US 11,781,070 B2
Mesogen compounds
Ramaiahgari Reddy, Murrysville, PA (US); Yannian Li, Murrysville, PA (US); and Alan M. Grubb, Pittsburgh, PA (US)
Assigned to Transitions Optical, Ltd., Tuam (IE)
Appl. No. 17/631,007
Filed by Transitions Optical, Ltd., Tuam (IE)
PCT Filed Jul. 30, 2019, PCT No. PCT/EP2019/070442
§ 371(c)(1), (2) Date Jan. 28, 2022,
PCT Pub. No. WO2021/018383, PCT Pub. Date Feb. 4, 2021.
Prior Publication US 2022/0275278 A1, Sep. 1, 2022
Int. Cl. G02F 1/1333 (2006.01); C09K 19/46 (2006.01); C07C 69/92 (2006.01); C09K 19/38 (2006.01); C09K 19/56 (2006.01); C09K 19/60 (2006.01); G02F 1/1337 (2006.01); C09K 19/04 (2006.01)
CPC C09K 19/46 (2013.01) [C07C 69/92 (2013.01); C09K 19/3857 (2013.01); C09K 19/56 (2013.01); C09K 19/60 (2013.01); G02F 1/1337 (2013.01); C09K 2019/0448 (2013.01)] 15 Claims
 
1. A mesogen-containing compound represented by the following Formula (I),
(Mesogen-1)-L1-(Mesogen-2)-L2-(Mesogen-3)  (I)
wherein
(A) Mesogen-1 and Mesogen-3 are each independently represented by the following Formula (II),

OG Complex Work Unit Chemistry
wherein for Formula (II),
P is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, acrylamido, methacrylamido, oxirane, hydroxyl, primary amino, carboxylic acid, or carboxylic acid ester;
(B) Mesogen-2 is represented by the following Formula (III),

OG Complex Work Unit Chemistry
wherein independently for each of Formula (II) and Formula (III)
S1, S2, S3, and S4, for each occurrence, are independently selected from a spacer unit chosen from —CH2—; —O—; —C(O)—; —N═N—; —CH═CH—; —C≡C—; —CH═N—; —CF2—; or —NH—, provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other;
d is 0 to 20;
e, f, and g, for each occurrence, are independently 0 to 3;
Q1, Q2, and Q3, for each occurrence, are independently a divalent group selected from the group consisting of unsubstituted or substituted cycloaliphatic group; unsubstituted or substituted heterocycloaliphatic group; unsubstituted or substituted aryl; and unsubstituted or substituted heteroaryl; wherein the cycloaliphatic group substituents, heterocycloaliphatic group substituents, aryl substituents, and heteroaryl substituents are each independently selected from cyano or —(S1)d—P, where S1, d, and P are each as defined with regard to Formula (II); and
e″ and f″, for each occurrence, are independently from 0 to 6, provided the sum of e″ and f″ is at least 1; and
(C) -L1- and -L2- are each independently represented by the following Formula (IV),
-(A-B)y-E-  (IV)
wherein
(i) y is 0 to 30;
(ii) each A independently for each y is a divalent group selected from the group consisting of aliphatic group and haloaliphatic group;
(iii) each B independently for each y is a divalent group selected from the group consisting of —O—; —C(O)O—; —OC(O)O—; —C(O)N(R1)— where R1 is H or alkyl;
—NH—C(O)O—; —N(R2)C(O)N(R2)— where each R2 is independently selected from H or alkyl;

OG Complex Work Unit Chemistry
where n is 1 to 5, and each R3 independently for each n is selected from methyl, ethyl, or phenyl; and —Si(R4)(R4)— where each R4 is independently selected from methyl, ethyl, or phenyl; and
(iv) E is a divalent group selected from the group consisting of aliphatic group and haloaliphatic group,
provided that at least one of Mesogen-1, Mesogen-2, or Mesogen-3, include at least four cyclic groups, and
provided that -L1- and -L2- each independently comprise an average chain length of at least 20 bonds.