S17

437

S18

438

S19

439

S20

440

S21

441

S22

442

S23

443

[0469]

28

TABLE C1

A list of compounds (substituents R1˜R6)

R1
R2
R3
R4
R5
R6

S3
S1
S3
S1
S11
S11

S3
S2
S3
S1
S11
S11

S3
S2
S3
S2
S11
S11

S3
S1
S12
S1
S11
S11

S3
S2
S12
S1
S11
S11

S3
S2
S12
S2
S11
S11

S3
S1
S13
S1
S11
S11

S3
S2
S13
S1
S11
S11

S3
S2
S13
S2
S11
S11

S3
S11
S3
S2
S11
S11

S3
S1
S3
S1
S11
S13

S3
S1
S3
S1
S11
S12

S3
S2
S3
S1
S11
S13

S3
S2
S3
S1
S11
S12

S3
S1
S12
S1
S11
S13

S3
S1
S13
S1
S11
S12

S3
S2
S12
S1
S11
S13

S3
S2
S13
S1
S11
S12

S3
S1
S3
S1
S12
S13

S3
S1
S3
S1
S13
S12

S3
S2
S3
S1
S12
S13

S3
S2
S3
S1
S13
S12

S3
S1
S13
S1
S12
S13

S3
S1
S12
S1
S13
S13

S3
S2
S12
S1
S12
S13

S3
S2
S13
S1
S13
S12

S3
S1
S3
S1
S3
S18

S3
S1
S3
S1
S14
S15

S3
S1
S3
S1
S15
S14

S3
S1
S3
S1
S17
S13

S3
S1
S3
S1
S16
S12

S3
S1
S3
S1
S12
S11

S3
S1
S3
S1
S12
S13

S3
S1
S3
S1
S13
S11

S3
S1
S3
S1
S13
S12

S3
S2
S3
S1
S12
S11

S3
S2
S3
S1
S13
S11

S3
S1
S4
S2
S11
S13

S3
S6
S7
S4
S2
S12

S3
S10
S11
S6
S19
S16

S3
S2
S20
S10
S7
S11

[0470]

29

TABLE C2

A list of compounds (substituents R1˜R6)

R1
R2
R3
R4
R5
R6

S3
S3
S3
S3
S3
S18

S3
S20
S2
S11
S16
S3

S3
S11
S10
S7
S5
S13

S3
S7
S6
S1
S20
S15

S3
S4
S1
S20
S18
S20

S12
S1
S3
S1
S11
S13

S12
S1
S3
S1
S3
S18

S12
S2
S3
S1
S11
S13

S12
S1
S3
S1
S14
S15

S12
S1
S3
S1
S15
S14

S12
S1
S3
S1
S17
S13

S12
S1
S3
S1
S16
S12

S12
S1
S3
S1
S12
S11

S12
S1
S3
S1
S12
S13

S12
S1
S3
S1
S13
S11

S12
S1
S3
S1
S13
S12

S12
S1
S12
S1
S12
S11

S12
S1
S13
S1
S12
S13

S12
S1
S13
S1
S13
S11

S12
S1
S12
S1
S13
S12

S12
S1
S4
S2
S11
S13

S12
S6
S7
S4
S2
S12

S12
S10
S11
S6
S19
S16

S12
S2
S20
S10
S7
S11

S12
S3
S3
S3
S3
S18

S12
S20
S2
S11
S16
S3

S12
S11
S10
S7
S5
S13

S12
S7
S6
S1
S20
S15

S12
S4
S1
S20
S18
S20

S13
S1
S3
S1
S11
S13

S13
S1
S3
S1
S3
S18

S13
S2
S3
S1
S11
S13

S13
S1
S3
S1
S14
S15

S13
S1
S3
S1
S15
S14

S13
S1
S3
S1
S17
S13

S13
S1
S3
S1
S16
S12

S13
S1
S3
S1
S12
S11

S13
S1
S3
S1
S12
S13

S13
S1
S3
S1
S13
S11

S13
S1
S3
S1
S13
S12

S13
S2
S13
S1
S12
S11

[0471]

30

TABLE C3

A list of compounds (substituents R1˜R6)

R1
R2
R3
R4
R5
R6

S13
S1
S12
S1
S12
S13

S13
S2
S12
S1
S13
S11

S13
S1
S13
S1
S13
S12

S13
S1
S4
S2
S11
S13

S13
S6
S7
S4
S2
S12

S13
S10
S11
S6
S19
S16

S13
S2
S20
S10
S7
S11

S13
S3
S3
S3
S3
S18

S13
S20
S2
S11
S16
S3

S13
S11
S10
S7
S5
S13

S13
S7
S6
S1
S20
S15

S13
S4
S1
S20
S18
S20

S11
S1
S2
S20
S7
S11

S11
S6
S20
S7
S3
S18

S11
S1
S12
S2
S11
S13

S11
S10
S3
S1
S16
S3

S11
S2
S1
S6
S5
S13

S11
S3
S10
S2
S20
S15

S11
S20
S6
S4
S18
S20

S11
S11
S11
S11
S11
S13

S11
S7
S4
S10
S2
S12

S11
S4
S7
S3
S19
S16

S11
S1
S11
S1
S11
S13

S11
S2
S11
S1
S11
S13

S11
S1
S11
S1
S11
S12

S11
S2
S11
S1
S11
S12

S11
S1
S12
S1
S11
S13

S11
S2
S12
S1
S11
S13

S11
S1
S12
S1
S11
S12

S11
S2
S12
S1
S11
S12

S11
S1
S13
S1
S11
S13

S11
S2
S13
S1
S11
S13

S11
S1
S13
S1
S11
S12

S11
S2
S13
S1
S11
S12

S11
S1
S11
S1
S14
S15

S11
S1
S11
S1
S12
S11

S11
S1
S11
S1
S13
S11

S11
S2
S11
S1
S12
S11

S11
S2
S11
S1
S13
S11

S11
S1
S11
S1
S13
S13

S11
S1
S11
S1
S13
S12

[0472]

