Quantum dot article with reduced edge ingress and improved color stability

Patent metadata

Field	Value
Publication number	US-10167417-B2
Application number	US-201515323661-A
Country	US
Kind code	B2
Filing date	Jun 30, 2015
Priority date	Jul 3, 2014
Publication date	Jan 1, 2019
Grant date	Jan 1, 2019

Abstract

A quantum dot film article including a first barrier layer, a second barrier layer; and a quantum dot layer between the first barrier layer and the second barrier layer. The quantum dot layer includes quantum dots dispersed in a matrix including a cured adhesive composition. The adhesive composition includes an epoxide and a curing agent including: (a) a compound of Formula I: wherein A is a monocyclic or a polycyclic alkylene group, or a monocyclic or a polycyclic heteroalkylene group, and m and n are integers each independently selected from 0 to 5; and (b) a polyether amine compound including at least one of primary and secondary amino groups attached to a polyether backbone. The adhesive composition further includes a radiation curable methacrylate compound.

First claim

The invention claimed is:

1. A quantum dot film article comprising:
a first barrier layer;
a second barrier layer; and
a quantum dot layer between the first barrier layer and the second barrier layer, the quantum dot layer comprising quantum dots dispersed in a matrix comprising a cured adhesive composition, wherein the adhesive composition comprises:
an epoxide;
a curing agent comprising:
(a) a compound of Formula I:
H 2 N—C n H 2n -A-C m H 2m —NH 2   Formula 1

wherein A is a monocyclic or a polycyclic alkylene group, or a monocyclic or a polycyclic heteroalkylene group, and m and n are integers each independently selected from 0 to 5; and
(b) a polyether amine compound of Formula V or VI:
R 10 —(O—R 11 ) q —NH 2   Formula V

wherein, in Formula V, group R 10 is an alkyl having 1 to 4 carbon atoms, and R 11 is independently a branched or linear alkylene having 1 to 4 carbon atoms, and q is equal to at least 2
H 2 N—R 12 —(OR 13 ) p —NH 2   Formula VI

wherein, in Formula VI, R 12 and R 13 are each independently a branched or linear alkylene having 1 to 4 carbon atoms, and p is equal to at least 2; and
a radiation curable methacrylate compound.

2. The film article of claim 1 , wherein the epoxide comprises a bisphenol-F backbone.

3. The film article of claim 1 , wherein the epoxide is a diepoxide.

4. The film article of claim 1 , wherein A in Formula I is the group of Formula II:

wherein R 1 , R 2 , R 3 , and R 4 , each represent either a hydrogen atom or a methyl group; x and y are each independently selected from 0 or 1; and the asterisks (*) represent attachment positions to Formula I.

5. The film article of claim 1 , wherein A in Formula I is the group of Formula III:

wherein R 5 and R 6 each represent either a hydrogen or a methyl group; x and y are each independently selected from 0 or 1, and the asterisks (*) represent the attachment positions to Formula I.

6. The film article of claim 1 , wherein the compound of Formula I is represented by one of the following:
(a) 3(or 4), 8(or 9)-diaminomethyltricyclo(5,2,1,0 2.6 ) decane:

(b) 4,9(or 10)-diaminomethyltetracyclo(6,2,1,1 3.6 ,0 2.7 ) dodecane:

or,
(c) 2,5(or 6)-diaminomethyl bicyclo(2,2,1)heptane:

7. The film article of claim 1 , wherein the adhesive composition further comprises a photoinitiator.

8. The film article of claim 1 , wherein the polyether backbone of the polyether amine compound comprises repeat units of propylene glycol (PG), ethylene glycol (EG), polytetramethylene glycol (PTMEG), and combinations thereof.

9. The film article of claim 1 , wherein the polyether amine compound is 4,7,10-trioxatridecane-1,13,-diamine.

10. The film article of claim 1 , wherein the ratio of the compound of Formula 1 to the polyether amine compound in the adhesive composition is about 1:1 to about 1:10 to about 10:1 to about 1:1.

11. The film article of claim 1 , wherein the matrix comprises about 5 wt % to about 25 wt % of the methacrylate compound and 70 to 90 wt % of an epoxy polymer formed from the reaction of the epoxide and the curing agent.

