IP Library Granted Patent US 8,637,627
Granted Patent B2
US 8,637,627 · App. 12/315,682 · Granted Jan 28, 2014

Phenoxyphenyl polysiloxane composition and method for making and using same

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Quick Facts
Patent No.
US 8,637,627
App. No.
12/315,682
Granted
Jan 28, 2014
Kind
B2
Abstract

A curable phenoxyphenyl polysiloxane composition is disclosed. A cured phenoxyphenyl polysiloxane composition is further disclosed, along with a method of making that cured phenoxyphenyl polysiloxane composition from the curable phenoxyphenyl silicon composition. An encapsulated semiconductor device, and a method of making that encapsulated semiconductor device by coating a semiconductor element of a semiconductor device with cured phenoxyphenyl polysiloxane are further disclosed.

Claims (85)

1. A curable phenoxyphenyl polysiloxane composition comprising:

A. a branched multialkenyl phenoxyphenyl polysiloxane represented by average compositional formula II,

(R 6 3 SiO 1/2 ) c (R 7 2 SiO 2/2 ) d (R 8 SiO 3/2 ) e (SiO 4/2 ) f   (II),

wherein:

R 6 3 SiO 1/2 , R 7 2 SiO 2/2 , R 8 SiO 3/2 , and SiO 4/2 are, respectively, an M-unit, a D-unit, a T-unit, and a Q-unit, all of which are primary siloxane units;

each of R 6 , each of R 7 , and each of R 8 is, independently, a silicon bonded organic group selected from alkenyl, phenoxyphenyl, aryl other than phenoxyphenyl, alkyl, hydroxy, alkoxy, aryloxy, other organic radical, hydrogen, and combinations thereof;

at least two silicon bonded organic groups are alkenyl;

the alkenyl group is CH2=CH-Xs- wherein s=0 or 1, and X is independently selected from: linear, branched or cyclic saturated C 1 -C 16 hydrocarbon radical, o-phenyl, m-phenyl, p-phenyl, and combinations thereof;

the alkenyl group is present in an amount of 1 mole percent to no more than 20 mole percent, based on total moles of the silicon bonded organic group of the multialkylene phenoxyphenyl polysiloxane;

at least one silicon bonded organic group is a phenoxyphenyl group selected from o-phenoxyphenyl, m-phenoxyphenyl, p-phenoxyphenyl, and combinations thereof;

the silicon bonded phenoxyphenyl group is present in an amount of greater than 0 mole percent and no more than 99 mole percent, based on the total moles of silicon bonded organic groups in the alkenyl phenoxyphenyl polysiloxane;

subscripts c, d, e, and f are selected to conform with the mole fractions of R 6 3 SiO 1/2 , R 7 2 SiO 2/2 , R 8 SiO 3/2 , and SiO 4/2 , respectively;

0.001≦c≦1; 0≦d≦0.999; 0≦e≦0.20; 0≦f≦0.10; c+d+e+f=1; and e+f>0;

and

the multialkenyl phenoxyphenyl polysiloxane has:

i) a number average molecular weight of at least 500 grams/mole and no more than 5,000 grams/mole; and

ii) a viscosity of at least 10 and no more than 7,000,000 centipoise at 25° C.;

B. a multihydrido silicon compound having at least two silicon bonded hydrogen atoms;

C. a hydrosilation catalyst in an amount effective to catalyze hydrosilation; and

D. a reactive diluent.

2. The curable phenoxyphenyl polysiloxane composition of claim 1 , having a refractive index of at least 1.59 and no more than 1.64.

3. The curable phenoxyphenyl polysiloxane composition of claim 1 ,

wherein:

when 0.00≦e≦0.03, 0.00≦f≦0.03, and 0.00≦e+f≦0.03,

the silicon bonded phenoxyphenyl group is present in an amount of at least 15 mole percent and no more than 99 mole percent, based on total moles of the silicon bonded organic groups of the multialkenyl phenoxyphenyl polysiloxane;

when 0.00≦e≦0.07, 0.00≦f<0.07, and 0.03<e+f<0.07,

the silicon bonded phenoxyphenyl group is present in an amount of at least 5 mole percent and no more than 99 mole percent, based on total moles of the silicon bonded organic groups of the multialkenyl phenoxyphenyl polysiloxane; and

when 0.00≦e≦0.20, 0.00≦f≦10, and 0.07≦e+f≦0.20,

the silicon bonded phenoxyphenyl group is present in an amount of greater than 0 mole percent and no more than 99 mole percent, based on total moles of the silicon bonded organic groups of the multialkenyl phenoxyphenyl polysiloxane.

