Organic Thin Film Ink Compositions and Methods

• US 20160024322A1
• Filed: 07/22/2015
• Published: 01/28/2016
• Est. Priority Date: 07/25/2014
• Status: Active Grant

• Current Assignee: Kateeva, Inc.
• Original Assignee: Kateeva, Inc.
• Inventors: Jain, Rajsapan, Chan, Michelle, Tregub, Inna, Chen, Jianglong
• Granted Patent: US 9,909,022 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: C09D 11/101 Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
• CPC Class Codes: C09D 11/30 Inkjet printing inks
• CPC Class Codes: C09D 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: H01L 21/823431 with a particular manufacturing method of transistors with a horizontal current flow in a vertical sidewall of a semiconductor body, e.g. FinFET, MuGFET
• CPC Class Codes: H10K 50/844 Encapsulations
• CPC Class Codes: H10K 59/873 Encapsulations
• CPC Class Codes: H10K 71/00 Manufacture or treatment specially adapted for the organic devices covered by this subclass
• CPC Class Codes: H10K 71/13 using printing techniques, e.g. ink-jet printing or screen printing
• CPC Class Codes: H10K 71/15 characterised by the solvent used

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 can be printed using an industrial inkjet printing system that can be housed in a gas enclosure, which gas enclosure defines an interior that has a controlled environment maintained as an inert and substantially low-particle process environment. Patterned printing of an organic thin film on a substrate, for example, but not limited by, an OLED device substrate, in such a controlled environment can ensure a high-volume, high yield process for a variety of OLED devices.

Claims

1. An ink composition comprising:

75-95 wt. % of a polyethylene glycol dimethacrylate monomer, a 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;

4-10 wt. % of pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, or a combination thereof; and

1-15 wt. % of a spreading modifier having a viscosity in the range from about 14 to about 18 cps at 22°

C. and a surface tension in the range from about 35 to about 39 dynes/cm at 22°

C.

2. The ink composition of claim 1, wherein the spreading modifier has a viscosity in the range from about 14 to about 16 cps at 22°

C. and a surface tension in the range from about 35 to about 38 dynes/cm at 22°

C.

3. The ink composition of claim 1, wherein the spreading modifier comprises an alkoxylated aliphatic diacrylate monomer, an alkoxylated aliphatic dimethacrylate monomer, or a combination thereof.

4. The ink composition of claim 2, wherein the spreading modifier comprises an alkoxylated aliphatic diacrylate monomer, an alkoxylated aliphatic dimethacrylate monomer, or a combination thereof.

5. The ink composition of claim 1, characterized in that:

the spreading modifier has a maximum stable inkjet jetting frequency of at least 23 kHz at 22°

C.; and

the spreading modifier has a maximum drop volume variation of no greater than 15% and a maximum drop velocity variation of no greater than 15% up to its maximum stable inkjet jetting frequency at 22°

C.

6. The ink composition of claim 1 having a maximum stable inkjet jetting frequency of at least 25 kHz at 25°

C.

7. The ink composition of claim 1, further comprising a crosslinking photoinitiator present in an amount that results in a volume change of no greater than 1% when a film printed from the ink composition is cured.

8. The ink composition of claim 7, wherein the photoinitiator is 2,4,6-trimethylbenzoyl-diphenylphosphine oxide.

9. The ink composition of claim 8, wherein the 2,4,6-trimethylbenzoyl-diphenylphosphine oxide is present in an amount in the range from about 3.75 to about 4.25 wt. % of the ink composition.

10. The ink composition of claim 3, wherein the photoinitiator is 2,4,6-trimethylbenzoyl-diphenylphosphine oxide.

11. The ink composition of claim 10, comprising 75-95 wt. % of a polyethylene glycol dimethacrylate monomer having a number average molecular weight of about 330 g/mole, and 4-10 wt. % of the pentaerythritol tetraacrylate, wherein the spreading modifier comprises the alkoxylated aliphatic diacrylate monomer.

12. 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 having an inorganic thin film formed thereupon;

providing an ink composition comprising;

75-95 wt. % of a polyethylene glycol dimethacrylate monomer, a 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;

4-10 wt. % of pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, or a combination thereof;

1-15 wt. % of a spreading modifier having a viscosity in the range from about 14 to about 18 cps at 22°

C. and a surface tension in the range from about 35 to about 39 dynes/cm at 22°

C.; and

0.1-5 wt. % of a photoinitiator,

printing a layer of the ink composition over a defined area of the substrate including the inorganic thin film, and

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

13. The process of claim 12, wherein the spreading modifier comprises an alkoxylated aliphatic diacrylate monomer, an alkoxylated aliphatic dimethacrylate monomer, or a combination thereof.

14. The process of claim 12, wherein the volume difference between the layer of printed ink composition and the organic polymeric thin film is no greater than 1%.

15. The process of claim 12, wherein the volume difference between the layer of printed ink composition and the organic polymeric thin film is no greater than 0.5%.

16. The process of claim 12, wherein the photoinitiator is 2,4,6-trimethylbenzoyl-diphenylphosphine oxide.

17. The process of claim 13, wherein the photoinitiator is 2,4,6-trimethylbenzoyl-diphenylphosphine oxide.

18. The process claim 12, 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.

19. The process of claim 12, wherein the inert process environment is provided using an inert gas selected from nitrogen, any of the noble gases, and combinations thereof.

20. The process of claim 12, wherein the inert process environment has water vapor content and oxygen content each at less than 100 ppm.