Articles including a (co)polymer reaction product of a urethane (multi)-(meth)acrylate (multi)-silane

Patent metadata

Field	Value
Publication number	US-9790396-B2
Application number	US-201314416303-A
Country	US
Kind code	B2
Filing date	Mar 1, 2013
Priority date	Aug 8, 2012
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

Urethane (multi)-(meth)acrylate (multi)-silane compositions, and articles including a (co)polymer reaction product of at least one urethane (multi)-(meth)acrylate (multi)-silane precursor compound. The disclosure also articles including a substrate, a base (co)polymer layer on a major surface of the substrate, an oxide layer on the base (co)polymer layer; and a protective (co)polymer layer on the oxide layer, the protective (co)polymer layer including the reaction product of at least one urethane (multi) (meth)acrylate (multi)-silane precursor compound. The substrate may be a (co)polymeric film or an electronic device such as an organic light emitting device, electrophoretic light emitting device, liquid crystal display, thin film transistor, or combination thereof. Methods of making urethane (multi)-(meth)acrylate (multi)-silane precursor compounds and their use in composite multilayer barrier films are also described. Methods of using such barrier films in articles selected from a solid state lighting device, a display device, and combinations thereof, are also described.

First claim

The invention claimed is:

1. An article, comprising:
a substrate selected from a (co)polymeric film or an electronic device, the electronic device further comprising an organic light emitting device (OLED), an electrophoretic light emitting device, a liquid crystal display, a thin film transistor, a photovoltaic device, or a combination thereof;
a base (co)polymer layer on a major surface of the substrate;
an oxide layer on the base (co)polymer layer; and
a protective (co)polymer layer on the oxide layer, wherein the protective (co)polymer layer comprises the reaction product of at least one urethane (multi)-(meth)acrylate (multi)-silane precursor compound of the formula:
R S —N(H)—C(O)—O—R A or R S —O—C(O)—N(H)—R A , wherein:
R S is a silane containing group of the formula —R 1 —[Si(Y p )(R 2 ) 3−p ] q , further wherein:
R 1 is a multivalent alkylene, arylene, alkarylene, or aralkylene group, said alkylene, arylene, alkarylene, or aralkylene groups optionally containing one or more catenary oxygen atoms,
each Y is a hydrolysable group,
R 2 is a monovalent alkyl or aryl group;
p is 1, 2, or 3, and
q is 1-5; and
R A is a (meth)acryl group containing group of the formula R 11 -(A) n , wherein:
R 11 is a polyvalent alkylene, arylene, alkarylene, or aralkylene group, said alkylene, arylene, alkarylene, or aralkylene groups optionally containing one or more catenary oxygen atoms,
A is a (meth)acryl group comprising the formula X 2 —C(O)—C(R 3 )═CH 2 , further wherein:
X 2 is —O, —S, or —NR 3 ,
R 3 is H, or C 1 -C 4 , and
n=1 to 5.

2. The article of claim 1 , wherein Y is individually selected from the group consisting of alkoxy groups, acetate groups, aryloxy groups, and halogens.

3. The article of claim 1 , wherein Y is selected from alkoxy groups.

4. The article of claim 1 , further comprising a plurality of alternating layers of the oxide layer and the protective (co)polymer layer on the base (co)polymer layer.

5. The article of claim 1 , wherein the substrate comprises a flexible transparent (co)polymeric film, optionally wherein the substrate comprises polyethylene terephthalate (PET), polyethylene napthalate (PEN), heat stabilized PET, heat stabilized PEN, polyoxymethylene, polyvinylnaphthalene, polyetheretherketone, fluoro(co)polymer, polycarbonate, polymethylmethacrylate, poly α-methyl styrene, polysulfone, polyphenylene oxide, polyetherimide, polyethersulfone, polyamideimide, polyimide, polyphthalamide, or combinations thereof.

6. The article of claim 1 , wherein the base (co)polymer layer comprises a (meth)acrylate smoothing layer.

7. The article of claim 1 , wherein the oxide layer comprises oxides and optionally any one or more of nitrides, carbides or borides of atomic elements from Groups IIA, IIIA, IVA, VA, VIA, VIIA, IB, or IIB, metals of Groups IIIB, IVB, or VB, rare-earth metals, or combinations thereof.

8. The article of claim 1 , further comprising an oxide layer applied to the protective (co)polymer layer, optionally wherein the oxide layer comprises silicon aluminum oxide.

9. An electronic device incorporating the article according to claim 1 , wherein the article is selected from a solid state lighting device, a display device, and combinations thereof.