4. The curable phenoxyphenyl polysiloxane composition of claim 1 , wherein the multihydrido silicon compound is selected from:

i) a multihydrido silicon compound having the average compositional formula III,

(R 9 3 SiO 1/2 ) g (R 10 2 SiO 2/2 ) h (R 11 SiO 3/2 ) j (SiO 4/2 ) k   (III),

wherein:

R 9 3 SiO 1/2 , R 10 2 SiO 2/2 , R 11 O 3/2 , and SiO 4/2 are, respectively, an M-unit, a D-unit, a T-unit, and a Q-unit, all of which are primary siloxane units;

subscripts g, h, j, and k are selected to conform with the mole fraction of R 9 3 SiO 1/2 , R 10 2 SiO 2/2 , R 11 SiO 3/2 , and SiO 4/2 , respectively;

0≦g≦1; 0≦h≦1; 0≦j≦0.50; 0≦f≦0.10; and g+h+j+k=1;

at least two silicon bonded hydrogen atoms are present in the multihydrido silicon compound;

a silicon bonded hydrogen atom is present in the hydrido silicon compound in an amount of at least 1 mole percent and no more than 60 mole percent, based on total moles of the silicon bonded organic groups of the multihydrido silicon compound; and

each of R 9 , each of R 10 , and each of R 11 is, independently, a silicon bonded organic group selected from hydrogen atom, aryl other than phenoxyphenyl, alkyl, hydroxy, alkoxy, aryloxy, phenoxyphenyl, other organic radical, alkenyl, and combinations thereof; and

ii) a hydrido silicon compound having the formula IV:

R 12 m SiH (4-m)   (IV)

wherein:

m=1 or 2; and

each R 12 is, independently, a silicon bonded organic group selected from aryl other than phenoxyphenyl, alkyl, hydroxy, alkoxy, aryloxy, phenoxyphenyl, other organic radical, alkenyl, and combinations thereof;

and combinations thereof.

5. The curable phenoxyphenyl polysiloxane composition of claim 1 , wherein:

the reactive diluent is present in the curable phenoxyphenyl polysiloxane composition in an amount of greater than 0 weight percent and no more than 30 weight percent, based on the weight of the curable phenoxyphenyl polysiloxane composition; and

the diluent has a viscosity of at least 1 centipoise and no more than 10,000 centipoise at 25° C.

6. The curable phenoxyphenyl polysiloxane composition of claim 1 , wherein the hydrosilation catalyst is present in an amount, expressed as a Group VIII element equivalent value, of least 0.005 ppm and no more than 3.0 ppm, based on the weight of the curable phenoxyphenyl polysiloxane composition.

7. A method of making a cured phenoxyphenyl polysiloxane composition, comprising the steps of:

A. providing a branched multialkenyl phenoxyphenyl polysiloxane represented by average compositional formula II,

(R 6 3 SiO 1/2 ) c (R 7 2 SiO 2/2 ) d (R 8 SiO 3/2 ) e (SiO 4/2 ) f   (II),

wherein:

R 6 3 SiO 1/2 , R 7 2 SiO 2/2 , R 8 SiO 3/2 , and SiO 4/2 are, respectively, an M-unit, a D-unit, a T-unit, and a Q-unit, all of which are primary siloxane units;

each of R 6 , each of R 7 , and each of R 8 is, independently, a silicon bonded organic group selected from alkenyl, phenoxyphenyl, aryl other than phenoxyphenyl, alkyl, hydroxy, alkoxy, aryloxy, other organic radical, hydrogen, and combinations thereof;

at least two silicon bonded organic groups are alkenyl;

the alkenyl group is CH2=CH-Xs- wherein s=0 or 1, and X is selected from: linear, branched, or cyclic C 1 -C 16 alkyl, o-phenyl, m-phenyl, p-phenyl, and combinations thereof;

the alkenyl group is present in an amount of 1 mole percent to no more than 20 mole percent, based on total moles of the silicon bonded organic group of the multialkylene phenoxyphenyl polysiloxane;