31

TABLE C4

A list of compounds (substituents R1˜R6)

R1
R2
R3
R4
R5
R6

S11
S1
S11
S1
S12
S13

S11
S1
S11
S1
S13
S13

S11
S1
S12
S1
S12
S11

S11
S1
S12
S1
S13
S11

S11
S2
S12
S1
S12
S11

S11
S2
S12
S1
S13
S11

S11
S1
S12
S1
S12
S12

S11
S1
S12
S1
S13
S12

S11
S1
S12
S1
S12
S13

S11
S1
S12
S1
S13
S13

S11
S1
S13
S1
S12
S11

S11
S1
S13
S1
S13
S11

S11
S2
S13
S1
S12
S11

S11
S2
S13
S1
S13
S11

S11
S1
S13
S1
S12
S12

S11
S1
S13
S1
S13
S12

S11
S1
S13
S1
S12
S13

S11
S1
S13
S1
S13
S13

S11
S11
S11
S1
S11
S13

S11
S1
S7
S1
S11
S13

S15
S1
S15
S1
S11
S13

S17
S1
S11
S1
S11
S13

S11
S1
S11
S1
S12
S11

S11
S1
S11
S1
S13
S11

S13
S1
S13
S1
S11
S13

S8
S1
S2
S1
S11
S13

S21
S8
S1
S11
S13

S21
S8
S1
S12
S11

S21
S3
S1
S11
S13

S21
S21
S11
S13

S22
S21
S11
S12

S23
S9
S1
S11
S13

S2
S2
S2
S1
S14
S15

S2
S2
S2
S1
S11
S13

S2
S1
S11
S7
S20
S15

S2
S1
S11
S7
S12
S11

S2
S6
S4
S1
S18
S20

S2
S10
S7
S20
S5
S13

S2
S2
S2
S2
S2
S12

S2
S3
S20
S4
S19
S16

S2
S3
S20
S4
S13
S11

[0473]

32

TABLE C5

A list of compounds (substituents R1˜R6)

R1
R2
R3
R4
R5
R6

S2
S3
S13
S4
S13
S11

S2
S20
S3
S6
S11
S13

S2
S11
S1
S10
S3
S18

S2
S7
S10
S3
S16
S3

S2
S4
S6
S11
S7
S11

S20
S1
S7
S10
S16
S3

S20
S6
S22
S3
S7
S22

S20
S10
S4
S22
S3
S18

S20
S2
S3
S7
S18
S20

S20
S3
S2
S1
S5
S13

S20
S20
S20
S20
S20
S15

S20
S20
S20
S20
S12
S11

S20
S11
S6
S2
S19
S16

S20
S11
S6
S2
S13
S11

S20
S7
S1
S4
S11
S13

S20
S4
S10
S6
S2
S12

S1
S1
S1
S1
S19
S16

S1
S1
S1
S1
S13
S11

S1
S6
S10
S20
S11
S13

S1
S10
S6
S7
S2
S12

S1
S2
S11
S4
S16
S3

S1
S3
S4
S6
S7
S11

S1
S20
S7
S2
S3
S18

S1
S11
S2
S3
S18
S20

S1
S7
S20
S11
S5
S13

S1
S4
S3
S10
S20
S15

S1
S4
S3
S10
S12
S11

S6
S1
S10
S4
S3
S18

S6
S6
S6
S6
S16
S3

S6
S10
S1
S2
S7
S11

S6
S2
S4
S3
S20
S15

S6
S2
S4
S3
S12
S11

S6
S3
S7
S11
S18
S20

S6
S20
S11
S10
S5
S13

S6
S11
S20
S1
S2
S12

S6
S7
S3
S20
S19
S16

S6
S7
S3
S20
S13
S11

S6
S4
S2
S7
S11
S13

S10
S1
S6
S3
S5
S13

S10
S6
S1
S11
S20
S15

S10
S6
S1
S11
S12
S11

[0474]

33

TABLE C6

A list of compounds (substituents R1˜R6)

R1
R2
R3
R4
R5
R6

S10
S10
S10
S10
S18
S20

S10
S2
S7
S1
S11
S13

S10
S3
S11
S20
S2
S12

S10
S20
S4
S7
S19
S16

S10
S20
S4
S7
S13
S11

S10
S11
S3
S4
S7
S11

S10
S7
S2
S6
S3
S18

S10
S4
S20
S2
S16
S3

S7
S1
S20
S6
S18
S20

S7
S6
S3
S2
S5
S13

S7
S10
S2
S4
S20
S15

S7
S10
S2
S4
S12
S11

S7
S2
S10
S11
S19
S16

S7
S2
S10
S11
S13
S11

S7
S3
S6
S10
S11
S13

S7
S20
S1
S3
S2
S12

S7
S11
S4
S20
S16
S3

S7
S7
S7
S7
S7
S11

S7
S4
S11
S1
S3
S18

S4
S1
S3
S11
S2
S12

S4
S6
S2
S10
S19
S16

S4
S6
S2
S10
S13
S11

S4
S10
S20
S3
S11
S13

S4
S2
S6
S20
S3
S18

S4
S3
S1
S7
S16
S3

S4
S20
S10
S1
S7
S11

S4
S11
S7
S6
S20
S15

S4
S11
S7
S6
S12
S11

S4
S7
S11
S2
S18
S20

S4
S4
S4
S4
S5
S13

[0475]

34

TABLE C7

A list of compounds (substituents R1˜R6)

