Black dichroic dye
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 Ar 1 —N═N—[Ar 2 —N═N—] q Ar 3 —N═N—Ar 4 (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.
1. A composition, comprising:
a dye of formula A:
and
a dye of formula B:
Ar 1 —N═N—[Ar 2 —N═N—] q Ar 3 —N═N—Ar 4 (B),
wherein each of n, m, and p is from 0 to 2;
q is 0 or 1;
Ar 1 is one of the formulae:
Ar 2 and Ar a are independently 1,4-phenylene, 1,4-phenylene substituted by one or two R 5 , or 1,4-naphthylene;
Ar 4 is naphthyl substituted by one or two residues C 1 -C 8 alkylamino, one or two residues di(C 1 -C 8 alkyl)amino, one or two residues di(C 1 -C 8 alkyl)amino whose alkyl groups are linked together to form one common bridging group C 1 -C 8 alkylene or C 2 -C 8 alkylene interrupted by O or S or NR′ 3 or any combination thereof, or two residues C 1 -C 8 alkylamino whose alkyl groups are linked together to form one common bridging group C 1 -C 8 alkylene or C 2 -C 8 alkylene interrupted by O or S or NR′ 3 or any combination thereof; or thiophenyl substituted by R 11 and optionally further substituted by C 1 -C 8 alkyl, phenyl, halogen, or CN, wherein
R 11 is NR′R″, with R′ and R″ independently selected from H or C 1 -C 4 alkyl or C 3 -C 12 cycloalkyl or phenyl or substituted phenyl; or R′ and R″ together forming one common bridging group C 1 -C 8 alkylene or C 2 -C 8 alkylene interrupted by O, S and/or NR′ 3
either R 1 is substituted or unsubstituted C 1 -C 12 alkyl, substituted or unsubstituted C 3 -C 12 cycloalkyl, or substituted or unsubstituted C 3 -C 5 cycloalkyl interrupted by O, S, or NR′ 3 ; and R 3 is H, substituted or unsubstituted C 1 -C 12 alkyl, substituted or unsubstituted C 3 -C 12 cycloalkyl, or substituted or unsubstituted C 3 -C 5 cycloalkyl interrupted by O, S, or NR′ 3 ; or
R 1 and R 3 together are substituted or unsubstituted C 2 -C 12 alkylene, substituted or unsubstituted C 2 -C 8 alkylene 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 C 1 -C 8 alkyl;
each of R 4 , R 5 , and R 6 , are independently selected from the group consisting of unsubstituted or substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, and CN;
X is H, Hal, or COOR 2 ;
Xb is Hal, COOR 2 , CN, phenyl, R 8 -substituted phenyl, C 3 -C 12 cycloalkyl, or C 1 -C 12 alkyl-cyclohexyl,
Hal is CF 3 , or halogen;
R 2 is unsubstituted or substituted C 1 -C 12 alkyl;
R 8 is C 1 -C 12 alkyl with an optionally substituted alkyl moiety, C 1 -C 12 alkoxy with an optionally substituted alkyl moiety, C 1 -C 12 alkyl-phenyl with an optionally substituted alkyl moiety, C 1 -C 12 alkyl-cyclohexyl with an optionally substituted alkyl moiety, C 1 -C 12 alkoxy-cyclohexyl with an optionally substituted alkyl moiety, C 3 -C 12 cycloalkyl, phenyl, CN, or Hal;
R 12 and R 13 are independently H; Hal; nitro; formyl; SCN; CN; COOR 2 ; COR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; C 1 -C 12 alkyl-SO 2 ; phenyl; phenoxy; phenyl-SO 2 ; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; phenoxy substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; phenyl-SO 2 substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy interrupted by O; C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; or R 12 and R 13 together are C 3 -C 4 alkylene;
R 14 is H; Hal; CN; SCN; COOR 2 ; COR 2 ; C 1 -C 12 alkyl; C 3 -C 12 cycloalkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; C 1 -C 12 alkylamino; di(C 1 -C 12 alkyl)amino; pyrrolidinyl; piperidinyl; morpholinyl; phenyl; phenyl-SO 2 ; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy interrupted by O; C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ;
R 15 is H; Hal; OCF 3 ; CN; COOR 2 ; COR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; C 1 -C 12 alkylamino; di(C 1 -C 12 alkyl)amino; C 1 -C 12 alkyl-CONH; C 1 -C 12 alkyl-SO 2 ; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl-SO 2 ; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, CN, CF 3 , or OCF 3 ; phenyl-SO 2 substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, CN, CF 3 , or OCF 3 ; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy interrupted by O; C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , COR 2 , phenyl, R 8 -substituted phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , COR 2 , phenyl, R 8 -substituted phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , COR 2 , phenyl, R 8 -substituted phenyl, fluoro, or CF 3 ; C 1 -C 8 alkylthio substituted by CN, COOR 2 , COR 2 , phenyl, R 8 -substituted phenyl, fluoro, or CF 3 ; or C 1 -C 8 alkyl-SO 2 substituted by CN, COOR 2 , COR 2 , phenyl, R 8 -substituted phenyl, fluoro, or CF 3 ;
R 16 and R 17 are independently H, halogen, nitro, C 1 -C 12 alkyl, or C 1 -C 12 alkoxy.
