IP Library › Granted Patent US 10,703,946
Granted Patent B2
US 10,703,946 · App. 16/091,127 · Granted Jul 7, 2020

Adhesive delamination layer including at least one non-linear organopolysiloxane

Inventors: Ginam Kim (Midland, MI); Junying Liu (Midland, MI)
Assignee: Dow Silicones Corporation
C09J183/04C08G77/20C08L83/00C09J5/06G03F7/16G03F7/20G03F7/26H01L21/6835H01L27/1266C08G77/12C08G77/70H01L2221/6835
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Quick Facts
Patent No.
US 10,703,946
App. No.
16/091,127
Granted
Jul 7, 2020
Kind
B2
Abstract

An adhesive delamination layer including at least one non-linear organopolysiloxane and methods for display device substrate processing are disclosed. The method includes securing the display device substrate to a carrier substrate with an adhesive delamination layer including a cured product of curing a precursor adhesive composition. The precursor adhesive composition includes Component (A), a hydrogenorganopolysiloxane and Component (B), a (C 2 -C 20 )alkenyl-functionalized organopolysiloxane, wherein the (C 2 -C 20 )alkenyl group is uninterrupted or interrupted by 1, 2, or 3 groups independently chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 - wherein at least one of Component (A) and Component (B) is non-linear.

Claims (88)

1. A method of processing a display device substrate, the method comprising the step of:

securing the display device substrate to a carrier substrate with an adhesive delamination layer comprising a cured product of curing a precursor adhesive composition comprising:

Component (A), a hydrogenorganopolysiloxane; and

Component (B), a (C 2 -C 20 ) alkenyl-functionalized organopolysiloxane, wherein the (C 2 -C 20 ) alkenyl group is uninterrupted or interrupted by 1, 2, or 3 groups independently chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -;

wherein at least one of Component (A) and Component (B) is non-linear and wherein the securing provides a display device processing intermediate wherein an adhesion promoter layer is between the carrier substrate and the adhesive delamination layer and/or a release layer is between the adhesive delamination layer and the display device substrate.

2. The method of claim 1 , wherein Component (A) is non-linear and Component (B) is linear; or wherein Component (A) is linear and Component (B) is non-linear.

3. The method of claim 1 , wherein Component (A) is non-linear and Component (A) is of formula:

(R A 3 SiO 1/2 ) w (R A 2 SiO 2/2 ) x (R A SiO 3/2 ) y (SiO 4/2 ) z ,

wherein

at each occurrence, R A is independently selected from —H and —R 1 ,

at least one R A in Component (A) is —H,

at each occurrence R 1 is independently a substituted or unsubstituted (C 1 -C 20 ) hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -,

y and z are independently 0 to 5,000,

at least one of y and z is greater than 0,

w is 0 to 500, and

x is 0 to 5,000.

4. The method of claim 1 , wherein Component (A) is linear and Component (A) is of formula:

(R A 3 SiO 1/2 ) 2 (R A 2 SiO 2/2 ) x ,

wherein

at each occurrence, R A is independently selected from —H and —R 1 ,

at least one R A in Component (A) is —H,

at each occurrence R 1 is independently a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -, and

x is 0 to 5,000.

5. The method of claim 1 , wherein Component (B) is non-linear and Component (B) is of formula:

(R B 3 SiO 1/2 ) w (R B 2 SiO 2/2 ) x (R B SiO 3/2 ) y (SiO 4/2 ) z

wherein

at each occurrence, R B is independently selected from R 1 and R 2 ,

at least one R B is R 2 ,

at each occurrence R 1 is independently a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -,

at each occurrence R 2 is independently a substituted or unsubstituted (C 2 -C 20 )alkenyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -,

y and z are independently 0 to 5,000,

at least one of y and z is greater than 0,

w is 0 to 500, and

x is 0 to 5,000.

6. The method of claim 1 , wherein Component (B) is linear and Component (B) is of formula:

(R B 3 SiO 1/2 ) 2 (R B 2 SiO 2/2 ) x ,

wherein

at each occurrence, R B is independently selected from —R 1 and —R 2 ,

at least one R B is R 2 ,

at each occurrence R 1 is independently a substituted or unsubstituted (C 1 -C 20 ) hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -,

at each occurrence R 2 is independently a substituted or unsubstituted (C 2 -C 20 ) alkenyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -, and

x is 0 to 5,000.

