US 8,013,052 B2Granted

Curable resin, production method thereof, epoxy resin composition, and electronic device

AssigneeHitachi Chemical Company, Ltd.

InventorsShinya Nakamura, Tomoya Masuda, Mitsuo Katayose

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Abstract

A curable resin which exhibits excellent heat resistance while including an extremely smaller amount of volatile component is disclosed, and an electronic component device having excellent reliability in heat resistance and the like which contains the above curable resin is provided. A curable resin obtained in reaction of at least one compound (a) selected from the group consisting of the silane compounds represented by the following Formula (I-1) and the partial condensates thereof with a phenol compound (b), comprising a remaining volatile component in an amount of 10 wt % or less with respect to the total weight of the curable resin is used as a curing agent. [Formula 1] R1nSiR2(4-n) (I-1) (Wherein, n denotes a number of 0 to 2; R1 represent a hydrogen atom, or substituted or unsubstituted hydrocarbon groups having 1 to 18 carbon atoms; R2 represent a halogen atom, a hydroxyl group, substituted or unsubstituted oxy groups, amino groups, and carbonyloxy groups having 1 to 18 carbon atoms; and two or more of R1 and R2 may bind to each other to form a cyclic structure).

Claims23

Dependent claims

A method of producing a curable resin, comprising a step of:

allowing at least one compound (a) selected from the group consisting of the silane compounds represented by the following Formula (I-1) and the partial condensates thereof to react with phenol compounds (b):
R1nSiR2(4-n) (I-1)
(Wherein,
n denotes a number of 0 or 1;
R1 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted hydrocarbon groups having 1 to 18 carbon atoms, and may be identical or different from each other;
R2 each independently represents a group selected from the group consisting of a halogen atom, a hydroxyl group, substituted or unsubstituted oxy groups having 1 to 18 carbon atoms, substituted or unsubstituted amino groups having 1 to 18 carbon atoms, and carbonyloxy groups having 2 to 18 carbon atoms, and may be identical or different from each other;
and
two or more of R1 and R2 may bind to each other to form a cyclic structure);
wherein the phenol compounds (b) include a phenol compound cyclizable with the at least one compound (a) in a total amount of 50 wt % or more with respect to the total weight of the phenol compounds, and the cyclizable phenol compound is selected from the group consisting of compounds shown in Formulas (I-1b) and (I-1g) below:
(Wherein, R7 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
and two or more R7 may bind to each other to form a cyclic structure);
and
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms;
and n is an average number of higher than 1).

13 more elements

A method of producing a curable resin, comprising a step of

allowing at least one compound (a) selected from the group consisting of the silane compounds represented by the following Formula (I-1) and partial condensates thereof to react with a phenol compound (b), under the presence of a catalyst selected from the group consisting of phosphine compounds, phosphonium salt compounds, cyclic amidine compounds, and cyclic amidinium salts:
R1nSiR2(4-n) (I-1)
(Wherein,
n denotes a number of 0 to 2;
R1 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted hydrocarbon groups having 1 to 18 carbon atoms, and may be identical or different from each other;
R2 each independently represents a group selected from the group consisting of a halogen atom, a hydroxyl group, substituted or unsubstituted oxy groups having 1 to 18 carbon atoms, substituted or unsubstituted amino groups having 1 to 18 carbon atoms, and carbonyloxy groups having 2 to 18 carbon atom, and may be identical or different from each other;
and
two or more of R1 and R2 may bind to each other to form a cyclic structure).

5 more elements

An epoxy resin composition, comprising an epoxy resin (A) and a curing agent (B), wherein the curing agent (B) includes a curable resin obtained in reaction of at least one compound (a) selected from the group consisting of the silane compounds represented by the following Formula (I-1) and the partial condensates thereof with phenol compounds (b),

a remaining volatile component in an amount of 10 wt % or less with respect to the total weight of the curable resin, and
the number of the unreacted R2 groups in an amount of 10% or less with respect to the total number of the R2 groups in the silane compound (a) when the reaction is initiated;
R1nSiR2(4-n) (I-1)
(Wherein,
n denotes a number of 0 or 1;
R1 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted hydrocarbon groups having 1 to 18 carbon atoms, and may be identical or different from each other;
R2 each independently represents a group selected from the group consisting of a halogen atom, a hydroxyl group, substituted or unsubstituted oxy groups having 1 to 18 carbon atoms, substituted or unsubstituted amino groups having 1 to 18 carbon atoms, and carbonyloxy groups having 2 to 18 carbon atoms, and may be identical or different from each other;
and
two or more of R1 and R2 may bind to each other to form a cyclic structure);
wherein the phenol compounds (b) include a phenol compound (b1) which reacts with the at least one compound (a) to form a cyclic structure, in a total amount of 50 wt % or more with respect to the total weight of the phenol compounds (b), and the phenol compound (b1) is selected from the group consisting of compounds shown in Formulas (I-1b) and (I-1g) below:
(Wherein, R7 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
and two or more R7 may bind to each other to form a cyclic structure);
and
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms;
and n is an average number of higher than 1).

