US 11,987,557 B2
Phenalene-1-one-containing photosensitizer composition, phenalene-1-one compound and the use thereof
Andreas Späth, Regensburg (DE); and Anja Eichner, Regensburg (DE)
Assigned to TRIOPTOTEC GMBH, Regensburg (DE)
Filed by TriOptoTec GmbH, Regensburg (DE)
Filed on Oct. 13, 2021, as Appl. No. 17/500,593.
Application 17/500,593 is a division of application No. 16/494,836, granted, now 11,186,545, previously published as PCT/EP2018/056653, filed on Mar. 16, 2018.
Claims priority of application No. 17161718 (EP), filed on Mar. 17, 2017.
Prior Publication US 2022/0064114 A1, Mar. 3, 2022
Int. Cl. C07D 213/30 (2006.01); C07C 49/755 (2006.01); C07C 69/56 (2006.01); C07C 69/76 (2006.01); C07C 211/62 (2006.01); C07C 233/18 (2006.01); C07C 233/20 (2006.01); C07C 309/14 (2006.01); C07C 317/22 (2006.01); C07D 303/14 (2006.01); C07D 303/18 (2006.01); C07D 309/14 (2006.01); C07F 7/02 (2006.01); C07F 7/18 (2006.01)
CPC C07D 213/30 (2013.01) [C07C 49/755 (2013.01); C07C 69/56 (2013.01); C07C 69/76 (2013.01); C07C 211/62 (2013.01); C07C 233/18 (2013.01); C07C 233/20 (2013.01); C07C 317/22 (2013.01); C07D 303/18 (2013.01); C07D 309/14 (2013.01); C07F 7/025 (2013.01); C07F 7/1804 (2013.01)] 8 Claims
 
1. A phenalen-1-one compound with the general formula (1a):

OG Complex Work Unit Chemistry
wherein the residues R1a to R8a, which respectively independently of one another may be identical to or different from each other, respectively represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, alkylaryl containing 5 to 20 C atoms, aryl containing 5 to 20 C atoms, *—O-alkyl containing 1 to 12 C atoms, *—O-alkylaryl containing 5 to 20 C atoms, *—O-aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms, a residue with the formula *—O—C(═O)—R(Ia), a residue with the formula *—C(═O)—R(Ib), or an organic residue W1a which contains at least one reactive functional group, with the proviso that at least one of the residues R1a or R2a is an organic residue W1a, wherein the organic residue W1a respectively independently of each other represents a residue with the general formula (2a) to (6a):
*—[(C(D)(E))d-B]e—(C(D)(E))m-Xa  (2a)
*-A-[(C(D)(E))d-B]c—(C(D)(E))m-Xa  (3a)
*—(C(D)(E))d-Ar—(C(D)(E))n-Xa  (4a)
*—[(C(D)(E))d-B]b—(C(D)(E))g-Ar—(C(D)(E))n-Xa  (5a)
*-A-[(C(D)(E))d-B]f—(C(D)(E))g-Ar—(C(D)(E))n-Xa  (6a)
wherein the residue A respectively independently of each other represents sulphur or a residue with the general formula (10a) to (11a):

OG Complex Work Unit Chemistry
wherein*ph respectively denotes a linkage from the residue with the general formula (10a) to (11a) to a C atom of the phenalene ring and *c respectively denotes a linkage from the residue with the general formula (10a) to (11 a) to a C atom of the residue (C(D)(E)),
wherein the residue B respectively independently of each other represents oxygen, sulphur or a residue with the general formula (10) to (12):

OG Complex Work Unit Chemistry
and wherein the residues R(Ia), R(Ib), R(11a) and R(12a) respectively independently of each other represent methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, n-pentyl, phenyl or benzyl, and wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group consisting of chlorine, bromine, fluorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, and combinations thereof, and
wherein the residues D and E respectively independently of each other represent hydrogen, halogen, hydroxyl, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, hydroxyalkyl which may be linear or branched, containing 1 to 5 carbon atoms and 1 to 5 OH groups, phenyl, benzyl, a residue with the formula *-L-R(II), a residue with the formula *-L-C(=L)-R(III), a residue with the formula *—(CH2)q—Xa, a residue with the formula *-L-(CH2)q—Xa, or a residue with the formula *—(CH2)s-L-(CH2)t—Xa, wherein the residue L respectively independently of each other represents oxygen or sulphur, wherein the residues R(II) and R(III) respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, n-pentyl, phenyl or benzyl, and wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group consisting of chlorine, bromine, fluorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, and combinations thereof, the indices q, s and t respectively independently of each other representing a whole number from 1 to 5,
wherein the indices c, g, f and n respectively independently of each other represent a whole number from 0 to 5, and
wherein the indices b, d, e and m respectively independently of each other represent a whole number from 1 to 5,
wherein the residue Ar respectively independently of each other represents a substituted or unsubstituted aromatic residue or a substituted or unsubstituted heteroaromatic residue which contains no N atoms, and
wherein the residue Xa respectively independently of each other represents a reactive functional group *—OH, *—SH, *—NCO, *—NCS, *—Si(R(VIII))(R(IX))—[O—Si(R(X))(R(XI))]p—Z, or a residue with the general formula (20) to (24):

OG Complex Work Unit Chemistry
wherein the residues R(20a), R(20b), R(20c), R(21a), R(22a), R(22b), R(22c), R(23a), R(24a), R(24b), and R(24c) respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, or n-pentyl, and wherein the indices 1 and k respectively independently of each other represent a whole number from 0 to 4, wherein the residues R(VIII), R(IX), R(X) and R(XI) respectively independently of each other represent hydrogen, alkyl which may be linear or branched, containing 1 to 5 carbon atoms, —O-alkyl which may be linear or branched, containing 1 to 5 carbon atoms, phenyl or benzyl, wherein phenyl and benzyl respectively independently of each other may be unsubstituted or substituted with one or more residues selected from the group consisting of chlorine, bromine, fluorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, and combinations thereof, wherein the residue Z respectively independently of each other represents halogen, hydroxyl, alkoxyl containing 1 to 4 carbon atoms or alkylcarboxyl containing 1 to 4 carbon atoms, and wherein the index p respectively independently of each other represents a whole number from 0 to 4.