Radiation curable composition for water scavenging layer, and method of manufacturing the same

Patent metadata

Field	Value
Publication number	US-10559777-B2
Application number	US-201314415475-A
Country	US
Kind code	B2
Filing date	Jul 16, 2013
Priority date	Jul 19, 2012
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

Abstract

A radiation curable resin composition comprising:
(A) metal oxide particles; (B) at least one photoinitiator, preferably a radical photoinitiator, or any mixture thereof; (C) at least one acrylate or methacrylate component with a ClogP higher than 2, preferably higher than 4, more preferably higher than 5, or any mixture thereof; (D) at least one monofunctional acrylate or methacrylate diluent component, preferably with a viscosity below 40 mPa·s at 20° C., or any mixture thereof; (E) at least one acrylate or methacrylate component with functionality equal or higher than 3, preferably 3 or 4, or any mixture thereof;

can be advantageously used, for example, in multilayer barrier stacks for the production of organic opto-electric or opto-electronic device, such as Organic Light Emitting Diode (OLED).

First claim

The invention claimed is:

1. A photocurable resin composition comprising:
(A) 1-30% by weight of alkaline earth metal oxide particles selected from the group consisting of dehydrated CaO, dehydrated BaO and dehydrated MgO particles;
(B) 0.1-10% by weight of at least one photoinitiator, or any mixture thereof;
(C) 30-80% by weight of at least one acrylate or methacrylate component with a ClogP higher than 2, or any mixture thereof;
(D) 5-40% by weight of at least one monofunctional acrylate or methacrylate diluent component, or any mixture thereof;
(E) 5-30% by weight of at least one acrylate or methacrylate component with functionality equal or higher than 3, or any mixture thereof;
(F) 0.1-30% by weight of a polybutadiene acrylate or methacrylate, a silicone acrylate or methacrylate, or a two-mole ethoxylated bisphenol A di(meth)acrylate, or any mixture thereof;
based on the total weight of the composition;
wherein the photocurable resin exhibits a water content of less than 1000 ppm by weight;
wherein Mica is excluded from the group of (A) alkaline earth metal oxide particles; and
wherein the photocurable resin composition does not comprise any urethane (meth)acrylate, polyester (meth)acrylate, or polyethylene glycol (PEG) (meth)acrylate.

2. A photocurable resin composition according to claim 1 , wherein the alkaline earth metal oxide particles A exhibit an average particle diameter of 10 to 1000 nm.

3. A photocurable resin composition according to claim 1 , which exhibits a viscosity at 20° C. below 500 mPa·s,
and/or which exhibits a pot life at 60° C. longer than 29 days.

4. A photocurable resin composition according to claim 1 , wherein component (D) exhibits a ClogP higher than 2,
component (E) exhibits a ClogP higher than 1,
and/or component (F) exhibits a ClogP higher than 4.

5. A photocurable resin composition according to claim 1 , wherein component C is a 1,n-diol di(meth)acrylate of a diol of the formula HO—(CH 2 ) n —OH, whereby n is higher than 3.

6. A photocurable resin composition according to claim 1 , which, after curing, is transparent.

7. A photocurable resin composition according to claim 1 comprising at least:
(A) 4-20% by weight of dehydrated CaO, dehydrated BaO and/or dehydrated MgO particles (component A);
(B) 0.1-5% by weight of the photo initiator B;
(C) 40-70% by weight of component C;
(D) 10-30% by weight of the monofunctional (meth)acrylate diluent component D;
(E) 7-20% by weight of the (meth)acrylate component E with functionality equal or higher than 3; and
(F) 0.3-25% by weight of component F;
based on the total weight of the composition.

8. Method for preparing a photocurable resin composition according to claim 1 , comprising the steps of:
h) mixing and stirring together components C, D, E, and optionally F, in order to produce a mixture h, which is optionally dried, wherein component F is a polybutadiene acrylate or methacrylate, a silicone acrylate or methacrylate, or a two-mole ethoxylated bisphenol A di(meth)acrylate, or any mixture thereof;
i) incorporating dehydrated calcium, dehydrated barium and/or dehydrated magnesium oxide (component A) into the produced mixture h, so as to obtain a mixture i;
j) milling and/or grinding the produced mixture i, in order to downsize the average diameter of dehydrated calcium, dehydrated barium and/or dehydrated magnesium oxide particles, so as to produce a mixture j;
k) adding the photoinitiator B to the produced mixture j, so as to obtain a mixture k.

9. Method for preparing a photocurable resin composition according to claim 8 , wherein during the milling step j) the average particle diameter of the dehydrated CaO, dehydrated BaO and/or dehydrated MgO particles is reduced to the range of 10 to 1000 nm, and/or wherein the produced photocurable resin k exhibits a water content less than 1000 ppm by weight.

10. Method for manufacturing a multi layer barrier stack against water and oxygen penetration and diffusion, comprising the steps of:
m) depositing a first inorganic layer;
n) depositing onto said first inorganic layer, a first organic layer of the photocurable resin composition according to claim 1 ;
o) exposing said first organic layer to ultraviolet radiation, so as to solidify said first organic layer and to produce a transparent layer exhibiting water scavenging properties;
p) applying onto said first solidified organic layer, a second organic layer of a photocurable resin not containing metal oxide particles;
q) exposing said second organic layer to UV radiation, so as to solidify said second organic layer and to produce a transparent layer exhibiting planarization properties;
r) depositing onto said second solidified organic layer a second inorganic layer.

11. Method for manufacturing a multi layer barrier stack according to claim 10 , whereby the first organic layer exhibits a thickness between 10 and 100 micrometers, and/or whereby the second organic layer exhibits a thickness between 10 and 100 micrometers.

12. A method for manufacturing an opto-electric device, comprising the steps of:
providing an opto-electric element and/or layer,
providing an encapsulation comprising a multi layer barrier stack produced according to the method of claim 10 .

13. A multi layer barrier stack or opto-electric device, obtained by a method according to claim 10 .

14. A photocurable resin composition according to claim 1 , wherein component A comprises dehydrated CaO.

15. A photocurable resin composition according to claim 1 , wherein at least two (meth)acrylate functionalities are exhibited by component (F).

16. A photocurable resin composition according to claim 1 , wherein component (F) exhibits a ClogP higher than 2.

17. The photocurable resin composition according to claim 14 , wherein said dehydrated CaO have a calcium hydroxide content of less than 5% by weight and a calcium carbonate content of less than 1% by weight.

Assignees

• Basf Coatings Gmbh

Inventors

• Galand Emilie
• Belbakra Zakaria
• Cherkaoui Zoubair
• Frantz Richard

Classifications

• C09D11/30

  Inkjet printing inks · CPC title

• H01L51/56

  Electricity · mapped topic

• H01L51/0043

  Electricity · mapped topic

• H01L51/5253 Primary

  Electricity · mapped topic

• C08K2003/2206

  of calcium, strontium or barium · CPC title