Binaphthyl compounds and thermoplastic resins

Abstract

The present invention relates to binaphthyl compounds of formula (I) that are suitable as monomers for preparing thermoplastic resins, such as polycarbonate resins, that have beneficial optical and mechanical properties and can be used to manufacture optical devices. [Formula 1] TIFF2026503334000063.tif3762, X 1 and X 2 -CHOH and -C(O)OR x are independently selected from R x is selected from the group consisting of hydrogen, phenyl, benzyl and C1-C4-alkyl; A 1 and A 2 are independently, for example, monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members or monocyclic or polycyclic hetarylene having a total of 5 to 26 ring atoms; R 1 and R 2 is halogen, C2-C3-alkynyl, CN, R, OR, CH S R' 3-s , NR2, C(O)R and CH=CHR", and when p+q>1, R 1 and R 2 can be the same or different, s at each occurrence is 0, 1 or 2; p and q are independently 0, 1 or 2.

Description

[Technical Field]

[0001] The present invention relates to binaphthyl compounds that have beneficial optical and mechanical properties and are suitable as monomers for preparing thermoplastic resins, such as polycarbonate resins, that can be used to manufacture optical devices. [Background technology]

[0002] Optical devices, such as optical lenses, made from optical resins instead of optical glass have the advantage of being mass-produced by injection molding. Recently, optical resins, particularly transparent polycarbonate resins, have been frequently used in the manufacture of camera lenses. In this regard, resins with higher refractive indices are highly desirable because they allow for the reduction of the size and weight of the final product. In general, using optical materials with higher refractive indices allows for the same optical power to be achieved with a lens element having a smaller surface curvature, thereby reducing the amount of aberrations that occur at this surface. As a result, it is possible to reduce the number of lenses, decrease the lens's decentering sensitivity, and / or reduce the lens thickness, thereby achieving weight reduction.

[0003] U.S. Pat. No. 9,360,593 describes polycarbonate resins having repeating units derived from binaphthyl monomers of formula (A):

[0004] [ka] (wherein Y is a C1-C4-alkanediyl, particularly 1,2-ethanediyl.) Polycarbonate resins are said to have beneficial optical properties in terms of high refractive index, low Abbe number, high transparency, low birefringence, and glass transition temperature suitable for injection molding.

[0005] Copolycarbonates of monomers of formula (A) and 10,10-bis(4-hydroxyphenyl)anthrone monomers and their use to prepare optical lenses are described in US Patent Application Publication No. 2016 / 0319069.

[0006] WO 2019 / 043060 describes a thermoplastic resin for producing an optical material, the thermoplastic resin comprising a polymerized compound of formula (B):

[0007] [ka] (In the formula, X is, for example, C2-C4-alkanediyl; R and R' are the same or different and are selected from optionally substituted monocyclic or polycyclic aryl having 6 to 36 carbon atoms and optionally substituted monocyclic or polycyclic hetaryl having a total of 5 to 36 atoms.

[0008] However, as observed by the present inventors, despite their multiple advantages, binaphthyl-derived monomers, such as those of Formulas A and B, suffer from the drawback of forming a significant proportion of undesirable cyclic oligomers when used as monomers in the production of thermoplastic resins, such as polyesters and polycarbonates. These cyclic oligomers can impair molecular weight growth and / or impair the resin's product properties, such as reduced mechanical strength, lower glass transition temperature, and / or optical properties. Unfortunately, these cyclic components are rarely able to be efficiently removed from the resin. To reduce the formation of such cyclic compounds, it is typically necessary to polymerize the binaphthyl-containing monomer with a relatively large amount of comonomer.

[0009] Without being bound by theory, it is believed that the reason for the increased formation of cyclic compounds when these monomers are used is particularly related to their flexible, typically short linker units (see moieties -Y-OH and -X-OH in Formulas A and B). Summary of the Invention

[0010] The inventors have now found that these problems can be alleviated by compounds of formula (I) as described below: The use of compounds of formula (I) as monomers in the production of thermoplastic resins, in particular polycarbonates, results in resins having a reduced content of undesirable cyclic oligomers and / or a higher molecular weight and a higher refractive index, and therefore improved optical and / or mechanical properties.

[0011] Thus, a first aspect of the present invention relates to the use of a compound of formula (I) or a mixture thereof as a monomer for producing a thermoplastic resin, in particular for producing a polyester, in particular for producing a polycarbonate:

[0012] [ka] (In the formula, X 1 and X 2 -CHOH and -C(O)OR x are independently selected from R x is selected from the group consisting of hydrogen, phenyl, benzyl and C1-C4-alkyl; A 1 and A 2represents a monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members and a monocyclic or polycyclic hetarylene having a total of 5 to 26 ring atoms, wherein 1, 2, 3, or 4 of the ring atoms of the hetarylene are selected from nitrogen, sulfur, and oxygen, and the remainder of the ring atoms of the hetarylene are carbon atoms, and the monocyclic or polycyclic arylene and the monocyclic or polycyclic hetarylene are unsubstituted or have 1, 2, 3, or 4 R Ar and independently selected from the group consisting of: R 1 and R 2 is halogen, C2-C3-alkynyl, CN, R, OR, CH s R' 3-s , NR2, C(O)R and CH=CHR", and when p+q>1, R 1 and R 2 may be the same or different, and s is 0, 1, or 2 for each occurrence; p and q are independently 0, 1, or 2; R Ar R, OR, CH t R' 3-t , NR2 and CH=CHR", R Ar may be the same or different when present more than once on the same (hetaryl)arylene group, and t is 0, 1 or 2 at each occurrence; R is selected from the group consisting of C1-C4-alkyl, phenyl, naphthyl, phenanthrenyl and triphenylenyl, where phenyl, naphthyl, phenanthrenyl and triphenylenyl are unsubstituted or substituted with 1, 2, 3 or 4 identical or different R''' groups; R' is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, and triphenylenyl, wherein phenyl, naphthyl, phenanthrenyl, and triphenylenyl are unsubstituted or substituted with 1, 2, 3, or 4 identical or different R''' groups; R" is selected from hydrogen, methyl, phenyl and naphthyl, wherein phenyl and naphthyl are unsubstituted or substituted with 1, 2, 3 or 4 identical or different R'" groups; R''' is selected from the group consisting of phenyl, halogen, OCH3, CH3, N(CH3)2 and C(O)CH3).

[0013] The compound of formula (I) is A 1 and A 2 are both unsubstituted phenylene, p and q are both 0, and X 1 and X 2 Both are -CH2OH or C(O)OR x (R x is hydrogen, methyl or ethyl). These compounds are known from S. Florea et al., Revista de Chimie 2003, 54(12), 972-973; P. Rajakumar et al., Bioorganic & Medicinal Chemistry Letters 2007, 17(18), 5270-5273; P. Rajakumar et al., Tetrahedron 2007, 63(36), 8891-8901; and P. Rajakumar et al., Tetrahedron Letters (2005), 46(36), 6127-6130.

[0014] Thus, the second aspect relates to novel compounds of formula (I). In other words, the second aspect relates to compounds of formula (I) 1 , A 2 , p, q, X 1 and X 2 with respect to compounds of formula (I), excluding compounds of formula (I) in which the combination of A 1 and A 2 are both unsubstituted phenylene, p and q are both 0, and X 1 and X 2 are both -CH2OH, C(O)OH, C(O)OCH3 or C(O)OCH2CH3.

[0015] A third aspect relates to a thermoplastic resin comprising polymerized units of a compound of formula (I), i.e., a thermoplastic resin comprising structural units represented by the following formula (II):

[0016] [ka] (In the formula, # represents the point of attachment to the adjacent structural unit; X 1a and X 2a is X 1 or X 2 -OH or -OR x by replacing the X group with an oxo (—O—) moiety, respectively. 1 and X 2 Induced by X 1 , X 2 , A 1 , A 2 , R 1 , R 2 , p and q are as defined hereinabove).

