JP2009265649A5 - - Google Patents

Claims (20)

(A) A pigment dispersion having a pigment dispersant, (B) a pigment, and (F) a solvent, wherein the (A) pigment dispersant is a nitrogen-containing monomer represented by the following general formula (I) And a graft copolymer comprising a polymer chain and a polymerizable oligomer comprising a group having an ethylenically unsaturated double bond at its terminal as a copolymerization component, and further the amino group contained in the nitrogen-containing monomer and the following general group A pigment dispersion for a color filter, wherein the organic phosphate compound represented by formula (II) is a graft copolymer in which a salt is formed.

[In the formulas (I) to (II), R ¹ Is a hydrogen atom or a methyl group, R ² And R ³ Are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, A is an alkylene group having 1 to 8 carbon atoms, and — [CH (R ⁶ ) -CH (R ⁷ -O] _x -CH (R ⁶ ) -CH (R ⁷ )-Or-[(CH ₂ ) _y -O] _z -(CH ₂ ) _y A divalent group represented by R, ⁴ And R ^{4 ’} Each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, or — [CH (R ⁹ ) -CH (R ¹⁰ -O] _a -R ⁸ ,-[(CH ₂ ) _b -O] _c -R ⁸ Or -O-R ^{4 "} A monovalent group represented by R ⁴ And R ^{4 ’} Any of which contains a carbon atom.
  R ^{4 "} Is an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group,-[CH (R ⁹ ) -CH (R ¹⁰ -O] _a -R ⁸ Or-[(CH ₂ ) _b -O] _c -R ⁸ It is a monovalent group shown by these. R ⁶ , R ⁷ , R ⁹ And R ¹⁰ Each independently represents a hydrogen atom or a methyl group, R ⁸ Is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, —CHO, —CH ₂ CHO, -CO-CH = CH ₂ , -CO-C (CH ₃ ) = CH ₂ Or -CH ₂ COOR ¹² A monovalent group represented by R ¹² Is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. R ⁴ , R ^{4 ’} , R ^{4 "} And R ⁸ In the above, each of the alkyl group, alkenyl group, aralkyl group and aryl group may have a substituent.
  x and a are integers of 0 to 18, y and b are integers of 1 to 5, and z and c are integers of 0 to 18. ] The pigment dispersion for a color filter according to claim 1, wherein the group having an ethylenically unsaturated double bond is a (meth) acryloyl group, a vinyl group, or an allyl group.   The pigment dispersion for a color filter according to claim 1 or 2, wherein the polymer chain has at least one structural unit represented by the following general formula (III) or general formula (IV).

[In the formulas (III) and (IV), R ^{1 ’} Is a hydrogen atom or a methyl group, R ⁵ Is an alkyl group having 1 to 18 carbon atoms, an alkylene group having 1 to 8 carbon atoms, an aralkyl group, an aryl group, a cyano group,-[CH (R ⁶ ) -CH (R ⁷ -O] _x -R ¹¹ ,-[(CH ₂ ) _y -O] _z -R ¹¹ ,-[CO- (CH ₂ ) _y -O] _z -R ¹¹ , -CO-O-R ^{5 ’} Or -O-CO-R ¹³ It is a monovalent group shown by these.
  R ^{5 ’} Is an alkyl group having 1 to 18 carbon atoms, an alkylene group having 1 to 8 carbon atoms, an aralkyl group, an aryl group, a cyano group,-[CH (R ⁶ ) -CH (R ⁷ -O] _x -R ¹¹ ,-[(CH ₂ ) _y -O] _z -R ¹¹ ,-[CO- (CH ₂ ) _y -O] _z -R ¹¹ Or -O-CO-R ¹³ A monovalent group represented by R ¹³ Represents an alkyl group having 1 to 18 carbon atoms.
  l represents an integer of 1 to 5, and m and m 'represent an integer of 5 to 200. R ⁶ , R ⁷ , X, y, z are the same as above and R ¹¹ Is the above R ⁸ Is the same. ]   R in the general formula (II) ⁴ And R ^{4 ’} The color filter pigment dispersion according to any one of claims 1 to 3, wherein any of the above is an aryl group or an aralkyl group which may have a substituent.   R in the general formula (II) ⁴ And R ^{4 ’} The colorant pigment dispersion according to any one of claims 1 to 4, which has a polymerizable group.   The pigment dispersion for a color filter according to claim 5, wherein the polymerizable group is a (meth) acryloyl group, a vinyl group, or an allyl group.   (B) The pigment particle dispersion for color filters according to any one of claims 1 to 6, wherein the pigment has an average particle diameter of 10 to 100 nm.   (A) As a pigment dispersant, a nitrogen-containing monomer represented by the following general formula (I) and a polymerizable oligomer composed of a polymer chain and a group having an ethylenically unsaturated double bond at its terminal are used as a copolymerization component. A step of preparing a graft copolymer that is a graft copolymer, further comprising a salt formed by the amino group of the nitrogen-containing monomer and an organic phosphate compound represented by the following general formula (II):
  (F) A method for producing a pigment dispersion for a color filter, comprising the step of adding the pigment dispersant (A) and the pigment (B) in a solvent and dispersing the pigment.