R1
R2
R3
R4
R5

S3
S1
S3
S1
S11

S3
S1
S12
S1
S11

S3
S1
S13
S1
S11

S3
S1
S3
S1
S3

S3
S2
S3
S1
S11

S3
S2
S12
S1
S11

S3
S2
S13
S1
S11

S3
S1
S3
S1
S14

S3
S1
S3
S1
S15

S3
S1
S3
S1
S17

S3
S1
S3
S1
S16

S3
S1
S3
S1
S12

S3
S1
S3
S1
S13

S3
S2
S3
S1
S12

S3
S2
S3
S1
S13

S3
S1
S4
S2
S11

S3
S6
S7
S4
S2

S3
S10
S11
S6
S19

S3
S2
S20
S10
S7

S3
S3
S3
S3
S3

S3
S20
S2
S11
S16

S3
S11
S10
S7
S4

S3
S7
S6
S1
S20

S3
S4
S1
S20
S15

S12
S1
S3
S1
S11

S12
S1
S3
S1
S3

S12
S2
S3
S1
S11

S12
S1
S12
S1
S11

S12
S1
S13
S1
S11

S12
S1
S12
S1
S3

S12
S1
S13
S1
S3

S12
S2
S12
S1
S11

S12
S2
S13
S1
S11

S12
S1
S3
S1
S14

S12
S1
S3
S1
S15

S12
S1
S3
S1
S17

S12
S1
S3
S1
S16

S12
S1
S3
S1
S12

S12
S1
S3
S1
S13

S12
S1
S12
S1
S12

S12
S1
S13
S1
S13

[0476]

35

TABLE C8

A list of compounds (substituents R1˜R5)

R1
R2
R3
R4
R5

S12
S1
S12
S1
S13

S12
S1
S13
S1
S12

S12
S1
S4
S2
S11

S12
S6
S7
S4
S2

S12
S10
S11
S6
S19

S12
S2
S20
S10
S7

S12
S3
S3
S3
S3

S12
S20
S2
S11
S16

S12
S11
S10
S7
S4

S12
S7
S6
S1
S20

S12
S4
S1
S20
S15

S13
S1
S3
S1
S11

S13
S1
S3
S1
S3

S13
S2
S3
S1
S11

S13
S1
S12
S1
S11

S13
S1
S12
S1
S3

S13
S2
S12
S1
S11

S13
S1
S13
S1
S11

S13
S1
S13
S1
S3

S13
S2
S13
S1
S11

S13
S1
S3
S1
S14

S13
S1
S3
S1
S15

S13
S1
S3
S1
S17

S13
S1
S3
S1
S16

S13
S1
S3
S1
S12

S13
S1
S3
S1
S13

S13
S1
S12
S1
S12

S13
S1
S12
S1
S13

S13
S1
S13
S1
S12

S13
S1
S13
S1
S13

S13
S1
S4
S2
S11

S13
S6
S7
S4
S2

S13
S10
S11
S6
S19

S13
S2
S20
S10
S7

S13
S3
S3
S3
S3

S13
S20
S2
S11
S16

S13
S11
S10
S7
S4

S13
S7
S6
S1
S20

S13
S4
S1
S20
S15

S11
S1
S2
S20
S7

S11
S6
S20
S7
S3

[0477]

36

TABLE C9

A list of compounds (substituents R1˜R5)

R1
R2
R3
R4
R5

S11
S1
S12
S2
S11

S11
S10
S3
S1
S16

S11
S2
S1
S6
S4

S11
S3
S10
S2
S20

S11
S20
S6
S4
S15

S11
S11
S11
S11
S11

S11
S7
S4
S10
S2

S11
S4
S7
S3
S19

S11
S1
S11
S1
S11

S11
S2
S11
S1
S11

S11
S1
S11
S1
S14

S11
S1
S11
S1
S12

S11
S1
S11
S1
S13

S11
S1
S12
S1
S11

S11
S2
S12
S1
S11

S11
S1
S12
S1
S14

S11
S1
S12
S1
S12

S11
S1
S12
S1
S13

S11
S1
S13
S1
S11

S11
S2
S13
S1
S11

S11
S1
S13
S1
S14

S11
S1
S13
S1
S12

S11
S1
S13
S1
S13

S11
S11
S11
S1
S11

S11
S1
S7
S1
S11

S15
S1
S15
S1
S11

S17
S1
S11
S1
S11

S11
S1
S11
S1
S12

S11
S1
S11
S1
S13

S13
S1
S13
S1
S11

S8
S1
S2
S1
S11

S21
S8
S1
S11

S21
S8
S1
S12

S21
S3
S1
S11

S21
S21
S11

S22
S21
S11

S23
S9
S1
S11

S2
S2
S2
S1
S14

S2
S2
S2
S1
S11

S2
S1
S11
S7
S20

S2
S1
S11
S7
S12

[0478]

37

TABLE C10

A list of compounds (substituents R1˜R5)

R1
R2
R3
R4
R5

S2
S6
S4
S1
S15

S2
S10
S7
S20
S4

S2
S2
S2
S2
S2

S2
S3
S20
S4
S19

S2
S3
S20
S4
S13

S2
S3
S13
S4
S13

S2
S20
S3
S6
S11

S2
S11
S1
S10
S3

S2
S7
S10
S3
S16

S2
S4
S6
S11
S7

S20
S1
S7
S10
S16

S20
S6
S11
S3
S7

S20
S10
S4
S11
S3

S20
S2
S3
S7
S15

S20
S3
S2
S1
S4

S20
S20
S20
S20
S20

S20
S20
S20
S20
S12

S20
S11
S6
S2
S19

S20
S11
S6
S2
S13

S20
S7
S1
S4
S11

S20
S4
S10
S6
S2

S1
S1
S1
S1
S19

S1
S1
S1
S1
S13

S1
S6
S10
S20
S11

S1
S10
S6
S7
S2

S1
S2
S11
S4
S16

S1
S3
S4
S6
S7

S1
S20
S7
S2
S3

S1
S11
S2
S3
S15

S1
S7
S20
S11
S4

S1
S4
S3
S10
S20

S1
S4
S3
S10
S12

S6
S1
S10
S4
S3

S6
S6
S6
S6
S16

S6
S10
S1
S2
S7

S6
S2
S4
S3
S20

S6
S2
S4
S3
S12

S6
S3
S7
S11
S15

S6
S20
S11
S10
S4

S6
S11
S20
S1
S2

S6
S7
S3
S20
S19

[0479]