7. The method of claim 1 , wherein Component (A) is chosen from (HR 1 2 SiO 1/2 ) 2 (R 1 2 SiO 2/2 ) 1-2000 and (HR 1 2 SiO 1/2 ) m1 (R 1 3 SiO 1/2 ) m2 (HR 1 SiO 2/2 ) d1 (R 1 2 SiO 2/2 ) d2 (R 1 SiO 3/2 ) t1 (HSiO 3/2 ) t2 (SiO 4/2 ) q1 ,

wherein subscripts m1, m2, d1, d2, t1, t2, and q1 represent mole fractions of their respective repeat units such that the sum of m1+m2+d1+d2+t1+t2+q1=1; wherein m1 is from 0 to 0.8, m2 is from 0 to 0.8, d1 is from 0 to 0.999, d2 is from 0 to 0.9999, t1 is from 0 to 0.8, t2 is from 0 to 0.8, and q1 is from 0 to 0.99, and

wherein at each occurrence R 1 is independently a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -.

8. The method of claim 1 , wherein Component (B) is chosen from (R 2 R 1 2 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 1-2000 and (R 2 R 1 2 SiO 1/2 ) m1 (R 1 3 SiO 1/2 ) m2 (R 2 R 1 SiO 2/2 ) d1 (R 1 2 SiO 2/2 ) d2 (R 1 SiO 3/2 ) t1 (R 2 SiO 3/2 ) t2 (SiO 4/2 ) q1 ,

wherein subscripts m1, m2, d1, d2, t1, t2, and q1 represent mole fractions of their respective repeat units such that the sum of m1+m2+d1+d2+t1+t2+q1=1; wherein m1 is from 0 to 0.8, m2 is from 0 to 0.8, d1 is from 0 to 0.9999, d2 is from 0 to 0.9999, t1 is from 0 to 0.8, t2 is from 0 to 0.8, and q1 is from 0 to 0.99, and

wherein

at each occurrence R 1 is independently a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -, and

at each occurrence R 2 is independently a substituted or unsubstituted (C 2 -C 20 )alkenyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -.

9. The method of claim 1 , wherein:

Component (A) is of formula: (Me 3 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 1-6 (HMeSiO 2/2 ) 3-9 , and Component (B) is of formula: (ViMe 2 SiO 1/2 ) 2-8 (Me 2 SiO 2/2 ) 50-200 (SiO 4/2 ) 1-2 ; or

Component (A) is of formula: (Me 3 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 3-4 (HMeSiO 2/2 ) 5-6 , and Component (B) is of formula: (ViMe 2 SiO 1/2 ) 4 (Me 2 SiO 2/2 ) 120 (SiO 4/2 ); or

Component (A) is of formula: (HMe 2 SiO 1/2 ) 1-3 (SiO 4/2 ) wherein the unit subscripts indicate mole ratios thereof, and Component (B) is of formula: (ViMe 2 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 50-300 ; or

Component (A) is of formula: (HMe 2 SiO 1/2 ) 1.58 (SiO 4/2 ) wherein the unit subscripts indicate mole ratios thereof, and Component (B) is of formula: (ViMe 2 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 150 ; or

Component (A) is of formula: (HMe 2 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 50-300 , and Component (B) is of formula: (ViMe 2 SiO 1/2 ) 5-20 (Me 3 SiO 1/2 ) 10-50 (SiO 4/2 ) 20-80 ; or

Component (A) is of formula: (HMe 2 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 100 , and Component (B) is of formula: (ViMe 2 SiO 1/2 ) 11 (Me 3 SiO 1/2 ) 34 (SiO 4/2 ) 55 .

10. The method of claim 1 , wherein the precursor adhesive composition further comprises at least one of a silane, an organosilane, a siloxane, an organosiloxane, silicone carbinol fluid, a rubber, a polyurethane, a polyisobutylene, a polyamide, a silyl-modified polyamide, a polyester, a polycarbonate, a polycarbamate, a polyether having at least one alkenyl or akynyl group per molecule, water soluble or water dispersible silicone polyether composition, wax, wax-like material, shellac, a urethane, a precursor that is curable to form of any one of the foregoing, a curing agent and/or a catalyst to cure said precursor when said precursor is present, and a reaction product of any one of the foregoing.

