Black dichroic dye
AssigneeBASF SE
InventorsJean-Pierre Bacher, Gerardus De Keyzer, Urs Lehmann
Life of this patent
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Abstract
Described is a black dichroic dye composition comprising 2 or more dyes, wherein at least one dye, generally a red dye and optionally a yellow dye, conforms to the formula A and at least one dye, usually a blue dye, conforms to the formula B Ar1—N═N—[Ar2—N═N—]qAr3—N═N—Ar4 (B) with symbols as defined in present claims. The dye composition is well suited for combination with liquid crystal material for use, inter alia, as polarizing film and/or in liquid crystal displays, showing, inter alia, high dichroic ratio and excellent compatibility with the LC material.
Claims19
A composition, comprising:
- a dye of formula A:
- and a dye of formula B:
- Ar1—N═N—[Ar2—N═N—]qAr3—N═N—Ar4 (B),
- wherein each of n, m, and p is from 0 to 2;
- q is 0 or 1;
- Ar1 is one of the formulae:
- Ar2 and Ar3 are independently 1,4-phenylene, 1,4-phenylene substituted by one or two R5, or 1,4-naphthylene;
- Ar4 is naphthyl substituted by one or two residues C1-C8alkylamino, one or two residues di(C1-C8alkyl)amino, one or two residues di(C1-C8alkyl)amino whose alkyl groups are linked together to form one common bridging group C1-C8alkylene or C2-C8alkylene interrupted by O or S or NR′3 or any combination thereof, or two residues C1-C8alkylamino whose alkyl groups are linked together to form one common bridging group C1-C8alkylene or C2-C8alkylene interrupted by O or S or NR′3 or any combination thereof;
- or thiophenyl substituted by R11 and optionally further substituted by C1-C8alkyl, phenyl, halogen, or CN;
- either R1 is substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, or substituted or unsubstituted C3-C5cycloalkyl interrupted by O, S, or NR′3;
- and R3 is H, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, or substituted or unsubstituted C3-C5cycloalkyl interrupted by O, S, or NR′3;
- or
- R1 and R3 together are substituted or unsubstituted C2-C12alkylene, substituted or unsubstituted C2-C8allylene interrupted by O, S, NR′3, or any combination thereof, thus forming, together with a nitrogen atom, an aliphatic N-heterocyclic residue of 2 to 12 carbon atoms;
- R′3 is H or C1-C8alkyl;
- each of R4, R5 and R6, are independently selected from the group consisting of unsubstituted or substituted C1-C4alkyl, C1-C4alkoxy, halogen, and CN;
- X is H, Hal, or COOR2;
- Xb is Hal, COOR2, CN, phenyl, R8-substituted phenyl, C3-C12cycloalkyl, or C1-C12alkyl-cyclohexyl,
- Hal is CF3, or halogen;
- R2 is unsubstituted or substituted C1-C12alkyl;
- R8 is C1-C12alkyl with an optionally substituted alkyl moiety, C1-C12alkoxy with an optionally substituted alkyl moiety, C1-C12alkyl-phenyl with an optionally substituted alkyl moiety, C1-C12alkyl-cyclohexyl with an optionally substituted alkyl moiety, C1-C12alkoxy-cyclohexyl with an optionally substituted alkyl moiety, C3-C12cycloalkyl, phenyl, CN, or Hal;
- R12 and R13 are independently H;
- Hal;
- nitro;
- formyl;
- SCN;
- CN;
- COOR2;
- COR2;
- C1-C12alkyl;
- C1-C12alkoxy;
- C1-C12alkylthio;
- C1-C12alkyl-SO2;
- phenyl;
- phenoxy;
- phenyl-SO2;
- phenyl substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, or C1-C8alkylthio;
- phenoxy substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, or C1-C8alkylthio;
- phenyl-SO2 substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, or C1-C8alkylthio;
- C2-C12alkyl interrupted by O;
- C3-C12alkoxy interrupted by O;
- C3-C12alkylthio interrupted by O;
- C1-C8alkyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C2-C3alkenyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C1-C8alkoxy substituted by CN, COOR2, phenyl, fluoro, or CF3;
- or C1-C8alkylthio substituted by CN, COOR2, phenyl, fluoro, or CF3;
- or R12 and R13 together are C3-C4alkylene;
- R14 is H;
- Hal;
- CN;
- SCN;
- COOR2;
- COR2;
- C1-C12alkyl;
- C3-C12cycloalkyl;
- C1-C12alkoxy;
- C1-C12alkylthio;
- C1-C12alkylamino;
- di(C1-C12alkyl)amino;
- pyrrolidinyl;
- piperidinyl;
- morpholinyl;
- phenyl;
- phenyl-SO2;
- phenyl substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, or C1-C8alkylthio;
- C2-C12alkyl interrupted by O;
- C3-C12alkoxy interrupted by O;
- C3-C12alkylthio interrupted by O;
- C1-C8alkyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C2-C3alkenyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C1-C8alkoxy substituted by CN, COOR2, phenyl, fluoro, or CF3;
- or C1-C8alkylthio substituted by CN, COOR2, phenyl, fluoro, or CF3;
- R15 is H;
- Hal;
- OCF3;
- CN;
- COOR2;
- COR2;
- C1-C12alkyl;
- C1-C12alkoxy;
- C1-C12alkylthio;
- C1-C12alkylamino;
- di(C1-C2alkyl)amino;
- C1-C2alkyl-CONH;
- C1-C12alkyl-SO2;
- pyrrolidinyl di(C1-C4alkyl)amino;
- morpholinyl;
- phenyl;
- phenyl-SO2;
- phenyl substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, C1-C8alkylthio, CN, CF3, or OCF3;
- phenyl-SO2 substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, C1-C8alkylthio, CN, CF3, or OCF3;
- C2-C12alkyl interrupted by O;
- C3-C12alkoxy interrupted by O;
- C3-C12alkylthio interrupted by O;
- C1-C8alkyl substituted by CN, COOR2, COR2, phenyl, R8-substituted phenyl, fluoro, or CF3;
- C2-C3alkenyl substituted by CN, COOR2, COR2, phenyl, R8-substituted phenyl, fluoro, or CF3;
- C1-C8alkoxy substituted by CN, COOR2, COR2, phenyl, R8-substituted phenyl, fluoro, or CF3;
- C1-C8alkylthio substituted by CN, COOR2, COR2, phenyl, R8-substituted phenyl, fluoro, or CF3;
- or C1-C8alkyl-SO2 substituted by CN, COOR2, COR2, phenyl, R8-substituted phenyl, fluoro, or CF3;
- R16 and R17 are independently H, halogen, nitro, C1-C12alkyl, or C1-C12alkoxy.
