Resin composition, solid imaging element obtained using same, and process for producing same

Patent metadata

Field	Value
Publication number	US-10316146-B2
Application number	US-201615546873-A
Country	US
Kind code	B2
Filing date	Jan 20, 2016
Priority date	Jan 30, 2015
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

A resin composition which includes (a) a solvent, (b) silica particles, (c) a polysiloxane, and (d) a secondary or tertiary amine compound, wherein the solvent (a) includes an organic acid. From the resin composition, an even film is easily formed even on bases having protrusions and recesses, such as lens shapes. The resin composition has satisfactory storage stability.

First claim

The invention claimed is:

1. A resin composition comprising a solvent (a), silica particles (b), a polysiloxane (c) and a secondary or tertiary amine compound (d), wherein:
the solvent (a) contains an organic acid; and
the polysiloxane (c) is a polysiloxane obtained by hydrolyzing and/or polycondensing at least one alkoxysilane compound which includes at least one compound represented by general formula (8):

wherein m represents an integer of 0 to 2, R 7 represents an alkylene group having 1 to 4 carbon atoms, and each of R 8 s independently represents hydrogen or an alkyl group having 1 to 4 carbon atoms.

2. The resin composition according to claim 1 , wherein the organic acid contained in the solvent (a) is an organic acid having a pH of 4.0 to 6.8 when diluted 5-fold in terms of mass ratio with a 50% by mass aqueous ethanol solution.

3. The resin composition according to claim 1 , wherein the organic acid includes a solvent having a β-diketone structure represented by general formula (1):

wherein, in general formula (1), R 1 and R 2 each may be the same or different, and represent —CH 3 , —C 2 H 5 , —C 3 H 7 , —C 4 H 9 , —OCH 3 , —OC 2 H 5 , —OC 3 H 7 , or —OC 4 H 9 .

4. The resin composition according to claim 1 , wherein a proportion of the solvent having a β-diketone structure represented by general formula (1) in the solvent (a) is 10% by weight or more and less than 70% by weight.

5. The resin composition according to claim 1 , wherein the solvent having a β-diketone structure represented by general formula (1) has a boiling point of 50° C. or more and 200° C. or less.

6. The resin composition according to claim 1 , wherein the silica particles (b) each have a particle size of 1 to 100 nm.

7. The resin composition according to claim 1 , wherein the secondary or tertiary amine compound (d) is a compound represented by general formula (9):

wherein R 9 and R 10 each may be the same or different, and represent an aliphatic hydrocarbon group having 2 to 12 carbon atoms, and R 11 is an aliphatic hydrocarbon group having 2 to 12 carbon atoms or a hydrogen atom.

8. The resin composition according to claim 1 , wherein a content of the secondary or tertiary amine compound (d) is 1 to 10% by weight based on a total amount of the silica particles (b) and the polysiloxane (c).

9. The resin composition according to claim 1 , wherein the at least one alkoxysilane compound additionally includes a compound represented by general formula (7):

wherein R 3 is a fluorinated alkyl group having 1 to 5 carbon atoms, and R 4 , R 5 and R 6 each independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms.

10. A solid imaging element comprising a photoelectric conversion portion, a lens provided above a light-receiving surface of the photoelectric conversion portion, and an anti-reflection film provided on the lens, wherein the anti-reflection film includes a cured film of a resin composition comprising a solvent (a), silica particles (b), a polysiloxane (c) and a secondary or tertiary amine compound (d), wherein the solvent (a) contains an organic acid.

11. The solid imaging element according to claim 10 , wherein when a thickness of the cured film in the lens top is defined as drop, when thicknesses of the cured film are defined as d 45L and d 45R at points where in the arbitrary cross section that passes through the lens top and that is orthogonal to the lens bottom surface, a line drawn perpendicularly to the lens bottom surface from the lens top intersects with the lens bottom surface and a line extending at 45° in a left direction and a line extending at 45° in a right direction from the intersecting point of the lens bottom surface intersect with the lens, and an average value of d 45L and d 45R is defined as d 45 , the d TOP and the d 45 satisfy 0≤(d 45 −d TOP )/d TOP )≤0.20.

12. The solid imaging element according to claim 10 , wherein the cured film has a film thickness in a range of 50 to 200 nm.

13. The solid imaging element according to claim 10 , wherein the cured film has a refractive index of 1.2 or more and 1.4 or less at a wavelength of 550 nm.

14. The solid imaging element according to claim 10 , wherein a difference in refractive index between the lens and the cured film is 0.2 to 0.8 at a wavelength of 550 nm.

15. A process for producing the solid imaging element according to claim 10 , the process comprising a step of applying the resin composition onto the lens, and a step of heating the resin composition.

16. The process for producing the solid imaging element according to claim 15 , wherein the applying step is a step of applying the resin composition onto the lens by a spin coating method.

Assignees

• Toray Industries

Inventors

• Hibino Toshiyasu
• Fujii Manami
• Suwa Mitsuhito

Classifications

• C09D183/04

  Polysiloxanes · CPC title

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title

• C08K5/10

  Esters; Ether-esters · CPC title

• C08K5/07

  Aldehydes; Ketones · CPC title

• C08J2383/04

  Polysiloxanes · CPC title