[0017] The invention further relates to an optical device made from a thermoplastic resin as defined above, in particular a polyester, especially a polycarbonate. DETAILED DESCRIPTION OF THE INVENTION

[0018] The compounds of formula (I) may have axial chirality due to restricted rotation along the bond between the naphthalene units, and therefore, the compounds of formula (I) may exist in the form of (S)-enantiomers and (R)-enantiomers. As a result, the compounds of formula (I) may exist as racemic mixtures or non-racemic mixtures or in the form of pure (S)- and (R)-enantiomers, respectively. The present invention relates to both racemic and non-racemic mixtures of the enantiomers of the compounds of formula (I), as well as to the pure (S)- and (R)-enantiomers, insofar as these enantiomers exist.

[0019] In the context of the present invention, the term "C1-C4-alkanediyl group", alternatively designated "C1-C4-alkylene group", refers to a divalent saturated aliphatic hydrocarbon group having 1, 2, 3 or 4 carbon atoms. Examples of C1-C4-alkanediyl are in particular straight-chain alkanediyls such as methylene (CH2), 1,2-ethanediyl (CH2CH2), 1,3-propanediyl (CH2CH2CH2) and 1,4-butanediyl (CH2CH2CH2CH2), but also branched alkanediyls such as 1-methyl-1,2-ethanediyl, 1-methyl-1,2-propanediyl, 2-methyl-1,2-propanediyl, 2-methyl-1,3-propanediyl and 1,3-butanediyl.

[0020] In the context of this invention, the term "monocyclic aryl" refers in particular to a monovalent aromatic monocyclic group such as phenyl.

[0021] In the context of this invention, the term "monocyclic hetaryl" refers to a monovalent heteroaromatic monocyclic group, i.e., a heteroaromatic monocyclic ring attached to the rest of the molecule by a single covalent bond, the ring atoms being part of a conjugated π-electron system, and the heteroaromatic monocyclic ring having 5 or 6 ring atoms (including 1, 2, 3, or 4 nitrogen atoms or 1 oxygen atom and 0, 1, 2, or 3 nitrogen atoms or 1 sulfur atom and 0, 1, 2, or 3 nitrogen atoms as heterocyclic ring members, the remaining ring atoms being carbon atoms). Examples include furyl (=furanyl), pyrrolyl (=1H-pyrrolyl), thienyl (=thiophenyl), imidazolyl (=1H-imidazolyl), pyrazolyl (=1H-pyrazolyl), 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, pyridyl (=pyridinyl), pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl.

[0022] In the context of this invention, the term "monocyclic or polycyclic aryl" refers to a monovalent aromatic monocyclic group or a monovalent aromatic polycyclic group as defined herein, i.e., a polycyclic arene attached to the rest of the molecule by a single covalent bond, wherein the polycyclic arene is: (i) aromatic polycyclic hydrocarbons, i.e., fully unsaturated polycyclic hydrocarbons in which each carbon atom is part of a conjugated π-electron system; (ii) a polycyclic hydrocarbon having at least one phenyl ring fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring; (iii) Polycyclic hydrocarbons having at least two phenyl rings covalently bonded to each other or directly fused to each other and / or fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring.

[0023] Monocyclic or polycyclic aryls have 6 to 26, usually 6 to 24, carbon atoms as ring atoms, for example 6, 9, 10, 12, 13, 14, 16, 17, 18, 19, 20, 22 or 24 carbon atoms, particularly 6 to 20 carbon atoms, especially 6, 10, 12, 13, 14, 16, 17 or 18 carbon atoms. Polycyclic aryls typically have 10 to 26, especially 10 to 20 carbon atoms, especially 10, 12, 13, 14, 16, 17 or 18 carbon atoms as ring atoms.

[0024] In this context, examples of polycyclic aryls having two, three, or four phenyl rings bonded to one another via single bonds include biphenylyl and terphenylyl. Examples of polycyclic aryls having two, three, or four phenyl rings directly fused to one another include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, triphenylenyl, chrysenyl, and benzo[c]phenanthrenyl. Examples of polycyclic aryls having two, three, or four phenyl rings fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring include 9H-fluorenyl, biphenylenyl, tetraphenylenyl, acenaphthenyl (1,2-dihydroacenaphthylenyl), acenaphthylenyl, 9,10-dihydroanthracen-1-yl, 1,2,3,4-tetrahydrophenanthrenyl, 5,6,7,8-tetrahydrophenanthrenyl, and benzo[c]phenanthrenyl. These include 9,10-dihydro-9,10[1',2']-benzenoanthracenyl, dibenzo[a,e][8]annulenyl, 9,9'-spirobi[9H-fluoren]yl, and spiro[1H-cyclobut[de]naphthalene-1,9'-[9H]fluoren]yl.

[0025] Examples of monocyclic or polycyclic aryl include phenyl, naphthyl, 9H-fluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysenyl, benzo[c]phenanthrenyl, acenaphthenyl, acenaphthylenyl, 2,3-dihydro-1H-indenyl, 5,6,7,8-tetrahydro-naphthalenyl, cyclopenta[fg]acenaphthylenyl, 2,3-dihydrophenalenyl, 9,10-dihydroanthracen-1-yl, 1,2,3,4-tetrahydrophenanthrenyl, 5,6,7,8-tetrahydrophenanthrenyl, fluoranthenyl, benzo[k]fluoranthenyl, biphenylenyl, triphenylenyl, tetraphenylenyl, 1,2-dihydroacenaphthylenyl, dibenzo[a,e][8]annulenyl, perylenyl, biphenylenyl, phenyl, terphenylyl, naphthylenephenyl, phenanthrylphenyl, anthracenylphenyl, pyrenylphenyl, 9H-fluorenylphenyl, di(naphthylene)phenyl, naphthylenebiphenyl, tri(phenyl)phenyl, tetra(phenyl)phenyl, pentaphenyl(phenyl), phenylnaphthyl, binaphthyl, phenanthrylnaphthyl, pyrenylnaphthyl, phenylanthracenyl, biphenylanthracenyl, naphthalenylanthracenyl, phenanthrylanthracenyl, dibenzo[a,e][8]annulenyl, 9,10-dihydro-9,10[1',2']benzanthracenyl, 9,9'-spirobi-9H-fluorenyl, and spiro[1H-cyclobuta[de]naphthalene-1,9'-[9H]fluorenyl]yl.

[0026] In the context of the present invention, the term "monocyclic or polycyclic hetaryl" refers to a monovalent heteroaromatic monocyclic group or a monovalent heteroaromatic polycyclic group as defined herein, i.e., a polycyclic hetaryl attached to the rest of the molecule by a single covalent bond; (i) the polycyclic hetarene has a heteroaromatic monocycle as defined above and at least one, e.g., 1, 2, 3, 4, or 5, further aromatic rings selected from phenyl and the heteroaromatic monocycles as defined above, wherein the aromatic rings of the polycyclic hetarene are covalently bonded to each other and / or directly fused to each other and / or fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring; or (ii) Polycyclic hetaranes are 5, 6, 7 or 8 saturated or partially or fully unsaturated ring-type hetaranes having 1, 2 or 3 heteroatoms selected from oxygen, sulfur and nitrogen as ring atoms, such as 2H-pyran, 4H-pyran, thiopyran, 1,4-dihydropyridine, 4H-1,4-oxazine, 4H-1,4-thiazine, 1,4-dioxine, oxepin, thiepin, dioxin, dithiin, dioxepin, dithiepin, dioxocine, dithiocine, etc. and at least one, e.g., 1, 2, 3, 4, or 5, aromatic rings selected from phenyl and heteroaromatic monocycles as defined above, wherein at least one aromatic ring is directly fused to a saturated or partially unsaturated 5- to 8-membered heterocyclic ring, and the aromatic rings of the polycyclic hetarene are covalently bonded to each other or are directly fused to each other and / or are fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring.

[0027] Monocyclic or polycyclic hetaryls have 5 to 26, usually 5 to 24, especially 5 to 20 ring atoms, including 1, 2, 3, or 4 atoms selected from nitrogen, sulfur, and oxygen, with the remaining ring atoms being carbon atoms. Polycyclic hetaryls generally have 9 to 26, usually 9 to 24, especially 9 to 20 ring atoms, including 1, 2, 3, or 4 atoms selected from nitrogen, sulfur, and oxygen, with the remaining ring atoms being carbon atoms.

