Polysiloxane formulations and coatings for optoelectronic applications

• US 10,544,329 B2
• Filed: 03/02/2016
• Issued: 01/28/2020
• Est. Priority Date: 04/13/2015
• Status: Active Grant

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Varaprasad, Desaraju, Mukhopadhyay, Sudip, Xie, Songyuan, Gebrehrhan, Amanuel H., Bien, Hai
• Primary Examiner(s): Loewe, Robert S
• Application Number:
  US15/522,419
• Publication Number:
  US 20180022957A1
• Time in Patent Office: 1,427 Days
• Field of Search: None
• CPC Class Codes: C08G 77/80 Siloxanes having aromatic substituents, e.g. phenyl side groups
• CPC Class Codes: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 2483/04 Polysiloxanes
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C08K 5/0025 Crosslinking or vulcanising agents; including accelerators
• CPC Class Codes: C08K 5/16 Nitrogen-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 183/04 Polysiloxanes

Abstract

A crosslinkable composition includes a first silicon-containing resin comprising alkyl groups and alkyl groups and a second silicon-containing resin comprising alkyl groups. The first silicon-containing resin has a weight average molecular weight from 1000 AMU to 10,000 AMU. The second silicon-containing resin has a weight average molecular weight from 900 AMU to 5000 AMU. The composition further includes at least one solvent and at least one heat-activated catalyst.

Claims

1. A crosslinkable composition, comprising:

a first polysiloxane resin comprising alkyl groups, wherein from 14% to 100% of the carbon atoms in the first polysiloxane resin are contained in the alkyl groups, the balance of carbon atoms contained in aryl groups, the first polysiloxane resin having a weight average molecular weight from 1000 AMU to 10,000 AMU;

a second polysiloxane resin comprising aryl groups, wherein all of the carbon atoms in the second polysiloxane resin are contained in the aryl groups, the second polysiloxane resin having a weight average molecular weight from 900 AMU to 5000 AMU;

at least one solvent; and

at least one heat-activated catalyst.

2. The crosslinkable composition of claim 1, further comprising at least one surfactant.

3. The crosslinkable composition of claim 1, further comprising at least one adhesion promoter.

4. The crosslinkable composition of claim 1, wherein the first polysiloxane resin comprises methylsiloxane, phenylsiloxane, and dimethyldiethoxysilane, and the second polysiloxane resin comprises phenylsiloxane.

5. The crosslinkable composition of claim 1, wherein the first polysiloxane resin further comprises a difunctional siloxane.

6. The crosslinkable composition of claim 5, wherein the difunctional siloxane is dimethyl siloxane.

7. The crosslinkable composition of claim 5, wherein the difunctional siloxane comprises at least 0.1 mol.% as a percent of the total moles of siloxane in the first polysiloxane resin.

8. The crosslinkable composition of claim 1, wherein the percentage of carbon atoms contained in alkyl groups ranges from 5% to 12% based on the total number of carbon atoms in the first and second polysiloxane resins.

9. A crosslinked film formed from the crosslinkable composition of claim 1, wherein the crosslinked film has a thickness of 1.5 μ

m or greater.

10. The crosslinked film of claim 9, wherein the crosslinked film has a thickness of 3.0 μ

m or greater.

11. The crosslinked film of claim 9, wherein the crosslinked film is cured at a temperature of 350°

C. or greater.

12. A device comprising a crosslinked film according to claim 9, wherein the device is selected from the group consisting of a transistor, a light-emitting diode, a color filter, a photovoltaic cell, a flat-panel display, a curved display, a touch-screen display, an x-ray detector, an active or passive matrix OLED display, an active matrix think film liquid crystal display, an electrophoretic display, a CMOS image sensor, and combinations thereof, and wherein the crosslinked film forms a passivation layer, a planarization layer, a barrier layer, or a combination thereof.

13. A method of forming a crosslinked film, the method comprising:

combining a first polysiloxane resin comprising alkyl groups, a second polysiloxane resin comprising aryl groups, a solvent, and a heat activated catalyst to form a crosslinkable composition, wherein from 14% to 100% of the carbon atoms in the first polysiloxane resin are contained in the alkyl groups, the balance of the carbon atoms contained in aryl groups, the first polysiloxane resin having a weight average molecular weight from 1000 AMU to 10,000 AMU, the second polysiloxane resin having a weight average molecular weight from 900 AMU to 5000 AMU, and all of the carbon atoms in the second polysiloxane resin are contained in the aryl groups;

depositing the composition on a substrate; and

curing the crosslinkable composition at a temperature of 350°

C. or greater to form a crosslinked film, wherein the crosslinked film has a thickness of 1.5 μ

m or greater.

14. The method of claim 13, wherein the first polysiloxane resin comprises methylsiloxane and phenylsiloxane and the second polysiloxane resin comprises phenylsiloxane.

15. The method of claim 14, wherein the first polysiloxane resin further comprises dimethyl siloxane.

16. The method of claim 13, wherein the crosslinked film has a thickness of 3.0 μ

m or greater.

17. The method of claim 13, wherein the crosslinked film is cured at a temperature of 350°

C. or greater.

18. The method of claim 13, wherein the crosslinked film is cured at a temperature of 390°

C. or greater.

19. The method of claim 13, wherein the first polysiloxane resin comprises methylsiloxane and phenylsiloxane and the second polysiloxane resin comprises phenylsiloxane, the method further comprising reacting a phenyl triethoxysilane-based polymer having a molecular weight of at least 1000 AMU in a solvent in the presence of a catalyst to form the second polysiloxane resin.

20. The method of claim 19, wherein the catalyst is a tetraorganoammonium compound.