2. The composition of claim 1 ,
wherein the dye of formula A comprises a red dye and optionally a yellow dye, and
the dye of formula B comprises a blue dye,
which composition is a black dichroic dye composition.
3. The composition of claim 1 ,
wherein the dye of formula A is of formula A1:
wherein m is 0 or 1;
R 4 and R 5 are independently selected from C 1 -C 4 alkyl;
Hal is F, or CF 3 ;
n is from 0 to 2;
either R 1 is substituted or unsubstituted C 1 -C 12 alkyl, substituted or unsubstituted C 3 -C 12 cycloalkyl, or substituted or unsubstituted C 3 -C 5 cycloalkyl interrupted by O, S, or NR′ 3 ; and R 3 is H, substituted or unsubstituted C 1 -C 12 alkyl, substituted or unsubstituted C 3 -C 12 cycloalkyl, or substituted or unsubstituted C 3 -C 5 cycloalkyl interrupted by O, S, or NR′ 3 ; or
R 1 and R 3 together are substituted or unsubstituted C 2 -C 12 alkylene, substituted or unsubstituted C 2 -C 8 alkylene 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 C 1 -C 8 alkyl; and
X is H, Hal, or COOR 2 .
4. The composition of claim 2 ,
wherein the yellow dye is present and has formula A, wherein N(R 1 )R 3 is morpholinyl and any of R 4 , R 5 , or R 6 , is methyl; and
in the red dye of formula A, N(R 1 )R 3 is pyrrolidinyl, piperidinyl, or di(C 1 -C 4 alkyl)amino, and any of R 4 , R 5 , or R 6 , is methyl; and
the dye of formula B is a blue dye, of any of the formulae B1, B2, B3, or B4:
wherein,
q is 0 or 1;
Ar is 1,4-phenylene, 1,4-phenylene substituted by methyl, or 1,4-naphthylene;
Ar 1 is one of the formulae:
Ar 3 is 1,4-phenylene, 1,4-phenylene substituted by one or two methyl, or 1,4-naphthylene;
Xb is Hal, COOR 2 , CN, phenyl, R 8 -substituted phenyl, cyclohexyl, or C 1 -C 12 alkyl-cyclohexyl;
Hal is CF 3 or fluoro;
R 2 is C 1 -C 8 alkyl;
R 8 is C 1 -C 8 alkyl, cyclohexyl, or C 1 -C 8 alkyl-cyclohexyl;
R 11 is pyrrolidinyl, piperidinyl, di(C 1 -C 4 alkyl)amino, or morpholinyl;
R 12 and R 13 are independently H; Hal; CN; COOR 2 ; C 1 -C 8 alkyl; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, or C 1 -C 8 alkoxy; C 2 -C 8 alkyl interrupted by O; or C 3 -C 8 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN or COOR 2 ; vinyl substituted by CN or COOR 2 ; or
R 12 and R 13 together are C 3 -C 4 alkylene;
R 14 is CF 3 ; CN; COOR 2 ; C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 alkylthio; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl or C 1 -C 8 alkyl; C 2 -C 8 alkyl interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, or CF 3 ; vinyl substituted by CN, COOR 2 , phenyl, or CF 3 , or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, or CF 3 ;
R 15 is CF 3 ; OCF 3 ; CN; COOR 2 ; C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 alkylthio; C 1 -C 8 alkyl-SO 2 ; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl or C 1 -C 8 alkyl; C 2 -C 8 alkyl interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, or CF 3 ; vinyl substituted by CN, COOR 2 , phenyl, or CF 3 ; C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, or CF 3 ; or C 1 -C 8 alkyl-SO 2 substituted by CN, COOR 2 , phenyl, or CF 3 ;
R 16 and R 17 are independently H, halogen, or nitro;
either R 18 is H or C 1 -C 8 alkylamino; and
R 19 is C 1 -C 8 alkyl;
or the alkyl groups of R 18 and R 19 form a common bridging group C 1 -C 3 alkylene; and
R 20 is H or C 1 -C 8 alkyl.