[0028] Examples of polycyclic hetaryls include benzofuryl, benzothienyl, dibenzofuranyl (=dibenzo[b,d]furanyl), dibenzothienyl (=dibenzo[b,d]thienyl), naphthofuryl, naphthothienyl, furo[3,2-b]furanyl, furo[2,3-b]furanyl, furo[3,4-b]furanyl, thieno[3,2-b]thienyl, thieno[2,3-b]thienyl, thieno[3,4-b]thienyl, oxanthrenyl, thianthrenyl, indolyl (=1H-indolyl), isoindolyl (=2H-isoindolyl), carbazolyl, indolizinyl. benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzo[c,d]indolyl, 1H-benzo[g]indolyl, quinolinyl, isoquinolinyl, acridinyl, phenazinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, fentiazinyl, benzo[b][1,5]naphthyridinyl, cinnolinyl, 1,5-naphthyridinyl, 1,8-naphthyridinyl, phenylpyrrolyl, naphthylpyrrolyl, dipyridyl, phenylpyridyl, naphthylpyridyl, pyrido[4,3-b]indolyl, pyrido[3,2-b]indolyl Doryl, pyrido[3,2-g]quinolinyl, pyrido[2,3-b][1,8]naphthyridinyl, pyrrolo[3,2-b]pyridinyl, pteridinyl, pryl, 9H-xanthenyl, 9H-thioxanthenyl, 2H-chromenyl, 2H-thiochromenyl, phenanthridinyl, phenanthrolinyl, benzo[1,2-b:4,3-b']difuranyl, benzo[1,2-b:6,5-b']difuranyl, benzo[1,2-b:5,4-b']difuranyl, benzo[1,2-b:4,5-b']difuranyl, naphthofuranyl, benzo[b]naphtho[1,2-d]furanyl nyl, benzo[b]naphtho[2,3-d]furanyl, benzo[b]naphtho[2,1-d]furanyl, tribenzo[b,d,f]oxepinyl, dibenzo[b,d]thienyl, naphtho[1,2-b]thienyl, naphtho[2,3-b]thienyl, naphtho[2,1-b]thienyl, benzo[b]naphtho[1,2-d]thienyl, benzo[b]naphtho[2,3-d]thienyl, benzo[b]naphtho[2,1-d]thienyl, 6H-dibenzo[b,d]thiopyranyl, 5H,9H-[1]benzothiopyrano[5,4,3-c,d,e][2]benzothiopyranyl, 5H,10H-[1]benzothiopyrano[5,4,3-c,d,e][2]benzothiopyranyl, benzo[1,2-b:4,3-b']bisthienyl, benzo[1,2-b:6,5-b']bisthienyl, benzo[1,2-b:5,4-b']bisthienyl, benzo[1,2-b:4,5-b']bisthienyl, 1,4-benzodithiinyl, naphtho[1,2-b][1,4]dithiinyl, naphtho[2,3-b][1,4]dithiinyl, thianthrenyl, Benzo[a]thianthrenyl, benzo[b]thianthrenyl, dibenzo[a,c]thianthrenyl, dibenzo[a,h]thianthrenyl, dibenzo[a,i]thianthrenyl, dibenzo[a,j]thianthrenyl, dibenzo[b,i]thianthrenyl, 2H-naphtho[1,8-b,c]thienyl, 5H-phenanthro[4,5-b,c,d]thiopyranyl, 10,11-dihydrodibenzo[b,f]thiepinyl, 6,7-dihydrodibenzo[b,d ]thiepinyl, dibenzo[b,f]thiepinyl, dibenzo[b,d]thiepinyl, 6H-dibenzo[d,f][1,3]dithiepinyl, tribenzo[b,d,f]thiepinyl, benzothieno[3,4-c,d]thieno[2,3,4-j,k][2]benzothiepinyl, dinaphtho[1,8-bc:1',8'-f,g][1,5]dithiocinyl, furo[3,2-g]quinolinyl, furo[2,3-g]quinolinyl, furo[2,3-g]quinoxalinyl, Examples include, but are not limited to, benzo[g]chromenyl, thieno[3,2-f][1]benzothienyl, thieno[2,3-f][1]benzothienyl, thieno[3,2-g]quinolinyl, thieno[2,3-g]quinolinyl, thieno[2,3-g]quinoxalinyl, benzo[g]thiochromenyl, pyrrolo[3,2,1-h,i]indolyl, benzo[g]quinoxalinyl, benzo[f]quinoxalinyl, and benzo[h]isoquinolinyl.

[0029] In the context of this invention, the term "monocyclic arylene" refers in particular to a divalent aromatic monocyclic group such as phenylene.

[0030] In the context of this invention, the term "monocyclic hetaryl" refers to a divalent heteroaromatic monocyclic group, i.e., a heteroaromatic monocyclic ring linked to two remaining parts of the molecule by two single covalent bonds, the ring atoms being part of a conjugated π-electron system, and the heteroaromatic monocyclic ring having 5 or 6 ring atoms (including 1, 2, 3, or 4 nitrogen atoms or 1 oxygen atom and 0, 1, 2, or 3 nitrogen atoms or 1 sulfur atom and 0, 1, 2, or 3 nitrogen atoms as heterocyclic ring members, the remaining ring atoms being carbon atoms). Examples include furylene (=furanylene), pyrrolylene (=1H-pyrrolylene), thienylene (=thiophenylene), imidazolylene (=1H-imidazolylene), pyrazolylene (=1H-pyrazolylene), 1,2,3-triazolylene, 1,2,4-triazolylene, tetrazolylene, oxazolylene, thiazolylene, isoxazolylene, isothiazolylene, 1,3,4-oxadiazolylene, 1,3,4-thiadiazolylene, pyridylene (=pyridinylene), pyrazinylene, pyridazinylene, pyrimidinylene and triazinylene.

[0031] In the context of the present invention, the term "monocyclic or polycyclic arylene" refers to a divalent aromatic monocyclic group or a divalent aromatic polycyclic group as defined herein, i.e., a polycyclic arene attached to two remaining parts of the molecule by two single covalent bonds, wherein the polycyclic arene is: (i) aromatic polycyclic hydrocarbons, i.e., fully unsaturated polycyclic hydrocarbons in which each carbon atom is part of a conjugated π-electron system; (ii) a polycyclic hydrocarbon having at least one phenyl ring fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring; (iii) Polycyclic hydrocarbons having at least two phenyl rings bonded to each other by a covalent bond, an oxygen atom, or a sulfur atom, or directly fused to each other and / or fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring.

[0032] Monocyclic or polycyclic arylenes have 6 to 26, usually 6 to 24, carbon atoms as ring atoms, for example 6, 9, 10, 12, 13, 14, 16, 17, 18, 19, 20, 22 or 24 carbon atoms, particularly 6 to 20 carbon atoms, especially 6, 10, 12, 13, 14, 16, 17 or 18 carbon atoms. Polycyclic arylenes typically have 10 to 26, especially 10 to 20 carbon atoms, especially 10, 12, 13, 14, 16, 17 or 18 carbon atoms as ring atoms.

[0033] In this context, polycyclic arylenes having two, three, or four phenyl rings bonded to one another via single bonds or oxygen or sulfur atoms include, for example, biphenylylene, terphenylylene, 1,1'-oxydiphenylene, and 1,1'-thiodiphenylene. Polycyclic arylenes having two, three, or four phenyl rings directly fused to one another include, for example, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, triphenylenylene, chrysenylene, and benzo[c]phenanthrenylene. Examples of polycyclic arylenes having 2, 3, or 4 phenyl rings fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring include 9H-fluorenylene, biphenylenylene, tetraphenylenylene, acenaphthenylene (1,2-dihydroacenaphthylenylene), acenaphthylenylene, 9,10-dihydroanthracen-1-ylene, 1,2,3,4-tetrahydrophenanthrenylene, 5,6,7,8-tetrahydrophenanthrenylene, 1,2,3,4 ... Examples include phenanthrenylene, cyclopenta[fg]acenaphthylenylene, phenalenylene, fluoranthenylene, benzo[k]fluoranthenylene, perylenylene, 9,10-dihydro-9,10[1',2']-benzenoanthracenylene, dibenzo[a,e][8]annurenylene, 9,9'-spirobi[9H-fluoren]ylene, and spiro[1H-cyclobut[de]naphthalene-1,9'-[9H]fluoren]ylene.

