Polymerizable compounds

Patent metadata

Field	Value
Publication number	US-11760935-B2
Application number	US-202117215873-A
Country	US
Kind code	B2
Filing date	Mar 29, 2021
Priority date	Aug 3, 2020
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

Polymerizable compounds, processes and intermediates for their preparation, compositions containing them, polymers made from the compounds or compositions, and uses of the polymerizable compounds, compositions and polymers.

First claim

The invention claimed is:

1. A compound selected from compounds of the following formulae:

wherein
L 11 to L 20 is, each independently, L or A,
L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or a branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—,

in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by P-Sp-, F or Cl,
R 0 , R 00 is, each independently, H or alkyl having 1 to 12 C atoms,
r1, r2, r3, r4 is, each independently, 0, 1, 2, 3 or 4,
r5, r6, is, each independently, 0, 1, 2 or 3,
r7 is 1, 2, 3 or 4,
r8 is 0, 1 or 2,
r9 is 0, 1, 2 or 3,
r10 is 1, 2 or 3,
P is a polymerizable group,
Sp is a spacer group or a single bond,
A is —SCH 3 , —SC 2 H 5 or —SC 3 H 7 , and
R is F, Cl, —CN, or a straight chain alkyl having 1 to 25 C atoms or a branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—,

in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl or P-Sp-,
wherein
in formulae I1A, I1C and I1E, r1+r2≥1,
in formula I1B, I1D and I1F, r1+r5≥1,
in formula I1G, I3A and I3C, r5+r6≥1,
in formulae I2A, I2D, I2E, I5A and I5C, r1+r2+r3≥1,
in formulae I2B, I2C, I2F, I5B and I5D, r1+r3+r5≥1,
in formula I2G, r3+r5+r6≥1,
in formula I4A, I4C and 14E, r4+r5+r6≥1,
in formula I4D, r5+r6+r9≥1,
in formula I3B, r5+r8≥1,
and in formula, I4B r4+r5+r8≥1,
wherein the compound contains at least one group L 11 to L 20 that denotes A.

2. A compound selected from compounds of the following formulae:

wherein
L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or a branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—,

in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by P-Sp-, F or Cl,
R 0 , R 00 is, each independently, H or alkyl having 1 to 12 C atoms,
P is a polymerizable group,
Sp is a spacer group or a single bond,
A is —SCH 3 , —SC 2 H 5 or —SC 3 H 7 , and
R is F, Cl, —CN, or a straight chain alkyl having 1 to 25 C atoms or a branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—,

in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl or P-Sp-.

3. The compound according to claim 1 , wherein A denotes —SCH 3 .

4. The compound according to claim 3 , wherein P is selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide.

5. The compound according to claim 3 , wherein Sp, when being different from a single bond, are selected from the group consisting of —(CH 2 ) p1 —, —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 , and —CO—O—(CH 2 ) p1 , wherein p1 is 2, 3, 4, 5 or 6, and, if Sp is —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 or —CO—O—(CH 2 ) p1 the O-atom or CO-group, respectively, is linked to the benzene ring.

6. A compound, which is selected from the following compounds:

7. A composition comprising one or more compounds of claim 3 .

8. A polymer obtained by polymerizing a compound of claim 3 , optionally by UV photopolymerization.

9. A method comprising incorporating a compound according to claim 3 into a liquid crystalline media for a protective, decorative or optoelectronic application.

10. A method of preparing a polymer, comprising polymerizing a compound according to claim 3 .

11. The compound according to claim 6 , which is the following compound

12. The compound according to claim 6 , which is the following compound

Assignees

• Merck Patent Gmbh

Inventors

• Kodek Thorsten
• Heppert Oliver
• Uebel Timo
• Fortte Rocco
• Weegels Leo

Classifications

• C07C321/28 Primary

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

• C07C323/22 Primary

  containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• C09K19/542 Primary

  Macromolecular compounds · CPC title

• C07C319/14

  of sulfides · CPC title

• C07C319/20

  by reactions not involving the formation of sulfide groups · CPC title