Photosensitive resin composition and cured film comprising the same

1. A photosensitive resin composition comprising:

a poly(imide-benzoxazine) block copolymer comprising one or more repeat units selected from the group consisting of a repeat unit represented by the following Chemical Formula 1 and a repeat unit represented by the following Chemical Formula 2; and

a photo-curable multifunctional acrylic compound:

in Chemical Formulas 1 and 2,

Y 1 is a C6-20 tetravalent aliphatic cyclic group; a C6-20 tetravalent aromatic cyclic group; or a C4-20 tetravalent heteroaromatic cyclic group comprising one or more heteroatoms selected from the group consisting of N, O, and S; the tetravalent aliphatic cyclic group, tetravalent aromatic cyclic group, or tetravalent heteroaromatic cyclic group is unsubstituted or substituted with at least one of —OH, —F, —Cl, —Br, —I, —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —NO 2 , —CN, —COCH 3 , CH 3 COO—, and —CO 2 C 2 H 5 ; the aliphatic cyclic group, aromatic cyclic group, or heteroaromatic cyclic group optionally has, two or more rings conjugated to form a condensed ring, or two or more rings linked by —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p , —(CF 2 ) q —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or —C(═O)NH—, wherein 1≤p≤10 and 1≤q≤10,

Y 2 includes a C6-20 divalent aliphatic cyclic group or a C6-20 divalent aromatic cyclic group; the divalent aliphatic or aromatic cyclic group is unsubstituted or substituted with at least one of —OH, —F, —Cl, —Br, —I, —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —NO 2 , —CN, —COCH 3 , CH 3 COO—, and —CO 2 C 2 H 5 ; the divalent aliphatic or aromatic cyclic group optionally has two or more rings conjugated to form a condensed ring, or two or more rings linked by —O—, —S—,—C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or —C(═O)NH—, wherein 1≤p≤10 and 1≤q≤10,

R 1 's are each independently a hydrogen atom, 2-hydroxybenzyl, 3-hydroxybenzyl, or 4-hydroxybenzyl,

A 1 and A 2 are each independently a direct bond; a C6-20 divalent aliphatic cyclic group; a C6-20 divalent aromatic cyclic group; or a C4-20 tetravalent heteroaromatic cyclic group comprising one or more heteroatoms selected from the group consisting of N, O, and S,

X 1 and X 2 are each independently a group represented by the following Chemical Formula 3a or 3b:

the mark

indicates a part where the group represented by Chemical Formula 3a or 3b is linked to an adjacent atom in the Chemical Formula 1, and

m and n are each independently a number of 5 to 10,000.

2. The photosensitive resin composition according to claim 1 , wherein Y 1 is a tetravalent group selected from the group consisting of the following structural formulas:

and in the structural formulas,

each cyclic group is unsubstituted or substituted with —OH, —F, —Cl, —Br, —I, —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —NO 2 , —CN, —COCH 3 , CH 3 COO—, and —CO 2 C 2 H 5 ,

each L 1 is independently —O—, —S—,—C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or —C(═O)NH—, wherein 1≤p≤10 and 1≤q≤10, and

is a part where the tetravalent group is linked to an adjacent atom in the Chemical Formula 1.

3. The photosensitive resin composition according to claim 1 , wherein Y 2 is a divalent group selected from the group consisting of the following structural formulas:

and in the structural formulas,

each cyclic group is unsubstituted or substituted with —OH, —F, —Cl, —Br, —I, —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —NO 2 , —CN, —COCH 3 , CH 3 COO—, and —CO 2 C 2 H 5 ,

each L 2 is independently, a —O—, —S—,—C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or —C(═O)NH—, wherein 1≤p≤10 and 1≤q≤10, and

is a part where the divalent group is linked to an adjacent atom in the Chemical Formula 1.

4. The photosensitive resin composition according to claim 1 , wherein A 1 and A 2 are each independently a direct bond or a divalent group selected from the group consisting of the following structural formulas:

and in the structural formulas,

each L 3 is independently —O—, —S—,—C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or —C(═O)NH—, wherein 1≤p≤10 and 1≤q≤10, and

is a part where the divalent group is linked to an adjacent atom in the Chemical Formula 1.

5. The photosensitive resin composition according to claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 4:

and in Chemical Formula 4,

A 1 , A 2 , X 1 , X 2 , m, and n are each independently as defined in claim 1 , and

L 1 and L 2 are each independently —O—, —S—,—C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or —C(═O)NH—, wherein 1≤p≤10 and 1≤q≤10.

6. The photosensitive resin composition according to claim 1 , wherein in the poly(imide-benzoxazine) block copolymer, the weight ratio of the repeat unit having a polymerization degree m and the repeat unit having a polymerization degree n is 1:0.01 to 1:100.

7. The photosensitive resin composition according to claim 1 , wherein the poly(imide-benzoxazine) block copolymer has a weight average molecular weight of 5000 to 100,000 g/mol.

8. The photosensitive resin composition according to claim 1 , wherein the photocurable multifunctional acrylic compound includes one or more acrylic compounds selected from the group consisting of an acrylate-based compound, a polyester acrylate based compound, a polyurethane acrylate based compound, an epoxy acrylate based compound, and a caprolactone modified acrylate based compound.

9. The photosensitive resin composition according to claim 1 , wherein the composition comprises 1 to 50 parts by weight of the photocurable multifunctional acrylic compounds, based on 100 parts by weight of the poly(imide-benzoxazine) block copolymer.

10. A method of preparing a film comprising curing the photosensitive resin composition of claim 1 .

11. The method of claim 10 , wherein the curing is performed at a temperature of from 160 to 220° C.

12. A film formed by the method of claim 10 .