[0034] Examples of monocyclic or polycyclic arylenes include phenylene, naphthylene, 9H-fluorenylene, phenanthrylene, anthracenylene, pyrenylene, chrysenylene, benzo[c]phenanthrenylene, acenaphthenylene, acenaphthylenylene, 2,3-dihydro-1H-indenylene, 5,6,7,8-tetrahydro-naphthalenylene, cyclopenta[fg]acenaphthylenylene, 2,3-dihydro-1H-indenylene, 5,6,7,8-tetrahydro-naphthalenylene, cyclopenta[fg]acenaphthylenylene, 2,3-dihydro-1H-indenylene, 5,6,7,8-tetrahydro-1H-inden ... Phenalenylene, 9,10-dihydroanthracen-1-ylene, 1,2,3,4-tetrahydrophenanthrenylene, 5,6,7,8-tetrahydrophenanthrenylene, fluoranthenylene, benzo[k]fluoranthenylene, biphenylenylene, triphenylenylene, tetraphenylenylene, 1,2-dihydroacenaphthylenylene, dibenzo[a,e][8]annulenylene, perylenylene, biphenylenylene Rylene, terphenylylene, naphthylenephenylene, phenanthrylphenylene, anthracenylphenylene, pyrenylphenylene, 9H-fluorenylphenylene, di(naphthylene)phenylene, naphthylenebiphenylene, tri(phenyl)phenylene, tetra(phenyl)phenylene, pentaphenyl(phenylene), phenylnaphthylene, binaphthylene, phenanthrylnaphthylene, pyrenylnaphthylene Examples include phenylanthracenylene, biphenylanthracenylene, naphthalenylanthracenylene, phenanthrylanthracenylene, dibenzo[a,e][8]annulenylene, 9,10-dihydro-9,10[1',2']benzoanthracenylene, 9,9'-spirobi-9H-fluorenylene, and spiro[1H-cyclobut[de]naphthalene-1,9'-[9H]fluorenylene]ylene.

[0035] In the context of the present invention, the term "monocyclic or polycyclic hetarylene" refers to a divalent heteroaromatic monocyclic group or a divalent heteroaromatic polycyclic group as defined herein, i.e., a polycyclic hetarene attached to two remaining parts of the molecule by two single covalent bonds, (i) the polycyclic hetarene has a heteroaromatic monocycle as defined above and at least one, e.g., 1, 2, 3, 4, or 5, further aromatic rings selected from phenyl and the heteroaromatic monocycles as defined above, wherein the aromatic rings of the polycyclic hetarene are covalently bonded to each other and / or directly fused to each other and / or fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring; or (ii) Polycyclic hetaranes are 5, 6, 7 or 8 saturated or partially or fully unsaturated ring-type hetaranes having 1, 2 or 3 heteroatoms selected from oxygen, sulfur and nitrogen as ring atoms, such as 2H-pyran, 4H-pyran, thiopyran, 1,4-dihydropyridine, 4H-1,4-oxazine, 4H-1,4-thiazine, 1,4-dioxine, oxepin, thiepin, dioxin, dithiin, dioxepin, dithiepin, dioxocine, dithiocine, etc. and at least one, e.g., 1, 2, 3, 4, or 5, aromatic rings selected from phenyl and heteroaromatic monocycles as defined above, wherein at least one aromatic ring is directly fused to a saturated or partially unsaturated 5- to 8-membered heterocyclic ring, and the aromatic rings of the polycyclic hetarene are covalently bonded to each other or are directly fused to each other and / or are fused to a saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydrocarbon ring.

[0036] Monocyclic or polycyclic hetaryl rings generally have 5 to 26, usually 5 to 24, and especially 5 to 20 ring atoms, including 1, 2, 3, or 4 atoms selected from nitrogen, sulfur, and oxygen, with the remaining ring atoms being carbon atoms. Polycyclic hetaryl rings generally have 9 to 26, usually 9 to 24, and especially 9 to 20 ring atoms, including 1, 2, 3, or 4 atoms selected from nitrogen, sulfur, and oxygen, with the remaining ring atoms being carbon atoms.

[0037] Examples of polycyclic hetarylenes include benzofurylene, benzothienylene, dibenzofuranylene (=dibenzo[b,d]furanylene), dibenzothienylene (=dibenzo[b,d]thienylene), naphthofurylene, naphthothienylene, furo[3,2-b]furanylene, furo[2,3-b]furanylene, furo[3,4-b]furanylene, thieno[3,2-b]thienylene, thieno[2,3-b]thienylene, thieno[3,4-b]thienylene, oxanthrene (=dibenzo[1,4]dioxinylene), thianthrenylene, and indolylene (=1H-indo). benzo[c,d]indolylene, 1H-benzo[g]indolylene, quinolinylene, isoquinolinylene, acridinylene, phenazinylene, quinazolinylene, quinoxalinylene, phenoxazinylene, phenthiazinylene, benzo[b][1,5]naphthyridinylene, cinnolinylene, 1,5-naphthyridinylene, 1,8-naphthyridinylene, phenylpyrrolylene , naphthylpyrrolylene, dipyridylene, phenylpyridylene, naphthylpyridylene, pyrido[4,3-b]indolylene, pyrido[3,2-b]indolylene, pyrido[3,2-g]quinolinylene, pyrido[2,3-b][1,8]naphthyridinylene, pyrrolo[3,2-b]pyridinylene, pteridinylene, purylene, 9H-xanthenylene, 9H-thioxanthenylene, 2H-chromenylene, 2H-thiochromenylene, phenanthridinylene, phenanthrolinylene, benzo[1,2-b:4,3-b']difuranylene, benzo[1,2-b:6,5- b']difuranylene, benzo[1,2-b:5,4-b']difuranylene, benzo[1,2-b:4,5-b']difuranylene, naphthofuranylene, benzo[b]naphtho[1,2-d]furanylene, benzo[b]naphtho[2,3-d]furanylene, benzo[b]naphtho[2,1-d]furanylene, tribenzo[b,d,f]oxepinylene, dibenzo[b,d]thienylene, naphtho[1,2-b]thienylene, naphtho[2,3-b]thienylene, naphtho[2,1-b]thienylene, benzo[b]naphtho[1,2-d]thienylene, benzo[b]naphtho[2,3-d]thienylene, benzo[b]naphtho[2,1-d]thienylene, 6H-dibenzo[b,d]thiopyranylene, 5H,9H-[1]benzothiopyrano[5,4,3-c,d,e][2]benzothiopyranylene, 5H,10H-[1]benzothiopyrano[5,4,3-c,d,e][2]benzothiopyranylene, benzo[1,2-b:4,3-b']bisthienylene, benzo[1,2-b:6,5-b']bisthienylene, benzo[1,2-b:5,4-b']bisthienylene, benzo[1,2-b:4,5-b']bis Thienylene, 1,4-benzodithiinylene, naphtho[1,2-b][1,4]dithiinylene, naphtho[2,3-b][1,4]dithiinylene, thianthrenylene, benzo[a]thianthrenylene, benzo[b]thianthrenylene, dibenzo[a,c]thianthrenylene, dibenzo[a,h]thianthrenylene, dibenzo[a,i]thianthrenylene, dibenzo[a,j]thianthrenylene, dibenzo[b,i]thianthrenylene, 2H-naphtho[1,8-b,c]thienylene, 5H-phenanthro[4,5-b,c,d]thio Pyranylene, 10,11-dihydrodibenzo[b,f]thiepinylene, 6,7-dihydrodibenzo[b,d]thiepinylene, dibenzo[b,f]thiepinylene, dibenzo[b,d]thiepinylene, 6H-dibenzo[d,f][1,3]dithiepinylene, tribenzo[b,d,f]thiepinylene, benzothieno[3,4-c,d]thieno[2,3,4-j,k][2]benzothiepinylene, dinaphtho[1,8-bc:1',8'-f,g][1,5]dithiocinylene, furo[3,2-g]quinolinylene, furo[2,3-g]quinolinylene Examples of quinoxalinylene include, but are not limited to, benzo[g]chromenylene, furo[2,3-g]quinoxalinylene, benzo[g]chromenylene, thieno[3,2-f][1]benzothienylene, thieno[2,3-f][1]benzothienylene, thieno[3,2-g]quinolinylene, thieno[2,3-g]quinolinylene, thieno[2,3-g]quinoxalinylene, benzo[g]thiochromenylene, pyrrolo[3,2,1-h,i]indolylene, benzo[g]quinoxalinylene, benzo[f]quinoxalinylene, and benzo[h]isoquinolinylene.