at least one silicon bonded organic group is a phenoxyphenyl group selected from o-phenoxyphenyl, m-phenoxyphenyl, p-phenoxyphenyl, and combinations thereof;

the silicon bonded phenoxyphenyl group is present in an amount of greater than 0 mole percent and no more than 99 mole percent, based on the total moles of silicon bonded organic groups in the alkenyl phenoxyphenyl polysiloxane;

subscripts c, d, e, and f are selected to conform with the mole fractions of R 6 3 SiO 1/2 , R 7 2 SiO 2/2 , R 8 SiO 3/2 , and SiO 4/2 , respectively;

0.001≦c≦1; 0≦d≦0.999; 0≦e≦0.20; 0≦f≦0.10; and c+d+e+f=1; and

the multialkenyl phenoxyphenyl polysiloxane has:

i) a number average molecular weight of at least 500 grams/mole and no more than 5,000 grams/mole; and

ii) a viscosity of at least 10 and no more than 7,000,000 centipoise at 25° C.;

B. providing a multihydrido silicon compound having at least two silicon bonded hydrogen atoms;

C. providing a hydrosilation catalyst in an amount effective to catalyze hydrosilation;

D. providing a reactive diluent wherein:

the reactive diluent is present in the curable phenoxyphenyl polysiloxane composition in an amount of greater than 0 weight percent and no more than 30 weight percent, based on the weight of the curable phenoxyphenyl polysiloxane composition; and

the diluent has a viscosity of at least 1 centipoise and no more than 10,000 centipoise at 25° C.;

E. optionally, providing a hydrosilation inhibitor in an amount in an amount sufficient to inhibit hydrosilation under conditions of shipment and storage of the curable phenoxyphenyl polysiloxane composition;

F. combining the multialkenyl phenoxyphenyl polysiloxane, the multihydrido silicon compound, the hydrosilation catalyst, the optional diluent, and the optional hydrosilation inhibitor to form a curable phenoxyphenyl polysiloxane composition; and

G. curing the curable phenoxyphenyl polysiloxane composition.

8. The method of claim 7 , further comprising the steps of:

C. providing a semiconductor device comprising semiconductor elements; and

D. forming a coating on at least one surface of at least one of the semiconductor elements by a technique comprising steps selected from:

applying the curable phenoxyphenyl silicon composition to the surface before or during the step (B) of curing;

applying the cured phenoxyphenyl polysiloxane composition to the surface; and

combinations thereof.

9. The curable phenoxyphenyl polysiloxane composition of claim 5 , further comprising an inert diluent, wherein:

the inert diluent is present in the curable phenoxyphenyl polysiloxane composition in an amount of greater than 0 weight percent and no more than 40 weight percent, based on the weight of the curable phenoxyphenyl polysiloxane composition;

the combination of the reactive diluent and the inert diluent is present in the curable phenoxyphenyl polysiloxane composition in an amount of greater than 0 weight percent and no more than 40 weight percent, based on the weight of the curable phenoxyphenyl polysiloxane composition.

10. The method of claim 7 , further comprising providing an inert diluent, wherein:

the inert diluent is present in the curable phenoxyphenyl polysiloxane composition in an amount of equal to or greater than 0 weight percent and no more than 40 weight percent, based on the weight of the curable phenoxyphenyl polysiloxane composition; and

the combination of the reactive diluent and the inert diluent the inert diluent is present in the curable phenoxyphenyl polysiloxane composition in an amount of greater than 0 weight percent and no more than 40 weight percent, based on the weight of the curable phenoxyphenyl polysiloxane composition.

Assignments (5)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
NUNC PRO TUNC ASSIGNMENT Recorded Jun 27, 2025
From: ROHM AND HAAS COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US 8, LLC
Reel/Frame 071738/0004 →
CHANGE OF ADDRESS Recorded Jun 27, 2025
From: ROHM AND HAAS COMPANY
To: ROHM AND HAAS COMPANY
Reel/Frame 072156/0067 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2008
From: AULD, KATHLEEN A.; CONNER, DAVID M.; KHANARIAN, GARO; MOSLEY, DAVID WAYNE
To: ROHM AND HAAS COMPANY
Reel/Frame 022007/0714 →