11. The method of claim 1 , wherein the precursor adhesive composition further comprises at least one of a natural adhesive, an epoxy-based adhesive, a furan-based adhesive, a phenolic-based adhesive, an aldehyde-based adhesive, a urea-aldehyde adhesive, an acrylic acid-based adhesive, a phenol/phenol formaldehyde/furfuryl alcohol adhesive, adhesion promoter, a surfactant, emulsifier, foam stabilizer, dispersant, crosslinking agent, rheology modifier, density modifier, cure modifier, hydrosilylation catalyst inhibitor, free radical initiator, acid acceptor, antioxidant, UV stabilizer, aziridine stabilizers, heat stabilizer, flame retardant, scavenging agent, silylating agent, diluent, solvent, plasticizer, thickening agent, filler, inorganic particle, pigment, dye, desiccants, and a flow control additive.

12. The method of claim 1 , further comprising at least one of the steps of: (a) washing, drying, forming a film, applying a liquid photoresist, exposure to light, development, etching, resist removal, sealing, vapor deposition, adhesion treatment, heating, annealing, irradiating, cooling the display device substrate, and at least one of the steps of (b) placing, forming and modifying on the display device substrate at least one of a semiconductor material, a semiconductor device, a diode, a light emitting diode, a transistor, a transistor array, a capacitor, a conductive pathway, a circuit pattern, a gate line, a data line, an electrical connector, an electrode, a transparent electrode, an electrical insulator, an electrically insulating layer, a protective layer, a color filter, a liquid crystal, a hole injection layer, a hole transporting layer, a light emitting layer, a passivation layer, an electrophoretic film, and an electron transporting layer.

13. The method of claim 1 , further comprising removing the display device substrate from the carrier substrate.

14. A method of processing a display device substrate, the method comprising:

securing the display device substrate to a carrier substrate with an adhesive delamination layer comprising a cured product of curing a precursor adhesive composition comprising:

0.1 wt % to 99 wt % Component (A), wherein Component (A) is a hydrogenorganopolysiloxane chosen from (HR 1 2 SiO 1/2 ) 2 (R 1 2 SiO 2/2 ) 1-2000 and (HR 1 2 SiO 1/2 ) m1 (R 1 3 SiO 1/2 ) m2 (HR 1 SiO 2/2 ) d1 (R 1 2 SiO 2/2 ) d2 (R 1 SiO 3/2 ) t1 (HSiO 3/2 ) t2 (SiO 4/2 ) q1 , wherein subscripts m1, m2, d1, d2, t1, t2, and q1 represent mole fractions of their respective repeat units such that the sum of m1+m2+d1+d2+t1+t2+q1=1; wherein m1 is from 0 to 0.8, m2 is from 0 to 0.8, d1 is from 0 to 0.999, d2 is from 0 to 0.9999, t1 is from 0 to 0.8, t2 is from 0 to 0.8, and q1 is from 0 to 0.99; and

0.1 wt % to 99.9 wt % Component (B), wherein Component (B) is an alkenyl-functionalized organopolysiloxane chosen from (R 2 R 1 2 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 1-2000 and (R 2 R 1 2 SiO 1/2 ) m1 (R 1 3 SiO 1/2 ) m2 (R 2 R 1 SiO 2/2 ) d1 (R 1 2 SiO 2/2 ) d2 (R 1 SiO 3/2 ) t1 (R 2 SiO 3/2 ) t2 (SiO 4/2 ) q1 , wherein subscripts m1, m2, d1, d2, t1, t2, and q1 represent mole fractions of their respective repeat units such that the sum of m1+m2+d1+d2+t1+t2+q1=1; wherein m1 is from 0 to 0.8, m2 is from 0 to 0.8, d1 is from 0 to 0.9999, d2 is from 0 to 0.9999, t1 is from 0 to 0.8, t2 is from 0 to 0.8, and q1 is from 0 to 0.99;

wherein

at least one of Component (A) and Component (B) is non-linear,

at each occurrence in Component (A) and (B) R 1 is independently a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -, and

at each occurrence in Component (B), R 2 is independently a substituted or unsubstituted (C 2 -C 20 )alkenyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -;

and wherein the securing provides a display device processing intermediate wherein an adhesion promoter layer is between the carrier substrate and the adhesive delamination layer and/or a release layer is between the adhesive delamination layer and the display device substrate.