12. The film article of claim 1 , wherein the stoichiometric ratio of epoxy to amine in the curing agent is about 0.6 to about 1.4 epoxy to amine hydrogen.

13. The film article of claim 1 , wherein the matrix further comprises scattering particles having an average size in a range from 1 to 10 micrometers.

14. The film article of claim 1 , wherein at least one of the first and the second barrier layer comprises at least one polymeric film.

15. The film article of claim 1 , wherein the matrix has a moisture and oxygen ingress of less than about 0.5 mm after 500 hours at 85° C.

16. The film article of claim 1 , wherein the matrix has a color shift d(x,y) using the CIE1931 (x,y) convention of less than about 0.02 after 100 hours at 85° C.

17. The film article of claim 16 , wherein the matrix has a color change d(x,y) using the CIE 1931 (x,y) convention of less than about 0.005 after 100 hours at 85° C.

18. A display device comprising the film article of claim 1 .

19. A method of forming a film article, comprising coating a quantum dot material on a first polymeric film, the quantum dot material comprising quantum dots in an adhesive composition comprising:
an epoxide;
a curing agent comprising:
(a) an amino-functional compound of Formula I:
H 2 N—C n H 2n -A-C m H 2m —NH 2   Formula I

wherein A is a monocyclic or a polycyclic alkylene group, or a monocyclic or a polycyclic heteroalkylene group, and m and n are integers each independently selected from 0 to 5; and
(b) a polyether diamine compound comprising at least one of primary and secondary amino groups attached to a polyether backbone, wherein the backbone comprises repeat units of propylene glycol (PG), ethylene glycol (EG), polytetramethylene glycol (PTMEG), and combinations thereof;
a radiation curable methacrylate compound; and
a photoinitiator.

20. The method of claim 19 , further comprising curing the adhesive composition.

21. The method of claim 20 , further comprising applying a second polymeric film on the adhesive composition.

22. The method of claim 21 , further comprising curing the adhesive composition.

23. The method of claim 19 , wherein the adhesive composition is cured by applying to the composition heat and UV light.

24. The method of claim 19 , wherein the polyether diamine compound is represented by Formula VI:
H 2 N—R 12 —(OR 13 ) p —NH 2   Formula VI

wherein, in Formula VI, R 12 and R 13 are each independently a branched or linear alkylene having 1 to 4 carbon atoms, and p is equal to at least 2.

25. The method of claim 24 , wherein the polyether diamine compound is 4,7,10-trioxatridecane-1,13,-diamine.

26. The method of claim 19 , wherein the stoichiometric ratio of epoxy to amine in the curing agent is about 0.6 to about 1.4 epoxy to amine hydrogen.

27. An adhesive composition, comprising:
an epoxide;
a curing agent comprising:
(a) an amino-functional compound of Formula I:
H 2 N—C n H 2n -A-C m H 2m —NH 2   Formula I

wherein A is a monocyclic or a polycyclic alkylene group, or a monocyclic or a polycyclic heteroalkylene group, and m and n are integers each independently selected from 0 to 5 and
(b) a polyether diamine compound represented by Formula VI:
H 2 N—R 12 —(OR 13 ) p —NH 2   Formula VI

wherein, in Formula VI, R 12 and R 13 are each independently a branched or linear alkylene having 1 to 4 carbon atoms, and p is equal to at least 2;
a radiation curable methacrylate compound;
a photoinitiator; and
quantum dots.

28. An adhesive composition, comprising:
an epoxide;
a curing agent comprising a blend of:
(a) an amino-functional compound of Formula I:
H 2 N—C n H 2n -A-C m H 2m —NH 2   Fo

Assignees

• 3M Innovative Properties Co

Inventors

• Pieper Joseph M
• Nelson Eric W
• Eckert Karrisa L
• Mahoney Wayne S

Classifications

• G02F2202/36

  Micro- or nanomaterials · CPC title

• G02F1/133615

  Edge-illuminating devices, i.e. illuminating from the side · CPC title

• G02F1/1336

  Illuminating devices · CPC title

• C09K11/08

  containing inorganic luminescent materials · CPC title

• C09K11/02 Primary

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title