RED PIGMENT COMPOSITION FOR COLOR FILTER

1 . A pigment composition, comprising:

a pigment of formula (I):

wherein

Ar 1 is each independently selected from the group consisting of an unsubstituted phenylene, a substituted phenylene substituted with R 1 , an unsubstituted C 2 -C 6 -heteroarylene, and a C 2 -C 6 -heteroarylene substituted with R 1 ;

Ar 2 is each independently selected from the group consisting of an un substituted C 6 -C 10 -aryl, a substituted C 6 -C 10 -aryl, an unsubstituted C 2 -C 6 -heteroaryl, and a substituted C 2 -C 6 -heteroaryl, wherein the substituted C 6 -C 10 -aryl and the substituted C 2 -C 6 -heteroaryl are substituted with R 2 and/or R 3 ;

R 1 is at least one selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN;

R 2 and R 3 are each independently selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN; or

R 2 and R 3 together with the aryl or heteroaryl ring to which they are bonded form an aromatic 5- or 6-membered ring or a heteroaromatic 5- or 6-membered ring, wherein the aromatic 5- or 6-membered ring or the heteroaromatic 5- or 6-membered ring is unsubstituted or substituted with R 4 ; and

R 4 is Cl or C 1 -C 4 -alkyl; and

a pigment derivative of formula (II):

(P 1 )—(X 1 ) m   (II),

wherein:

P 1 is a residue of a colorant chromophore,

X 1 is a group comprising at least one selected from the group consisting of an aliphatic carboxamide group, an aliphatic sulfonamide group, a carboxylic acid group, and a salt thereof, and

m is 1, 2, 3, or 4.

2 . The pigment composition of claim 1 , wherein X 1 is a group of formula

-A 1 -D-G  (III) or

-A 2 -E  (IV),

wherein:

A 1 and A 2 are each independently a direct bond or a C 1 -C 4 -alkylene;

D is at least one selected from the group consisting of —NH—CO—, —NH—SO 2 —, —CO—NR 5 —, and —SO 2 —NR 5 —;

G is —(C 1 -C 6 -alkylene)-NR 6 R 7 or —(C 1 -C 6 -alkylene)-NH—NR 6 R 7 , wherein the C 1 -C 6 -alkylene is optionally interrupted by —NH—;

R 5 is H; or

G and R 5 together with a linking nitrogen form a 5- or 6-membered ring, wherein the 5- or 6-membered ring is unsubstituted or substituted with C 1 -C 4 -alkyl and/or interrupted by at least one selected from the group consisting of NR 8 , O, and S;

R 6 and R 7 are each independently H or C 1 -C 4 -alkyl; or

R 6 and R 7 together with the linking nitrogen form a 5- or 6-membered ring, wherein the 5- or 6-membered ring is unsubstituted or substituted with C 1 -C 4 -alkyl and/or interrupted by at least one selected from the group consisting of NR 8 , O, and S;

R 8 is H or C 1 -C 4 -alkyl; and

E is C 6 -C 12 -aryl substituted with CO 2 H or a salt thereof.

3 . The pigment composition of claim 1 , wherein the pigment derivative of formula (II) is a diketopyrrolopyrrole derivative of formula (IIa):

wherein

m is 1 or 2;

r is 0, 1, or 2;

R 9 is each independently selected from the group consisting of Cl, Br, CF 3 , CN, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, SC 1 -C 4 -alkyl, Ar 3 , OAr 3 , and SAr 3 ;

Ar 3 is each independently C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl, wherein the C 6 -C 10 -aryl and/or the C 2 -C 6 -heteroaryl are unsubstituted or substituted with R 10 and/or R 11 ;

R 10 and R 11 are each independently selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN; or

R 10 and R 11 together with the C 6 -C 10 -aryl and/or the C 2 -C 6 -heteroaryl ring to which they are bonded form an aromatic or heteroaromatic ring, wherein the aromatic or heteroaromatic ring is unsubstituted or substituted with Cl or C 1 -C 4 -alkyl;

X 1 is a group of formula (III):

-A 1 -D-G  (III),

wherein A 1 is a direct bond or methylene;

D is at least one selected from the group consisting of —NH—CO—, —CO—NR 5 —, and —SO 2 —NR 5 —;

G is —(C 1 -C 4 -alkylene)-NR 6 R 7 , wherein the C 1 -C 4 -alkylene is optionally interrupted by —NH—;

R 5 is H; or

G and R 5 together with a linking nitrogen form a 6-membered ring, wherein the 6-membered ring is optionally substituted by C 1 -C 4 -alkyl and/or interrupted by at least one selected from the group consisting of NR 8 , O, and S;

R 6 and R 7 are each independently H or C 1 -C 4 -alkyl, or

R 6 and R 7 together with a linking nitrogen form a 6-membered ring, wherein the 6-membered ring is optionally substituted by C 1 -C 4 -alkyl and/or interrupted by at least one selected from the group consisting of NR 8 , O, and S; and

R 8 is H or C 1 -C 4 -alkyl.

