Compound and polymer compound containing the compound

Patent metadata

Field	Value
Publication number	US-11560383-B2
Application number	US-201916977128-A
Country	US
Kind code	B2
Filing date	Mar 4, 2019
Priority date	Mar 5, 2018
Publication date	Jan 24, 2023
Grant date	Jan 24, 2023

Abstract

Provided is a compound having higher fluorescence quantum yield and higher optical stability than a conventional FLAP and a polymer compound containing the compound.A: seven or eight-membered ring structure,Y1, Y2, Y3: halogen atom or the like,a1: number of Y1, a2: number of Y2,B: number of Y3,0≤m and n≤3: when 1≤m≤3, Y1 may be substituted with a structure portion defined by m, when 1≤n≤3, Y2 may be substituted with a structure portion defined by n, andB1, B2: Formulas (2-1) to (2-3).C1, C2, C3: structure containing a cyclic hydrocarbon compound,D1, D2, D3: substructure that inhibits aggregation,E1, E2, E3: polymerizable substructure,Z1: hydrogen atom or the like,c: number of substituent groups Z1,Z2, Z3: hydrogen atom or the like, and may form a ring with C2.

First claim

The invention claimed is:

1. A compound represented by a following general Formula (1):

wherein in general Formula (1),
A is represented by general Formula (3) and forms a conjugated system with a benzene ring bound to A:

m and n each denote, independently, an integer greater than or equal to 0 and less than or equal to 3,
B 1 and B 2 each denote, independently, a structure represented by general Formula (5-2), said structure having a —C═C— bond between two nitrogen atoms as a position to connect to the remaining of general Formula (1),

wherein in general Formula (5-2),
D 2 denotes a substructure that inhibits aggregation and has any of following structures:

wherein R 1 to R 7 each denote H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF 3 , CCl 3 , CN, or OCH 3 , and R 1 to R 7 may be the same or different,
E 2 denotes a polymerizable substituent group and is any of Formulas (E-1) to (E-18):

wherein in the Formulas (E-12) and (E-13), X denotes amide or ester but may not be included, R 1 in the Formulas (E-12) and (E-13) is the same as R 1 according to D 2 , R in Formulas (E-1) to (E-18) denotes a linear, branched, or cyclic alkyl group with 1-20 carbons or an aryl group with 6-20 carbons, R in Formulas (E-1) to (E-11) may not be included, and each filled circle represents D 2 ,
wherein one atom contained in R 1 to R 7 of D 2 can be replaced with E 2 in order to form E 2 -D 2 - existing in general Formula (5-2),
Z 2 and Z 3 each denote, independently, a substituent group selected from a hydrogen atom, a halogen atom, an alkyl group with 1-20 carbons that may have a substituent group, an alkynyl group with 2-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, and a cyano group,
wherein Z 4 in general Formula (5-2) is the same as the Z 2 and Z 3 .

2. A polymer compound made by polymerizing a compound represented by following general Formula (1):

wherein in general Formula (1),
A is represented by general Formula (3) and forms a conjugated system with a benzene ring bound to A:

m and n each denote, independently, an integer greater than or equal to 0 and less than or equal to 3,
B 1 and B 2 each denote, independently, a structure represented by general Formula (5-2), said structure having a —C═C— bond between two nitrogen atoms as a position to connect to the remaining of general Formula (1),

wherein in general Formula (5-2),
D 2 denotes a substructure that inhibits aggregation and has any of following structures:

wherein R 1 to R 7 each denote H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF 3 , CCl 3 , CN, or OCH 3 , and R 1 to R 7 may be the same or different,
E 2 denotes a polymerizable substituent group and is any of Formulas (E-1) to (E-18):

wherein in the Formulas (E-12) and (E-13), X denotes amide or ester but may not be included, R 1 in the Formulas (E-12) and (E-13) is the same as R 1 according to D 2 , R in Formulas (E-1) to (E-18) denotes a linear, branched, or cyclic alkyl group with 1-20 carbons or an aryl group with 6-20 carbons, R in Formulas (E-1) to (E-11) may not be included, and each filled circle represents D 2 ,
wherein one atom contained in R 1 to R 7 of D 2 can be replaced with E 2 in order to form E 2 -D 2 - existing in general Formula (5-2),
Z 2 and Z 3 each denote, independently, a substituent group selected from a hydrogen atom, a halogen atom, an alkyl group with 1-20 carbons that may have a substituent group, an alkynyl group with 2-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, and a cyano group, wherein Z 4 in general Formula (5-2) is the same as the Z 2 and Z 3 .

3. The polymer compound according to claim 2 , wherein the compound is bound via a urethane binding in the polymer compound.

4. A polymer compound made by polymerizing a compound represented by following general Formula (1):

wherein in general Formula (1),
A is represented by general Formula (3) and forms a conjugated system with a benzene ring bound to A:

m and n each denote, independently, an integer greater than or equal to 0 and less than or equal to 3,
B 1 and B 2 each denote, independently, a structure represented by general Formula (5-2), said structure having a —C═C— bond between two nitrogen atoms as a position to connect to the remaining of general Formula (1),

wherein in general Formula (5-2),
D 2 denotes a substructure that inhibits aggregation and has any of following structures:

wherein R 1 to R 7 each denote H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF 3 , CCl 3 , CN, or OCH 3 , and R 1 to R 7 may be the same or different,
E 2 denotes a polymerizable substituent group and is any of Formulas (E-1) to (E-18):

wherein in the Formulas (E-12) and (E-13), X denotes amide or ester but may not be included, R 1 in the Formulas (E-12) and (E-13) is the same as R 1 according to D 2 , R in Formulas (E-1) to (E-18) denotes a linear, branched, or cyclic alkyl group with 1-20 carbons or an aryl group with 6-20 carbons, R in Formulas (E-1) to (E-11) may not be included, and each filled circle represents D 2 ,
wherein one atom contained in R 1 to R 7 of D 2 can be replaced with E 2 in order to form E 2 -D 2 - existing in general Formula (5-2),
Z 2 and Z 3 each denote, independently, a substituent group selected from a hydrogen atom, a halogen atom, an alkyl group with 1

Assignees

• Japan Science & Tech Agency

Inventors

• Saito Shohei
• Yabu Hiroshi
• Abe Hiroya

Classifications

• C07D471/06

  Peri-condensed systems · CPC title

• C07D313/14

  [b,f]-condensed · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C08G18/3281

  containing three hydroxy groups · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title