US2004142261A1PendingUtilityA1
Charge-transfer material and process for producing the same, electron-transfer agent, photoreceptor for electrophotography and organic electroluminescence element using said charge-transfer material
Est. expiryMar 30, 2021(expired)· nominal 20-yr term from priority
H10K 85/611C07D 231/22G03G 5/0629G03G 5/0612G03G 5/062G03G 5/0661G03G 5/0631G03G 5/065G03G 5/0609G03G 5/06G03G 5/0637G03G 5/0638H10K 85/655H10K 85/653H10K 30/00H10K 85/657H10K 85/621H10K 85/654
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Claims
Abstract
A photosensitive layer contains an electron-transfer agent that makes use of a compound represented by the following general formula (1): wherein R 1 through R 4 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.
Claims
exact text as granted — not AI-modified1 . A compound represented by a following general formula (4):
wherein R 1 through R 6 are each independently selected from a 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 except that R 1 and R 3 are tert-butyl, R 2 , R 4 and R 6 are hydrogen, R 5 is methyl; X is selected from a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur.
2 . A compound represented by a following general formula (6):
wherein R 1 through R 6 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur.
3 . A compound represented by a following general formula (44):
wherein R 1 through R 6 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur.
4 . A compound represented by a following chemical formula (7):
5 . A compound represented by a following chemical formula (8):
6 . A compound represented by a following chemical formula (9):
7 . A compound represented by a following chemical formula (10):
8 . A compound represented by a following chemical formula (11):
9 . A compound represented by a following chemical formula (12):
10 . A compound represented by a following chemical formula (13):
11 . A compound represented by a following chemical formula (14):
12 . A compound represented by a following chemical formula (16):
13 . A compound represented by a following chemical formula (29):
14 . A compound represented by a following chemical formula (30):
15 . A compound represented by a following chemical formula (31):
16 . A compound represented by a following chemical formula (32):
17 . A compound represented by a following chemical formula (33):
18 . A compound represented by a following chemical formula (34):
19 . A compound represented by a following chemical formula (35):
20 . A compound represented by a following chemical formula (36):
21 . A compound represented by a following chemical formula (37):
22 . A compound represented by a following chemical formula (38):
23 . A compound represented by a following chemical formula (39):
24 . A compound represented by a following chemical formula (40):
25 . A compound represented by a following chemical formula (41):
26 . A compound represented by a following chemical formula (42):
27 . A compound represented by a following chemical formula (43):
28 . A compound represented by a following chemical formula (45):
29 . A compound represented by a following chemical formula (46):
30 . A compound represented by a following chemical formula (47):
31 A compound represented by a following chemical formula (48):
32 A compound represented by a following chemical formula (49):
33 . A compound represented by a following chemical formula (50):
34 . A compound represented by a following chemical formula (51):
35 . A compound represented by a following chemical formula (52):
36 . A compound represented by a following chemical formula (53):
37 . A compound represented by a following chemical formula (54):
38 . A compound represented by a following chemical formula (55):
39 . A compound represented by a following chemical formula (56):
40 . A compound represented by a following chemical formula (57):
41 . A compound represented by a following chemical formula (58):
42 . A compound represented by a following chemical formula (59):
43 . A compound represented by a following chemical formula (60):
44 . A process for producing a compound represented by a following general formula (1):
wherein R 1 to R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has the structure shown in a following general formula (1′) that replaces the general formula (1) above:
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 comprising a step of reacting in the presence of a base catalyst a benzoquinone compound represented by a following general formula (17):
wherein R 1 through R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ,
with a compound having an active methylene represented by a following general formula (18):
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.
45 . A process for producing a compound represented by a following general formula (2):
wherein R 1 and R 3 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (2′) that replaces the general formula (2) above:
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 comprising a step of reacting in the presence of a base catalyst a benzoquinone compound represented by a following general formula (19):
wherein R 1 and R 3 are each independently selected from a group consisting of hydrogen, alkyl with 1 to 6 carbon atoms, and phenyl; and X is selected from a group consisting of oxygen, sulfur, and ═C(CN) 2 ,
with a compound having an active methylene represented by a following general formula (18):
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.
46 . A process for producing a compound represented by a following general formula (3):
wherein X is selected from a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (3′) that replaces the general formula (3) above:
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 comprising a step of reacting in the presence of a base catalyst a benzoquinone compound represented by a following general formula (20):
wherein X is selected from a group consisting of oxygen, sulfur, and ═C(CN) 2 ,
with a compound having an active methylene represented by a following general formula (18):
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.
