US 10,947,384 B2Granted

Curable resin composition, cured product thereof, and semiconductor device

AssigneeDaicel Corporation

InventorsYasunobu Nakagawa, Shinya Yabuno

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Abstract

An objective of the present invention is to provide a curable resin composition for forming a cured product having excellent heat resistance, light resistance, flexibility, and toughness. The present invention provides a curable resin composition containing the following components in specific blended amounts. (A): A polyorganosiloxane represented by average unit formula: (SiO4/2)a1(R1SiO3/2)a2(R12SiO2/2)a3(R13SiO1/2)a4 R1 is alkyl, aryl, alkenyl, or the like; a proportion of the alkyl is from 30 to 98 mol %, a proportion of the aryl is from 1 to 50 mol %, and a proportion of the alkenyl is from 1 to 20 mol % relative to a total amount of R1; and a1>0, a2>0, a3≥0, a4>0, 0.01≤a1/a2≤10, and a1+a2+a3+a4=1. (B): A polyorganosiloxane having not more than 10 silicon atoms and having a proportion of an alkenyl group relative to a total amount (100 mol %) of the organic groups bonded to the silicon atom from 20 to 60 mol %. (C): An organopolysiloxane represented by average unit formula below: (RxSiO3/2)x1(Rx2SiO2/2)x2(Rx2SiRARx2SiO2/2)x3(Rx3SiO1/2)x4 where Rx is alkyl, aryl, alkenyl, or the like; a proportion of the aryl relative to a total amount of Rx is from 1 to 50 mol %, and at least two of all the Rx moieties are alkenyl; RA is a divalent hydrocarbon group; and 0.05>x1≥0, x2+x3>0, x4>0, and x1+x2+x3+x4=1. (D) A polyorganosiloxane represented by average composition formula below: R2mHnSiO[(4-m-n)/2] where R2 is alkyl or aryl, and at least two silicon atoms are bonded to hydrogen atoms; and 0.7≤m≤2.1, 0.001≤n≤1, and 0.8≤m+n≤3. (E): A hydrosilylation catalyst.

Claims22

Dependent claims

A curable resin composition comprising:

a component (A), a component (B), a component (C), a component (D), and a component (E) below;
a content of the component (B) per 100 parts by weight of the component (A) being from 5 to 50 parts by weight;
a content of the component (C) per 100 parts by weight of the component (A) being from 0 to 10 parts by weight;
a content of the component (D) being an amount that makes the amount of an SiH group (hydrosilyl group) present in the component (D) from 0.5 to 5 mol per 1 mol of an alkenyl group present in the component (A), the component (B), and the component (C);
and
a total content of the component (B), the component (C), and the component (D) per 100 parts by weight of the component (A) being not greater than 80 parts by weight;
(A):
a polyorganosiloxane represented by Average Unit Formula (I) below:
(SiO4/2)a1(R1SiO3/2)a2(R12SiO2/2)a3(R13SiO1/2)a4 (I)
wherein R1 is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
in the case where a proportion of the alkyl group is X mol %, a proportion of the aryl group is Y mol %, and a proportion of the alkenyl group is Z mol % relative to a total amount (100 mol %) of R1, X is from 30 to 98 mol %, Y is from 1 to 50 mol %, and Z is from 1 to 20 mol %;
a ratio of X to Y (X/Y) is from 5.5 to 25, and a1, a2, a3, and a4 are each a number satisfying a1>0, a2>0, a3≥0, a4>0, 0.01≤a1/a2≤10, and a1+a2+a3+a4=1;
(B):
a polyorganosiloxane having not more than 10 silicon atoms and having a proportion of an alkenyl group relative to a total amount (100 mol %) of the organic groups bonded to the silicon atom from 20 to 60 mol %;
(C):
an organopolysiloxane represented by Average Unit Formula (X) below:
(RxSiO3/2)x1(Rx2SiO2/2)x2(Rx2SiRARx2SiO2/2)x3(Rx3SiO1/2)x4 (X)
wherein Rx is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
a proportion of the aryl group relative to a total amount (100 mol %) of Rx is from 1 to 50 mol %, and at least two of all the Rx moieties are alkenyl groups;
RA is a divalent hydrocarbon group;
and x1, x2, x3, and x4 are each a number satisfying 0.05>x1≥0, x2+x3>0, x4>0, and x1+x2+x3+x4=1;
(D) a polyorganosiloxane represented by Average Composition Formula (II) below:
R2mHnSiO[(4-m-n)/2] (II)
wherein R2 is, the same or different, an alkyl group having from 1 to 10 carbons or an aryl group having from 6 to 14 carbons, and at least two hydrogen atoms are bonded to the silicon atom;
and m and n are each a number satisfying 0.7≤m≤2.1, 0.001≤n≤1, and 0.8≤m+n≤3;
and
(E):
a hydrosilylation catalyst.

