Triarylmethane compounds

Patent metadata

Field	Value
Publication number	US-12570593-B2
Application number	US-202318231676-A
Country	US
Kind code	B2
Filing date	Aug 8, 2023
Priority date	Feb 9, 2018
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

Abstract

The present invention relates to triarylmethane compounds of the formula (I), which suitable as monomers for preparing thermoplastic resins having beneficial optical properties and which can be used for producing optical devices. R 1 , R 2 are e.g. hydrogen; Y is an alkylene group having 2, 3 or 4 carbon atoms, Ar is selected from mono- or polycyclic aryl and mono- or polycyclic hetaryl; X 1 , X 2 , X 3 , X 4 are CH, C—R x or N, provided that in each ring at most two of X 1 , X 2 , X 3 , X 4 are N; R x is e.g. halogen, CN or CH═CH 2 . The invention also relates to thermoplastic resins comprising a polymerized unit of the compound of formula (I).

First claim

We claim:

1 . A compound of the formula (I)

where
R 1 , R 2 are hydrogen, a radical R a or R 1 and R 2 together with the carbon atoms to which they are bound may also form a fused benzene ring, which is unsubstituted or substituted by one radical Ra,
Y represents an alkylene group having 2, 3 or 4 carbon atoms,
Ar is selected from the group consisting of mono-or polycyclic aryl having from 6 to 26 carbon atoms and mono-or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of these atoms are selected from nitrogen, sulphur and oxygen, while the remainder of these atoms are carbon atoms,
where mono-or polycyclic aryl and mono-or polycyclic hetaryl are unsubstituted or carry 1, 2, 3 or 4 radicals R Ar ,

X 1 , X 2 , X 3 , X 4 are CH;
R a is selected from the group consisting of fluorine, cyclopropyl, cyclobutyl, CN, R, OR, CH n R 3-n , NR 2 , C(O)R, C(O)NH 2 , CH═CH 2 , CH═CHR′, CH 2 -CH═CH 2 , CH 2 —CH═CHR′, CH 2 —C≡CH and CH 2 —C≡CR′;
R Ar is selected from the group consisting of fluorine, cyclopropyl, cyclobutyl, CN, R, OR, CH n R 3-n , NR 2 , C(O)R, C(O)NH 2 , CH═CH 2 , CH═CHR′, CH 2 —CH═CH 2 , CH 2 —CH═CHR′, CH 2 —C≡CH and CH 2 —C≡CR′, wherein each R Ar is identical or different if more than one R Ar is present on each ring;
R is selected from methyl and mono-or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of the ring atoms of hetaryl are selected from nitrogen and oxygen, while the remainder of these atoms are carbon atoms, where mono-or polycyclic aryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R″;
R′ is selected from methyl, mono-or polycyclic aryl having from 6 to 26 carbon atoms and mono-or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of the ring atoms of hetaryl are selected from nitrogen and oxygen, while the remainder of these atoms are carbon atoms, where mono-or polycyclic aryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R″;
R″ is selected from fluorine, cyclopropyl, cyclobutyl, phenyl, CN, OCH 3 , CH 3 , N(CH 3 ) 2 , C(O)CH 3 , CH═CH 2 , CH═CHCH 3 , CH 2 —CH═CH 2 , CH 2 —CH═CH—CH 3 , CH 2 —C═CH and CH 2 —C≡C—CH 3 ; and
n on each occurrence is 0, 1, 2 or 3;
where monocyclic aryl is phenyl;
where polycyclic aryl is:
a completely unsaturated polycyclic hydrocarbon radical, where each of the carbon atoms is part of a conjugate x-electron system,
a polycyclic hydrocarbon radical which bears 1 phenyl ring which is fused to a saturated or unsaturated 4 to 10-membered mono-or bicyclic hydrocarbon ring, or a polycyclic hydrocarbon radical which bears at least 2 phenyl rings which are fused to each other directly and/or which are fused to a saturated or unsaturated 4 to 10-membered mono-or bicyclic hydrocarbon ring;

where monocyclic hetaryl is a heteroaromatic monocycle, where the ring member atoms are part of a conjugate π-electron system, where the heteroaromatic monocycle has 5 or 6 ring atoms, which comprise 1, 2, 3 or 4 nitrogen atoms or 1 oxygen atom and 0, 1, 2 or 3 nitrogen atoms, or 1 sulphur atom and 0, 1, 2 or 3 nitrogen atoms, where the remainder of the ring atoms are carbon atoms; and
where polycyclic hetaryl is:
a heteroaromatic polycyclic radical, which bears a monocyclic hetaryl ring as defined above and at least one further aromatic ring selected from phenyl and heteroaromatic monocycles as defined above, where the aromatic rings of polycyclic hetaryl are linked to each other by a covalent bond and/or fused to each other directly and/or fused to a saturated or unsaturated 4 to 10-membered mono-or bicyclic hydrocarbon ring, or
a heteroaromatic polycyclic radical, which bears at least one saturated or partially unsaturated 5- or 6-membered heterocyclic ring bearing 1 or 2 heteroatoms selected from oxygen, sulphur and nitrogen as ring atoms, and at least one further aromatic ring selected from phenyl and heteroaromatic monocycles, where at least one of the further aromatic rings is directly fused to the saturated or partially unsaturated 5- or 6-membered heterocyclic radical and where the remainder of further aromatic rings of polycyclic hetaryl are linked to each other by a covalent bond or fused to each other directly and/or fused to a saturated or unsaturated 4 to 10-membered mono-or bicyclic hydrocarbon ring.