47 . A process for producing a compound represented by a following general formula (4):
wherein R 1 through R 6 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur,
the process comprising a step of reacting in the presence of a base catalyst a benzoquinone compound represented by a following general formula (17):
wherein R 1 through R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ,
with a compound having an active methylene represented by a following general formula (21):
wherein R 5 and R 6 are each independently selected from a 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.
48 . A process for producing a compound represented by a following general formula (5):
wherein R 1 through R 6 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur,
the process comprising a step of reacting in the presence of a base catalyst a benzoquinone compound represented by a following general formula (17):
wherein R 1 through R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ,
with a compound having an active methylene represented by a following general formula (22):
wherein R 5 and R 6 are each independently selected from a 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.
49 . A process for producing a compound represented by a following general formula (6):
wherein R 1 through R 6 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur,
the process comprising a step of reacting in the presence of a base catalyst a benzoquinone compound represented by a following general formula (17):
wherein R 1 through R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ,
with a compound having an active methylene represented by a following general formula (23):
wherein R 5 and R 6 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur.
50 . A process for producing a compound represented by a following general formula (44):
wherein R 1 through R 6 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and Y is oxygen or sulfur,
the process comprising a step of reacting in the presence of a base catalyst a benzoquinone compound represented by a following general formula (17):
wherein R 1 through R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 , with a compound having an active methylene represented by a following general formula (61):
wherein R 5 and R 6 are each independently selected from a 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.
51 . The process for producing a compound according to claim 44 wherein 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 a group consisting of water, alcohol, and saturated hydrocarbon solvent.
52 . The process for producing a compound according to claim 45 , wherein 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 a group consisting of water, alcohol, and saturated hydrocarbon solvent.
53 . The process for producing a compound according to claim 46 , wherein 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 a group consisting of water, alcohol, and saturated hydrocarbon solvent.
54 . The process for producing a compound according to claim 47 , wherein 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 a group consisting of water, alcohol, and saturated hydrocarbon solvent.
55 . The process for producing a compound according to claim 48 , wherein 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 a group consisting of water, alcohol, and saturated hydrocarbon solvent.
56 . The process for producing a compound according to claim 49 , wherein 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 a group consisting of water, alcohol, and saturated hydrocarbon solvent.
57 . The process for producing a compound according to claim 50 , wherein 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 a group consisting of water, alcohol, and saturated hydrocarbon solvent.
58 . The process for producing a compound according to claim 44 , wherein 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 formula (1).
59 . The process for producing a compound according to claim 45 , wherein 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 formula (2).
60 . The process for producing a compound according to claim 46 , wherein 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 Ig of the compound of the general formula (3).
61 . The process for producing a compound according to claim 47 , wherein 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 formula (4).
62 . The process for producing a compound according to claim 48 , wherein 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 formula (5).
63 . The process for producing a compound according to claim 49 , wherein 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 formula (6).
64 . The process for producing a compound according to claim 50 , wherein 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 formula (44).
65 . An electron-transfer agent comprising a resin and as a charge-transfer material a compound represented by the following general formula (1):
wherein R 1 to R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (1′) that replaces the general formula (1) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
66 . An electron-transfer agent comprising a resin and as a charge-transfer material a compound represented by the following general formula (2):
wherein R 1 and R 3 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring having a structure shown in a following general formula (2′) that replaces the general formula (2) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
67 . An electron-transfer agent comprising a resin and as a charge-transfer material a compound represented by the following general formula (3):
wherein X is selected from a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (3′) that replaces the general formula (3) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
68 . 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 a following general formula (1):
wherein R 1 to R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has the structure shown in a following general formula (1′) that replaces the general formula (1) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
69 . 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 a following general formula (2):
wherein R 1 and R 3 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (2′) that replaces the general formula (2) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
70 . 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):
wherein X is selected from a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (3′) that is to replace the general formula (3) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
71 . An organic electroluminescence element comprising 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 a following general formula (1):
wherein R 1 through R 4 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4 - to 8-membered ring and has a structure shown in a following general formula (1′) that replaces the general formula (1) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
72 . An organic electroluminescence element comprising 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 a following general formula (2):
wherein R 1 and R 3 are each independently selected from a 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 a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (2′) that replaces the general formula (2) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.
73 . An organic electroluminescence element comprising 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 a following general formula (3):
wherein X is selected from a group consisting of oxygen, sulfur, and ═C(CN) 2 ; and W is a 4- to 8-membered ring and has a structure shown in a following general formula (3′) that replaces the general formula (3) above:
wherein Y is oxygen or sulfur, and Z is a structure that has 2 or more atoms and forms a part of the ring.Join the waitlist — get patent alerts
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