Curable resin composition, and cured product of same

Patent metadata

Field	Value
Publication number	US-9646904-B2
Application number	US-201414758480-A
Country	US
Kind code	B2
Filing date	Jan 9, 2014
Priority date	Jan 9, 2013
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

The curable resin composition according to the present invention includes a polyorganosiloxane (A), a silsesquioxane (B), an isocyanurate compound (C), and a silane coupling agent (D). The polyorganosiloxane (A) is a polyorganosiloxane approximately devoid of aryl groups. The silsesquioxane (B) includes a ladder-like silsesquioxane. The curable resin composition has excellent heat resistance, transparency and flexibility. It offers superior reflow resistance and barrier properties to a corrosive gas.

First claim

The invention claimed is:

1. A curable resin composition comprising:
a polyorganosiloxane (A);
a silsesquioxane (B);
an isocyanurate compound (C); and
a silane coupling agent (D),
the polyorganosiloxane (A) comprising both:
a polyorganosiloxysilalkylene comprising a structure represented by Formula (I-1); and
a polyorganosiloxysilalkylene comprising a structure represented by Formula (I-2), Formulae (I-1) and (I-2) expressed as follows:

wherein R a to R f are, independently in each occurrence, selected from the group consisting of hydrogen, an aryl-free monovalent hydrocarbon group, and a monovalent heterocyclic group, where at least one of R a to R f is a monovalent group comprising an aliphatic carbon-carbon unsaturated bond; R g represents, independently in each occurrence, a C 2 -C 4 alkylene group; and s1 and s2 each independently represent an integer of 1 or more,

wherein R a to R f are, independently in each occurrence, selected from the group consisting of hydrogen, an aryl-free monovalent hydrocarbon group, and a monovalent heterocyclic group, where at least one of R a to R f is hydrogen; R g represents, independently in each occurrence, a C 2 -C 4 alkylene group; and s1 and s2 each independently represent an integer of 1 or more,
the silsesquioxane (B) comprising
a ladder-like silsesquioxane.

2. The curable resin composition according to claim 1 ,
wherein the silsesquioxane (B) comprises a ladder-like silsesquioxane comprising an aliphatic carbon-carbon double bond in molecule.

3. The curable resin composition according to claim 1 ,
wherein the silsesquioxane (B) comprises a ladder-like silsesquioxane comprising a Si—H bond in molecule.

4. The curable resin composition according to claim 1 ,
wherein the silsesquioxane (B) comprises a ladder-like silsesquioxane comprising an aryl group in molecule.

5. The curable resin composition according to claim 1 ,
wherein the isocyanurate compound (C) comprises an isocyanurate compound represented by Formula (1):

wherein R x , R y , and R z are each, identically or differently, selected from a group represented by Formula (2) and a group represented by Formula (3):

wherein R 1 and R 2 are each, identically or differently, selected from hydrogen and C 1 -C 8 straight or branched chain alkyl.

6. The curable resin composition according to claim 5 ,
wherein one or two of R x , R y , and R z in Formula (1) are independently the group represented by Formula (3).

7. The curable resin composition according to claim 1 ,
wherein the silane coupling agent (D) comprises an epoxy-containing silane coupling agent.

8. A cured product of the curable resin composition according to claim 1 .

9. An encapsulating agent comprising
the curable resin composition according to claim 1 .

10. A semiconductor device obtained by using the encapsulating agent according to claim 9 .

11. The curable resin composition according to claim 1 ,
wherein R g represents an ethylene group.

12. A curable resin composition comprising:
a polyorganosiloxane (A);
a silsesquioxane (B);
an isocyanurate compound (C);
a silane coupling agent (D); and
a hydrosilylation catalyst,
the polyorganosiloxane (A) being a polyorganosiloxane approximately devoid of aryl groups and epoxy groups,
the silsesquioxane (B) comprising a ladder-like silsesquioxane approximately devoid of epoxy groups,
the isocyanurate compound (C) comprising an isocyanurate compound represented by Formula (1):

wherein R x , R y , and R z are each, identically or differently, selected from a group represented by Formula (2) and a group represented by Formula (3), where one or two of R x , R y , and R z are independently the group represented by Formula (3), Formulae (2) and (3) expressed as follows:

wherein R 1 and R 2 are each, identically or differently, selected from hydrogen and C 1 -C 8 straight or branched chain alkyl.

13. The curable resin composition according to claim 12 ,
wherein the polyorganosiloxane (A) comprises both:
a polyorganosiloxysilalkylene comprising a structure represented by Formula (I-1); and
a polyorganosiloxysilalkylene comprising a structure represented by Formula (I-2), Formulae (I-1) and (I-2) expressed as follows:

wherein R a to R f are, independently in each occurrence, selected from the group consisting of hydrogen, an aryl-free monovalent hydrocarbon group, and a monovalent heterocyclic group, where at least one of R a to R f is a monovalent group comprising an aliphatic carbon-carbon unsaturated bond; R g represents, independently in each occurrence, an aryl-free divalent hydrocarbon group; and s1 and s2 each independently represent an integer of 1 or more,

wherein R a to R f are, independently in each occurrence, selected from the group consisting of hydrogen, an aryl-free monovalent hydrocarbon group, and a monovalent heterocyclic group, where at least one of R a to R f is hydrogen; R g represents, independently in each occurrence, an aryl-free divalent hydrocarbon group; and s1 and s2 each independently represent an integer of 1 or more.

14. The curable resin composition according to claim 12 ,
wherein the silane coupling agent (D) comprises an epoxy-containing silane coupling agent.

15. A cured product of the curable resin composition according to claim 12 .

16. An encapsulating agent comprising
the curable resin composition according to claim 12 .

17. A semiconductor device obtained by using the encapsulating agent according to claim 16 .

18. A curable resin composition comprising:
a polyorganosiloxane (A);
a silsesquioxane (B);
an isocyanurate compound (C); and
a silane coupling agent (D),
the polyorganosiloxane (A) comprising
a polyorganosiloxysilalkylene comprising a structure represented by Formula (I):

wherein R a , R b , R c , R d , R e , and R f are, independently in each occurrence, selected from the group consisting of hydrogen, an aryl-free monovalent hydrocarbon group, and a monovalent heterocyclic group; R g represents, independently in each occurrence, an aryl-free divalent hydrocarbon group; and s1 and s2 each independently represent an integer of 1 or more,
the silsesquioxane (B) comprising
a ladder-like silsesquioxane,

the isocyanurate compound (C) comprising an isocyanurate compound represented by Formula (1):

wherein R x , R y , and R z are each, identically or differently, selected from a group represented by Formula (2) and a group re

Assignees

• Daicel Corp

Inventors

• Nakagawa Yasunobu
• Kamuro Shigeaki

Classifications

• H10W74/476 Primary

  Organic materials comprising silicon · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• H01L23/296 Primary

  Electricity · mapped topic

• C09J183/04

  Polysiloxanes · CPC title

• C08L83/14

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence) · CPC title