Conductive die attach film for large die semiconductor packages and compositions useful for the preparation thereof

Patent metadata

Field	Value
Publication number	US-9449938-B2
Application number	US-201615010531-A
Country	US
Kind code	B2
Filing date	Jan 29, 2016
Priority date	Sep 30, 2013
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

Provided herein are conductive die attach films having advantageous properties for use in a variety of applications, e.g., for the preparation of large die semiconductor packages. Also provided are formulations useful for the preparation of such films, as well as methods for making such formulations. In additional aspects of the present invention, there are provided conductive networks prepared from compositions according to the present invention. In additional aspects, the invention further relates to articles comprising such conductive die attach films adhered to a suitable substrate therefor.

First claim

That which is claimed is:

1. A composition comprising:
a first maleimide, nadimide or itaconimide, wherein said first maleimide, nadimide or itaconimide has an aromatic backbone, and the degree of substitution of imide moieties on the backbone of said first maleimide, nadimide or itaconimide is at least 0.5 imide moieties per repeat unit of said backbone,
a second maleimide, nadimide or itaconimide, wherein said second maleimide, nadimide or itaconimide has a flexible aliphatic or aliphatic/aromatic backbone, wherein the backbone of said second maleimide, nadimide or itaconimide includes straight or branched chain hydrocarbyl segments, wherein each hydrocarbyl segment has at least 20 carbons,
a first epoxy resin, wherein said first epoxy resin is rubber or elastomer-modified,
a second epoxy resin, wherein said second epoxy resin has a flexible aliphatic or aliphatic/aromatic backbone, wherein the backbone of said second epoxy resin includes straight or branched chain hydrocarbyl segments, wherein each hydrocarbyl segment has at least 20 carbons, backbone,
a conductive filler,
a curing agent; and
optionally a non-reactive organic diluent therefore;

wherein:
said composition, when cured, has a modulus less than about 1 GPa when tested by dynamic mechanical analysis (DMA) at 260° C.

2. The composition of claim 1 optionally further comprising one or more flow additives, adhesion promoters, conductivity additives, rheology modifiers, or mixtures of any two or more thereof.

3. The composition of claim 1 wherein the degree of substitution of imide moieties on the backbone of said first maleimide, nadimide or itaconimide is at least 0.8 imide moieties per repeat unit of said backbone.

4. The composition of claim 1 wherein said first maleimide, nadimide or itaconimide has the structure:

respectively, wherein:
m is 1-15,
p is 0-15,
each R 2 is independently selected from hydrogen or lower alkyl, and
J is a monovalent or a polyvalent radical selected from:
aromatic hydrocarbyl or substituted aromatic hydrocarbyl species having in the range of about 6 up to about 300 carbon atoms, where the aromatic hydrocarbyl species is selected from aryl, alkylaryl, arylalkyl, aryalkenyl, alkenylaryl, arylalkynyl or alkynylaryl;
aromatic hydrocarbylene or substituted aromatic hydrocarbylene species having in the range of about 6 up to about 300 carbon atoms, where the aromatic hydrocarbylene species are selected from arylene, alkylarylene, arylalkylene, arylalkenylene, alkenylarylene, arylalkynylene or alkynylarylene,
heterocyclic or substituted heterocyclic species having in the range of about 6 up to about 300 carbon atoms,
polysiloxane, or
polysiloxane-polyurethane block copolymers, as well as

combinations of one or more of the above with a linker selected from a covalent bond, —O—, —S—, —NR—, —NR—C(O)—, —NR—C(O)—O—, —NR—C(O)—NR—, —S—C(O)—, —S—C(O)—O—, —S—C(O)—NR—, —O—S(O) 2 —, —O—S(O) 2 —O—, —O—S(O) 2 —NR—, —O—S(O)—, —O—S(O)—O—, —O—S(O)—NR—, —O—NR—C(O)—, —O—NR—C(O)—O—, —O—NR—C(O)—NR—, —NR—O—C(O)—, —NR—O—C(O)—O—, —NR—O—C(O)—NR—, —O—NR—C(S)—, —O—NR—C(S)—O—, —O—NR—C(S)—NR—, —NR—O—C(S)—, —NR—O—C(S)—O—, —NR—O—C(S)—NR—, —O—C(S)—, —O—C(S)—O—, —O—C(S)—NR—, —NR—C(S)—, —NR—C(S)—O—, —NR—C(S)—NR—, —S—S(O) 2 —, —S—S(O) 2 —O—, —S—S(O) 2 —NR—, —NR—O—S(O)—, —NR—O—S(O)—O—, —NR—O—S(O)—NR—, —NR—O—S(O) 2 —, —NR—O—S(O) 2 —O—, —NR—O—S(O) 2 —NR—, —O—NR—S(O)—, —O—NR—S(O)—O—, —O—NR—S(O)—NR—, —O—NR—S(O) 2 —O—, —O—NR—S(O) 2 —NR—, —O—NR—S(O) 2 —, —O—P(O)R 2 —, —S—P(O)R 2 —, or —NR—P(O)R 2 —;
where each R is independently hydrogen, alkyl or substituted alkyl.

