IP Library Granted Patent US 10,040,968
Granted Patent B2
US 10,040,968 · App. 15/214,115 · Granted Aug 7, 2018

Di- and mono(meth)acrylate based organic thin film ink compositions

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Quick Facts
Patent No.
US 10,040,968
App. No.
15/214,115
Granted
Aug 7, 2018
Kind
B2
Abstract

The present teachings relate to various embodiments of an ink composition, which once printed and cured forms an organic thin film on a substrate such as, but not limited by, an OLED device substrate. Various embodiments of the ink compositions comprise polyethylene glycol di(meth)acrylate monomers, mono(meth)acrylate monomers and multifunctional crosslinking agents.

Claims (35)

1. A process of forming a polymeric thin film layer on a substrate, the method comprising:

providing an inert processing environment;

providing an OLED device substrate;

providing an ink composition, the ink composition comprising:

40 wt. % to 60 wt. % polyethylene glycol dimethacrylate monomer, polyethylene glycol diacrylate monomer, or a combination thereof, wherein the polyethylene glycol dimethacrylate monomer and the polyethylene glycol diacrylate monomer have number average molecular weights in the range from about 230 g/mole to about 430 g/mole;

25 wt. % to 50 wt. % monoacrylate monomer, monomethacrylate monomer, or a combination thereof, having a viscosity in the range from about 10 cps to about 27 cps at 22° C.;

4 wt. % to 10 wt. % multifunctional acrylate crosslinking agent, a multifunctional methacrylate crosslinking agent, or a combination thereof; and

0.1 wt. % to 10 wt. % crosslinking photoinitiator,

the ink composition having a surface tension of between about 32 dynes/cm and about 45 dynes/cm at 22° C.;

printing a layer of the ink composition over a defined area of the substrate, and

curing the layer of printed ink, wherein an organic polymeric thin film is formed.

2. The process claim 1 , further comprising before the step of providing an OLED device substrate:

providing an industrial printing system housed within the interior of a gas enclosure, wherein the industrial printing system comprises:

a printhead assembly comprising at least one printhead;

a substrate support system for supporting a substrate; and

a motion system for the precise positioning of the substrate relative to the printhead assembly; and

a UV curing module.

3. The process of claim 1 , wherein the inert process environment is provided using an inert gas selected from nitrogen, any of the noble gases, and combinations thereof.

4. The process of claim 1 , wherein the inert process environment has water vapor content and oxygen content each at less than 100 ppm.

5. The process of claim 1 , wherein the cured layer of printed ink has a thickness of no greater than 6 μm.

6. The process of claim 1 , wherein the ink composition further comprises 1 wt. % to 15 wt. % of a spreading modifier having a viscosity in the range from about 10 cps to about 20 cps at 22° C. and a surface tension in the range from about 35 dynes/cm to about 39 dynes/cm at 22° C.

7. The process of claim 6 , wherein the spreading modifier comprises an alkoxylated aliphatic diacrylate monomer, an alkoxylated aliphatic dimethacrylate monomer, or a combination thereof.

8. The process of claim 1 , wherein the ink composition comprises 45 wt. % to 57 wt. % polyethylene glycol dimethacrylate monomer, polyethylene glycol diacrylate monomer, or combination thereof and 30 wt. % to 40 wt. % monoacrylate monomer, monomethacrylate monomer, or combination thereof and has a viscosity in the range from about 10 cps to about 27 cps at 22° C.

9. The process of claim 1 , wherein the crosslinking photoinitiator comprises pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, di(trimethylolpropane) tetraacrylate, di(trimethylolpropane) tetramethacrylate or a combination thereof.

10. The process of claim 1 , wherein the crosslinking photoinitiator comprises 2,4,6-trimethylbenzoyl-diphenylphosphine oxide.

11. The process of claim 1 , wherein the monoacrylate monomer, monomethacrylate monomer, or combination thereof comprises a cyclic monoacrylate monomer, cyclic monomethacrylate monomer, or a combination thereof.

12. The process of claim 11 , wherein the cyclic monoacrylate monomer, cyclic monomethacrylate monomer, or combination thereof comprises dicyclopentenyloxyethyl acrylate, dicyclopentenyloxyethyl methacrylate, or a combination thereof.

13. The process of claim 12 , wherein the cyclic monoacrylate monomer, cyclic monomethacrylate monomer, or combination thereof further comprises isobornyl acrylate, isobornyl methacrylate, or a combination thereof.

14. The process of claim 13 , wherein less than 10 wt. % of the ink composition is comprised of the isobornyl acrylate, isobornyl methacrylate, or a combination thereof.

15. The process of claim 1 , wherein the monoacrylate monomer, monomethacrylate monomer, or combination thereof comprises an aliphatic monoacrylate monomer, aliphatic monomethacrylate monomer, or a combination thereof.

16. The process of claim 15 , wherein the aliphatic monoacrylate monomer, aliphatic monomethacrylate monomer or combination thereof comprises n-octadecyl acrylate, n-octadecyl methacrylate, or a combination thereof.

17. The process of claim 16 , wherein the ink composition comprises 29 wt. % to 40 wt. % of the n-octadecyl acrylate, n-octadecyl methacrylate, or a combination thereof.

18. The process of claim 1 , wherein the defined area of the substrate comprises an electroluminescent region of an OLED.

19. The process of claim 1 , wherein the organic polymeric thin film is part of an encapsulation stack on an active region of an OLED device, the encapsulation stack further comprising an inorganic device layer adjacent to the organic polymeric thin film.

20. The process of claim 1 , wherein the OLED device substrate is an electrode of an OLED pixel.

Assignments (6)
SECURITY INTEREST Recorded Apr 19, 2022
From: KATEEVA CAYMAN HOLDING, INC.
To: HB SOLUTION CO., LTD.
Reel/Frame 059727/0111 →
SECURITY INTEREST Recorded Mar 17, 2022
From: KATEEVA, INC.; KATEEVA CAYMAN HOLDING, INC.
To: SINO XIN JI LIMITED
Reel/Frame 059382/0053 →
SECURITY AGREEMENT Recorded Jan 23, 2020
From: KATEEVA, INC.
To: SINO XIN JI LIMITED
Reel/Frame 051682/0212 →
RELEASE OF SECURITY INTEREST Recorded Jan 22, 2020
From: EAST WEST BANK, A CALIFORNIA BANKING CORPORATION
To: KATEEVA, INC.
Reel/Frame 051664/0802 →
SECURITY INTEREST Recorded Apr 4, 2019
From: KATEEVA, INC.
To: EAST WEST BANK
Reel/Frame 048806/0639 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 19, 2016
From: JAIN, RAJSAPAN; YUWONO, CITRA; CHAN, MICHELLE; TREGUB, INNA
To: KATEEVA, INC.
Reel/Frame 039191/0543 →