4 . The pigment composition of claim 1 , wherein the pigment composition further comprises:

a pigment derivative of formula (V):

(P 2 )—(Y) n   (V),

wherein;

P 2 is a residue of a colorant chromophore;

Y is a group selected from the group consisting of OC 4 -C 25 -alkyl, SC 4 -C 25 -alkyl, OC 7 -C 25 -aralkyl, SC 7 -C 25 -aralkyl, OC 7 -C 25 -alkylaryl, SC 7 -C 25 -alkylaryl, and NR 12 R 13 ;

R 12 and R 13 are each independently selected from the group consisting of H, C 4 -C 25 -alkyl, C 7 -C 25 -aralkyl, and C 7 -C 25 -alkylaryl, with the proviso that the sum of carbon atoms of R 12 and R 13 is at least 8;

the alkyl group in Y is optionally interrupted by at least one selected from the group consisting of O, S, NR 14 , and phenylene;

R 14 is H or C 1 -C 4 -alkyl; and

n is 1, 2, 3, or 4.

5 . The pigment composition claim 4 , wherein the pigment derivative of formula (V) is a diketopyrrolopyrrole derivative of formula (Va):

wherein

n is 1;

s is 0, 1, or 2;

R 15 is each independently selected from the group consisting of Cl, Br, CF 3 , CN, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, SC 1 -C 4 alkyl, Ar 4 , OAr 4 , and SAr 4 ;

Ar 4 is C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl, wherein the C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl is unsubstituted or substituted with R 16 and/or R 17 ;

R 16 and R 17 are each independently selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN; or

R 16 and R 17 together with the aryl or heteroaryl ring to which they are bonded form an aromatic or heteroaromatic 5- or 6-membered ring, wherein the aromatic or heteroaromatic ring is unsubstituted or substituted with Cl or C 1 -C 4 -alkyl,

Y is selected from the group consisting of OC 8 -C 22 -alkyl, SC 8 -C 22 -alkyl, OC 12 -C 22 -aralkyl, SC 12 -C 22 -aralkyl, OC 12 -C 22 -alkylaryl, SC 12 -C 22 -alkylaryl, and NR 12 R 13 ,

R 12 and R 13 are each independently selected from the group consisting of H, C 8 -C 22 -alkyl, C 12 -C 22 -aralkyl, and C 12 -C 22 -alkylaryl;

each alkyl group in Y is optionally interrupted by at least one selected from the group consisting of O, S, NR 14 , and phenylene; and

R 14 is FT or C 1 -C 4 -alkyl.

6 . The pigment composition of claim 1 , wherein the amount of the pigment derivative of formula (I) is at least 65 wt %, and the amount of the pigment derivative of formula (II) is from 3 to 35 wt %, each amount based on the total weight of the pigment composition.

7 . The pigment composition of claim 1 , wherein the pigment composition further comprises

a pigment derivative of formula (VI):

(Z 2 ) p —(P 3 )—(A 3 -Z 1 ) q   (VI),

wherein;

P 3 is a residue of a colorant chromophore,

A 3 is C 1 -C 6 -alkylene;

Z 1 is a N-containing 5-membered heterocycle; and

Z 2 is SO 3 H or a salt thereof, or CO 2 H or a salt thereof,

p is a number of 0 to 2; and

q is a number of 1 or 2.

8 . The pigment composition of claim 7 , wherein Z 1 is at least one group selected from the group consisting of

wherein:

R 18 , R 19 , and R 20 are each independently selected from the group consisting of H, halogen, C 1 -C 18 -alkyl, C 1 -C 18 -alkyl substituted with halogen, C 1 -C 18 -alkyl substituted with OC 1 -C 6 -alkyl, C 1 -C 18 -alkyl substituted with di(C 1 -C 3 -alkyl)amino, C 6 -C 12 -aryl, C 6 -C 12 -aryl substituted with C 1 -C 18 -alkyl, C 6 -C 12 -aryl substituted with halogen, C 6 -C 12 -aryl substituted with nitro, and C 6 -C 12 -aryl substituted with OC 1 -C 6 -alkyl; and

two adjacent groups of R 18 , R 19 , and R 20 together with the heteroaryl ring to which they are bonded form at least one selected from the group consisting of a 5-7-membered alicyclic ring, a 5-7-membered aromatic ring, and a 5-7-membered heteroaromatic ring.

9 . The pigment composition of claim 1 , wherein the colorant chromophore of P 1 is at least one selected from the group consisting of a diketopyrrolopyrrole, a quinacridone, a dihydroquinacridone, a quinacridonequinone, an aminoanthraquinone, and a perylene; and

wherein the chromophore is unsubstituted or substituted.