2 . The compound of claim 1 , where the variable Y is a linear alkylene group having 2, 3 or 4 carbon atoms.

3 . The compound of claim 1 , where Ar is mono-or polycyclic aryl selected from the group consisting of phenyl, naphthyl, phenanthryl, 2,3-dihydro-1H-indenyl, 1H-indenyl, 5,6,7,8-tetrahydronaphthalenyl, 1,2-dihydroacenaphthylenyl, acenaphthylenyl, 9,10-dihydroanthracen-1-yl, 1,2,3,4-tetrahydrophenanthrenyl, 5,6,7,8-tetrahydrophenanthrenyl, fluorenyl, anthracenyl, pyrenyl, biphenylenyl, triphenylenyl, tetraphenylenyl, 5H-dibenzo[a,d][7]annulenyl, perylenyl, 9,9′-spirobi[9H-fluoren]yl and 10,11-dihydro-5H-dibenzo[a,d][7]annulenyl, dibenzo[a,e][8]annulenyl, where mono-or polycyclic aryl is unsubstituted or substituted by 1 radical R Ar .

4 . The compound of claim 3 , where Ar is is mono-or polycyclic aryl selected from the group consisting of phenyl, naphthyl, phenanthryl, biphenylenyl and 1,2-dihydroacenaphthylen-5-yl, where mono-or polycyclic aryl is unsubstituted or substituted by 1 radical R Ar .

5 . The compound of claim 1 , where Ar is mono-or polycyclic hetaryl selected from the group consisting of furyl, benzofuryl, benzothienyl, naphthofuryl, dibenzofuranyl, dibenzothienyl, 9H-xanthenyl, 2H-chromenyl, 4H-chromenyl, 2H-benzo[g]chromenyl, 4H-benzo[g]chromenyl, 3H-benzo[f]chromenyl, 1H-benzo[f]chromenyl, furo[3,2-b]furanyl, furo[2,3-b]furanyl, furo[3,4-b]furanyl, 2,3-dihydro-1,4-benzodioxinyl, oxanthrenyl, furo[3,2-f][1] benzofuranyl, furo[2,3-f][1] benzofuranyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolizinyl, benzo[cd]indolyl, 1H-benzo[g]indolyl, 3H-benzo[e]indolyl, 1H-benzo[f]indolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[f]isoquinolinyl, benzo[h]isoquinolinyl,imidazolyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, benzopyrazolyl, benzimidazolyl, quinazolinyl, quinoxalinyl, cinnolinyl, 1,5-naphthyridinyl, 1,8-naphthyridinyl, dipyridyl, pyrido[4,3-b]indolyl, pyrido[3,2-b]indolyl, pyrrolo [3,2-b]pyridinyl, phenazinyl, benzo[b][1,5] naphthyridinyl, phenanthrolinyl, benzo[b][1,8]naphthyridin-3-yl, pyrido[2,3-g]quinolinyl, pyrido[3,2-g]quinolinyl, benzo[g]quinoxalinyl, benzo[f]quinoxalinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, triazinyl, pyrido[2,3-b][1,8]naphthyridinyl, tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, benzoxazolyl, phenoxazinyl, furo[3,2-g]quinolinyl, furo[2,3-g]quinolinyl and furo[2,3-g]quinoxalinyl, where mono-or polycyclic hetaryl is unsubstituted or substituted by 1 radical R Ar .

6 . The compound of claim 5 , where Ar is mono-or polycyclic hetaryl selected from the group consisting of dibenzo[b,d]furanyl, dibenzo[b,d]thienyl, pyrrolyl, indolyl, pyridyl, quinolinyl, isoquinolinyl and pyrimidinyl, where mono-or polycyclic hetaryl is unsubstituted or substituted by 1 radical R Ar .

7 . The compound of claim 1 , which bears at least one radical R Ar , R 1 or R 2 which is selected from CN, CH═CH 2 and phenyl.

8 . The compound of claim 1 , where Ar is selected from the group consisting of radicals of the formulae Ar-1 to Ar-19;

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Reuter Karl
• Andrushko Vasyl
• Kantor Mark
• Stolz Florian
• SHIRATAKE Munenori
• Ishihara Kentaro
• Hirose Koji
• Ikeda Shinya
• Kato Noriyuki
• Kondo Mitsuteru
• Murata Shoko
• Oshima Kensuke

Classifications

• C08G63/193

  containing two or more aromatic rings · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• G02B1/041

  Lenses · CPC title