25 more elements

A curable resin composition comprising:

a component (A), a component (B), a component (C), a component (D), and a component (E) below;
a content of the component (B) per 100 parts by weight of the component (A) being from 5 to 50 parts by weight;
a content of the component (C) per 100 parts by weight of the component (A) being from 0 to 10 parts by weight;
a content of the component (D) being an amount that makes the amount of an SiH group (hydrosilyl group) present in the component (D) from 0.5 to 5 mol per 1 mol of an alkenyl group present in the component (A), the component (B), and the component (C);
and
a total content of the component (B), the component (C), and the component (D) per 100 parts by weight of the component (A) being not greater than 80 parts by weight;
(A):
a polyorganosiloxane represented by Average Unit Formula (I) below:
(SiO4/2)a1(R1SiO3/2)a2(R12SiO2/2)a3(R13SiO1/2)a4 (I)
wherein R1 is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
in the case where a proportion of the alkyl group is X mol %, a proportion of the aryl group is Y mol %, and a proportion of the alkenyl group is Z mol % relative to a total amount (100 mol %) of R1, X is from 30 to 98 mol %, Y is from 1 to 14 mol %, and Z is from 1 to 20 mol %;
and a1, a2, a3, and a4 are each a number satisfying a1>0, a2>0, a3≥0, a4>0, 0.01≤a1/a2≤10, and a1+a2+a3+a4=1;
(B):
a polyorganosiloxane having not more than 10 silicon atoms and having a proportion of an alkenyl group relative to a total amount (100 mol %) of the organic groups bonded to the silicon atom from 20 to 60 mol %;
(C):
an organopolysiloxane represented by Average Unit Formula (X) below:
(RxSiO3/2)x1(Rx2SiO2/2)x2(Rx2SiRARx2SiO2/2)x3(Rx3SiO1/2)x2 (X)
wherein Rx is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
a proportion of the aryl group relative to a total amount (100 mol %) of Rx is from 1 to 50 mol %, and at least two of all the Rx moieties are alkenyl groups;
RA is a divalent hydrocarbon group;
and x1, x2, x3, and x4 are each a number satisfying 0.05>x1≥0, x2+x3>0, x4>0, and x1+x2+x3+x4=1;
(D) a polyorganosiloxane represented by Average Composition Formula (II) below:
R2mHnSiO[(4-m-n)/2] (II)
wherein R2 is, the same or different, an alkyl group having from 1 to 10 carbons or an aryl group having from 6 to 14 carbons, and at least two hydrogen atoms are bonded to the silicon atom;
and m and n are each a number satisfying 0.7≤m≤2.1, 0.001≤n≤1, and 0.8≤m+n≤3;
and
(E):
a hydrosilylation catalyst.

25 more elements

A curable resin composition comprising:

a component (A), a component (B), a component (C), a component (D), and a component (E) below;
a content of the component (B) per 100 parts by weight of the component (A) being from 5 to 50 parts by weight;
a content of the component (C) per 100 parts by weight of the component (A) being from 1 to 10 parts by weight;
a content of the component (D) being an amount that makes the amount of an SiH group (hydrosilyl group) present in the component (D) from 0.5 to 5 mol per 1 mol of an alkenyl group present in the component (A), the component (B), and the component (C);
and
a total content of the component (B), the component (C), and the component (D) per 100 parts by weight of the component (A) being not greater than 80 parts by weight;
(A):
a polyorganosiloxane represented by Average Unit Formula (I) below:
(SiO4/2)a1(R1SiO3/2)a2(R12SiO2/2)a3(R13SiO1/2)a4 (I)
wherein R1 is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
in the case where a proportion of the alkyl group is X mol %, a proportion of the aryl group is Y mol %, and a proportion of the alkenyl group is Z mol % relative to a total amount (100 mol %) of R1, X is from 30 to 98 mol %, Y is from 1 to 50 mol %, and Z is from 1 to 20 mol %;
and a1, a2, a3, and a4 are each a number satisfying a1>0, a2>0, a3≥0, a4>0, 0.01≤a1/a2≤10, and a1+a2+a3+a4=1;
(B):
a polyorganosiloxane having not more than 10 silicon atoms and having a proportion of an alkenyl group relative to a total amount (100 mol %) of the organic groups bonded to the silicon atom from 20 to 60 mol %;
(C):
an organopolysiloxane represented by Average Unit Formula (X) below:
(RxSiO3/2)x1(Rx2SiO2/2)x2(Rx2SiRARx2SiO2/2)x3(Rx3SiO1/2)x4 (X)
wherein Rx is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
a proportion of the aryl group relative to a total amount (100 mol %) of Rx is from 1 to 50 mol %, and at least two of all the Rx moieties are alkenyl groups;
RA is a divalent hydrocarbon group;
and x1, x2, x3, and x4 are each a number satisfying 0.05>x1≥0, x2+x3>0, x4>0, and x1+x2+x3+x4=1;
(D) a polyorganosiloxane represented by Average Composition Formula (II) below:
R2mHnSiO[(4-m-n)/2] (II)
wherein R2 is, the same or different, an alkyl group having from 1 to 10 carbons or an aryl group having from 6 to 14 carbons, and at least two hydrogen atoms are bonded to the silicon atom;
and m and n are each a number satisfying 0.7≤m≤2.1, 0.001≤n≤1, and 0.8≤m+n≤3;
and
(E):
a hydrosilylation catalyst.