5. The composition of claim 4 wherein J is heterocyclic, oxyheterocyclic, thioheterocyclic, aminoheterocyclic, carboxyheterocyclic, oxyaryl, thioaryl, aminoaryl, carboxyaryl, heteroaryl, oxyheteroaryl, thioheteroaryl, aminoheteroaryl, carboxyheteroaryl, oxyalkylaryl, thioalkylaryl, aminoalkylaryl, carboxyalkylaryl, oxyarylalkyl, thioarylalkyl, aminoarylalkyl, carboxyarylalkyl, oxyarylalkenyl, thioarylalkenyl, aminoarylalkenyl, carboxyarylalkenyl, oxyalkenylaryl, thioalkenylaryl, aminoalkenylaryl, carboxyalkenylaryl, oxyarylalkynyl, thioarylalkynyl, aminoarylalkynyl, carboxyarylalkynyl, oxyalkynylaryl, thioalkynylaryl, aminoalkynylaryl or carboxyalkynylaryl, oxyarylene, thioarylene, aminoarylene, carboxyarylene, oxyalkylarylene, thioalkylarylene, aminoalkylarylene, carboxyalkylarylene, oxyarylalkylene, thioarylalkylene, aminoarylalkylene, carboxyarylalkylene, oxyarylalkenylene, thioarylalkenylene, aminoarylalkenylene, carboxyarylalkenylene, oxyalkenylarylene, thioalkenylarylene, aminoalkenylarylene, carboxyalkenylarylene, oxyarylalkynylene, thioarylalkynylene, aminoarylalkynylene, carboxy arylalkynylene, oxyalkynylarylene, thioalkynylarylene, aminoalkynylarylene, carboxyalkynylarylene, heteroarylene, oxyheteroarylene, thioheteroarylene, aminoheteroarylene, carboxyheteroarylene, heteroatom-containing di- or polyvalent cyclic moiety, oxyheteroatom-containing di- or polyvalent cyclic moiety, thioheteroatom-containing di- or polyvalent cyclic moiety, aminoheteroatom-containing di- or polyvalent cyclic moiety, or a carboxyheteroatom-containing di- or polyvalent cyclic moiety.

6. The composition of claim 1 wherein the backbone of said second maleimide, nadimide or itaconimide contains straight or branched chain hydrocarbyl segments, wherein each hydrocarbyl segment has at least 30 carbons, thereby enhancing the flexibility thereof.

7. The composition of claim 1 wherein said second maleimide, nadimide or itaconimide has the structure:

respectively, wherein:
m is 1-15,
p is 0-15,
each R 2 is independently selected from hydrogen or lower alkyl, and
J is a monovalent or a polyvalent radical selected from:
non-aromatic hydrocarbyl or substituted non-aromatic hydrocarbyl species having in the range of about 20 up to about 500 carbon atoms, where the non-aromatic hydrocarbyl species is selected from alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkenyl;
non-aromatic hydrocarbylene or substituted non-aromatic hydrocarbylene species having in the range of about 20 up to about 500 carbon atoms, where the non-aromatic hydrocarbylene species are selected from alkylene, alkenylene, alkynylene, cycloalkylene, or cycloalkenylene,
heterocyclic or substituted heterocyclic species having in the range of about 20 up to about 500 carbon atoms,
polysiloxane, or
polysiloxane-polyurethane block copolymers, as well as

combinations of one or more of the above with a linker selected from a covalent bond, —O—, —S—, —NR—, —NR—C(O)—, —NR—C(O)—O—, —NR—C(O)—NR—, —S—C(O)—, —S—C(O)—O—, —S—C(O)—NR—, —O—S(O) 2 —, —O—S(O) 2 —O—, —O—S(O) 2 —NR—, —O—S(O)—, —O—S(O)—O—, —O—S(O)—NR—, —O—NR—C(O)—, —O—NR—C(O)—O—, —O—NR—C(O)—NR—, —NR—O—C(O)—, —NR—O—C(O)—O—, —NR—O—C(O)—NR—, —O—NR—C(S)—, —O—NR—C(S)—O—, —O—NR—C(S)—NR—, —NR—O—C(S)—, —NR—O—C(S)—O—, —NR—O—C(S)—NR—, —O—C(S)—, —O—C(S)—O—, —O—C(S)—NR—, —NR—C(S)—, —NR—C(S)—O—, —NR—C(S)—NR—, —S—S(O) 2 —, —S—S(O) 2 —O—, —S—S(O) 2 —NR—, —NR—O—S(O)—, —NR—O—S(O)—O—, —NR—O—S(O)—NR—, —NR—O—S(O) 2 —, —NR—O—S(O) 2 —O—, —NR—O—S(O) 2 —NR—, —O—NR—S(O)—, —O—NR—S(O)—O—, —O—NR—S(O)—NR—, —O—NR—S(O) 2 —O—, —O—NR—S(O) 2 —NR—, —O—NR—S(O) 2 —, —O—P(O)R 2 —, —S—P(O)R 2 —, or —NR—P(O)R 2 —;
where each R is independently hydrogen, alkyl or substituted alkyl.

8. The composition of claim 7 wherein J is oxyalkyl, thioalkyl, aminoalkyl, carboxylalkyl, oxyalkenyl, thioalkenyl, aminoalkenyl, carboxyalkenyl, oxyalkynyl, thioalkynyl, aminoalkynyl, carboxyalkynyl, oxycycloalkyl, thiocycloalk

Assignees

• Henkel IP & Holding GmbH

Inventors

• Zhu Pukun
• Hoang Gina V
• Gupta Shashi K
• Laib Andrew

Classifications

• H10W90/736

  between a chip and a stacked lead frame, conducting package substrate or heat sink · CPC title

• H10W90/734

  between a chip and a stacked insulating package substrate, interposer or RDL · CPC title

• H10W72/07351

  characterised by changes in properties of the die-attach connectors during connecting · CPC title

• H10W72/07338

  hardening the adhesive by curing, e.g. thermosetting · CPC title

• H10W72/07332

  Compression bonding, e.g. thermocompression bonding · CPC title