Ultraviolet light absorbers

Patent metadata

Field	Value
Publication number	US-10619098-B2
Application number	US-201515514004-A
Country	US
Kind code	B2
Filing date	Sep 21, 2015
Priority date	Sep 30, 2014
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

Compounds that have ultraviolet light absorbing properties, and which can also have mesogenic properties. Compositions that include one or more such compounds. Articles of manufacture that include one or more such compounds, such as optical elements that include an optical substrate and a layer that includes at least one such compound.

First claim

What is claimed is:

1. A compound represented by at least one of the following Formulas (III), (IV), (V), (VIII), and (IX),

wherein independently for each of Formulas (III), (IV), (V), (VIII), and (IX),
R 1 independently for each x, and R 2 independently for each y, are in each case independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and —OR 7 , where each R 7 is independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl, wherein the hydrocarbyl and substituted hydrocarbyl of R 1 , R 2 , and R 7 are in each case independently and optionally interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —S(O)—, —SO 2 —, —N(R 9 )—, and —Si(R 9 )(R 10 )— wherein R 9 and R 10 are each independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl,
M 1 independently for each n, M 2 independently for each p, and M 4 independently for each g, are in each case independently represented by the following Formula (X),

wherein independently for each Formula (X),
L 1 in each case is independently selected from the group consisting of at least one of: a single bond; —O—; —S—; —C(O)—; —S(O)—; —SO 2 —; —N═N—; —N(R 11 ′)— where R 11 ′ is selected from hydrogen, hydrocarbyl or substituted hydrocarbyl; —Si(OR 8 ′) w (R 8 ′) e —, where w and e are each independently 0 to 2, provided that the sum of w and e is 2, and each R 8 ′ is independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl; hydrocarbyl, and substituted hydrocarbyl, each optionally and independently interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —S(O)—, —SO 2 —, —N═N—, —N(R 11 ′)— where R 11 ′ is selected from the group consisting of hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR 8 ′) w (R 8 ′) e —, where w and e are each independently 0 to 2, provided that the sum of w and e is 2, and each R 8 ′ is independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more thereof,
t is 1 to 4,
m is, independently for each t, from 0 to 8,
L 2 is independently for each m selected from the group consisting of divalent linear or branched C 1 -C 25 alkyl, divalent linear or branched C 1 -C 25 perhaloalkyl, and divalent linear or branched C 2 -C 25 alkenyl, in each case optionally interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —S(O)—, —SO 2 —, —N(R 9 )—, and —Si(R 9 )(R 10 )— wherein R 9 and R 10 are each independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl,
q is, independently for each t, from 0 to 8, provided that the sum of m and q is at least one for each t, and provided that q is at least 1 for at least one t,
L 3 independently for each q is represented by the following Formula (XI-1),

Y is, independently for each q, a divalent linking group selected from the group consisting of a single bond, —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —S(O)—, —SO 2 —, —N(R 9 )—, —N(R 9 )—C(O)—O—, —C(O)—N(R 9 )—, and —Si(R 9 )(R 10 ) wherein R 9 and R 10 are each independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl,
v and u are each independently, for each q, selected from 0 to 5, provided that the sum of v and u is at least 2 for each q that is greater than zero,
Z is, independently for each v, a divalent linking group selected from the group consisting of a single bond, —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —S(O)—, —SO 2 —, —N(R 9 )—, —N(R 9 )—C(O)—O—, —C(O)—N(R 9 )—, and —Si(R 9 )(R 10 )— wherein R 9 and R 10 are each independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl,
the divalent rings,

are each independently selected, for each v and each u, from the group consisting of divalent aryl, substituted divalent aryl, divalent heteroaryl, substituted divalent heteroaryl, divalent cycloalkyl, substituted divalent cycloalkyl, divalent heterocycloalkyl, and substituted divalent heterocycloalkyl,
E 1 is selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl each optionally interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —S(O)—, —SO 2 —, —N(R 9 )—, and —Si(R 9 )(R 10 )— wherein R 9 and R 10 are each independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl, and (meth)acryloyl,
provided that a direct L 1 -L 2 link between L 1 and L 2 is free of two heteroatoms linked together, a direct L 1 -L 3 link between L 1 and L 3 is free of two heteroatoms linked together, and each direct L 2 -L 3 link between each directly linked L 2 and L 3 is free of two heteroatoms linked together;

for Formula (III),
x is from 0 to 4,
n is from 0 to 4, provided that the sum of x and n is 4,
g is from 0 to 6, provided that the sum of n and g is at least 1, and
Ring-A is selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl,

for Formula (IV),
x is from 0 to 4,
n is from 1 to 4, provided that the sum of x and n is 4,
g is from 0 to 6, provided that the sum of n and g is at least 1,
Ring-B is selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl, and
D is selected from the group consisting of O, S, and N—R 2 ′, wherein R 2 ′ is selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl, each optionally and independently interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —S(O)—, —SO 2 —, —N═N—, —N(R 11 ′)— where R 11 ′ is selected from the group consisting of hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR 8 ′) w (R 8 ′) e —, where w and e are each independently 0 to 2, provided that the sum of w and e is 2, and each R 8 ′ is independently selected from the group consisting of hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more thereof,

for Formula (V),
x is from 0 to 5,
n is from 0 to 5, provided the sum of x and n is 5,
y is from 0 to 5, and
p is from 0 to 5, provided the sum of y and p is 5,
provided that the sum of n and p is at least 1,

for Formula (VIII),
x is from 0 to 3, and
n is from 1 to 4, provided that the sum of x and n is 4,

for Formula (IX),
x is from 0 to 3, and
n is from 1 to 4, provided that the sum of x and n is 4,

wherein at least one L 3 independently is a mesogenic group, and said compound is a mesogenic compound.

2. The compound of claim 1 wherein,
independently for each of Formulas (III), (IV), (V), (VIII), and (IX),
R 1 independently for each x, and R 2 independently for each y, are in each case independently selected from the group consisting of hydrogen, linear or branched C 1 -C 25 alkyl, linear or branched C 2 -C 25 alkenyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, aryl, heteroaryl, and —OR 7 , where each R 7 is independently selected from the group consisting of hydrogen, C 1 -C 25 alkyl, linear or branched C 2 -C 25 alkenyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, aryl, and heteroaryl,

Assignees

• Transitions Optical Inc

Inventors

• Reddy Ramaiahgari
• Brown Cory S
• Grubb Alan
• He Meng
• Kumar Anil
• Xu Ruisong

Classifications

• C09K19/2014

  containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n- · CPC title

• C07D239/74

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring · CPC title

• C07D251/24

  to three ring carbon atoms · CPC title

• C09K19/3444

  the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine · CPC title

• C09K19/2007 Primary

  the chain containing -COO- or -OCO- groups · CPC title