5. The composition of claim 1 , wherein the dye of formula A comprises a compound A2:
and a compound A3:
and the dye of formula B comprises a compound B6, B6′, B7, B8, B10, or any combination thereof:
wherein Hal is fluoro or CF 3 ;
n is from 0 to 2;
either R 19 is branched C 3 -C 6 alkyl; and R 20 is H, or
R 19 and R 20 are C 1 -C 4 alkyl;
R 2 is linear or branched C 1 -C 8 alkyl;
q is 0 or 1;
Ar 1 is phenyl substituted by Xb, or a heterocyclic residue of one of the formulae:
Ar 2 and Ar 3 are independently 1,4-phenylene, 1,4-phenylene substituted by C 1 -C 4 alkyl, or 1,4-naphthylene;
Xb is Hal, COOR 2 , CN, phenyl, R 8 -substituted phenyl, C 3 -C 12 cycloalkyl, C 1 -C 12 alkyl-cyclohexyl, or C 1 -C 12 alkoxy-cyclohexyl;
Hal is CF 3 or fluoro;
R 8 is C 1 -C 12 alkoxy, C 3 -C 12 cycloalkyl, phenyl, C 1 -C 12 alkyl-phenyl, C 1 -C 12 alkyl-cyclohexyl, or C 1 -C 12 alkoxy-cyclohexyl;
R 11 is pyrrolidinyl, piperidinyl, di(C 1 -C 4 alkyl)amino, or morpholinyl;
R 12 and R 13 are independently H; Hal; CN; COOR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; C 2 -C 12 alkyl interrupted by O, C 3 -C 12 alkoxy interrupted by O; C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; or R 12 and R 13 together are C 3 -C 4 alkylene;
R 14 is H; CF 3 ; CN; COOR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; pyrrolidinyl; piperidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, fluoro or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , phenyl, fluoro or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , phenyl, fluoro or CF 3 ; or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, fluoro or CF 3 ;
R 15 is H; CF 3 ; OCF 3 ; CN; COOR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; C r C 12 alkyl-SO 2 ; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 , or C 1 -C 8 alkyl-SO 2 substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; and
R 16 and R 17 are independently H, halogen, nitro, C 1 -C 12 alkyl, or C 1 -C 12 alkoxy.