[0038] In the context of the present invention, the suffix "-ylene" means, as is customary in the art, that the respective hetaryl (arene) moiety is in the form of a divalent radical. Thus, the suffix "-ylene", as in, for example, phenylene or 1,4-phenylene, is used herein synonymously with the suffix "-diyl", as in, for example, phendiyl or phen-1,4-diyl.

[0039] For purposes of the present invention, a "structural unit" is a structural element that occurs repeatedly in the polymer backbone of a thermoplastic resin. Thus, the terms "structural unit" and "repeating unit" are used interchangeably.

[0040] In the context of the present invention, the term "optical device" refers to a device that is transparent to visible light and manipulates light rays, particularly by refraction. Optical devices include, but are not limited to, prisms, lenses, optical films, and combinations thereof, particularly camera lenses and eyeglass lenses.

[0041] The remarks made below on preferred embodiments of the variables (substituents) of the compounds of formula (I) and of the structural units of formula (II) are valid both alone and preferably in combination with one another.

[0042] The remarks made below regarding preferred embodiments of the variables are furthermore valid, alone and preferably in combination with one another, for the compounds of formula (I) and structural units of formula (II) and, where applicable, for the uses according to the invention.

[0043] In formula (I) and similarly in formula (II), the variable X 1 , X 2 , A 1 , A 2 , R 1 , R 2 , p and q, alone or preferably in any combination, preferably have the following meanings:

[0044] -CHOH and -C(O)ORx (R x is selected from the group consisting of hydrogen and C1-C4-alkyl 1 and X 2 and thus variable X of formula (II) independently selected from —CHO— and —C(O)O—. 1a and X 2a is preferred.

[0045] In a preferred group (1) of embodiments, the variable X of formula (I) 1 and X 2 are both —CHOH, and therefore the variable X in formula (II) 1a and X 2a are both -CH2O-.

[0046] In another group (2) of embodiments, the variable X in formulas (I) and (II) 1 and X 2 are independently -C(O)OR x and therefore the variable X in formula (II) 1a and X 2a are both -C(O)O- (R x is R x and is selected from the meanings defined herein for (a) and (b) and is in particular selected from the group consisting of hydrogen, phenyl, benzyl and C1-C4-alkyl, preferably hydrogen and C1-C4-alkyl, more preferably hydrogen, methyl and ethyl, in particular hydrogen and methyl).

[0047] In a particular subgroup (2') of embodiments, the variable X of formula (I) 1 and X 2 is X 1 and X 2 has the same meaning as that defined in group (2) of embodiments.

[0048] In a preferred group (3) of embodiments, which is a combination of groups (1) and (2) of embodiments, the variable X of formula (I) is 1 and X 2-CHOH and -C(O)OR x (R x is hydrogen or C1-C4-alkyl), in particular independently selected from —CH2OH, —C(O)OH, —C(O)OCH3 and —C(O)OCH2CH3, specifically independently selected from —CH2OH, —C(O)OH and —C(O)OCH3. Correspondingly, in this preferred group (4) of embodiments, the variable X of formula (II) 1a and X 2a are independently selected from —CHO— and —C(O)O—.

[0049] In a particular subgroup (3') of embodiments, the variable X of formula (I) 1 and X 2 is X 1 and X 2 has the same meaning as defined herein, selected from the meanings mentioned as particularly preferred, in particular selected from the meanings defined in group (3) of embodiments, and similarly the variable X of formula (II) 1a and X 2a has the same meaning selected from the meanings defined in group (3) of embodiments.

[0050] In a preferred group (4) of embodiments, variable A of formulas (I) and (II) 1 and A 2 represents monocyclic or polycyclic arylenes having 6 to 22, especially 6 to 18, carbon atoms as ring members and monocyclic or polycyclic hetarylenes having 9 to 26 atoms as ring members, of which 1, 2, 3 or 4 are nitrogen, oxygen or sulfur atoms, especially 1, 2 or 3, for example 1 or 2, of these atoms are oxygen or sulfur atoms, and the remainder of these atoms are carbon atoms, and the monocyclic or polycyclic arylenes and monocyclic or polycyclic hetarylenes are unsubstituted or contain 1, 2, 3 or 4, especially 1 or 2, R Ar Group(R Ar are independently selected from the group consisting of: having one of the meanings defined herein, particularly one of the meanings mentioned as being preferred).

[0051] In a more preferred subgroup of embodiments (4.1), A 1 and A 2are phenylene, naphthylene, 1,2-dihydroacenaphthylene, biphenylylene, 1,1'-oxydiphenylene, 1,1'-thiodiphenylene, 9H-fluorenylene, 11H-benzo[a]fluorenylene, 11H-benzo[b]fluorenylene, 7H-benzo[c]fluorenylene, anthracylene, phenanthrylene, benzo[c]phenanthrylene, pyrenylene, chrysenylene, picenylene, triphenylenylene, furanylene, benzo[b]furanylene, dibenzo[b,d]furanylene, naphtho[1,2-b]furanylene, naphtho[2 ,3-b]furanylene, naphtho[2,1-b]furanylene, benzo[b]naphtho[1,2-d]furanylene, benzo[b]naphtho[2,3-d]furanylene, benzo[b]naphtho[2,1-d]furanylene, benzo[1,2-b:4,3-b']difuranylene, benzo[1,2-b:6,5-b']difuranylene, benzo[1,2-b:5,4-b']difuranylene, benzo[1,2-b:4,5-b']difuranylene, 9H-xantylene, tribenzo[b,d,f]oxepinylene, dibenzo[1,4]dioxenylene, 2H-naphtho[1,8 -d,e][1,3]dioxinylene, phenoxathienylene, dinaphtho[2,3-b:2',3'-d]furanylene, oxanthrenylene, benzo[a]oxanthrenylene, benzo[b]oxanthrenylene, thienylene, benzo[b]thienylene, dibenzo[b,d]thienylene, naphtho[1,2-b]thienylene, naphtho[2,3-b]thienylene, naphtho[2,1-b]thienylene, benzo[b]naphtho[1,2-d]thienylene, benzo[b]naphtho[2,3-d]thienylene, benzo[b]naphtho[2,1-d]thienylene, benzo [1,2-b:4,3-b']dithienylene, benzo[1,2-b:6,5-b']dithienylene, benzo[1,2-b:5,4-b']dithienylene, benzo[1,2-b:4,5-b']dithienylene, 9H-thioxanthrene, 6H-dibenzo[b,d]thiopyranylene, 1,4-benzodithiinylene, naphtho[1,2-b][1,4]dithiinylene, naphtho[2,3-b][1,4]dithiinylene, thianthrenylene, benzo[a]thianthrenylene, benzo[b]thianthrenylene, dibenzo[a,c]thianthrenylene, dibenzo[a,h]thianthrenylene, dibenzo[a,i]thianthrenylene, dibenzo[a,j]thianthrenylene, dibenzo[b,i]thianthrenylene, 2H-naphtho[1,8-b,c]thienylene, dibenzo[b,d]thiepinylene, dibenzo[b,f]thiepinylene, 5H-phenanthro[4,5-b,c,d]thiopyranylene, tribenzo[b,d,f]thiepinylene, 2,5-dihydronaphtho[1,8-b,c:4,5-b',c']dithienylene, 2,6-dihydronaphtho[1,8-b,c:5,4-b',c']dithienylene, tribenzo[a,c,i]thianylene and independently selected from the group consisting of threnylene, benzo[b]naphtho[1,8-e,f][1,4]dithiepinylene, dinaphtho[2,3-b:2',3'-d]thienylene, 5H-phenanthro[1,10-b,c]thienylene, 7H-phenanthro[1,10-c,b]thienylene, dibenzo[d,d']benzo[1,2-b:4,5-b']dithienylene and dibenzo[d,d']benzo[1,2-b:5,4-b']dithienylene (the aforementioned monocyclic or polycyclic arylene and monocyclic or polycyclic hetaryl are unsubstituted or contain one or two R, Ar (having a group).

