Polycycloolefin polymer compositions as optical materials

Patent metadata

Field	Value
Publication number	US-9944818-B2
Application number	US-201615253980-A
Country	US
Kind code	B2
Filing date	Sep 1, 2016
Priority date	Sep 1, 2015
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

Embodiments in accordance with the present invention encompass compositions encompassing components A and B which respectively contain a procatalyst and an activator along with one or more monomers which undergo vinyl addition polymerization when both components are mixed together to form a substantially transparent film. The monomers employed therein have a range of refractive index from 1.4 to 1.8 and thus these compositions can be tailored to form transparent films of varied refractive indices. Accordingly, compositions of this invention are useful in various opto-electronic applications, including as coatings, encapsulants, fillers, leveling agents, among others.

First claim

What is claimed is:

1. A composition comprising a Component A and a Component B, wherein each of said Component A and Component B contains 5-(2-([1,1′-biphenyl]-4-yl)ethyl)bicyclo[2.2.1]hept-2-ene (NBEtPhPh), 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and (bicyclo[2.2.1]hept-5-en-2-ylmethoxy)(methyl)diphenylsilane (NBCH 2 OSiMePh 2 ); and wherein Component A further contains palladium (II) bis(tricyclohexyl-phosphine) diacetate and Component B contains lithium tetrakis(pentafluorophenyl)borate etherate.

2. A kit for forming a substantially transparent film comprising:
a Component A; and
a Component B;
wherein each of said Component A and said Component B contains one or more monomers of formula (I) or formula (II) and wherein Component A further comprises a procatalyst and Component B further comprises an activator, wherein:
a) said monomer of formula (I) is:

wherein:
m is an integer 0, 1 or 2;
at least one of R 1 , R 2 , R 3 and R 4 is a group of formula (A):
—X-Aryl  (A)

wherein:
X is selected from the group consisting of:
O, CO, C(O)O, OC(O), OC(O)O, S, (CR 5 R 6 ) a , O(CR 5 R 6 ) a , (CR 5 R 6 ) a O, (CR 5 R 6 ) a O(SiR 5 R 6 ) a , (CR 5 R 6 ) a O(CR 5 R 6 ) a , C(O)(CR 5 R 6 ) a , (SiR 5 R 6 ) a O(SiR 5 R 6 ) a , (CR 5 R 6 ) a C(O), C(O)O(CR 5 R 6 ) a , (CR 5 R 6 ) a C(O)O, OC(O)(CR 5 R 6 ) a , (CR 5 R 6 ) a O C(O), (CR 5 R 6 ) a O C(O)O, (CR 5 R 6 ) a OC(O)O(CR 5 R 6 ) a , OC(O)O(CR 5 R 6 ) a , S(CR 5 R 6 ) a , (CR 5 R 6 ) a S, (SiR 5 R 6 ) a , O(SiR 5 R 6 ) a , (SiR 5 R 6 ) a O, where R 5 and R 6 are the same or different and each independently represents hydrogen, methyl, ethyl, linear or branched (C 3 -C 12 )alkyl and (C 6 -C 10 )aryl, and a is an integer from 0 to 12, inclusive;

Aryl is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl and substituted or unsubstituted fluorenyl;
the remaining R 1 , R 2 , R 3 and R 4 are the same or different and each independently represents hydrogen, halogen, a hydrocarbyl or halohydrocarbyl group selected from methyl, ethyl, linear or branched (C 3 -C 12 )alkyl, hydroxy(C 1 -C 12 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 1 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl or perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl;
b) said monomer of formula (II) is:

wherein:
n is an integer 0, 1 or 2;
R 7 , R 8 , R 9 and R 10 are the same or different and each independently selected from the group consisting of hydrogen, halogen, a hydrocarbyl or halohydrocarbyl group selected from methyl, ethyl, linear or branched (C 3 -C 16 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl and a group of formula (B):
—Y-Aryl 1   (B)

wherein:
Y is selected from the group consisting of:
(CR 5 R 6 ) a , O(CR 5 R 6 ) a and (CR 5 R 6 ) a O, where a, R 5 and R 6 are as defined above;

Aryl 1 is phenyl or phenyl substituted with one or more (C 1 -C 6 )alkyl;
and wherein
said monomer of formula (I) is having a refractive index greater than or equal to 1.6, said second monomer of formula (II) is having a refractive index less than 1.6 and viscosity below 100 centipoise, and said Component A and Component B are in a clear liquid form at room temperature.

3. The kit according to claim 2 , wherein each of Component A and Component B contains at least two monomers wherein first monomer is of formula (I) and second monomer is of formula (II), wherein monomer of formula (I) is completely soluble in monomer of formula (II), and wherein when Component A and Component B are mixed together at a temperature of from 50° C. to 100° C. for a sufficient length of time it forms a substantially transparent film having at least 90 percent of visible light transmission.

4. The kit according to claim 2 , wherein each of said Component A and Component B further comprises one or more monomers selected from monomer of formula (III) or monomer of formula (IV), wherein said monomer of formula (III) is:

wherein:
o is an integer from 0 to 2, inclusive;
D is SiR 14 R 15 R 16 or a group of formula (C):
—(CH 2 ) c —OSiR 14 R 15 R 16   (C); wherein

c is an integer from 1 to 10, inclusive, and where one or more of CH 2 is optionally substituted with (C 1 -C 10 )alkyl or (C 1 -C 10 )perfluoroalkyl;
R 11 , R 12 and R 13 are the same or different and independently of each other selected from hydrogen, halogen and hydrocarbyl, where hydrocarbyl is selected from methyl, ethyl, linear or branched (C 3 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 3 )alkyl, (C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy(C 1 -C 3 )alkyl or (C 6 -C 10 )aryloxy; and
R 14 , R 15 and R 16 are each independently of one another methyl, ethyl, linear or branched (C 3 -C 9 )alkyl, substituted or unsubstituted (C 6 -C 14 )aryl, methoxy ethoxy, linear or branched (C 3 -C 9 )alkoxy or substituted or unsubstituted (C 6 -C 14 )aryloxy;
said monomer of formula (IV) is:

wherein:
Z is an arylene selected from the following:

R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are the same or different and independently of each other selected from hydrogen, halogen and hydrocarbyl, where hydrocarbyl is selected from methyl, ethyl, linear or branched (C 3 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 3 )alkyl, (C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy(C 1 -C 3 )alkyl or (C 6 -C 10 )-aryloxy.

5. The kit according to claim 2 , wherein each of said Component A and said Component B contains 5-(2-([1,1′-biphenyl]-4-yl)ethyl)bicyclo[2.2.1]hept-2-ene (NBEtPhPh), 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and (bicyclo[2.2.1]hept-5-en-2-ylmethoxy)(methyl)diphenylsilane (NBCH 2 OSiMePh 2 ); and wherein Component A further contains palladium (II) bis(tricyclohexyl-phosphine) diacetate and Component B contains lithium tetrakis(pentafluorophenyl)borate etherate.

6. The kit according to claim 2 , wherein the monomer of formula (I) is selected from the group consisting of:

Assignees

• Promerus Llc

Inventors

• Rhodes Larry F
• Burgoon Hugh A

Classifications

• C08G63/189

  containing a naphthalene ring · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C09D145/00

  Coating compositions based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Coating compositions based on derivatives of such polymers (based on polymers of cyclic esters of polyfunctional acids C09D131/00; based on polymers of cyclic anhydrides or imides C09D135/00) · CPC title

• C09D165/00 Primary

  Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers · CPC title

• C08F232/08

  having condensed rings (coumarone-indene polymers C08F244/00) · CPC title