[In the formulas (I) to (II), R ¹ Is a hydrogen atom or a methyl group, R ² And R ³ Are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, A is an alkylene group having 1 to 8 carbon atoms, and — [CH (R ⁶ ) -CH (R ⁷ -O] _x -CH (R ⁶ ) -CH (R ⁷ )-Or-[(CH ₂ ) _y -O] _z -(CH ₂ ) _y A divalent group represented by R, ⁴ And R ^{4 ’} Each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, or — [CH (R ⁹ ) -CH (R ¹⁰ -O] _a -R ⁸ ,-[(CH ₂ ) _b -O] _c -R ⁸ Or -O-R ^{4 "} A monovalent group represented by R ⁴ And R ^{4 ’} Any of which contains a carbon atom.
  R ^{4 "} Is an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group,-[CH (R ⁹ ) -CH (R ¹⁰ -O] _a -R ⁸ Or-[(CH ₂ ) _b -O] _c -R ⁸ It is a monovalent group shown by these. R ⁶ , R ⁷ , R ⁹ And R ¹⁰ Each independently represents a hydrogen atom or a methyl group, R ⁸ Is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, —CHO, —CH ₂ CHO, -CO-CH = CH ₂ , -CO-C (CH ₃ ) = CH ₂ Or -CH ₂ COOR ¹² A monovalent group represented by R ¹² Is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. R ⁴ , R ^{4 ’} , R ^{4 "} And R ⁸ In the above, each of the alkyl group, alkenyl group, aralkyl group and aryl group may have a substituent.
  x and a are integers of 0 to 18, y and b are integers of 1 to 5, and z and c are integers of 0 to 18. ] Color filter negative having (A) pigment dispersant, (B) pigment, (C) alkali-soluble resin, (D) polyfunctional monomer, (E) photoinitiator, and (F) solvent. The (A) pigment dispersant comprises a nitrogen-containing monomer represented by the following general formula (I), a polymer chain, and a group having an ethylenically unsaturated double bond at its terminal. A graft copolymer containing a polymerizable oligomer as a copolymerization component, and a graft copolymer in which an amino group of the nitrogen-containing monomer and an organic phosphate compound represented by the following general formula (II) form a salt. A negative resist composition for color filters, which is a polymer.

[In the formulas (I) to (II), R ¹ is a hydrogen atom or a methyl group, R ² and R ³ are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and A is a carbon atom having 1 carbon atom. To 8 alkylene groups, — [CH (R ⁶ ) —CH (R ⁷ ) —O] _x —CH (R ⁶ ) —CH (R ⁷ ) — or — [(CH ₂ ) _y —O] _z — ( A divalent group represented by CH ₂ ) _y —, R ⁴ and R ^{4 ′} are each independently a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, 1 represented by an aryl group, — [CH (R ⁹ ) —CH (R ¹⁰ ) —O] _a —R ⁸ , — [(CH ₂ ) _b —O] _c —R ⁸ , or —O—R ^{4 ″} the valence of the group, one of R ⁴ and R ^{4 'comprises} a carbon atom.
R ^{4 ″} is an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, — [CH (R ⁹ ) —CH (R ¹⁰ ) —O] _a —R ⁸ , Or a monovalent group represented by — [(CH ₂ ) _b —O] _c —R ⁸ , wherein R ⁶ , R ⁷ , R ⁹ and R ¹⁰ are each independently a hydrogen atom or a methyl group, and R ⁸ is A hydrogen atom or an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, —CHO, —CH ₂ CHO, —CO—CH═CH ₂ , —CO—C (CH ₃ ) = a monovalent group represented by CH ₂ or —CH ₂ COOR ¹² , wherein R ¹² is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. R ⁴ , R ^{4 ′} , R ^{4 ″} and R ⁴ in ^8, an alkyl group, an alkenyl group, an aralkyl group, an aryl Each may have a substituent.
x and a are integers of 0 to 18, y and b are integers of 1 to 5, and z and c are integers of 0 to 18. ] The negative resist composition for a color filter according to claim 9 , wherein the group having an ethylenically unsaturated double bond is a (meth) acryloyl group, a vinyl group, or an allyl group. The negative resist composition for a color filter according to claim 9 or 10 , wherein the polymer chain has at least one structural unit represented by the following general formula (III) or general formula (IV).

