Bis (aminostyryl) naphthalene compound, synthesis intermediate thereof, and process for production thereof

A bis(aminostyryl)naphthalene compound represented by the general formula (6) below.

• 90
• (where Ar1, Ar2, Ar3, and Ar4 are identical or different, each denoting an aryl group which may have a substituent, said aryl group with a substituent being one which is selected from aryl groups represented by the general formula (7), (8), (9), (10), (11), (12), (12′), or (12″) below.
• 91
• (where R52, R53, and R54 each denotes a saturated or unsaturated hydrocarbon group having one or more carbons;
• R55, R56, R57, R58, R59, and R60 are identical or different, each denoting a saturated or unsaturated hydrocarbon group having one or more carbons;
• n is an integer of 0 to 6;
• m is an integer of 0 to 3;
• and 1 is an integer of 0 to 4.)

A bis(aminostyryl)naphthalene compound represented by the general formula (21) below.

• 105
• (where Ar1, Ar2, Ar3, and Ar4 are identical or different, each denoting an aryl group which may have a substituent, said aryl group with a substituent being one which is selected from aryl groups represented by the general formula (7), (8), (9), (10), (11), (12), (12′), or (12″) below.
• 106
• (where R52, R53, and R54 each denotes a saturated or unsaturated hydrocarbon group having one or more carbons;
• R55, R56, R57, R58, R59, and R60 are identical or different, each denoting a saturated or unsaturated hydrocarbon group having one or more carbons;
• n is an integer of 0 to 6;
• m is an integer of 0 to 3;
• and 1 is an integer of 0 to 4.)

A bis(aminostyryl)naphthalene compound which is represented by the general formula (30) below.

• 119
• (where Ar1, Ar2, Ar3, and Ar4 are identical or different, each denoting an aryl group which may have a substituent, said aryl group with a substituent being one which is selected from aryl groups represented by the general formula (7), (8), (9), (10), (11), (12), (12′), or (12″) below.
• 120
• (where R52, R53, and R54 each denotes a saturated or unsaturated hydrocarbon group having one or more carbons;
• R55, R56, R57, R58, R 59, and R60 are identical or different, each denoting a saturated or unsaturated hydrocarbon group having one or more carbons;
• n is an integer of 0 to 6;
• m is an integer of 0 to 3;
• and 1 is an integer of 0 to 4.)

A process for producing a bis(aminostyryl)naphthalene compound represented by the general formula [I], [II], [III], or [IV] below, said process comprising condensing at least one species of 4-(N,N-diarylamino)benzaldehyde represented by the general formula [V] or [VI] below and diphosphonic ester represented by the general formula [VII] below or diphosphonium represented by the general formula [VIII] below.

• 133
• (where R68 and R69 each denotes an aryl group corresponding to R1, R2, R12, R13 R23 R24 , R34 or R35 given below;
• and R70 and R71 each denotes an aryl group corresponding to R3, R4, R14, R15, R25, R26, R36 , or R37 given below.)
• 134
• (where R72 and R73 are identical or different, each denoting a hydrocarbon group;
• R74 and R75 each denotes a group corresponding to R5, R6, R16, R17, R27, R28, R38, or R39 given below;
• and X denotes a halogen atom.)
• 135
• (where R2 and R3 each denotes an unsubstituted aryl group, and R1 and R4 each denotes an aryl group represented by the general formula (1) below.)
• 136
• (where R7, R8, R9, R10, and R11 are identical or different groups, at least one of them being a saturated or unsaturated hydrocarbon oxy group, hydrocarbon group, or hydrocarbon amino group having one or more carbons;
• and R5 and R6 are identical or different groups, at least one of them being a hydrogen atom, cyano group, nitro group, trifluoromethyl group, or halogen atom.)
• 137
• (where R12, R13, R14, and R15 are identical or different groups, each denoting an aryl group represented by the general formula (2) below.)
• 138
• (where R18, R19, R20, R21, and R22 are identical or different groups, at least one of them being a saturated or unsaturated hydrocarbon oxy group or hydrocarbon group, or hydrocarbon amino group having one or more carbons;
• and R16 and R17 are identical or different groups, at least one of them being a hydrogen atom, cyano group, nitro group, trifluoromethyl group, or halogen atom.)
• 139
• (where at least one of R23, R24, R25, and R26 denotes an aryl group represented by the general formula (3) below, with the remainder being an unsubstituted aryl group.)
• 140
• (where R29, R30, R31, R32, and R33 are identical or different groups, at least one of them being a saturated or unsaturated hydrocarbon oxy group, hydrocarbon group, or hydrocarbon amino group;
• and R27 and R28 are identical or different groups, at least one of them being a hydrogen atom, cyano group, nitro group, trifluoromethyl group, or halogen atom.)
• 141
• (where R35 and R36 are identical or different groups, each denoting an aryl group represented by the general formula (4) below.)
• 142
• (where R40, R41, R42, R43, and R44 are identical or different groups, each denoting hydrogen or at least one of them being a saturated or unsaturated hydrocarbon oxy group, hydrocarbon group, or hydrocarbon amino group having one or more carbons;
• and R34 and R37 are identical or different groups, at least one of them being an aryl group represented by the general formula (5) below.)
• 143
• (where R45, R46, R47, R48, R49, R50, and R51 are identical or different groups, each denoting a hydrogen atom or at least one of them being a saturated or unsaturated hydrocarbon oxy group, hydrocarbon group, or hydrocarbon amino group having one or more carbons;
• and R38 and R39 are identical or different groups, at least one of them being a hydrogen atom, cyano group, nitro group, trifluoromethyl group, or halogen atom.)

A process for producing a diphosphonic ester or diphosphonium represented by the general formula [VII] or [VIII] below, said process comprising reacting an aryl halide compound represented by the general formula [IX] below and a trialkyl phosphite represented by the general formula [X] below or triphenyl phosphine (PPh3)

• 193
• (where R74 and R75s are identical or different, at least one of them denoting a hydrogen atom, cyano group, nitro group, trifluoromethyl group, or halogen atom, and X denotes a halogen atom.)
• P (OR76)3 or P (OR77 )3 General formula [X]
• (where R76 and R77 are identical or different, each denoting a hydrocarbon group.)
• 194
• (where R72 and R73 are identical or different, each denoting a hydrocarbon group;
• and R74, R75, and X are defined as above.)

A process for producing an aryl halide compound represented by the general formula [IX] below, said process comprising reacting an naphthalene compound represented by the general formula [XI] below with an N-halogenated succinimide represented by the general formula [XII] below.

• 199
• (where R74 and R75 are identical or different, at least one of them denoting a hydrogen atom, cyano group, nitro group, trifluoromethyl group, or halogen atom.)
• 200
• (where X denotes a halogen atom.)
• 201
• (where R74 and R75 are defined as above, and X denotes a halogen atom.)