10. A process, comprising:
(a) applying a base (co)polymer layer to a major surface of a substrate selected from a (co)polymeric film or an electronic device, the electronic device further comprising an organic light emitting device (OLED), an electrophoretic light emitting device, a liquid crystal display, a thin film transistor, a photovoltaic device, or a combination thereof;
(b) applying an oxide layer on the base (co)polymer layer; and
(c) depositing on the oxide layer a protective (co)polymer layer, wherein the protective (co)polymer layer comprises the reaction product of at least one urethane (multi)-(meth)acrylate (multi)-silane precursor compound of the formula:
R S —N(H)—C(O)—O—R A or R S —O—C(O)—N(H)—R A , wherein:
R S is a silane containing group of the formula —R 1 —[Si(Y p )(R 2 ) 3−p ] q , further wherein:
R 1 is a multivalent alkylene, arylene, alkarylene, or aralkylene group, said alkylene, arylene, alkarylene, or aralkylene groups optionally containing one or more catenary oxygen atoms,
each Y is a hydrolysable group,
R 2 is a monovalent alkyl or aryl group;
p is 1, 2, or 3, and
q is 1-5; and
R A is a (meth)acryl group containing group of the formula R 11 -(A) n , wherein:
R 11 is a polyvalent alkylene, arylene, alkarylene, or aralkylene group, said alkylene, arylene, alkarylene, or aralkylene groups optionally containing one or more catenary oxygen atoms,
A is a (meth)acryl group comprising the formula X 2 —C(O)—C(R 3 )═CH 2 , further wherein:
X 2 is —O, —S, or —NR 3 ,
R 3 is H, or C 1 -C 4 , and
n=1 to 5.

11. The process of claim 10 , wherein Y is selected from the group consisting of alkoxy groups, acetate groups, aryloxy groups, and halogens.

12. The process of claim 10 , wherein the at least one urethane (multi)-(meth)acrylate (multi)-silane precursor compound precursor compound undergoes a chemical reaction to form the protective (co)polymer layer at least in part on the oxide layer, optionally wherein the chemical reaction is selected from a free radical polymerization reaction, and a hydrolysis reaction.

13. The process of claim 10 , wherein step (a) comprises:
(i) evaporating the base (co)polymer precursor;
(ii) condensing the evaporated base (co)polymer precursor onto the substrate; and
(iii) curing the evaporated base (co)polymer precursor to form the base (co)polymer layer.

14. The process of claim 10 , wherein the base (co)polymer precursor comprises a (meth)acrylate monomer.

15. The process of claim 10 , wherein step (b) comprises depositing an oxide onto the base (co)polymer layer to form the oxide layer, wherein depositing is achieved using sputter deposition, reactive sputtering, chemical vapor deposition, or a combination thereof.

16. The process of claim 10 , wherein step (b) comprises applying a layer of an inorganic silicon aluminum oxide to the base (co)polymer layer.

17. The process of claim 10 , further comprising sequentially repeating steps (b) and (c) to form a plurality of alternating layers of the protective (co)polymer layer and the oxide layer on the base (co)polymer layer.

18. The process of claim 10 , wherein step (c) further comprises at least one of co-evaporating the at least one urethane (multi)-(meth)acrylate (multi)-silane precursor compound precursor compound with a (meth)acrylate compound from a liquid mixture, or sequentially evaporating the at least one urethane (multi)-(meth)acrylate (multi)-silane precursor compound precursor compound and a (meth)acrylate compound from separate liquid sources, optionally wherein the liquid mixture comprises no more than about 10 wt. % of the urethane (multi)-(meth)acrylate (multi)-silane precursor compound precursor compound.

19. The process of claim 10 , wherein step (c) further comprises at least one of co-condensing the urethane (multi)-(meth)acrylate (multi)-silane precursor compound precursor compound with the (meth)acrylate compound onto the oxide layer, or sequentially condensing the urethane (multi)-(meth)acrylate (multi)-silane precursor compound precursor compound and the (meth)acrylate compound on the oxide layer.

20. The process of claim 10 , wherein reacting the urethane (multi)-(meth)acrylate (multi)-silane precursor compound precursor compound with the (meth)acrylate compound t

Assignees

• 3M Innovative Properties Co
• 3M Innovation Properties Company

Inventors

• Klun Thomas P
• Nachtigal Alan K
• Spagnola Joseph C
• Roehrig Mark A
• Schnobrich Jennifer K
• Joly Guy D
• Lyons Christopher S

Classifications

• C08F130/08

  containing silicon · CPC title

• C23C16/40

  Oxides · CPC title

• Y10T428/31551

  Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.] · CPC title

• B05D3/067

  Curing or cross-linking the coating · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title