6. The composition of claim 1 , wherein the dye of formula A is of formula A4:
wherein X is H;
m is 1;
n is 0, 1, or 2;
R 4 and R 5 are methyl;
the moiety —N(R 1 )R 3 is pyrrolidinyl; and
the dye of formula B is one compound of formulae B1, B2, B3, or B4:
wherein
q is 0 or 1;
Ar is 1,4-phenylene, 1,4-phenylene substituted by methyl, or 1,4-naphthylene;
Ar 1 is one of the formulae:
Ar 3 is 1,4-phenylene, 1,4-phenylene substituted by one or two methyl, or 1,4-naphthylene;
Xb is Hal, COOR 2 , CN, phenyl, R 8 -substituted phenyl, cyclohexyl, or C 1 -C 12 alkyl-cyclohexyl;
Hal is CF 3 or fluoro;
R 2 is C 1 -C 8 alkyl;
R 8 is C 1 -C 8 alkyl, cyclohexyl, or C 1 -C 8 alkyl-cyclohexyl;
R 11 is pyrrolidinyl, piperidinyl, di(C 1 -C 4 alkyl)amino, or morpholinyl;
R 12 and R 13 are independently H; Hal; CN; COOR 2 ; C 1 -C 8 alkyl; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, or C 1 -C 8 alkoxy; C 2 -C 8 alkyl interrupted by O; or C 3 -C 8 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN or COOR 2 ; vinyl substituted by CN or COOR 2 ; or
R 12 and R 13 together are C 3 -C 4 alkylene;
R 14 is CF 3 ; CN; COOR 2 ; C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 alkylthio; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl or C 1 -C 8 alkyl; C 2 -C 8 alkyl interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, or CF 3 ; vinyl substituted by CN, COOR 2 , phenyl, or CF 3 or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, or CF 3 ;
R 15 is CF 3 ; OCF 3 ; CN; COOR 2 ; C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 alkylthio; C 1 -C 8 alkyl-SO 2 ; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl or C 1 -C 8 alkyl; C 2 -C 8 alkyl interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, or CF 3 ; vinyl substituted by CN, COOR 2 , phenyl, or CF 3 ; C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, or CF 3 ; or C 1 -C 8 alkyl-SO 2 substituted by CN, COOR 2 , phenyl, or CF 3 ;
R 16 and R 17 are independently H, halogen, or nitro;
either R 18 is H or C 1 -C 8 alkylamino; and
R 19 is C 1 -C 8 alkyl;
or the alkyl groups of R 18 and R 19 form a common bridging group C 1 -C 3 alkylene; and
R 20 is H or C 1 -C 8 alkyl.
7. The composition of claim 1 , further comprising a liquid crystal material, wherein the dyes are dissolved.
8. The composition of claim 1 , wherein a ratio of total weight parts of the dye of formula (A) to the dye of formula (B) is from 0.1:20 to 5:1.
9. The composition of claim 7 , comprising:
from 1 to 20 parts by weight in total of the dye of formula (B),
from 0.1 to 5 parts by weight in total of the dye of formula (A),
based on from 50 to 2000 parts by weight in total of liquid crystal material.
10. A liquid crystal display comprising the composition of claim 1 .
11. The liquid crystal display of claim 10 comprising the composition in a polarizing film.
12. A compound of formula B10:
wherein
q is 0 or 1;
Ar 1 is phenyl substituted by Xb, or a heterocyclic residue of one of the formulae:
Ar 2 and Ar 3 are independently 1,4-phenylene, 1,4-phenylene substituted by C 1 -C 4 alkyl, or 1,4-naphthylene;
Xb is Hal, COOR 2 , CN, phenyl, R 8 -substituted phenyl, C 3 -C 12 cycloalkyl, C 1 -C 12 alkyl-cyclohexyl, or C 1 -C 12 alkoxy-cyclohexyl;
Hal is CF 3 or fluoro;
R 2 is C 1 -C 8 alkyl;
R 8 is C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 12 cycloalkyl, phenyl, C 1 -C 12 alkyl-phenyl, C 1 -C 12 alkyl-cyclohexyl, or C 1 -C 12 alkoxy-cyclohexyl;
R 11 is pyrrolidinyl, piperidinyl, di(C 1 -C 4 alkyl)amino, or morpholinyl;
either R 12 and R 13 are independently H; Hal; CN; COOR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy interrupted by O; C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; or R 12 and R 13 together are C 3 -C 4 alkylene;
R 14 is H; CF 3 ; CN; COOR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; pyrrolidinyl; piperidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, or C 1 -C 8 alkylthio; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy interrupted by O; C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ; or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, fluoro, or CF 3 ;
R 15 is H; CF 3 ; OCF 3 ; CN; COOR 2 ; C 1 -C 12 alkyl; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; C 1 -C 12 alkyl-SO 2 ; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, CN, CF 3 , or OCF 3 ; C 2 -C 12 alkyl interrupted by O; C 3 -C 12 alkoxy C 3 -C 12 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , COR 2 , phenyl, fluoro, or CF 3 ; C 2 -C 3 alkenyl substituted by CN, COOR 2 , COR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkoxy substituted by CN, COOR 2 , COR 2 , phenyl, fluoro, or CF 3 ; C 1 -C 8 alkylthio substituted by CN, COOR 2 , COR 2 , phenyl, fluoro, or CF 3 ; or C 1 -C 8 alkyl-SO 2 substituted by CN, COOR 2 , COR 2 , phenyl, fluoro, or CF 3 ;
R 16 and R 17 are independently H, halogen, nitro, C 1 -C 12 alkyl, or C 1 -C 12 alkoxy,
with the proviso that a compound of formula:
wherein R 21 is F, CF 3 , or CN, is excluded.