38

TABLE C11

A list of compounds (substituents R1˜R5)

R1
R2
R3
R4
R5

S6
S7
S3
S20
S13

S6
S4
S2
S7
S11

S10
S1
S6
S3
S4

S10
S6
S1
S11
S20

S10
S6
S1
S11
S12

S10
S10
S10
S10
S15

S10
S2
S7
S1
S11

S10
S3
S11
S20
S2

S10
S20
S4
S7
S19

S10
S20
S4
S7
S13

S10
S11
S3
S4
S7

S10
S7
S2
S6
S3

S10
S4
S20
S2
S16

S7
S1
S20
S6
S15

S7
S6
S3
S2
S4

S7
S10
S2
S4
S20

S7
S10
S2
S4
S12

S7
S2
S10
S11
S19

S7
S2
S10
S11
S13

S7
S3
S6
S10
S11

S7
S20
S1
S3
S2

S7
S11
S4
S20
S16

S7
S7
S7
S7
S7

S7
S4
S11
S1
S3

S4
S1
S3
S11
S2

S4
S6
S2
S10
S19

S4
S6
S2
S10
S13

S4
S10
S20
S3
S11

S4
S2
S6
S20
S3

S4
S3
S1
S7
S16

S4
S20
S10
S1
S7

S4
S11
S7
S6
S20

S4
S11
S7
S6
S12

S4
S7
S11
S2
S15

S4
S4
S4
S4
S4

[0480]

39

TABLE D1

Synthesis examples obtained in production examples 7˜15

Reaction Temperature

Reaction Time

Production Example
A compound having an active methylene
Yield (%)

7

444

20° C. 20 hours 32

8

445

20° C. 20 hours 67

9

446

20° C. 20 hours 63

10

447

45° C. 3.5 hours 41

11

448

20° C. 20 hours 37

12

449

20° C. 20 hours 37

13

450

45° C. 8 hours 30

14

451

20° C. 20 hours 55

15

452

20° C. 30 minute 10

[0481]

40

TABLE D2

Compounds obtained in production examples 7˜15

Production Example
Compound
Name of compound

7

453

2,6-Di-tert-butyl-4-(3-methyl- 1-phenyl-5-oxo-4-pyrazolili- dene)-2,5-cyclohexadiene-1-one

8

454

2,6-Di-tert-butyl-4-[3-methyl- 1-(4-chlorophenyl)-5-oxo-4- pyrazolilidene]-2,5- cyclohexadiene-1-one

9

455

2,6-Di-tert-butyl-4-[3-methyl- 1-(4-bromophenyl)-5-oxo-4- pyrazolilidene]-2,5-cyclo- hexadiene-1-one

10

456

2,6-Di-tert-butyl-4-(3-trifluoro- methyl-1-phenyl-5-oxo-4- pyrazolilidene)-2,5-cyclo- hexadiene-1-one

11

457

2,6-Di-tert-butyl-4-[3-(2-furanyl)- 1-pheny1-5-oxo-4-pyrazo- lilidene]-2,5-cyclo- hexadiene-1-one

[0482]

41

TABLE D3

Compounds obtained in Production Examples

Production Example
Compound
Name of compound

12

458

2,6-Di-tert-butyl-4-[3-(2- thienyl-1-phenyl-5-oxo-4- pyrazolilidene]-2,5-cyclo- hexadiene-1-one

13

459

1,3-Bis-3-(2,6-di-tert-butyl-1- oxo-2,5-cyclohexadiene-4- ylidene)-1-phenyl-5-oxo-4- pyrazolylbenzene

14

460

2,6-Di-tert-butyl-4-(2,2-dimethyl- 1,3-dioxane-4,6-dione-5- ylidene)-2,5-cyclo- hexadiene-1-one

15

461

2,6-Di-tert-butyl-4-(1,3-diethyl-2- thioxo-4,6-dioxo-5-pyrimidin- ylidene)-2,5-cyclo- hexadiene-1-one

[0483]

42

TABLE E

The melting point and the results of the element analysis

for each compounds of the formulae (7)˜(16)

Com-
Melting
Results of the element analysis

pound
Point(° C.)
Calculated Value(%)
Observed Valve(%)

(7)
135.6˜136.4
C: 72.58, H: 8.33, N: 8.91
C: 72.32, H: 8.45, N: 8.71

(8)
165.7˜166.0
C: 76.56, H: 7.50, N: 7.44
C: 76.66, H: 7.67, N: 7.70

(9)
214.4˜215.1
C: 70.15, H: 6.62, N: 6.82
C: 70.35, H: 6.48, N: 6.61

(10)
212.6˜213.3
C: 63.30, H: 5.98, N: 6.15
C: 63.41, H: 5.88, N: 6.03

(11)
159.0˜159.5
C: 66.96, H: 5.85, N: 6.51
C: 67.11, H: 5.78, N: 6.34

(12)
200.5˜201.0
C: 75.68, H: 6.59, N: 6.54
C: 75.47, H: 6.79, N: 6.83

(13)
227.5˜228.1
C: 72.94, H: 6.35, N: 6.30
C: 72.82, H: 6.21, N: 6.45

(14)
316.9˜317.5
C: 78.17, H: 6.81, N: 7.01
C: 78.23, H: 6.63, N: 6.88

(Decom-

position)

(15)
153.8˜154.5
C: 69.34, H: 7.56
C: 69.27, H: 7.66

(16)
127.3˜128.2
C: 65.64, H: 7.51, N: 6.96
C: 65.71, H: 7.39, N: 6.81

[0484]

43

TABLE F

Measurement results of Electron Mobilities

for Example and Comparative Example

Electron Mobilities

Example
(cm2/V · sec)