[0052] In a particularly preferred subgroup (4.2) of embodiments, A 1 and A 2 are independently selected from the group consisting of phenylene, naphthylene, benzo[b]thienylene, benzo[b]furanylene, biphenylylene, 9H-fluorenylene, oxanthrene, phenoxathienylene, thianthrenylene, 9H-xanthrene and 9H-thioxanthrene (the aforementioned monocyclic or polycyclic arylene and monocyclic and polycyclic hetaryl are unsubstituted or are substituted by one or two R Ar (having a group).

[0053] In a particularly preferred subgroup (4.3) of embodiments, A 1 and A 2are independently selected from the group consisting of phenylene, naphthylene, dibenzo[b,d]thienylene, dibenzo[b,d]furanylene, biphenylylene, 9H-fluorenylene, oxanthrene, phenoxathiinylene and thianthrenylene, in particular 1,4-phenylene, 1,2-phenylene, 1,3-phenylene, 1,4-naphthylene, 1,5-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 2,3-naphthylene, 1,8-naphthylene, 1,7-naphthylene, 2,8-naphthylene, 1,6-naphthylene, 2,5-naphthylene, 2,4-naphthylene, dibenzo[b,d]thienylene, 1,3-naphthylene, 2,1-naphthylene, 1,2-naphthylene, 2,8-dibenzo[b,d]thienylene, 4,6-dibenzo[b,d]thienylene, 2,9-dibenzo[b,d]thienylene, 1,2-dibenzo[b,d]thienylene, 2,4-dibenzo[b,d]thienylene, 3,6-dibenzo[b,d]thienylene, 4,8-dibenzo[b,d]thienylene, 2,6-dibenzo[b,d]thienylene, 3,2-dibenzo[b,d]thienylene, 3,8-dibenzo[b,d]thienylene, 1,6-dibenzo[b,d]thienylene, 1,4-dibenzo[b,d]thienylene, Benzo[b,d]thienylene, 3,4-dibenzo[b,d]thienylene, 4,2-dibenzo[b,d]thienylene, 2,8-dibenzo[b,d]furanylene, 4,6-dibenzo[b,d]furanylene, 2,9-dibenzo[b,d]furanylene, 1,2-dibenzo[b,d]furanylene, 2,4-dibenzo[b,d]furanylene, 3,6-dibenzo[b,d]furanylene, 4,8-dibenzo[b,d]furanylene, 2,6-dibenzo[b,d]furanylene, 3,2-dibenzo[b,d]furanylene, 3,8-dibenzo[b,d]furanylene, 1,6-dibenzo[b,d]furanylene benzo[b,d]furanylene, 1,4-dibenzo[b,d]furanylene, 3,4-dibenzo[b,d]furanylene, 4,2-dibenzo[b,d]furanylene, 4,4'-biphenylylene, 3,4'-biphenylylene, 3,3'-biphenylylene, 4,3'-biphenylylene, 2,2'-biphenylylene, 4,2'-biphenylylene, 3,2'-biphenylylene, 2,4'-biphenylylene, 2,3'-biphenylylene, 9,9-9H-fluorenylene, 3,6-9H-fluorenylene, 1,6-9H-fluorenylene, 2,6-9H-fluorenylene, 4,6-9H-fluorenylene, 1,3-9H-fluorenylene, 4,3-9H-fluorenylene, 2,3-9H-fluorenylene, 3,8-9H-fluorenylene, 1,8-9H-fluorenylene, 2,8-9H-fluorenylene, 4,8-9H-fluorenylene, 3,1-9H-fluorenylene, 4,1-9H-fluorenylene, 2,1-9H-fluorenylene, 3,2-9H-fluorenylene, 1,2-9H-fluorenylene, 2,4-9H-fluorenylene, 4,7-9H-fluorenylene, 1,7-9H-fluorenylene, 2,7-9H-fluorenylene, 3,7-9H-fluorenylene, 3,5-9H-fluorenylene, 4,5-9H-fluorenylene, 2,5-9H-fluorenylene, 1,5-9H-fluorenylene, 1,4-9H-fluorenylene, 2,4-9H-fluorenylene, 3,4-9H-fluorenylene, 2,7-oxantrenylene , 2,8-oxantrenylene, 1,4-oxantrenylene, 2,3-oxantrenylene, 1,6-oxantrenylene, 1,9-oxantrenylene, 1,4-phenoxathiinylene, 4,1-phenoxathiinylene, 3,7-phenoxathiinylene, 2,8-phenoxathiinylene, 3,8-phenoxathiinylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,8-thianthrenylene, 1,7-thianthrenylene thianthrenylene, 1,3-thianthrenylene, 2,3-thianthrenylene, 1,2-thianthrenylene, 2,1-thianthrenylene, 2,4-thianthrenylene, 1,4-thianthrenylene, 2,9-thianthrenylene, 1,9-thianthrenylene, 2,6-thianthrenylene and 1,6-thianthrenylene (the aforementioned monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or are substituted by one or two R, Ar (having a group).

