Negative photosensitive resin composition, cured film obtained by curing same, method for producing cured film, optical device provided with cured film, and backside-illuminated CMOS image sensor

Patent metadata

Field	Value
Publication number	US-9977329-B2
Application number	US-201515113119-A
Country	US
Kind code	B2
Filing date	Jan 21, 2015
Priority date	Jan 24, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The present invention provides a negative photosensitive resin composition including the following (a) to (d): (a) metallic compound particles, (b) a polysiloxane compound, (c) a compound having at least 1 group containing an α,β-unsaturated carboxylate ester structure, and (d) a photopolymerization initiator, the composition also including (e) a compound containing maleimide group.

First claim

The invention claimed is:

1. A negative photosensitive resin composition comprising the following (a) to (d):
(a) metallic compound particles,
(b) a polysiloxane compound,
(c) a compound having at least 1 group containing an α,β-unsaturated carboxylate ester structure, and
(d) a photopolymerization initiator, the composition further comprising
(e) a compound containing maleimide group.

2. A negative photosensitive resin composition according to claim 1 wherein the polysiloxane compound (b) is a polysiloxane compound containing the structural unit represented by general formula (1) and/or (2):

wherein R 1 is an organic group containing carboxyl group and/or a dicarboxylic anhydride structure, R 2 is hydrogen, an alkyl group containing 1 to 6 carbon atoms, an acyl group containing 2 to 6 carbon atoms, or an aryl group containing 6 to 16 carbon atoms.

3. A negative photosensitive resin composition according to claim 2 wherein the polysiloxane compound (b) further contains a structural unit represented by general formula (3) and/or (4):

wherein R 3 is an organic group containing an alkenyl group containing 2 to 10 carbon atoms, R 4 is hydrogen, an alkyl group containing 1 to 6 carbon atoms, an acyl group containing 2 to 6 carbon atoms, an organic group containing an alkenyl group containing 2 to 10 carbon atoms, or an aryl group containing 6 to 16 carbon atoms.

4. A negative photosensitive resin composition according to claim 3 wherein R 3 is an allyl group, a vinyl group, (meth)acryloyl group, or styryl group.

5. A negative photosensitive resin composition according to claim 1 wherein the compound (c) having at least 1 group containing an α,β-unsaturated carboxylate ester structure is a compound selected from general formulae (5) to (10):

wherein in general formula (5), R 5 is single bond, a chain aliphatic group containing 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group containing 3 to 16 carbon atoms; the plurality of R 3 being independently the same or different; R 6 is hydrogen or methyl group, the plurality of R 6 being independently the same or different; h is an integer of 0 to 3; i and j are integer of 0 to 2, i+j being 1 to 2,

wherein in general formula (6), R 7 is single bond, a chain aliphatic group containing 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group containing 3 to 16 carbon atoms, the plurality of R 7 being independently the same or different, R 8 is hydrogen or methyl group, the plurality of R 8 being independently the same or different; and k is an integer of 1 to 2,

wherein in general formula (7), R 9 is single bond, a chain aliphatic group containing 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group containing 3 to 16 carbon atoms, the plurality of R 9 being independently the same or different; R 10 is hydrogen or methyl group, the plurality R 10 being independently the same or different; R 11 is hydrogen or a chain aliphatic group containing 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group containing 3 to 16 carbon atoms, the plurality of R 11 being independently the same or different; and l and m are an integer of 0 to 2, l+m being 1 to 2,

wherein in general formula (8), R 12 is single bond, a chain aliphatic group containing 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group containing 3 to 16 carbon atoms, the plurality of R 11 being independently the same or different; and o is an integer of 1 to 2,

wherein in general formula (9), R 13 is single bond, a chain aliphatic group containing 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group containing 3 to 16 carbon atoms, the plurality of R 12 being independently the same or different; and p is an integer of 1 to 2,

wherein in general formula (10), q is an integer of 0 to 3 and R 14 is a chain aliphatic group containing 1 to 10 carbon atoms and 1 to 3 oxygen atoms.

6. A negative photosensitive resin composition according to claim 1 wherein R 1 of the polysiloxane compound (b) is an organic group having a dicarboxylic anhydride represented by any one of general formula (11) to (13):

wherein in the general formula (11) to (13), R 15 , R 16 , and R 17 are single bond, a chain aliphatic hydrocarbon group containing 1 to 10 carbon atoms, a cyclic aliphatic hydrocarbon group containing 3 to 16 carbon atoms, an alkyl carbonyloxy group containing 2 to 6 carbon atoms, carbonyl group, ether group, ester group, amide group, an aromatic group containing 6 to 16 carbon atoms, or a divalent group having any one of these groups; the hydrogen atom of these groups being optionally substituted with an alkyl group containing 1 to 10 carbon atoms, an alkenyl group containing 2 to 10 carbon atoms, an aryl group containing 6 to 16 carbon atoms, an alkylcarbonyloxy group containing 2 to 6 carbon atoms, hydroxy group, amino group, carboxyl group, or thiol group; and r, s, t, and u represent an integer of 0 to 3.

7. A negative photosensitive resin composition according to claim 1 wherein ratio of molar amount of the Si atoms in the structural unit represented by the general formula (1) and/or (2) constituting the polysiloxane compound to molar amount of the Si atom of the polysiloxane compound (b) is at least 5 mol % to up to 30 mol %.

8. A negative photosensitive resin composition according to claim 1 wherein the metallic compound particles (a) is at least one metal compound particles selected from aluminum compound particles, tin compound particles, titanium compound particles, and zirconium compound particles; or a composite particles of at least one metallic compound selected from aluminum compound, tin compound, titanium compound, and zirconium compound with a silicon compound.

9. A negative photosensitive resin composition according to claim 1 wherein the metallic compound particles (a) and the polysiloxane compound (b) are partially bonded.

10. A negative photosensitive resin composition according to claim 1 wherein the metallic compound particles (a) have a number average particle diameter of 1 nm to 400 nm.

11. A negative photosensitive resin composition according to claim 1 wherein at least 10 parts by weight to up to 500 parts by weight of the metallic compound particles (a) is used in relation to 100 parts by weight of the polysiloxane compound (b).

12. A cured film prepared by curing the negative photosensitive resin composition of claim 1 .

13. An LED luminaire having the cured film of claim 12 .

14. An image sensor having the cured film of claim 12 .

Assignees

• Toray Industries

Inventors

• Iimori Hirokazu
• Hibino Toshiyasu
• Suwa Mitsuhito

Classifications

• G03F7/0757 Primary

  Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title

• F21Y2115/10

  Light-emitting diodes [LED] · CPC title

• G03F7/0047

  characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing · CPC title

• G03F7/031

  Organic compounds not covered by group G03F7/029 · CPC title

• G02B5/223

  containing organic substances, e.g. dyes, inks or pigments · CPC title