Example 1
2 × 10−8

Example 2
6 × 10−8

Example 3
1 × 10−8

Example 4
1 × 10−8

Example 5
6 × 10−8

Example 6
3 × 10−8

Example 7
6 × 10−8

Example 8
1 × 10−8

Example 9
1 × 10−8

Example 10
4 × 10−8

Comparative Example 1
1 × 10−9

[0485]

44

TABLE G

The amount of luminescence of the organic electro luminescence

Elements obtained in Application Examples 1˜10

The amount of

Example
luminescence (cd/m2)

Application Example 1
100

Application Example 2
120

Application Example 3
60

Application Example 4
60

Application Example 5
110

Application Example 6
90

Application Example 7
100

Application Example 8
80

Application Example 9
80

Application Example 10
100

[0486]

45

TABLE H

Electrical Potential and Half-decay exposure for Application

Examples 11˜20 and Comparative Example 2

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 11
640
3.4

Application Example 12
670
2.9

Application Example 13
620
4.8

Application Example 14
630
4.7

Application Example 15
660
3.3

Application Example 16
650
4.0

Application Example 17
650
3.6

Application Example 18
630
4.2

Application Example 19
620
4.3

Application Example 20
640
3.9

Comparative Example 2
580
6.1

[0487]

46

TABLE I

Electrical Potential and Half-decay exposure for Application

Examples 21˜30 and Comparative Example 3

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 21
580
1.8

Application Example 22
590
1.4

Application Example 23
540
2.3

Application Example 24
560
2.0

Application Example 25
570
1.5

Application Example 26
550
1.9

Application Example 27
570
1.6

Application Example 28
550
1.9

Application Example 29
580
2.1

Application Example 30
560
1.7

Comparative Example 3
550
2.8

[0488]

47

TABLE J

Electrical Potential and Half-decay exposure for Application

Examples 31˜40 and Comparative Example 4

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 31
530
2.0

Application Example 32
550
1.8

Application Example 33
520
2.3

Application Example 34
550
2.2

Application Example 35
570
1.7

Application Example 36
540
1.8

Application Example 37
530
1.9

Application Example 38
540
2.2

Application Example 39
550
2.1

Application Example 40
560
2.0

Comparative Example 4
540
3.0

[0489]

48

TABLE K

Electrical Potential and Half-decay exposure for Application

Example 41˜50 and Comparative Example 5

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 41
−600
1.5

Application Example 42
−590
1.2

Application Example 43
−610
2.0

Application Example 44
−600
2.1

Application Example 45
−580
1.3

Application Example 46
−600
1.6

Application Example 47
−590
1.2

Application Example 48
−610
1.9

Application Example 49
−600
2.0

Application Example 50
−570
1.8

Comparative Example 5
−620
3.5

[0490]

49

TABLE L1

Synthesis examples obtained in production examples 23˜31

Reaction

Temperature

Reaction

Production

Time

Example
A compound having an active methylene
Yield (%)

23

462

25 20 hours 49

24

463

25 16 hours 20

25

464

20 20 hours 64

26

465

25 20 hours 50

27

466

50 6 hours 5

28

467

50 6 hours 2

29

468

70 3 hours 9

30

469

25 20 hours 44

31

470

25 20 hours 39

[0491]

50

TABLE L2

Synthesis examples obtained in production examples 32˜37

Reaction

Pro-

Tem-

duc-

perature

tion

Reaction

Exam-

Time

ple
A compound having an active methylene
Yield (%)

32

471

25 20 hours 30

33

472

25 20 hours 49

34

473

25 20 hours 28

35

474

25 20 hours 38

36

475

25 20 hours 41

37

476

25 20 hours 36

[0492]

51

TABLE M1

Compounds obtained in production examples 23˜27

Production

Example
Compound
Name of Compound

23

477

2,6-Di-tert-butyl-4-[1-phenyl- 3-(4-trifluoro- methylphenyl)-5-oxo-4- pyrazolilidene]-2,5-cyclo- hexadiene-1-one

24

478

2,6-Di-tert-butyl-4-[3- (2-furanyl)-1-(1-naphthyl)- 5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

25

479

2,6-Di-tert-butyl-4-[1-(2- benzothiazolyl)-3-methyl- oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

26

480

2,6-Di-tert-butyl-4-(1- phenyl-3-propyl-5-oxo-4- pyrazolilidene)-2,5-cyclo- hexadiene-1-one

27

481

2,6-Di-tert-butyl-4-[1-tert- butyl-3-(2-thienyl)-5-oxo- 4-pyrazolilidene]-2,5- cyclohexadiene-1-one

[0493]

52

TABLE M2

Compounds obtained in production examples 28˜33

Production

Example
Compound
Name of Compound

28

482

2,6-Di-tert-butyl-4-[1-tert- butyl-3-(2-furanyl)-5-oxo- 4-pyrazolilidene]-2,5- cyclohexadiene-1-one

29

483

2,6-Di-tert-butyl-4-(1-tert-butyl-3- trifluoromethyl-5-oxo-4- pyrazolilidene)-2,5-cyclo- hexadiene-1-one

30

484

2,6-Di-tert-butyl-4-(3-iso- propyl-1-phenyl-5-oxo-4- pyrazolilidene)-2,5-cyclo- hexadiene-1-one

31

485

2,6-Di-tert-butyl-4-(3-butyl- 1-phenyl-5-oxo-4-pyra- zolilidene)-2,5-cyclohexa- diene-1-one

32

486

2,6-Di-tert-butyl-4-[3-methyl- 1-(2-methylphenyl)- 5-oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

33

487

2,6-Di-tert-butyl-4-[1-(2- methylphenyl)-3-propyl- 5-oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

[0494]

53

TABLE M3

Compounds obtained in production examples 34˜37

Production

Example
Compound
Name of Compound

34

488

2,6-Di-tert-butyl-4-[1-(2- methylphenyl)-3-(2-thienyl)- 5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

