UREA (MULTI)-URETHANE (METH)ACRYLATE-SILANE COMPOSITIONS AND ARTICLES INCLUDING THE SAME
Compositions of matter described as urea (multi)-urethane (meth)acrylate-silanes having the general formula R A —NH—C(O)—N(R 4 )—R 11 —[O—C(O)NH—R S ] n , or R S —NH—C(O)—N(R 4 )—R 11 —[O—C(O)NH—R A ] n . 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) urethane(meth)acrylate-silane precursor compound. 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 such urea (multi)-urethane(meth)acrylate-silane precursor compounds, and their use in composite films and electronic devices are also described. Methods of using multilayer composite films as barrier films in articles selected from solid state lighting devices, display devices, and photovoltaic devices are also described.
1 . A composition of matter, comprising:
at least one urea (multi)-urethane (meth)acrylate-silane compound of the formula:
R A —NH—C(O)—N(R 4 )—R 11 —[O—C(O)NH—R S ]n, wherein:
R A is a (meth)acryl containing group of the formula R 11 -(A) n , further 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 atom,
A is a (meth)acryl group comprising the formula X 2 —C(O)—C(R 3 )═CH 2 , additionally wherein:
X 2 is —O, —S, or —NR 3 ,
R 3 is independently H, or C 1 -C 4 , and
n=1 to 5;
R 4 is H, C 1 to C 6 alkyl, or C 1 to C 6 cycloalkyl;
Rs is a silane containing group of the formula —R 1 —[Si(Y p )(R 2 ) 3-q ] q , wherein:
R 1 is a polyvalent 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, and
p is 1,2, or 3.
2 . A composition of matter, comprising:
at least one urea (multi)-urethane (meth)acrylate-silane compound of the formula:
R S —NH—C(O)—N(R 4 )—R 11 —[O—C(O)NH—R A ] n , wherein:
R S is a silane containing group of the formula —R 1 —Si(Y p )(R 2 ) 3-p , wherein:
R 1 is a polyvalent 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, and
p is 1,2, or 3;
R 4 is H, C 1 to C 6 alkyl, or C 1 to C 6 cycloalkyl;
R A is a (meth)acryl group containing group of the formula R 11 -(A) n , further wherein:
R 11 is a polyvalent alkylene, arylene, alkarylene, or aralkylene group, said alkylene, arylene, alkarylene, or aralkylene group optionally containing one or more catenary oxygen atom,
A is a (meth)acryl containing group of the formula X 2 —C(O)—C(R 3 )═CH 2 , additionally wherein:
X 2 is —O, —S, or —NR 3 ,
R 3 is independently H, or C 1 -C 4 ; and
n=1 to 5.
3 . A composition of matter according to claim 1 , wherein each hydrolysable group Y is independently selected from an alkoxy group, an acetate group, an aryloxy group, and a halogen.
4 . (canceled)
5 . 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 urea (multi)-urethane (meth)acrylate-silane precursor compound of the formula:
R A —NH—C(O)—N(R 4 )—R 11 [O—C(O)NH—R S ] n , wherein:
R A is a (meth)acryl containing group of the formula R″-(A) n , further 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 atom,
A is a (meth)acryl group comprising the formula X 2 —C(O)—C(R 3 )═CH 2 , additionally wherein:
X 2 is —O, —S, or —NR 3 ,
R 3 is independently H, or C 1 -C 4 , and
n=1 to 5;
R 4 is H, C 1 to C 6 alkyl, or C 1 to C 6 cycloalkyl;
R S is a silane containing group of the formula —R 1 —Si(Y p )(R 2 )3-p, wherein:
R 1 is a polyvalent 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, and
p is 1,2, or 3.
6 . 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 urea (multi)-urethane (meth)acrylate-silane precursor compound of the formula:
R S —NH—C(O)—N(R 4 )—R 11 —[O—C(O)NH—R A ] n , wherein
R S is a silane containing group of the formula —R 1 —Si(Y p )(R 2 )3-p, wherein:
R 1 is a polyvalent 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, and
p is 1,2, or 3;
R 4 is H, C 1 to C 6 alkyl, or C 1 to C 6 cycloalkyl;
R A is a (meth)acryl group containing group of the formula R 11 -(A) n , further wherein:
R 11 is a polyvalent alkylene, arylene, alkarylene, or aralkylene group, said alkylene, arylene, alkarylene, or aralkylene group optionally containing one or more catenary oxygen atom,
A is a (meth)acryl containing group of the formula X 2 —C(O)—C(R 3 )═CH 2 , additionally wherein:
X 2 is —O, —S, or —NR 3 ,
R 3 is independently H, or C 1 -C 4 ; and
n=1 to 5.