15. A display device processing intermediate comprising:

a carrier substrate;

an adhesive delamination layer on the carrier substrate comprising a cured product of curing a precursor adhesive composition comprising

Component (A), a hydrogenorganopolysiloxane; and

Component (B), a (C 2 -C 20 )alkenyl-functionalized organopolysiloxane, wherein the (C 2 -C 20 )alkenyl group is uninterrupted or interrupted by 1, 2, or 3 groups independently chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -;

wherein at least one of Component (A) and Component (B) is non-linear; and

a display device substrate secured to the carrier substrate via the adhesive delamination layer;

and wherein the display device processing intermediate has an adhesion promoter layer between the carrier substrate and the adhesive delamination layer and/or a release layer between the adhesive delamination layer and the display device substrate.

16. The display device processing intermediate according to claim 15 ,

wherein the precursor adhesive composition comprises

0.1 wt % to 99 wt % Component (A), wherein Component (A) is a hydrogenorganopolysiloxane chosen from (HR 1 2 SiO 1/2 ) 2 (R 1 2 SiO 2/2 ) 1-2000 and (HR 1 2 SiO 1/2 ) m1 (R 1 3 SiO 1/2 ) m2 (HR 1 SiO 2/2 ) d1 (R 1 2 SiO 2/2 ) d2 (R 1 SiO 3/2 ) t1 (HSiO 3/2 ) t2 (SiO 4/2 ) q1 , wherein subscripts m1, m2, d1, d2, t1, t2, and q1 represent mole fractions of their respective repeat units such that the sum of m1+m2+d1+d2+t1+t2+q1=1; wherein m1 is from 0 to 0.8, m2 is from 0 to 0.8, d1 is from 0 to 0.999, d2 is from 0 to 0.9999, t1 is from 0 to 0.8, t2 is from 0 to 0.8, and q1 is from 0 to 0.99; and

0.1 wt % to 99.9 wt % Component (B), wherein Component (B) is an alkenyl-functionalized organopolysiloxane chosen from (R 2 R 1 2 SiO 1/2 ) 2 (Me 2 SiO 2/2 ) 1-2000 and (R 2 R 1 2 SiO 1/2 ) m1 (R 1 3 SiO 1/2 ) m2 (R 2 R 1 SiO 2/2 ) d1 (R 1 2 SiO 2/2 ) d2 (R 1 SiO 3/2 ) t1 (R 2 SiO 3/2 ) t2 (SiO 4/2 ) q1 , wherein subscripts m1, m2, d1, d2, t1, t2, and q1 represent mole fractions of their respective repeat units such that the sum of m1+m2+d1+d2+t1+t2+q1=1; wherein m1 is from 0 to 0.8, m2 is from 0 to 0.8, d1 is from 0 to 0.9999, d2 is from to 0.9999, t1 is from 0 to 0.8, t2 is from 0 to 0.8, and q1 is from 0 to 0.99;

wherein

at least one of Component (A) and Component (B) is non-linear,

at each occurrence in Component (A) and (B), R 1 is independently a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -, and

at each occurrence in Component (B), R 2 is independently a substituted or unsubstituted (C 2 -C 20 )alkenyl interrupted with 0, 1, 2, or 3 groups chosen from —O—, —S—, substituted or unsubstituted —NH—, —(O—(C 2 -C 3 )alkylene) n - wherein n is 1 to 1,000, —Si((C 1 -C 5 )alkoxy) 2 -, and —Si((C 1 -C 5 )alkyl) 2 -; and

a display device substrate secured to the carrier substrate via the adhesive delamination layer.

17. The method of claim 1 , wherein the precursor adhesive composition further comprises at least one of a thermoplastic material, a thermoset material, and a crosslinkable polymer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 28, 2020
From: KIM, GINAM; LIU, JUNYING
To: DOW SILICONES CORPORATION
Reel/Frame 052770/0454 →
Continuity (2)
Provisional Application 62336780 · May 16, 2016
Related Publication 20190119538A1 · Apr 25, 2019