35

489

2,6-Di-tert-butyl-4-[3-(2- furanyl)-1-(2-methylphenyl)- yl)-5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

36

490

2,6-Di-tert-butyl-4-[3-(2- furanyl)-1-(4-iso-propylphenyl)- 5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

37

491

2,6-Di-tert-butyl-4-[3-propyl- 1-(4-iso-propylphenyl)- 5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

[0495]

54

TABLE N

The melting point and the results of the element analysis

for each compounds of the formulae (29)˜(43)

Results of the element analysis

Melting Point
Calculated Value
Observed Value

Compound
(°C.)
(%)
(%)

(29)
261.0˜262.9
C: 71.13, H: 5.77, N: 5.53
C: 71.34, H: 5.42, N: 5.32

(30)
175.0˜175.5
C: 77.80, H: 6.32, N: 5.85
C: 77.67, H: 6.12, N: 5.65

(31)
260.9˜261.7
C: 69.26, H: 6.28, N: 9.69
C: 69.07, H: 6.48, N: 9.71

(32)
155.4˜156.1
C: 77.19, H: 7.97, N: 6.92
C: 77.23, H: 7.82, N: 6.67

(33)
179.9˜180.6
C: 70.72, H: 7.60, N: 6.60
C: 70.58, H: 7.48, N: 6.55

(34)
153.7˜154.4
C: 73.50, H: 7.90, N: 6.86
C: 73.24, H: 7.95, N: 6.77

(35)
130.7˜131.4
C: 64.37, H: 7.12, N: 6.82
C: 64.49, H: 7.02, N: 6.93

(36)
166.4˜167.1
C: 77.19, H: 7.97, N: 6.92
C: 77.35, H: 7.86, N: 6.83

(37)
149.6˜150.2
C: 77.48, H: 8.19, N: 6.69
C: 77.63, H: 8.35, N: 6.65

(38)
68.0˜70.0
C: 76.89, H: 7.74, N: 7.17
C: 76.65, H: 7.57, N: 7.01

(39)
87.1˜87.9
C: 77.48, H: 8.19, N: 6.69
C: 77.62, H: 8.34, N: 6.82

(40)
170.0˜170.7
C: 73.33, H: 6.59, N: 6.11
C: 73.37, H: 6.67, N: 6.34

(41)
154.0˜154.5
C: 75.99, H: 6.83, N: 6.33
C: 75.82, H: 6.97, N: 6.51

(42)
157.8˜158.5
C: 76.57, H: 7.28, N: 5.95
C: 76.77, H: 7.12, N: 6.01

(43)
75.0˜78.0
C: 77.99, H: 8.58, N: 6.27
C: 78.12, H: 8.45, N: 6.34

[0496]

55

TABLE O

Measurement results of Electron mobilities for

example 11˜25 and Comparative example

Example
Electron mobilities(cm2/V · sec)

Example 11
1 × 10−8

Example 12
3 × 10−8

Example 13
3 × 10−8

Example 14
1 × 10−7

Example 15
5 × 10−8

Example 16
2 × 10−7

Example 17
1 × 10−8

Example 18
1 × 10−7

Example 19
1 × 10−7

Example 20
8 × 10−8

Example 21
6 × 10−8

Example 22
2 × 10−7

Example 23
2 × 10−7

Example 24
4 × 10−8

Example 25
2 × 10−7

Comparative Example 1
1 × 10−9

[0497]

56

TABLE P

The amount of luminescence of the organic electro luminescence

elements obtained in Application Examples 51˜65

Example
The amount of luminescence (cd/m2)

Application example 51
60

Application example 52
100

Application example 53
90

Application example 54
140

Application example 55
110

Application example 56
150

Application example 57
80

Application example 58
130

Application example 59
150

Application example 60
130

Application example 61
120

Application example 62
130

Application example 63
120

Application example 64
70

Application example 65
130

[0498]

57

TABLE Q

Electrical Potential and half-decay exposure for Application

Examples 66˜80 and Comparative Examples 2

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application example 66
670
4.5

Application example 67
640
4.6

Application example 68
630
4.3

Application example 69
650
2.4

Application example 70
640
3.8

Application example 71
620
2.3

Application example 72
660
4.7

Application example 73
650
2.7

Application example 74
670
2.6

Application example 75
680
2.9

Application example 76
630
3.9

Application example 77
640
3.7

Application example 78
670
3.5

Application example 79
660
3.9

Application example 80
640
2.8

Comparative Example 2
580
6.1

[0499]

58

TABLE R

Electrical Potential and half-decay exposure for Application

Examples 81˜95 and Comparative Examples 3

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 8l
600
2.4

Application Example 82
570
2.3

Application Example 83
560
2.2

Application Example 84
570
1.3

Application Example 85
560
1.6

Application Example 86
590
1.2

Application Example 87
570
2.1

Application Example 88
580
1.4

Application Example 89
570
1.3

Application Example 90
590
1.5

Application Example 91
600
1.9

Application Example 92
560
1.7

Application Example 93
580
1.9

Application Example 94
580
2.3

Application Example 95
570
1.6

Comparative Example 3
550
2.8

[0500]

59

TABLE S

Electrical Potential and Half-decay exposure for Application

Example 96˜110 and Comparative Example 4

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 96
560
2.2

Application Example 97
540
2.1

Application Example 98
530
2.2

Application Example 99
550
1.6

Application Example 100
530
2.2

Application Example 101
540
1.5

Application Example 102
520
2.3

Application Example 103
550
1.7

Application Example 104
530
1.6

Application Example 105
570
1.8

Application Example 106
560
2.0

Application Example 107
530
1.9

Application Example 108
570
1.9

Application Example 109
560
2.2

Application Example 110
540
1.6

Comparative Example 4
540
3.0

[0501]

