Phosphonium compound, preparation method thereof, epoxy resin composition including the same, and semiconductor device prepared by using the same

Patent metadata

Field	Value
Publication number	US-9896465-B2
Application number	US-201615189057-A
Country	US
Kind code	B2
Filing date	Jun 22, 2016
Priority date	Jun 22, 2015
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

A phosphonium compound, a method of preparing the same, an epoxy resin composition including the same, and a semiconductor device encapsulated with the same, the compound being represented by Formula 1:

First claim

What is claimed is:

1. A phosphonium compound represented by Formula 1:

wherein:
R 1 , R 2 , R 3 , and R 4 are each independently a substituted or unsubstituted C 1 to C 30 aliphatic hydrocarbon group, a substituted or unsubstituted C 6 to C 30 aromatic hydrocarbon group, or a substituted or unsubstituted C 1 to C 30 hydrocarbon group including a hetero atom;
X and Y are each independently a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 10 cycloalkylene group, or a substituted or unsubstituted C 1 to C 20 alkylene group;
R 5 and R 6 are each independently hydrogen, a hydroxyl group, a C 1 to C 20 alkyl group, a C 6 to C 30 aryl group, a C 3 to C 30 heteroaryl group, a C 3 to C 10 cycloalkyl group, a C 3 to C 10 heterocycloalkyl group, a C 7 to C 30 arylalkyl group, or a C 1 to C 30 heteroalkyl group.

2. The phosphonium compound as claimed in claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each independently a substituted or unsubstituted C 6 to C 30 aryl group.

3. The phosphonium compound as claimed in claim 2 , wherein at least one of R 1 , R 2 , R 3 , and R 4 is a hydroxyl group-substituted C 6 to C 30 aryl group.

4. The phosphonium compound as claimed in claim 1 , wherein the phosphonium compound is represented by one of the following Formulae 1a to 1h.

5. An epoxy resin composition, comprising:
an epoxy resin,
a curing agent,
an inorganic filler, and
a curing catalyst, wherein the curing catalyst includes the phosphonium compound as claimed in claim 1 .

6. The epoxy resin composition as claimed in claim 5 , wherein the epoxy resin includes at least one of a bisphenol A epoxy resin, a bisphenol F epoxy resin, a phenol novolac epoxy resin, a tert-butyl catechol epoxy resin, a naphthalene epoxy resin, a glycidylamine epoxy resin, a cresol novolac epoxy resin, a biphenyl epoxy resin, a linear aliphatic epoxy resin, a cycloaliphatic epoxy resin, a heterocyclic epoxy resin, a spiro ring-containing epoxy resin, a cyclohexane dimethanol epoxy resin, a trimethylol epoxy resin, and a halogenated epoxy resin.

7. The epoxy resin composition as claimed in claim 5 , wherein the curing agent includes a phenol resin.

8. The epoxy resin composition as claimed in claim 5 , wherein the curing agent includes at least one of a phenol aralkyl phenol resin, a phenol novolac phenol resin, a xyloc phenol resin, a cresol novolac phenol resin, a naphthol phenol resin, a terpene phenol resin, a polyfunctional phenol resin, a dicyclopentadiene-based phenol resin, a novolac phenol resin synthesized from bisphenol A and resorcinol, a polyhydric phenolic compound, an acid anhydride, and an aromatic amine.

9. The epoxy resin composition as claimed in claim 5 , wherein the curing catalyst is present in the epoxy resin composition in an amount of about 0.01 wt % to about 5 wt %, in terms of solid content.

10. The epoxy resin composition as claimed in claim 5 , wherein the phosphonium compound is present in the curing catalyst in an amount of about 10 wt % to about 100 wt %, based on a total weight of the curing catalyst.

11. The epoxy resin composition as claimed in claim 6 , wherein the epoxy resin composition has a curing shrinkage rate of less than about 0.40%, as calculated according to Equation 1:
Curing shrinkage=(| C−D|/C )×100  Equation 1

wherein, in Equation 1, C is a length of a specimen obtained by transfer molding the epoxy resin composition at 175° C. under a load of 70 kgf/cm 2 , and D is a length of the specimen after post-curing the specimen at 170° C. to 180° C. for 4 hours and cooling.

12. The epoxy resin composition as claimed in claim 5 , wherein the epoxy resin composition has a storage stability after 72 hours of about 85% or more, as calculated according to Equation 2:
Storage stability=( F 1/ F 0)×100  Equation 2

wherein, in Equation 2, F1 is a flow length in inches of the epoxy resin composition, measured after storing the composition at 25° C./50% RH for 72 hours, using a transfer molding press at 175° C. and 70 kgf/cm 2 in accordance with EMMI-1-66, and F0 is an initial flow length in inches of the epoxy resin composition.

13. A semiconductor device encapsulated with the epoxy resin composition as claimed in claim 5 .

14. A method of preparing a phosphonium compound, the method comprising reacting a phosphonium cation-containing compound represented by Formula 2 with a phenylene-bis-benzamide anion-containing compound represented by Formula 3:

wherein, in Formula 2, R 1 , R 2 , R 3 , and R 4 are each independently a substituted or unsubstituted C 1 to C 30 aliphatic hydrocarbon group, a substituted or unsubstituted C 6 to C 30 aromatic hydrocarbon group, or a substituted or unsubstituted C 1 to C 30 hydrocarbon group including a hetero atom, and M is a halogen, and
wherein, in Formula 3, X and Y are each independently a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 10 cycloalkylene group, or a substituted or unsubstituted C 1 to C 20 alkylene group; R 5 and R 6 are each independently hydrogen, a hydroxyl group, a C 1 to C 20 alkyl group, a C 6 to C 30 aryl group, a C 3 to C 30 heteroaryl group, a C 3 to C 10 cycloalkyl group, a C 3 to C 10 heterocycloalkyl group, a C 7 to C 30 arylalkyl group, or a C 1 to C 30 heteroalkyl group; and Z is an alkali metal or Ag.

Assignees

• Samsung Sdi Co Ltd

Inventors

• Lee Dong Hwan
• Kim Min Gyum
• Kim So Yoon
• Na Woo Chul
• Lee Yoon Man
• Cho Ji Yoon
• Kwon Ki Hyeok
• Bae Kyoungchul
• Lee Eun Jung
• Chung Joo Young
• Cheon Jin Min
• Choi Jin Woo
• Han Seung

Classifications

• C08G59/688

  containing phosphorus · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C08G59/621

  Phenols · CPC title

• C07F9/5442 Primary

  Aromatic phosphonium compounds (P-C aromatic linkage) · CPC title

• C07C235/64

  having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring · CPC title