10 . A process for preparing the pigment composition of claim 4 , wherein P 1 and P 2 are each independently a residue of a diketopyrrolopyrrole chromophore,

wherein the process comprises reacting a succinic diester with a compound of formula (VIII):

NC—Ar 1 —S—Ar 2   (VIII);

a compound of formula (IX):

optionally a compound of formula (X):

wherein;

Ar 1 is phenylene or C 2 -C 6 -heteroarylene, wherein the phenylene or the C 2 -C 6 -heteroarylene is unsubstituted or substituted with R 1 ;

Ar 2 is C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl, wherein the C 6 -C 10 -aryl or the C 2 -C 6 -heteroaryl is unsubstituted or substituted with R 2 and/or R 3 ;

R 1 is at least one selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN;

R 2 and R 3 are each independently of one another selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN; or

R 2 and R 3 together with the aryl or heteroaryl ring to which they are bonded form an aromatic 5- or 6-membered ring or a heteroaromatic 5- or 6-membered ring, wherein the aromatic 5- or 6-membered ring or the heteroaromatic 5- or 6-membered ring is unsubstituted or substituted with R 4 ,

R 4 is Cl or C 1 -C 4 -alkyl;

X 1 is a group comprising an aliphatic carboxamide group or an aliphatic sulfonamide group;

Y is at least one group selected from the group consisting of OC 4 -C 25 -alkyl, SC 4 -C 25 -alkyl, OC 7 -C 25 -aralkyl, SC 7 -C 25 -aralkyl, OC 7 -C 25 -alkylaryl, SC 7 -C 25 -alkylaryl, and NR 12 R 13 ;

R 12 and R 13 are each independently selected from the group consisting of H, C 4 -C 25 -alkyl, C 7 -C 25 -aralkyl, and C 7 -C 25 -alkylaryl, with the proviso that the sum of carbon atoms of R 12 and R 13 is at least 8; and the alkyl group in Y is optionally interrupted by at least one selected from the group consisting of O, S, NR 14 , and phenylene; and

R 14 is H or C 1 -C 4 -alkyl.

11 . A pigment dispersion, comprising the pigment composition of claim 1 and a polymeric dispersant.

12 . A photosensitive resist formulation, comprising:

the pigment dispersion of claim 11 ,

a resin,

a photopolymerization initiator,

an ethylenically unsaturated monomer, and

a solvent.

13 . A color filter, comprising the pigment composition of claim 1 .

14 . A method of coloring a photosensitive resist formulation with the pigment composition of claim 1 , comprising:

contacting a photosensitive resist formulation with the pigment composition to produce at least one selected from the group consisting of a color filter, a printing ink, a liquid ink, a coating composition, a paint, a plastic, a film, and a fiber.

15 . A pigment derivative of formulae (XI) or (XII):

wherein:

m is 1 or 2;

X 1 is a group comprising an aliphatic carboxamide group or an aliphatic sulfonamide group;

Ar 3 is C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl, wherein the C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl is unsubstituted or substituted with R 10 and/or R 11 ;

R 10 and R 11 are each independently selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN; or

R 10 and R 11 together with the aryl or heteroaryl ring to which they are bonded form an aromatic 5- or 6-membered ring or a heteroaromatic 5- or 6-membered ring, wherein the aromatic 5- or 6-membered ring or the heteroaromatic 5- or 6-membered ring is unsubstituted or substituted with Cl or C 1 -C 4 -alkyl;

Ar 5 is phenylene or C 2 -C 6 -heteroarylene, wherein the phenylene or the C 2 -C 6 -heteroarylene is unsubstituted or substituted with R 21 ;

R 21 is at least one selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN;

Ar 6 is at each occurrence independently at least one selected from the group consisting of phenylene and C 2 -C 6 -heteroarylene, wherein the phenylene or the C 2 -C 6 -heteroarylene is unsubstituted or substituted with R 22 ;

R 22 is at least one selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN;

Ar 7 is at each occurrence independently at least one selected from the group consisting of C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl, wherein the C 6 -C 10 -aryl or C 2 -C 6 -heteroaryl is unsubstituted or substituted with R 23 and/or R 24 ;

R 23 and R 24 are each independently at least one selected from the group consisting of Cl, Br, C 1 -C 4 -alkyl, OC 1 -C 4 -alkyl, CF 3 , and CN; or

R 23 and R 24 together with the aryl or heteroaryl ring to which they are bonded form an aromatic 5- or 6-membered ring or a heteroaromatic 5- or 6-membered ring, wherein the aromatic 5- or 6-membered ring or the heteroaromatic 5- or 6-membered ring is unsubstituted or substituted with Cl or C 1 -C 4 -alkyl;

Z 2 is SO 3 H or a salt thereof;

t is a number of 1 to 4;

u is a number of 0 to 3; and

t+u is 1 to 4.

16 . A pigment dispersion, comprising a pigment composition and a polymeric dispersant, wherein the pigment composition is obtained by the process of claim 10 .