60

TABLE T

Electrical Potential and Half-decay exposure for Application

Example 111˜125 and Comparative Example 5

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 111
−610
2.1

Application Example 112
−580
1.9

Application Example 113
−580
1.7

Application Example 114
−590
1.1

Application Example 115
−570
1.6

Application Example 116
−580
1.0

Application Example 117
−560
2.2

Application Example 118
−600
1.2

Application Example 119
−580
1.1

Application Example 120
−620
1.3

Application Example 121
−610
1.7

Application Example 122
−580
1.5

Application Example 123
−600
1.4

Application Example 124
−590
1.9

Application Example 125
−570
1.3

Comparative Example 5
−620
3.5

[0502]

61

TABLE U1

Synthesis examples obtained in production 38˜46

Reaction

Temperature

Production

Reaction Time

Example
A compound having an active methylene
Yield (%)

38

492

25° C. 20 hours 53

39

493

25° C. 20 hours 34

40

494

25° C. 20 hours 31

41

495

25° C. 20 hours 36

42

496

25° C. 20 hours 29

43

497

25° C. 20 hours 32

44

498

25° C. 20 hours 21

45

499

25° C. 20 hours 25

46

500

25° C. 20 hours 31

[0503]

62

TABLE U2

Synthesis examples obtained in production 47˜53

Reaction

Temperature

Production

Reaction Time

Example
A compound having an active methylene
Yield (%)

47

501

20° C. 3 hours 41

48

502

20° C. 1.5 hours 53

49

503

20° C. 20 hours 30

50

504

20° C. 20 hours 32

51

505

20° C. 20 hours 18

52

506

20° C. 20 hours 57

53

507

20° C. 20 hours 36

[0504]

63

TABLE V1

Compounds obtained in production 38˜43

Production

Example
Compound
Name of Compound

38

508

2,6-Di-tert-butyl-4-[1-(4- methylphenyl)-3-methyl-5- oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

39

509

2,6-Di-tert-butyl-4-[3-(4- methylphenyl)-1-propyl-5- oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

40

510

2,6-Di-tert-butyl-4-[1-(2-chloro- phenyl)-3-methyl-5-oxo- 4-pyrazolilidene]-2,5- cyclohexadiene-1-one

41

511

2,6-Di-tert-butyl-4-[1-(2-chloro- phenyl)-3-propyl-5-oxo-4- pyrazolilidene]-2,5-cyclo- hexadiene-1-one

42

512

2,6-Di-tert-butyl-4-[1-(2- chlorophenyl)-3- (2-thienyl)-5- oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

43

513

2,6-Di-tert-butyl-4-[1-(2- chlorophenyl)-3-(2-furanyl)-5-oxo- 4-pyrazolilidene]-2,5- cyclohexadiene-1-one

[0505]

64

TABLE V2

Compounds obtained in production 44˜49

Production

Example
Compound
Name of compound

44

514

2,6-Di-tert-butyl-4-[3-methyl- 1-(2-pyridinyl)-5-oxo-4- pyrazolilidene]-2,5-cyclo- hexadiene-1-one

45

515

2,6-Di-tert-butyl-4-[3-propyl- 1-(2-pyridinyl)-5-oxo-4- pyrazolilidene]-2,5-cyclo- hexadiene-1-one

46

516

2,6-Di-tert-butyl-4-[3- (2-furanyl)-1-(2-pyridinyl)- 5-oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

47

517

2,6-Di-tert-butyl-4-[1- (3-chlorophenyl)-3-methyl- 5-oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

48

518

2,6-Di-tert-butyl-4-[1- (3-chlorophenyl)-3-propyl- 5-oxo-4-pyrazolilidene]-2,5- cyclohexadiene-1-one

49

519

2,6-Di-tert-butyl-4-[1- (3-chlorophenyl)-3- (2-thienyl)- 5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

[0506]

65

TABLE V3

Compounds obtained in production 50˜53

Production

Example
Compound
Name of compound

50

520

2,6-Di-tert-butyl-4-[1- (2,5-dichlorophenyl)-3-propyl- 5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

51

521

2,6-Di-tert-butyl-4-[1- (2,5-dichlorophenyl)-3-(2- thienyl)-5-oxo-4-pyrazolilidene]- 2,5-cyclohexadiene-1-one

52

522

2,6-Di-tert-butyl-4-(1,2- diphenyl-3,5-dioxo-4-pyrazo- lilidene)-2,5-cyclo- hexadiene-1-one

53

523

2,6-Di-tert-butyl-4-(1,2-di- methyl-3,5-dioxo-4-pyrazo- lilidene)-2,5-cyclohexa- diene-1-one

[0507]

66

TABLE W

The melting point and the results of the element analysis

for each compounds of the formulae(45) ˜ (60)

Melting Point
Results of the element analysis

Compound
(° C.)
Calculated Value (%)
Observed Value (%)

