Aromatic substituted alkane-core monomers and polymers thereof for volume Bragg gratings

Patent metadata

Field	Value
Publication number	US-11780819-B2
Application number	US-202017098130-A
Country	US
Kind code	B2
Filing date	Nov 13, 2020
Priority date	Nov 27, 2019
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

Abstract

The disclosure provides recording materials including aromatic substituted alkane-core derivatized monomers and polymers for use in volume Bragg gratings, including, but not limited to, volume Bragg gratings for holography applications. Several structures are disclosed, including Formula I. When used in Bragg gratings applications, the monomers and polymers disclosed lead to materials with higher refractive index, low birefringence, and high transparency. The disclosed derivatized monomers and polymers can be used in any volume Bragg gratings materials, including two-stage polymer materials where a matrix is cured in a first step, and then the volume Bragg grating is written by way of a second curing step of a monomer.

First claim

The invention claimed is:

1. A compound of Formula I:

wherein in Formula I:
Alk is a C 1-12 alkyl core;
Ar is aryl;
at each independent occurrence, R is hydrogen or a substituent comprising one or more groups selected from optionally substituted alkyl, optionally substituted heteroalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, hydroxy, halo, cyano, trifluoromethyl, trifluoromethoxy, nitro, trimethylsilanyl, optionally substituted epoxide, optionally substituted glycidyl, optionally substituted acrylate, optionally substituted methacrylate, —OR a , —SR a , —OC(O)—R a , —N(R a ) 2 , —C(O)R a , —C(O)OR a , —C(O)SR a , —SC(O)R a , —OC(O)OR a , —OC(O)N(R a ) 2 , —C(O)N(R a ) 2 , —N(R a )C(O)OR a , —N(R a )C(O)R a , —N(R a )C(O)N(R a ) 2 , —N(R a )C(NR a )N(R a ) 2 , —N(R a )S(O) t R a , —S(O) t R a , —S(O) t OR a , —S(O) t N(R a ) 2 , —S(O) t N(R a )C(O)R a , —O(O)P(OR a ) 2 , and —O(S)P(OR a ) 2 ;
m is an integer from 1 to 4;
n is independently at each occurrence an integer from 0 to 5;
t is 1 or 2;
each R a is independently selected from hydrogen, optionally substituted alkyl, optionally substituted heteroalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, and optionally substituted heteroarylalkyl; and
wherein the compound of Formula I comprises at least one R substituent
selected from:

2. The compound of claim 1 , wherein Alk is selected from methane, ethane, propane, and butane.

3. The compound of claim 1 , wherein Ar is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, phenalenyl, tetracenyl, chrysenyl, triphenylenyl, and pyrenyl.

4. The compound of claim 1 , wherein Ar is phenyl and m is 2 or 3.

5. A recording material for writing a volume Bragg grating, the material comprising a resin mixture comprising a first polymer precursor comprising the compound of claim 1 , wherein the first polymer precursor is partially or totally polymerized or crosslinked.

6. A volume Bragg grating recorded on the recording material of claim 5 , wherein the grating is characterized by a Q parameter equal to or greater than 1, wherein

Q
=

2
⁢
π
⁢

λ
0

⁢
d

n
0

⁢

Λ
2

and wherein λ 0 is a recording wavelength, d is the thickness of the recording material, n 0 is a refractive index of the recording material, and Λ is a grating constant.

7. A compound selected from

Assignees

• Meta Platforms Tech Llc

Inventors

• Purvis Lafe
• Lane Austin
• Colburn Matthew E

Classifications

• C07D303/18 Primary

  by etherified hydroxyl radicals · CPC title

• C07C271/54

  to carbon atoms of hydrocarbon radicals substituted by carboxyl groups · CPC title

• C07C271/58

  with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C321/20

  of an unsaturated carbon skeleton containing rings · CPC title

• C07C321/28

  Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings · CPC title