7 . The article of claim 5 , wherein each hydrolysable group Y is independently selected from an alkoxy group, an acetate group, an aryloxy group, and a halogen.
8 . (canceled)
9 . The article of claim 5 , further comprising a plurality of alternating layers of the oxide layer and the protective (co)polymer layer on the base (co)polymer layer.
10 . The article of claim 5 , 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.
11 . The article of claim 5 , wherein the base (co)polymer layer comprises an acrylate smoothing layer.
12 . The article of claim 5 , wherein the oxide layer comprises oxides, 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.
13 . The article of claim 5 , further comprising an oxide layer applied to the protective (co)polymer layer, optionally wherein the oxide layer comprises silicon aluminum oxide.
14 . An electronic device incorporating the article according to claim 5 , wherein the substrate is a (co)polymer film and the electronic device is selected from a solid state lighting device, a display device, and combinations thereof.
15 - 16 . (canceled)
17 . 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 urea (multi)-urethane (meth)acrylate-silane precursor compound of the formula:
R A —NH—C(O)—N(R 4 )—R 11 —[O—C(O)NH—R S ] n , wherein:
R A is a (meth)acryl containing group of the formula R 11 -(A) n , further 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 atom,
A is a (meth)acryl group comprising the formula X 2 —C(O)—C(R 3 )═CH 2 , additionally wherein:
X 2 is —O, —S, or —NR 3 ,
R 3 is independently H, or C 1 -C 4 , and
n=1 to 5;
R 4 is H, C 1 to C 6 alkyl, or C 1 to C 6 cycloalkyl;
R S is a silane containing group of the formula —R 1 —Si(Y p )(R 2 ) 3-p , wherein:
R 1 is a polyvalent 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, and
p is 1,2, or 3.
18 . 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 urea (multi)-urethane (meth)acrylate-silane precursor compound of the formula:
R S —NH—C(O)—N(R 4 )—R 11 [O—C(O)NH—R A ] n , wherein:
R S is a silane containing group of the formula —R 1 —Si(Y p )(R 2 ) 3-p , wherein:
R 1 is a polyvalent 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, and
p is 1,2, or 3;
R 4 is H, C 1 to C 6 alkyl, or C 1 to C 6 cycloalkyl;
RA is a (meth)acryl group containing group of the formula R 11 -(A) n , further wherein:
R 11 is a polyvalent alkylene, arylene, alkarylene, or aralkylene group, said alkylene, arylene, alkarylene, or aralkylene group optionally containing one or more catenary oxygen atom,
A is a (meth)acryl containing group of the formula X 2 —C(O)—C(R 3 )═CH 2 , additionally wherein:
X 2 is —, —S, or —NR 3 ,
R 3 is independently H, or C 1 -C 4 ; and
n=1 to 5.
19 . The process of claim 17 , wherein each hydrolysable group Y is independently selected from an alkoxy group, an acetate group, an aryloxy group, and a halogen.
20 . (canceled)
21 . The process of claim 17 , wherein step (a) comprises:
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.
22 . (canceled)
23 . The process of claim 17 , 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.
24 . (canceled)
25 . The process of claim 17 , 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.
26 . The process of claim 17 , wherein step (c) further comprises at least one of co-evaporating the at least one urea (multi)-urethane (meth)acrylate-silane precursor compound with a (meth)acrylate compound from a liquid mixture, or sequentially evaporating the at least one urea (multi)-urethane (meth)acrylate-silane 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 urea (multi)-urethane (meth)acrylate-silane precursor compound.
27 . The process of claim 17 , wherein step (c) further comprises at least one of co-condensing the urea (multi)-urethane (meth)acrylate-silane precursor compound with the (meth)acrylate compound onto the oxide layer, or sequentially condensing the urea (multi)-urethane (meth)acrylate-silane precursor compound and the (meth)acrylate compound on the oxide layer.
28 . (canceled)