(45)
188.6˜189.2
C: 76.89, H: 7.74, N: 7.17
C: 76.68, H: 7.45, N: 7.22

(46)
154.6˜155.0
C: 77.48, H: 8.19, N: 6.69
C: 77.67, H: 8.01, N: 6.59

(47)
71.7˜72.4
C: 70.15, H: 6.62, N: 6.82
C: 70.22, H: 6.72, N: 6.70

(48)
116.8˜117.5
C: 71.14, H: 7.12, N: 6.38
C: 71.18, H: 7.34, N: 6.48

(49)
179.0˜179.3
C: 67.70, H: 5.68, N: 5.85
C: 67.56, H: 5.60, N: 5.92

(50)
178.8˜179.3
C: 70.05, H: 5.88, N: 6.05
C: 70.20, H: 5.81, N: 6.00

(51)
193.2˜193.8
C: 73.18, H: 7.21, N: 11.13
C: 73.30, H: 7.24, N: 11.24

(52)
138.4˜139.1
C: 74.04, H: 7.70, N: 10.36
C: 74.24, H: 7.81, N: 10.26

(53)
222.5˜222.9
C: 72.71, H: 6.34, N: 9.78
C: 72.62, H: 6.15, N: 9.82

(54)
162.9˜163.5
C: 70.15, H: 6.62, N: 6.82
C: 70.31, H: 6.32, N: 6.68

(55)
165.8˜166.3
C: 71.14, H: 7.12, N: 6.38
C: 71.26, H: 7.03, N: 6.42

(56)
179.7˜181.2
C: 67.70, H: 5.68, N: 5.85
C: 67.81, H: 5.61, N: 5.78

(57)
131.5˜132.1
C: 65.96, H: 6.39, N: 5.92
C: 65.83, H: 6.49, N: 5.81

(58)
137.6˜138.9
C: 63.16, H: 5.10, N: 5.46
C: 63.33, H: 5.21, N: 5.34

(59)
174.8˜175.8
C: 76.63, H: 6.65, N: 6.16
C: 76.68, H: 6.56, N: 6.19

(60)
162.8˜164.0
C: 69.06, H: 7.93, N: 8.48
C: 69.15, H: 7.82, N: 8.28

[0508]

67

TABLE X

Measurement results of electron mobilities for example 26˜41

and Comparative examples

Example
Electron Mobilities(cm2/V · sec)

Example 26
1 × 10−7

Example 27
1 × 10−7

Example 28
4 × 10−8

Example 29
7 × 10−7

Example 30
1 × 10−7

Example 31
2 × 10−7

Example 32
2 × 10−7

Example 33
1 × 10−7

Example 34
8 × 10−8

Example 35
2 × 10−8

Example 36
4 × 10−8

Example 37
4 × 10−8

Example 38
2 × 10−8

Example 39
1 × 10−7

Example 40
7 × 10−8

Example 41
6 × 10−8

Comparative examples 1
1 × 10−9

[0509]

68

TABLE Y

The amount of luminescence of the organic electro luminescence

elements obtained in Application Examples 126˜141

Example
The amount of luminescence (cd/m2)

Application Example 126
100

Application Example 127
110

Application Example 128
70

Application Example 129
150

Application Example 130
120

Application Example 131
120

Application Example 132
90

Application Example 133
120

Application Example 134
80

Application Example 135
70

Application Example 136
90

Application Example 137
80

Application Example 138
60

Application Example 139
120

Application Example 140
90

Application Example 141
100

[0510]

69

TABLE Z

Electrical potential and half-decay exposure for Application

Examples 142˜157 and Comparative example 2

Half-decay exposure

Example
Electrical potential (V)
(Lux · sec)

Application Example 142
650
3.5

Application Example 143
630
3.2

Application Example 144
620
4.5

Application Example 145
690
2.2

Application Example 146
640
3.4

Application Example 147
670
3.0

Application Example 148
650
3.0

Application Example 149
660
3.2

Application Example 150
680
4.3

Application Example 151
670
4.5

Application Example 152
680
4.2

Application Example 153
620
4.0

Application Example 154
650
4.6

Application Example 155
630
3.3

Application Example 156
650
4.4

Application Example 157
680
4.5

Comparative example 2
580
6.1

[0511]

70

TABLE AA

Electrical potential and half-decay exposure for Application

Example 158˜173 and Comparative example 3

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 158
600
1.6

Application Example 159
540
1.3

Application Example 160
570
2.5

Application Example 161
600
1.1

Application Example 162
580
1.6

Application Example 163
610
1.3

Application Example 164
590
1.2

Application Example 165
580
1.3

Application Example 166
600
2.3

Application Example 167
570
2.4

Application Example 168
580
2.2

Application Example 169
560
2.1

Application Example 170
570
2.3

Application Example 171
590
1.4

Application Example 172
560
2.4

Application Example 173
580
2.5

Comparative example 3
550
2.8

[0512]

71

TABLE AB

Electrical potential and half-decay exposure for Application

Example 174˜189 and Comparative example 4

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 174
550
2.2

Application Example 175
530
1.9

Application Example 176
540
2.4

Application Example 177
580
1.5

Application Example 178
530
1.8

Application Example 179
560
1.6

Application Example 180
550
1.6

Application Example 181
570
1.8

Application Example 182
540
2.6

Application Example 183
580
2.4

Application Example 184
570
2.0

Application Example 185
520
1.9

Application Example 186
560
2.1

Application Example 187
550
1.7

Application Example 188
590
2.3

Application Example 189
580
2.5

Comparative example 4
540
3.0

[0513]

72

TABLE AC

Electrical potential and half-decay exposure for Application

Example 190˜205 and Comparative example 5

Electrical Potential
Half-decay exposure

Example
(V)
(Lux · sec)

Application Example 190
−590
1.9

Application Example 191
−570
1.8

Application Example 192
−560
2.3

Application Example 193
−600
1.1

Application Example 194
−570
1.6

Application Example 195
−590
1.5

Application Example 196
−550
1.7

Application Example 197
−590
1.6

Application Example 198
−580
1.9

Application Example 199
−590
2.1

Application Example 200
−570
1.9

Application Example 201
−560
2.0

Application Example 202
−580
2.3

Application Example 203
−570
1.7

Application Example 204
−620
2.0

Application Example 205
−610
2.1

Comparative Example 5
−620
3.5

Number	Date	Country	Kind
2001-98301	Mar 2001	JP
2001-274861	Sep 2001	JP

	Number	Date	Country
Parent	PCT/JP02/02965	Mar 2002	US
Child	10673405	Sep 2003	US

Charge-transfer material and process for producing the same, electron-transfer agent, photoreceptor for electrophotography and organic electroluminescence element using said charge-transfer material

Information

Publication Number

Date Filed

Date Published

Inventors

Original Assignees

CPC

US Classifications

International Classifications

Abstract

Description

Claims

Priority Claims (2)

Parent Case Info

Continuations (1)