[0054] In a particularly preferred subgroup (4.4) of embodiments, A 1 and A 2are phenylene, naphthylene, biphenylylene, 9H-fluorenylene, dibenzo[b,d]thienylene, dibenzo[b,d]furanylene and thianthrenylene, such as 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,4-naphthylene, 1,5-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 2,3-naphthylene, 1,8-naphthylene, 1,7-naphthylene, 2,8-naphthylene, 1,6-naphthylene, 2,5-naphthylene, 2,4-naphthylene, 1,3-naphthylene, 2,1-naphthylene, 1,2-naphthylene, 4 ,4'-biphenylylene, 3,4'-biphenylylene, 3,3'-biphenylylene, 4,3'-biphenylylene, 2,2'-biphenylylene, 4,2'-biphenylylene, 3,2'-biphenylylene, 2,4'-biphenylylene, 2,3'-biphenylylene, 3,6-9H-fluorenylene, 1,6-9H-fluorenylene, 2,6-9H-fluorenylene, 4,6-9H-fluorenylene, 1,3-9H-fluorenylene, 4,3-9H-fluorenylene, 2,3-9H-fluorenylene, 3,8-9H-fluorenylene, 1,8-9H-fluorenylene fluorenylene, 2,8-9H-fluorenylene, 4,8-9H-fluorenylene, 3,1-9H-fluorenylene, 4,1-9H-fluorenylene, 2,1-9H-fluorenylene, 3,2-9H-fluorenylene, 1,2-9H-fluorenylene, 2,4-9H-fluorenylene, 4,7-9H-fluorenylene, 1,7-9H-fluorenylene, 2,7-9H-fluorenylene, 3,7-9H-fluorenylene, 3,5-9H-fluorenylene, 4,5-9H-fluorenylene, 2,5-9H-fluorenylene, 1,5-9H-fluorenylene, 1,4-9H- Fluorenylene, 2,4-9H-fluorenylene, 3,4-9H-fluorenylene, 2,8-dibenzo[b,d]thienylene, 4,6-dibenzo[b,d]thienylene, 2,9-dibenzo[b,d]thienylene, 1,2-dibenzo[b,d]thienylene, 2,4-dibenzo[b,d]thienylene, 3,6-dibenzo[b,d]thienylene, 4,8-dibenzo[b,d]thienylene, 2,6-dibenzo[b,d]thienylene, 3,2-dibenzo[b,d]thienylene, 3,8-dibenzo[b,d]thienylene, 1,6-dibenzo[b,d]thienylene, 1,4-Dibenzo[b,d]thienylene, 3,4-dibenzo[b,d]thienylene, 4,2-dibenzo[b,d]thienylene, 2,8-dibenzo[b,d]furanylene, 4,6-dibenzo[b,d]furanylene, 2,9-dibenzo[b,d]furanylene, 1,2-dibenzo[b,d]furanylene, 2,4-dibenzo[b,d]furanylene, 3,6-dibenzo[b,d]furanylene, 4,8-dibenzo[b,d]furanylene, 2,6-dibenzo[b,d]furanylene, 3,2-dibenzo[b,d]furanylene, 3,8-dibenzo[b,d]furanylene benzo[b,d]furanylene, 1,6-dibenzo[b,d]furanylene, 1,4-dibenzo[b,d]furanylene, 3,4-dibenzo[b,d]furanylene, 4,2-dibenzo[b,d]furanylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,8-thianthrenylene, 1,7-thianthrenylene, 1,3-thianthrenylene, 2,3-thianthrenylene, 1,2-thianthrenylene, 2,1-thianthrenylene, 2,4-thianthrenylene, 1,4-thianthrenylene, 2,9-thianthrenylene, 1 ,9-thianthrenylene, 2,6-thianthrenylene or 1,6-thianthrenylene, in particular phenylene, naphthylene, biphenylylene, dibenzo[b,d]thienylene and thianthrenylene, such as 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,4-naphthylene, 1,5-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 2,4-naphthylene, 1,3-naphthylene, 2,3-naphthylene, 1,2-naphthylene, 2,1-naphthylene, 4,4'-biphenylylene, 4,4'-bibenzo[b,d]thienylene and 4,4'-biphenyl .... phenylylene, 3,4'-biphenylylene, 3,3'-biphenylylene, 4,3'-biphenylylene, 2,2'-biphenylylene, 4,2'-biphenylylene, 3,2'-biphenylylene, 2,4'-biphenylylene, 2,3'-biphenylylene, 2,8-dibenzo[b,d]thienylene, 4,6-dibenzo[b,d]thienylene, 2,8-thianthrenylene or 1,9-thianthrenylene, wherein the aforementioned monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or can be substituted by one or two R, Ar (having a group).

[0055] In a particular subgroup (4') of embodiments, variable A of formula (I) and (II) 1 and A 2 is A 1 and A 2 has the same meaning as defined herein, in particular selected from the meanings mentioned as preferred, in particular selected from the meanings defined in groups of embodiments (4), (4.1), (4.2), (4.3) and (4.4).

[0056] A preferred subgroup (4a) of the embodiment group (4) is the moiety A 1 and A 2 Each of X contains a phenylene ring which may have one or two fused rings selected from a fused benzene ring and a fused 5- or 6-membered heteroaromatic ring. 1 or X 2 group and -CH2- group, 1 or A 2 Preferred are compounds in which the phenylene ring is bonded at the para position. These compounds are also referred to as para isomers of embodiment group (4a). Mixtures of the para isomers of the compounds of formula (I) of embodiment group (4a) with the corresponding meta or ortho isomers are also preferred. Among the compounds of embodiment group (4a), A 1 and A 2 Particularly preferred are compounds of formula (I) in which both are 1,4-phenylene or both are 1,4-phenylene and a mixture of one or both of its isomers, ie, 1,2-phenylene and 1,3-phenylene.

[0057] In a preferred group (5) of embodiments, the variable R of formulas (I) and (II) 1 and R 2 are, if present, independently of one another, halogen, C2-C3-alkynyl, CN, R, OR and CH s R' 3-sand more preferably selected from the group consisting of fluorine, CN, R and OR, where s is 1 or 2, especially 2, and the variables R and R' each have one of the meanings defined herein, especially the preferred meanings.

[0058] In a particularly preferred subgroup (5.1) of embodiments, R 1 and R 2 is, when present, independently selected from the group consisting of fluorine, CN, methyl, methoxy, phenyl, naphthyl, such as 1-naphthyl or 2-naphthyl, and phenanthrenyl, such as 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl or 9-phenanthrenyl, in particular from the group consisting of fluorine, phenyl or naphthyl, such as 1-naphthyl or 2-naphthyl.

[0059] In a particular subgroup (5′) of embodiments, the variable R of formulas (I) and (II) 1 and R 2 is R 1 and R 2 has the same meaning as defined herein, selected from the meanings mentioned as being particularly preferred, and in particular selected from the meanings defined in groups (5) and (5.1) of embodiments.

[0060] Variables p and q in formulae (I) and (II) having the same meaning selected from 0, 1 and 2 are preferred.

[0061] In a preferred group (6) of embodiments, the variables p and q in formulas (I) and (II) are both 0, i.e., the binaphthyl moieties in formulas (I) and (II) are not substituted by the substituent R 1 The substituent R 2 It does not have either.

[0062] In a preferred group (7) of embodiments, the variables p and q of formulas (I) and (II) are both 1, i.e., the binaphthyl moieties of formulas (I) and (II) contain one substituent R 1 and one substituent R 2Furthermore, in this group (7) of embodiments, the variable portion R 1 and R 2 has the same meaning, preferably selected from the meanings defined herein, in particular from the meanings mentioned herein as preferred, preferably selected from the meanings defined in group (5), in particular from the meanings defined in group (5.1) of embodiments.

[0063] In a particularly preferred subgroup (7.1) of embodiment group (7), two substituents R 1 and R 2 are bonded to the corresponding positions of each naphthyl unit, i.e., R 1 is attached to the 5-position of the binaphthyl moiety of formula (I) or (II), R 2 is attached to the 5' position of the moiety.

[0064] In a particularly preferred subgroup (7.2) of embodiments, two substituents R 1 and R 2 are attached to the 6- and 6'-positions, respectively, of the binaphthyl moiety of formula (I) or (II).

[0065] In a preferred group (8) of embodiments, the variables p and q in formulas (I) and (II) are both 2, i.e., the binaphthyl moieties in formulas (I) and (II) are each substituted by two substituents R 1 and two substituents R 2 Furthermore, in this group (8) of embodiments, the variable portion R 1 and R 2 has the same meaning as defined herein, particularly selected from the meanings mentioned herein as preferred, more preferably selected from the meanings defined in group (5), particularly from the meanings defined in group (5.1) of embodiments. Furthermore, in this group (8) of embodiments, two substituents R 1 and R 2 are preferably attached to corresponding positions of each naphthyl unit, i.e., two substituents R 1is attached to the 3- and 6-positions of the binaphthyl moiety of formula (I) or (II), two substituents R 2 are attached to the 3' and 6' positions of the moiety.

[0066] Those skilled in the art will recognize that in formulas (I) and (II), X as given in embodiment group (1) 1 and X 2 The meaning of A according to one or more of the groups (4), (4.1), (4.2), (4.3), (4.4) and (4') of the embodiments 1 and A 2 R according to one or more of the groups (5), (5.1) and (5′) of the embodiments 1 and R 2 It will be readily understood that the meaning of X given in one of the groups (2) and (2') of embodiments in formulas (I) and (II) can be combined with the meaning of p and q according to one or more of the groups (6), the groups (7), the groups (7.1) and (7.2), or the groups (8). 1 and X 2 The meaning of A according to one or more of the groups (4), (4.1), (4.2), (4.3), (4.4) and (4') of the embodiments 1 and A 2 R according to one or more of the groups (5), (5.1) and (5′) of the embodiments 1 and R 2 It will also be understood that the meaning of p and q in formulas (I) and (II) can be combined with the meaning of X given in one of the groups of embodiments (3) and (3') and with the meaning of p and q according to one or more of the groups of embodiments (6), the groups of embodiments (7), (7.1) and (7.2), or the group of embodiments (8). 1 and X 2 The meaning of A according to one or more of the groups (4), (4.1), (4.2), (4.3), (4.4) and (4') of the embodiments 1 and A 2R according to one or more of the groups (5), (5.1) and (5′) of the embodiments 1 and R 2 It will also be understood that the meanings of p and q may be combined with the meanings of p and q according to any of group of embodiments (6), group of embodiments (7), one or more of (7.1) and (7.2), or group of embodiments (8).

