Bis (aminostyryl) anthracene compound, synthesis is intermediate thereof, and process for production thereof
View Patent ↗A bis(aminostyryl)anthracene compound represented by the general formula [I] or the like below. (where R 2 and R 3 each denotes an unsubstituted aryl group; R 1 and R 4 each denotes an aryl group having a specific substituent such as methoxy group; and R 5 and R 6 each denotes a cyano group or the like.) A process for producing a bis(aminostyryl)anthracene compound represented by the general formula [I] by condensation of, for example, 4-(N,N-diarylamino)benzaldehyde with diphosphonic ester or diphosphonium. The bis(aminostyryl)anthracene compound emits intense yellow or red light. The process permits efficient production of the bis(aminostyryl)anthracene compound. The bis(aminostyryl)anthracene compound emits intense yellow or red light. The process permits efficient production of the bis(aminostyryl)anthracene compound.
1. A bis(aminostyryl)anthracene compound represented by formula [I], [II], [III], or [IV]
where R 2 and R 3 each denotes an unsubstituted aryl group, and R 1 and R 4 each denotes an aryl group represented by formula (1)
where R 7 , R 8 , R 9 , R 10 , and R 11 are identical or different groups, at least one of them being a saturated or unsaturated hydrocarbon oxy group or hydrocarbon group having at least one carbon; and R 5 and R 6 are identical or different groups, at least one of them being a hydrogen atom, cyano group, nitro group, or halogen atom
where R 12 , R 13 , R 14 , and R 15 are identical or different groups, each denoting an aryl group represented by formula (2)
where R 18 , R 19 , R 20 , R 21 , and R 22 are identical or different groups, at least one of them being a saturated or unsaturated hydrocarbon oxy group or hydrocarbon group having at least one carbon; and R 16 and R 17 are identical or different groups, at least one of them being a hydrogen atom, cyano group, nitro group, or halogen atom
where at least one of R 23 , R 24 , R 25 , and R 26 denotes an aryl group represented by formula (3), with the remainder being an unsubstituted aryl group
where R 29 , R 30 , R 31 , R 32 , and R 33 are identical or different groups, at least one of them being a saturated or unsaturated hydrocarbon amino group; and R 27 and R 28 are identical or different groups, at least one of them being a hydrogen atom, cyano group, nitro group, or halogen atom.
2. A bis(aminostyryl)anthracene compound represented by formula (6)
where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different each denoting an aryl group which may have a substituent, and if a substituent is present, said aryl group being one which is selected from aryl groups represented by formula (7), (8)
where R 52 , R 53 , each denotes a saturated or unsaturated hydrocarbon group having one or more carbons; n is an integer of 0 to 6.
3. A bis(aminostyryl)anthracene compound as defined in claim 2 , wherein R 52 , R 53 , each has from 1 to 6 carbons.
4. A bis(aminostyryl)anthracene compound as defined in claim 1 or 2 which is represented by formula (13), (13′), (14), (15)
where R 61 denotes a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms
where R 61 denotes a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms
where R 62 denotes a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms
where R 63 denotes a saturated or unsaturated hydrocarbon group or hydrocarbon oxy group having 1 to 6 carbon atoms.
5. A bis(aminostyryl)anthracene compound as defined in claim 1 or 2 which is represented by formulae (18)-1, (18)-2, (18)-2′, (18)-3, (18)-4 or (18)-11
6. A bis(aminostyryl)anthracene compound represented by formula (19)
where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different, each denoting an aryl group which may have a substituent, and if a substituent is present, said aryl group being one which is selected from aryl groups represented by the general formula (7), (8)
where R 52 , R 53 each denotes a saturated or unsaturated hydrocarbon group having one or more carbons; n is an integer of 0 to 6.
7. A bis(aminostyryl)anthracene compound as defined in claim 6 , wherein R 52 , R 53 each has 1 to 6 carbon atoms.
8. A bis(aminostyryl)anthracene compound as defined in claim 1 or 6 which is represented by formula (20), (21), (22)
where R 61 denotes a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms
where R 62 denotes a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms
where R 63 denotes a saturated or unsaturated hydrocarbon group or hydrocarbon oxy group having 1 to 6 carbon atoms.
9. A bis(aminostyryl)anthracene compound as defined in claim 1 or 6 which is represented by formulae (25)-1, (25)-2, (25)-2′, (25)-3, (25)-4, or 25-(11)
10. A bis(aminostyryl)anthracene compound which is represented by formula (26)
where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different, each denoting an aryl group which may have a substituent, and if a substituent is present, said aryl group being one which is selected from aryl groups represented by the general formula (7) or (8)
where R 52 , R 53 denotes a saturated or unsaturated hydrocarbon group having one or more carbons; n is an integer of 0 to 6.
11. A bis(aminostyryl)anthracene compound as defined in claim 10 , wherein R 52 , R 53 each has 1 to 6 carbon atoms.
12. A bis(aminostyryl)anthracene compound as defined in claim 1 or 10 which is represented by formulae (27), (28), (29)
where R 61 denotes a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms
where R 62 denotes a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms
where R 63 denotes a saturated or unsaturated hydrocarbon group or hydrocarbon oxy group having 1 to 6 carbon atoms.
13. A bis(aminostyryl)anthracene compound as defined in claim 1 or 10 which is represented by formulae (32)-1, (32)-2, (32)-2′, (32)-3, (32)-4.