Urea (multi)-(meth)acrylate (multi)-silane compositions and articles including the same

Patent metadata

Field	Value
Publication number	US-9982160-B2
Application number	US-201314419303-A
Country	US
Kind code	B2
Filing date	Mar 1, 2013
Priority date	Aug 8, 2012
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

Urea (multi)-(meth)acrylate (multi)-silane precursor compounds, synthesized by reaction of (meth)acrylated materials having isocyanate functionality with aminosilane compounds, either neat or in a solvent, and optionally with a catalyst, such as a tin compound, to accelerate the reaction. Also described are 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 urea (multi) (meth)acrylate (multi)-silane precursor compound synthesized by reaction of (meth)acrylated materials having isocyanate functionality with aminosilane compounds. The substrate may be a (co)polymer 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 the urea (multi)-(meth)acrylate (multi)-silanes and their use in composite films and electronic devices are 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 10 wt % or less the reaction product of at least one urea (multi)-(meth)acrylate (multi)-silane precursor compound of the formula:
R S —N(R 5 )—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 ,

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 3-5;
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; and
R 5 is H, C 1 to C 6 alkyl, C 3 to C 6 cycloalkyl, or R S .

2. The article of claim 1 , wherein each hydrolysable group Y is independently selected from an alkoxy group, an acetate group, an aryloxy group, and a halogen.

3. The article of claim 2 , wherein at least some of the hydrolysable groups Y are chlorine.

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, a 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 oxid layer comprises at least one oxide, nitride, carbide or boride of atomic elements selected from Groups IIA, IIIA, IVA, VA, VIA, VIIA, IB, or IIB, metals of Groups IIIB, IVB, or VB, rare-earth metals, or a combination or mixture thereof.

7. 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.

8. 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 101 wt % or less a (co)polymer formed as the reaction product of at least one urea (multi)-(meth)acrylate (multi)-silane precursor compound of the formula:
R S —N(R 5 )—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 ,

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,
Y is a hydrolysable group,
R 2 is a monovalent alkyl or aryl group,
p is 1, 2, or 3, and
q is 3-5;
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 wherein:
X 2 is —O, —S, or —NR 3 , wherein R 3 is H, or C 1 -C 4 and n=1 to 5; and
R 5 is H, C 1 to C 6 alkyl, C 3 to C 6 or cycloalkyl, R S .

9. The process of claim 8 , wherein the at least one urea (multi)-(meth)acrylate (multi)-silane 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.

10. The process of claim 8 , wherein each hydrolysable group Y is independently selected from an alkoxy group, an acetate group, an aryloxy group, and a halogen.

11. The process of claim 10 , wherein at least some of the hydrolysable groups Y are chlorine.

12. The process of claim 8 , wherein step (a) comprises:
(i) evaporating a 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.

13. The process of claim 8 , 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.

14. The process of claim 8 , 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.

15. The process of claim 8 , wherein step (c) further comprises at least one of co-evaporating the at least one urea (multi)-(meth)acrylate (multi)-silane precursor compound with a (meth)acrylate compound from a liquid mixture, or sequentially evaporating the at least one urea (multi)-(meth)acrylate (multi)-silane precursor compound and a (meth)acrylate compound from separate liquid sources.

Assignees

• 3M Innovative Properties Co

Inventors

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

Classifications

• C23C14/08

  Oxides (C23C14/10 takes precedence) · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C08J2333/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• Y10T428/31551

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

• B05D1/60

  Deposition of organic layers from vapour phase (vapour phase deposition in general C23C14/00, C23C16/00) · CPC title