25 more elements

A curable resin composition comprising:

a component (A), a component (B), a component (C), a component (D), a component (E), and a component (F) below;
a content of the component (B) per 100 parts by weight of the component (A) being from 5 to 50 parts by weight;
a content of the component (C) per 100 parts by weight of the component (A) being from 0 to 10 parts by weight;
a content of the component (D) being an amount that makes the amount of an SiH group (hydrosilyl group) present in the component (D) from 0.5 to 5 mol per 1 mol of an alkenyl group present in the component (A), the component (B), and the component (C);
and
a total content of the component (B), the component (C), and the component (D) per 100 parts by weight of the component (A) being not greater than 80 parts by weight;
(A):
a polyorganosiloxane represented by Average Unit Formula (I) below:
(SiO4/2)a1(R1SiO3/2)a2(R12SiO2/2)a3(R13SiO1/2)a4 (I)
wherein R1 is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
in the case where a proportion of the alkyl group is X mol %, a proportion of the aryl group is Y mol %, and a proportion of the alkenyl group is Z mol % relative to a total amount (100 mol %) of X is from 30 to 98 mol %, Y is from 1 to 50 mol %, and Z is from 1 to 20 mol %;
and a1, a2, a3, and a4 are each a number satisfying a1>0, a2>0, a3>0, a4>0, 0.01≤a1/a2≤10, and a1+a2+a3+a4=1;
(B):
a polyorganosiloxane having not more than 10 silicon atoms and having a proportion of an alkenyl group relative to a total amount (100 mol %) of the organic groups bonded to the silicon atom from 20 to 60 mol %;
(C):
an organopolysiloxane represented by Average Unit Formula (X) below:
(RxSiO3/2)x1(Rx2SiO2/2)x2(Rx2SiRARx2SiO2/2)x3(Rx3SiO1/2)x4 (X)
wherein Rx is, the same or different, an alkyl group having from 1 to 10 carbons, an aryl group having from 6 to 14 carbons, an alkenyl group having from 2 to 8 carbons, an alkoxy group having from 1 to 10 carbons, or a hydroxy group;
a proportion of the aryl group relative to a total amount (100 mol %) of Rx is from 1 to 50 mol %, and at least two of all the Rx moieties are alkenyl groups;
RA is a divalent hydrocarbon group;
and x1, x2, x3, and x4 are each a number satisfying 0.05>x1≥0, x2+x3>0, x4>0, and x1+x2+x3+x4=1;
(D) a polyorganosiloxane represented by Average Composition Formula (II) below:
R2mHnSiO[(4-m-n)/2] (II)
wherein R2 is, the same or different, an alkyl group having from 1 to 10 carbons or an aryl group having from 6 to 14 carbons, and at least two hydrogen atoms are bonded to the silicon atom;
and m and n are each a number satisfying 0.7≤m≤2.1, 0.001≤n≤1, and 0.8≤m+n≤3;
and
(E):
a hydrosilylation catalyst;
and
(F):
a silsesquioxane having at least one alkenyl group and at least one aryl group in a molecule.

28 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/331,078Filed 24 Aug 2017
Priority: JP JP2016-1747517 Sep 2016
Published: US 2019/0218346 A118 Jul 2019
Granted: 16 Mar 2021
Term ends: Not estimatedThe source records don’t support an estimate.

Classification17 codes

C08L 83/04
Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with…
C08G 77/045
Polysiloxanes: containing less than 25 silicon atoms
C08K 5/5419
Containing at least one Si—O bond: containing at least one Si—C bond
H10H 20/854
Encapsulations: characterised by their material, e.g. epoxy or silicone resins