Bis (aminostyryl) naphthalene compound, synthesis intermediate thereof, and process for production thereof
View Patent ↗A bis(aminostyryl)naphthalene 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)naphthalene 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)naphthalene compound emits intense yellow or red light. The process permits efficient production of the bis(aminostyryl)naphthalene compound.
1. A method of manufacturing a material for an electroluminescent element, the method comprising the steps of:
(A) producing one or more compounds represented by the formula [I], [II], [III], or [IV], said producing comprising condensing at least one species of 4-(N,N-diarylamino)benzaldehyde represented by the formula [V] or [VI] and a diphosphonic ester of formula [VII] or a diphosphonium of formula [VIII]:
where R 68 and R 69 each denotes an aryl group corresponding to R 1 , R 2 , R 12 , R 13 , R 23 , R 24 , R 34 , or R 35 ; and R 70 and R 71 each denotes an aryl group corresponding to R 3 , R 4 , R 14 , R 15 , R 25 , R 26 , R 36 , or R 37 ;
where R 72 and R 73 are identical or different, each denoting a hydrocarbon group; R 74 and R 75 are identical or different groups, at least one being a cyano group, a nitro group, a trifluoromethyl group, or a halogen atom, and the remainder being hydrogen atoms; and X denotes a halogen atom
wherein Formula [I] is
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 the formula (1):
where R 7 , R 8 , R 9 , R 10 , and R 11 are identical or different groups, at least one being a saturated or unsaturated hydrocarbon oxy group, a hydrocarbon group, or a hydrocarbon amino group having one or more carbons; and R 5 and R 6 identical or different groups, at least one being a cyano group, a nitro group, a trifluoromethyl group, or a halogen atom, the remainder being hydrogen atoms;
wherein Formula [II] is
where R 12 , R 13 , R 14 , and R 15 are identical or different groups, each denoting an aryl group of 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 a hydrocarbon group, or a hydrocarbon amino group having one or more carbons; and R 16 and R 17 are identical or different groups, at least one them being a cyano group, a nitro group, a trifluoromethyl group, or a halogen atom, the remainder being hydrogen atoms,
wherein Formula [III] is
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 thereof being a saturated or unsaturated hydrocarbon oxy group, a hydrocarbon group, or a hydrocarbon amino group; and R 27 and R 28 are identical or different groups, at least one being a cyano group, a nitro group, a trifluoromethyl group, or a halogen atom, the remainder being hydrogen atoms
wherein Formula [IV] is
where R 35 and R 36 are identical or different groups, each denoting an aryl group of formula (4):
where R 40 , R 41 , R 42 , R 43 , and R 44 are identical or different groups, each denoting hydrogen or at least one being a saturated or unsaturated hydrocarbon oxy group, a hydrocarbon group, or a hydrocarbon amino group having one or more carbons; and R 34 and R 37 are identical or different groups, at least one being an aryl group of formula (5):
where R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , and R 51 are identical or different groups, each denoting a hydrogen atom or at least one being a saturated or unsaturated hydrocarbon oxy group, a hydrocarbon group, or a hydrocarbon amino group having one or more carbons;
and R 38 and R 39 are identical or different groups, at least one being a cyano group, a nitro group, a trifluoromethyl group, or a halogen atom, the remainder being hydrogen atoms; and
(B) adding one or more fluorescent materials to the one or more compounds produced in step (A).
2. A material manufactured according to the method of claim 1 .
3. The material of claim 2 , wherein said material is a luminescent material.
4. A luminescent layer comprising the material of claim 3 .
5. The material of claim 2 , wherein said material is an electron transfer material.
6. An electron transfer layer comprising the material of claim 5 .
7. The material of claim 2 , wherein said material is a hole transfer material.
8. A hole transfer layer comprising the material of claim 7 .