A compound of formula B10:
- wherein
- q is 0 or 1;
- Ar1 is phenyl substituted by Xb, or a heterocyclic residue of one of the formulae:
- Ar2 and Ar3 are independently 1,4-phenylene, 1,4-phenylene substituted by C1-C4alkyl, or 1,4-naphthylene;
- Xb is Hal, COOR2, CN, phenyl, R8-substituted phenyl, C3-C12cycloalkyl, C1-C12alkyl-cyclohexyl, or C1-C12alkoxy-cyclohexyl;
- Hal is CF3 or fluoro;
- R2 is C1-C8alkyl;
- R8 is C1-C12alkyl, C1-C12alkoxy, C3-C12cycloalkyl, phenyl, C1-C12alkyl-phenyl, C1-C12alkyl-cyclohexyl, or C1-C12alkoxy-cyclohexyl;
- R11 is pyrrolidinyl, piperidinyl, di(C1-C4alkyl)amino, or morpholinyl;
- either R12 and R13 are independently H;
- Hal;
- CN;
- COOR2;
- C1-C12alkyl;
- C1-C12alkoxy;
- C1-C12alkylthio;
- phenyl;
- phenyl substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy or C1-C8alkylthio;
- C2-C12alkyl interrupted by O;
- C3-C12alkoxy interrupted by O;
- C3-C12alkylthio each of which is interrupted by O;
- C1-C8alkyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C2-C3alkenyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C1-C8alkoxy substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C1-C8alkylthio substituted by CN, COOR2, phenyl, fluoro, or CF3;
- or R12 and R13 together are C3-C4alkylene;
- R14 is H;
- CF3;
- CN;
- COOR2;
- C1-C12alkyl;
- C1-C12alkoxy;
- C1-C12alkylthio;
- pyrrolidinyl;
- piperidinyl;
- di(C1-C4alkyl)amino;
- morpholinyl;
- phenyl;
- phenyl substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, or C1-C8alkylthio;
- C2-C12alkyl interrupted by O;
- C3-C12alkoxy interrupted by O;
- C3-C12alkylthio interrupted by O;
- C1-C8alkyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C2-C3alkenyl substituted by CN, COOR2, phenyl, fluoro, or CF3;
- C1-C8alkoxy substituted by CN, COOR2, phenyl, fluoro, or CF3;
- or C1-C8alkylthio substituted by CN, COOR2, phenyl, fluoro, or CF3;
- R15 is H;
- CF3;
- OCF3;
- CN;
- COOR2;
- C1-C12alkyl;
- C1-C12alkoxy;
- C1-C12alkylthio;
- C1-C12alkyl-SO2;
- pyrrolidinyl;
- di(C1-C4alkyl)amino;
- morpholinyl;
- phenyl;
- phenyl substituted by phenyl, C1-C8alkyl, cyclohexyl, C1-C8alkoxy, C1-C8alkylthio, CN, CF3, or OCF3;
- C2-C12alkyl interrupted by O;
- C3-C12alkoxy C3-C12alkylthio interrupted by O;
- C1-C8alkyl substituted by CN, COOR2, COR2, phenyl, fluoro, or CF3;
- C2-C3alkenyl substituted by CN, COOR2, COR2, phenyl, fluoro, or CF3;
- C1-C8alkoxy substituted by CN, COOR2, COR2, phenyl, fluoro, or CF3;
- C1-C8alkylthio substituted by CN, COOR2, COR2, phenyl, fluoro, or CF3;
- or C1-C8alkyl-SO2 substituted by CN, COOR2, COR2, phenyl, fluoro, or CF3;
- R16 and R17 are independently H, halogen, nitro, C1-C12alkyl, or C1-C12alkoxy,
- with the proviso that a compound of formula:
- wherein R21 is F, CF3, or CN, is excluded.
(canceled)
Dependencies are inferred from the claim text.