14 more elements

An epoxy resin composition, comprising an epoxy resin (A) and a curing agent (B), wherein the curing agent (B) includes a curable resin having an aryloxysilyl (ArO—Si) bond, the curable resin comprising at least one structural unit selected from the group consisting of the structural units represented by the following Formulas (I-2a), (I-3a), (I-2b), and (I-3b):

(Wherein, Ar represents a divalent organic group which is derived from phenol compounds);
(Wherein, Ar represents a divalent organic group which is derived from phenol compounds, and n denotes a number of 0 or more);
(Wherein, Ar2 represents a (m+2)-valent organic group which is derived from phenol compounds;
and m denotes an integer of one or more);
and
(Wherein, Ar2 represents a (m+2)-valent organic group which is derived from phenol compounds;
n denotes a number of 0 or more;
and m denotes an integer of one or more);
wherein the phenol compounds are selected from the group consisting of compounds shown in Formulas (I-1b), (I-1c) and (I-1g) below:
(Wherein, R7 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
and two or more R7 may bind to each other to form a cyclic structure);
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms);
and
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms;
and n is an average number of higher than 1).

16 more elements

A method of producing a curable resin, comprising a step of

allowing at least one compound (a) selected from the group consisting of the silane compounds represented by the following Formula (I-1) and the partial condensates thereof to react with phenol compounds (b):
R1nSiR2(4-n) (I-1)
(Wherein,
n denotes 0;
R1 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted hydrocarbon groups having 1 to 18 carbon atoms, and may be identical or different from each other;
R2 each independently represents a group selected from the group consisting of a halogen atom, a hydroxyl group, substituted or unsubstituted oxy groups having 1 to 18 carbon atoms, substituted or unsubstituted amino groups having 1 to 18 carbon atoms, and carbonyloxy groups having 2 to 18 carbon atom, and may be identical or different from each other;
and
two or more of R1 and R2 may bind to each other to form a cyclic structure);
wherein the phenol compounds (b) include a phenol compound cyclizable with the at least one compound (a) in a total amount of 50 wt % or more with respect to the total weight of the phenol compounds, and the cyclizable phenol compound is selected from the group consisting of compounds shown in Formulas (I-1b), (I 1c) and (I-1g) below:
(Wherein, R7 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
and two or more R7 may bind to each other to form a cyclic structure);
and
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms;
and n is an average number of higher than 1).

13 more elements

An epoxy resin composition, comprising an epoxy resin (A) and a curing agent (B), wherein the curing agent (B) includes a curable resin, the curable resin comprising at least one of a compound having the structural unit represented by the following Formula (I-4a) and a compound having the structural unit represented by the following Formula (I-4b):

(Wherein, Ar represents a divalent organic group which is derived from phenol compounds);
and
(Wherein, Ar2 represents a (m+2)-valent organic group which is derived from phenol compounds, and each m independently denotes an integer of 1 or more);
wherein the phenol compounds (b) are selected from the group consisting of a compounds shown in Formulas (I-1b), (I-1c) and (I-1g) below:
(Wherein, R7 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
and two or more R7 may bind to each other to form a cyclic structure);
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms);
and
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms;
and n is an average number of higher than 1).

11 more elements

A method of producing a curable resin, comprising a step of

allowing at least one compound (a) selected from the group consisting of the silane compounds represented by the following Formula (I-1) and partial condensates thereof to react with phenol compounds (b), under the presence of a catalyst selected from the group consisting of phosphine compounds, phosphonium salt compounds, cyclic amidine compounds, and cyclic amidinium salts:
R1nSiR2(4-n) (I-1)
(Wherein,
n denotes a number of 0 to 2;
R1 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted hydrocarbon groups having 1 to 18 carbon atoms, and may be identical or different from each other;
R2 each independently represents a group selected from the group consisting of a halogen atom, a hydroxyl group, substituted or unsubstituted oxy groups having 1 to 18 carbon atoms, substituted or unsubstituted amino groups having 1 to 18 carbon atoms, and carbonyloxy groups having 2 to 18 carbon atom, and may be identical or different from each other;
and
two or more of R1 and R2 may bind to each other to form a cyclic structure);
wherein the phenol compounds (b) include a phenol compound (b1) which reacts with the at least one compound (a) to form a cyclic structure, in a total amount of 50 wt % or more with respect to the total weight of the phenol compounds (b), and the phenol compound (b1) is selected from the group consisting of compounds shown in Formulas (I-1b), (I-1c) and (I-1g) below:
(Wherein, R7 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
and two or more R7 may bind to each other to form a cyclic structure);
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms);
and
(Wherein, R8 each independently represents a group selected from the group consisting of a hydrogen atom and substituted or unsubstituted organic groups having 1 to 18 carbon atoms and may be identical or different from each other;
two or more of R8 may bind to each other to form a cyclic structure;
and R9 represents a divalent organic group having 1 to 18 carbon atoms;
and n is an average number of higher than 1).

16 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/816,571Filed 31 Jan 2006
Priority: JP P2005-04210818 Feb 2005
Published: US 2009/0023855 A122 Jan 2009
Granted: 6 Sep 2011
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C08G 59/302
Containing atoms other than carbon, hydrogen, oxygen and nitrogen: containing sulfur
C08G 59/4261
Polymers with carboxylic terminal groups: macromolecular compounds obtained by reactions involving only unsaturated carbon-to-carbon bindings
C08G 77/52
By carbon linkages: containing aromatic rings
C09J 163/00
Adhesives based on epoxy resins