13. The composition of claim 5 , wherein the compound of formula B10 is of formula B11, B12, or B13:
wherein
q is 0 or 1;
Ar 5 is a heterocyclic residue of the formula:
Ar 6 is a heterocyclic residue of one of the formulae:
wherein
Xb is Hal, COOR 2 , CN, phenyl, or R 8 -substituted phenyl;
Hal is CF 3 or fluoro;
R 2 is C 1 -C 8 alkyl;
R 8 is C 1 -C 8 alkyl, cyclohexyl, phenyl, C 1 -C 8 alkyl-phenyl, or C 1 -C 8 alkyl-cyclohexyl;
R 11 is pyrrolidinyl, di(C 1 -C 4 alkyl)amino, or morpholinyl;
either R 12 and R 13 are independently H; Hal; CN; COOR 2 ; C 1 -C 8 alkyl; phenyl; phenyl substituted by phenyl, C 1 -C 8 alkyl, cyclohexyl, or C 1 -C 8 alkoxy; C 2 -C 8 alkyl interrupted by O; C 3 -C 8 alkylthio interrupted by O; C 1 -C 8 alkyl substituted by CN or COOR 2 ; or vinyl substituted by CN or COOR 2 ; or R 12 and R 13 together are C 3 -C 4 alkylene;
R 14 is CF 3 ; CN; COOR 2 ; C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 alkylthio; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl or C 1 -C 8 alkyl; C 2 -C 8 alkyl interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, or CF 3 ; vinyl substituted by CN, COOR 2 , phenyl, or CF 3 ; or C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, or CF 3 ;
R 15 is CF 3 ; OCF 3 ; CN; COOR 2 ; C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 alkylthio; C 1 -C 8 alkyl-SO 2 ; pyrrolidinyl; di(C 1 -C 4 alkyl)amino; morpholinyl; phenyl; phenyl substituted by phenyl or C 1 -C 8 alkyl; C 2 -C 8 alkyl interrupted by O; C 1 -C 8 alkyl substituted by CN, COOR 2 , phenyl, or CF 3 ; vinyl substituted by CN, COOR 2 , phenyl, or CF 3 ; C 1 -C 8 alkylthio substituted by CN, COOR 2 , phenyl, or CF 3 ; or C 1 -C 8 alkyl-SO 2 substituted by CN, COOR 2 , phenyl, or CF 3 ;
R 16 and R 17 are independently H, halogen, or nitro.
14. A process for the preparation of a polarizing film or a liquid crystal display, comprising:
dissolving the composition of claim 1 in liquid crystal material.
15. The composition of claim 1 , wherein Ar 4 is of formula:
wherein R 11 is NR′R″, with R′ and R″ independently selected from the group consisting of H, C 1 -C 4 alkyl, C 3 -C 12 cycloalkyl, phenyl, and substituted phenyl, or R′ and R″ are together a common bridging group C 1 -C 8 alkylene, C 2 -C 8 alkylene interrupted by O, S, NR′ 3 , or any combination thereof.
16. The composition of claim 1 , wherein Hal is CF 3 or fluoro.
17. The composition of claim 15 , wherein R 11 is pyrrolidinyl, piperidinyl, di(C 1 -C 4 alkyl)amino, or morpholinyl.
18. The composition of claim 1 , wherein any substituent of alkyl moieties is selected from the group consisting of halogen, CF 3 , CN, OH, C 1 -C 4 alkoxy, and phenyl; C 1 -C 8 dialkylamino; or a N-bonded aliphatic or aromatic heterocyclic ring containing from 2 to 5 carbon ring atoms and optionally one oxygen ring atom besides the bonding nitrogen atom.