US 11,702,597 B2
Azo dye
Peer Kirsch, Seeheim-Jugenheim (DE); Kerstin Altenburg, Darmstadt (DE); René Lutz, Brensbach (DE); Susann Gunst, Darmstadt (DE); Michael Junge, Pfungstadt (DE); and Ursula Patwal, Reinheim (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 17/278,953
Filed by MERCK PATENT GMBH, Darmstadt (DE)
PCT Filed Sep. 23, 2019, PCT No. PCT/EP2019/075458
§ 371(c)(1), (2) Date Mar. 23, 2021,
PCT Pub. No. WO2020/064591, PCT Pub. Date Apr. 2, 2020.
Claims priority of application No. 18196594 (EP), filed on Sep. 25, 2018.
Prior Publication US 2023/0056437 A1, Feb. 23, 2023
Int. Cl. G02F 1/1333 (2006.01); C09K 19/60 (2006.01); C09K 19/30 (2006.01); C09K 19/34 (2006.01); C09K 19/04 (2006.01)
CPC C09K 19/601 (2013.01) [C09K 19/3003 (2013.01); C09K 19/3068 (2013.01); C09K 19/3402 (2013.01); C09K 2019/0466 (2013.01); C09K 2019/301 (2013.01); C09K 2019/3009 (2013.01); C09K 2019/3016 (2013.01); C09K 2019/3021 (2013.01); C09K 2019/3025 (2013.01); C09K 2019/3071 (2013.01); C09K 2019/3078 (2013.01); C09K 2019/3422 (2013.01)] 16 Claims
 
1. A compound of formula I

OG Complex Work Unit Chemistry
in which
W11, W12 identically or differently, denote O, S or Se,

OG Complex Work Unit Chemistry
 on each occurrence, identically or differently, denotes

OG Complex Work Unit Chemistry
R11, R12, identically or differently, denote H, F, C1-25-straight-chain or C3-25-branched alkyl, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —N(Rz)—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN,
Rz on each occurrence, identically or differently, denotes H, halogen, C1-25-straight-chain or C3-25-branched alkyl, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl,
A11, A12 each, independently of one another, denote an aryl or heteroaryl group, which may be substituted by one or more radicals L,
A21, A22 are each, independently of one another, defined like A11 or denote a cyclic alkyl group having 3 to 10 C atoms, in which 1 to 4 CH2 groups may be replaced by O in such a way that no two O atoms are adjacent,
L on each occurrence, identically or differently, denotes OH, CH2OH, F, Cl, Br, I, —CN, —NO2, SF5, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rz)2, —C(═O)Rz, —N(Rz)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or C1-25-straight-chain or C3-25-branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, in which, in addition, one or more H atoms may be replaced by F or Cl, an aryl or heteroaryl group, which may be substituted by one or more radicals L, and alternatively two adjacent groups L together also denote a C2-10-straight-chain or C3-10-branched alkylene group, in which one, several or all H atoms may be replaced by F and in which one or more —CH2CH2— groups can be replaced by —CH═CH—,
Z10, Z11, Z12 on each occurrence, identically or differently, denote a single bond, —N═N—, —CH═N—, —N═CH—, —N═N(O)—, —N(O)═N—, —CRx1═CRx2—, —(CRx1═CRx2)2—, —C≡C—, —C(═O)—, —CH═CH—C(═O)—, —C(═O)—CH═CH—, —CH═CH—COO— or —OCO—CH═CH—,
Z21, Z22 on each occurrence, identically or differently, have one of the meanings of Z10 or denote —O—, —S—, —CRy1Ry2—, —CF2O—, —OCF2—, —C(O)—O—, —O—C(O)—, —O—C(O)—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, or —(CF2)n1—,
Rx1, Rx2, independently of one another, denote H, F, Cl, CN or alkyl having 1-12 C atoms,
Ry1, Ry2 each, independently of one another, denote H or alkyl having 1-12 C atoms,
Rx11, Rx12, Rx13, Rx14 independently of one another, denote H, F, Cl, CN, C1-12-alkyl, C2-12-alkenyl, C1-2-alkoxy or C2-12-alkenyloxy,
r and t, independently of one another, denote 0, 1 or 2,
s 0 or 1, and
n1 denotes 1, 2, 3 or 4,
and wherein one or more of Z10, Z11, Z12, Z21, Z22, denote —N═N—.