[In the formulas (III) and (IV), R ^{1 ′} is a hydrogen atom or a methyl group, R ⁵ is an alkyl group having 1 to 18 carbon atoms, an alkylene group having 1 to 8 carbon atoms, an aralkyl group, an aryl group, a cyano group. , — [CH (R ⁶ ) —CH (R ⁷ ) —O] _x —R ¹¹ , — [(CH ₂ ) _y —O] _z —R ¹¹ , — [CO— (CH ₂ ) _y —O] _z A monovalent group represented by —R ¹¹ , —CO—O—R ^{5 ′} or —O—CO—R ¹³ .
R ^{5 ′} is an alkyl group having 1 to 18 carbon atoms, an alkylene group having 1 to 8 carbon atoms, an aralkyl group, an aryl group, a cyano group, — [CH (R ⁶ ) —CH (R ⁷ ) —O] _x —. A monovalent group represented by R ¹¹ , — [(CH ₂ ) _y —O] _z —R ¹¹ , — [CO— (CH ₂ ) _y —O] _z —R ^11, or —O—CO—R ¹³ ; Yes, R ¹³ represents an alkyl group having 1 to 18 carbon atoms.
l represents an integer of 1 to 5, and m and m ′ represent an integer of 5 to 200. R ⁶ , R ⁷ , x, y, and z are the same as described above, and R ¹¹ is the same as R ⁸ described above. ] The color filter negative according to any one of claims 9 to 11 , wherein any one of R ⁴ and R ^{4 '} in the general formula (II) is an aryl group or an aralkyl group which may have a substituent. Type resist composition. The negative resist composition for color filter according to any one of claims 9 to 12 , wherein R ⁴ and R ^{4 '} in the general formula (II) have a polymerizable group. The negative resist composition for a color filter according to claim 13 , wherein the polymerizable group is a (meth) acryloyl group, a vinyl group, or an allyl group. The negative resist composition for a color filter according to any one of claims 9 to 14 , wherein (B) the pigment has an average particle size of 10 to 100 nm. (D) The negative resist composition for a color filter according to any one of claims 9 to 15 , wherein the polyfunctional monomer is a compound having two or more ethylenically unsaturated bonds. The negative resist composition for a color filter according to claim 16 , wherein the compound having two or more ethylenically unsaturated bonds is a polyfunctional (meth) acrylate.   (A) As a pigment dispersant, a nitrogen-containing monomer represented by the following general formula (I) and a polymerizable oligomer composed of a polymer chain and a group having an ethylenically unsaturated double bond at its terminal are used as a copolymerization component. A step of preparing a graft copolymer that is a graft copolymer, further comprising a salt formed by the amino group of the nitrogen-containing monomer and an organic phosphate compound represented by the following general formula (II):
  (F) In the solvent, adding the (A) pigment dispersant and (B) the pigment, and dispersing the pigment to prepare a pigment dispersion;
  A negative type for color filter, comprising the step of adding and mixing (C) an alkali-soluble resin, (D) a polyfunctional monomer, and (E) a photopolymerization initiator to the pigment dispersion obtained in the above step. A method for producing a resist composition.

[In the formulas (I) to (II), R ¹ Is a hydrogen atom or a methyl group, R ² And R ³ Are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, A is an alkylene group having 1 to 8 carbon atoms, and — [CH (R ⁶ ) -CH (R ⁷ -O] _x -CH (R ⁶ ) -CH (R ⁷ )-Or-[(CH ₂ ) _y -O] _z -(CH ₂ ) _y A divalent group represented by R, ⁴ And R ^{4 ’} Each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, or — [CH (R ⁹ ) -CH (R ¹⁰ -O] _a -R ⁸ ,-[(CH ₂ ) _b -O] _c -R ⁸ Or -O-R ^{4 "} A monovalent group represented by R ⁴ And R ^{4 ’} Any of which contains a carbon atom.
  R ^{4 "} Is an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group,-[CH (R ⁹ ) -CH (R ¹⁰ -O] _a -R ⁸ Or-[(CH ₂ ) _b -O] _c -R ⁸ It is a monovalent group shown by these. R ⁶ , R ⁷ , R ⁹ And R ¹⁰ Each independently represents a hydrogen atom or a methyl group, R ⁸ Is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, an aryl group, —CHO, —CH ₂ CHO, -CO-CH = CH ₂ , -CO-C (CH ₃ ) = CH ₂ Or -CH ₂ COOR ¹² A monovalent group represented by R ¹² Is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. R ⁴ , R ^{4 ’} , R ^{4 "} And R ⁸ In the above, each of the alkyl group, alkenyl group, aralkyl group and aryl group may have a substituent.
  x and a are integers of 0 to 18, y and b are integers of 1 to 5, and z and c are integers of 0 to 18. ] A colored layer formed using the negative resist composition for color filters according to any one of claims 9 to 17 , or the negative resist composition for color filters obtained by the production method according to claim 18. A color filter comprising: A liquid crystal display device comprising the color filter according to claim 19 .