Compound containing phosphonium ion, epoxy resin composition containing same, and device manufactured by using same

Patent metadata

Field	Value
Publication number	US-10047191-B2
Application number	US-201414907643-A
Country	US
Kind code	B2
Filing date	Feb 27, 2014
Priority date	Jul 23, 2013
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

The present invention relates to a compound containing phosphonium ion of a chemical formula 1, an epoxy resin composition containing the same, and a device manufactured by using the same.

First claim

The invention claimed is:

1. A phosphonium ion-containing compound represented by Formula 1:

wherein, in Formula 1,
R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, or a substituted or unsubstituted C 7 to C 21 arylalkyl group, provided that at least one of R 1 , R 2 , R 3 , or R 4 is an unsubstituted C 6 to C 20 aryl group;
R 5 is hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 2 to C 20 heterocycloalkyl group, a substituted or unsubstituted C 7 to C 20 arylalkyl group, a substituted or unsubstituted C 3 to C 20 heteroaryl group, or a group represented by Formula 2:

wherein, in Formula 2, * is a binding site to N in Formula 1, and R 11 is a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, or a substituted or unsubstituted C 7 to C 20 arylalkyl group; and

R 6 , R 7 , R 8 , R 9 , and R 10 are each independently hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 7 to C 21 arylalkyl group, or —NR′R″ in which R′ and R″ are each independently hydrogen, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group, or a C 7 to C 21 arylalkyl group.

2. The phosphonium ion-containing compound according to claim 1 , wherein the phosphonium ion-containing compound decomposes as in Reaction Formula 1 at about 90° C. to about 175° C.:

wherein, in Reaction Formula 1, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are the same as defined in Formula 1.

3. The phosphonium ion-containing compound according to claim 1 , wherein R 5 is a substituted or unsubstituted C 1 to C 4 alkyl group, a substituted or unsubstituted C 3 to C 20 heteroaryl group, or a compound represented by Formula 2 in which R 11 is a substituted or unsubstituted C 1 to C 5 alkyl group or a substituted or unsubstituted C 6 to C 10 aryl group.

4. The phosphonium ion-containing compound according to claim 1 , wherein:
R 1 , R 2 , R 3 , and R 4 each independently include a substituted or unsubstituted C 6 to C 20 aryl group, at least one of R 1 , R 2 , R 3 , or R 4 being an unsubstituted C 6 to C 20 aryl group, and
R 6 is —NR′R″ in which R′ and R″ are each independently hydrogen, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group, or a C 7 to C 21 arylalkyl group.

5. An epoxy resin composition, comprising:
an epoxy resin, a curing agent, and a curing catalyst, the curing catalyst including the phosphonium ion-containing compound according to claim 1 .

6. The epoxy resin composition according to claim 5 , wherein the epoxy resin includes an epoxy resin having two or more epoxy groups and one or more hydroxyl groups per molecule.

7. The epoxy resin composition according to claim 5 , wherein the epoxy resin includes one or more of a bisphenol epoxy resin, a phenol novolac epoxy resin, a tert-butyl catechol epoxy resin, a naphthalene epoxy resin, a glycidyl amine epoxy resin, a phenol aralkyl epoxy resin, a cresol novolac epoxy resin, a biphenyl epoxy resin, a linear aliphatic epoxy resin, an alicyclic epoxy resin, a heterocyclic epoxy resin, a spiro ring-containing epoxy resin, a cyclohexane dimethanol epoxy resin, or a halogenated epoxy resin.

8. The epoxy resin composition according to claim 5 , wherein the curing agent includes a phenol resin.

9. The epoxy resin composition according to claim 5 , wherein the curing agent includes one or more of a phenolaralkyl 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 multifunctional phenol resin, a dicyclopentadiene-based phenol resin, a novolac phenol resin prepared from bisphenol A and resol, tris(hydroxyphenyl)methane, dihydroxybiphenyl, an acid anhydride, meta-phenylenediamine, diaminodiphenylmethane, or diaminodiphenylsulfone.

10. The epoxy resin composition according to claim 5 , wherein the phosphonium ion-containing compound is present in an amount of about 0.01 wt % to about 5 wt % in the epoxy resin composition.

11. The epoxy resin composition according to claim 5 , wherein the phosphonium ion-containing compound is present in an amount of about 10 wt % to 100 wt % in the curing catalyst.

12. The epoxy resin composition according to claim 5 , further comprising an inorganic filler.

13. The epoxy resin composition according to claim 5 , wherein the epoxy resin composition has a curing initiation temperature of about 90° C. to about 120° C.

14. The epoxy resin composition according to claim 5 , wherein the epoxy resin composition has a rate of viscosity change of about 16% or less, as calculated according to Equation 1:
Rate of viscosity change=| B−A|/A× 100  [Equation 1]

wherein, in Equation 1, A is the viscosity (unit: cPs) of the epoxy resin composition as measured at 25° C., and B is the viscosity (unit: cPs) of the epoxy resin composition as measured at 25° C. after leaving the epoxy resin composition at 25° C. for 24 hours.

15. The epoxy resin composition according to claim 5 , wherein the epoxy resin composition has a flow length of about 59 to about 75 inches as measured using a transfer molding press at 175° C. under a load of 70 kgf/cm 2 in accordance with EMMI-1-66.

16. The epoxy resin composition according to claim 5 , wherein the epoxy resin composition has a curing shrinkage of less than about 0.4% as calculated according to Equation 2:
Curing shrinkage=| C−D|/C× 100  [Equation 2]

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

17. An epoxy resin composition for encapsulating a semiconductor device comprising the epoxy resin composition according to claim 5 .

18. An apparatus manufactured using the epoxy resin composition according to claim 5 .

19. A curing catalyst represented by Formula 1:

wherein, in Formula 1,
R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, or a substituted or unsubstituted C 7 to C 21 arylalkyl group, provided that at least one of R 1 , R 7 , R 3 , or R 4 is an unsubstituted C 6 to C 20 aryl group;
R 5 is hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubs

Assignees

• Samsung Sdi Co Ltd

Inventors

• Cheon Jin Min
• Kim Min Gyum
• Kim Jung Seob
• Lee Dong Hwan
• Cheon Hwan Sung
• Han Seung

Classifications

• C07C311/51

  Y being a hydrogen or a carbon atom · CPC title

• C07F9/5442

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

• C08G59/621

  Phenols · CPC title

• C08G59/688 Primary

  containing phosphorus · CPC title

• C08L2205/05

  containing polymer components which can react with one another · CPC title