[0067] Apart from that, unless otherwise specified, variable part R Ar , R, R', R" and R'" may be used alone or preferably in combination with each other and the variable X 1 , X 1 , A 1 , A 2 , R 1 , R 2 In combination with the meanings and preferred meanings of p and q, the following meanings are given:

[0068] R Ar is preferably R, OR and CH t R' 3-t and more preferably from the group consisting of R and OR, where t is 1 or 2, especially 2, and the variables R and R' each have one of the meanings defined herein, especially the preferred meanings. In particular, R Ar The group is selected from the group consisting of methyl, methoxy, phenyl, naphthyl, phenanthrenyl and triphenylenyl, in particular phenyl, naphthyl, e.g., 1-naphthyl or 2-naphthyl, and phenanthrenyl, e.g., 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl or 9-phenanthrenyl.

[0069] R is preferably selected from the group consisting of methyl, ethyl, phenyl, naphthyl, phenanthrenyl and triphenylenyl, unsubstituted or substituted with 1, 2 or 3 identical or different R'" groups, where R'" has, independently at each occurrence, one of the meanings defined herein, particularly the preferred meanings. More preferably, R is selected from the group consisting of phenyl, naphthyl, such as 1-naphthyl or 2-naphthyl, and phenanthrenyl, such as 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl or 9-phenanthrenyl, which is unsubstituted.

[0070] R' is preferably selected from the group consisting of phenyl, naphthyl, phenanthrenyl and triphenylenyl, unsubstituted or substituted with 1, 2 or 3 identical or different R'" groups, where R'" has, independently at each occurrence, one of the meanings defined herein, particularly the preferred meanings. More preferably, R' is selected from the group consisting of phenyl, naphthyl, such as 1-naphthyl or 2-naphthyl, and phenanthrenyl, such as 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl or 9-phenanthrenyl, which is unsubstituted.

[0071] R" is preferably selected from the group consisting of hydrogen, methyl, phenyl and naphthyl, which phenyl and naphthyl are unsubstituted or substituted with 1, 2 or 3, in particular 1 or 2, identical or different R'" groups, where R'" on each occurrence independently has one of the meanings defined herein, in particular the preferred meanings. More preferably, R" is unsubstituted phenyl or unsubstituted naphthyl, for example 1-naphthyl or 2-naphthyl.

[0072] R''' is preferably selected from the group consisting of phenyl, OCH3 and CH3.

[0073] In particular subgroup (6a) of groups (6), (3′) and (4′) of embodiments, in formula (I), variables p and q are both 0 and X 1 and X 2 The groups have the same meaning, and A 1 and A 2 When the groups have the same meaning, the compound of formula (I) is a compound of formula (Ia):

[0074] [ka] (wherein X is the same X 1 and X 2 A represents the same A 1 and A 2 represents a group, and X 1 , X 2 , A 1 , and A 2 have the meanings defined herein, particularly those mentioned herein as preferred).

[0075] In this subgroup (6a) of groups (6), (3′) and (4′) of embodiments, the structural unit of formula (II) is a structural unit of formula (IIa):

[0076] [ka] (wherein # represents a point of attachment to an adjacent structural unit, and X a are the same X 1a and X 2a A represents the same A 1 and A 2 represents a group, and the variable X 1a , X 2a , A 1 and A 2 have the meanings defined herein, particularly those mentioned as preferred).

[0077] Preferably, the moiety X of formula (Ia) and the moiety X of formula (IIa) ais defined as either embodiment group (1), embodiment group (2) or embodiment group (3). Thus, the moiety X of formula (Ia) is herein defined as, in particular, —CHOH (i.e., hydroxymethyl) and —C(O)OR x (R x is hydrogen or C1-C4-alkyl), in particular selected from —CH2OH, —C(O)OH, —C(O)OCH3 and —C(O)OCH2CH3, specifically selected from —CH2OH, —C(O)OH and —C(O)OCH3. Thus, the moiety X of formula (IIa) a is herein selected from the group consisting of —CHO— and —C(O)O—.

[0078] Also preferred are compounds of formula (Ia) and structural units of formula (IIa) in which moiety A is defined as one of the embodiments (4), (4.1), (4.2), (4.3) and (4.4). More preferably, moiety A of formula (Ia) and formula (IIa) is defined as the embodiment group (4.4). Thus, moiety A of formulae (Ia) and (IIa) may here in particular be 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,4-naphthylene, 1,5-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 2,3-naphthylene, 1,8-naphthylene, 1,7-naphthylene, 2,8-naphthylene, 1,6-naphthylene, 2,5-naphthylene, 2,4-naphthylene, 1,3-naphthylene, 2,1-naphthylene, 1,2-naphthylene, 4,4'-biphenylylene, 3,4 '-biphenylylene, 3,3'-biphenylylene, 4,3'-biphenylylene, 2,2'-biphenylylene, 4,2'-biphenylylene, 3,2'-biphenylylene, 2,4'-biphenylylene, 2,3'-biphenylylene, 3,6-9H-fluorenylene, 1,6-9H-fluorenylene, 2,6-9H-fluorenylene, 4,6-9H-fluorenylene, 1,3-9H-fluorenylene, 4,3-9H-fluorenylene, 2,3-9H-fluorenylene, 3,8-9H-fluorenylene Fluorenylene, 1,8-9H-fluorenylene, 2,8-9H-fluorenylene, 4,8-9H-fluorenylene, 3,1-9H-fluorenylene, 4,1-9H-fluorenylene, 2,1-9H-fluorenylene, 3,2-9H-fluorenylene, 1,2-9H-fluorenylene, 2,4-9H-fluorenylene, 4,7-9H-fluorenylene, 1,7-9H-fluorenylene, 2,7-9H-fluorenylene, 3,7-9H-fluorenylene, 3,5-9H-fluorenylene , 4,5-9H-fluorenylene, 2,5-9H-fluorenylene, 1,5-9H-fluorenylene, 1,4-9H-fluorenylene, 2,4-9H-fluorenylene, 3,4-9H-fluorenylene, 2,8-dibenzo[b,d]thienylene, 4,6-dibenzo[b,d]thienylene, 2,9-dibenzo[b,d]thienylene, 1,2-dibenzo[b,d]thienylene, 2,4-dibenzo[b,d]thienylene, 3,6-dibenzo[b,d]thienylene, 4,8-dibenzo[b,d]thienylene, 2,6-dibenzo[b,d]thienylene, 3,2-dibenzo[b,d]thienylene, 3,8-dibenzo[b,d]thienylene, 1,6-dibenzo[b,d]thienylene, 1,4-dibenzo[b,d]thienylene, 3,4-dibenzo[b,d]thienylene, 4,2-dibenzo[b,d]thienylene, 2,8-dibenzo[b,d]furanylene, 4, 6-dibenzo[b,d]furanylene, 2,9-dibenzo[b,d]furanylene, 1,2-dibenzo[b,d]furanylene, 2,4-dibenzo[b,d]furanylene, 3,6-dibenzo[b,d]furanylene, 4,8-dibenzo[b,d]furanylene, 2,6-dibenzo[b,d]furanylene, 3,2-dibenzo[b,d]furanylene, 3,8-dibenzo[b,d] and 1,6-dibenzo[b,d]furanylene, 1,4-dibenzo[b,d]furanylene, 3,4-dibenzo[b,d]furanylene, 4,2-dibenzo[b,d]furanylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,8-thianthrenylene, 1,7-thianthrenylene, 1,3-thianthrenylene, 2,3-thianthrenylene, 1,2-thianthrenylene, 2,1-thianthrenylene, 2,4-thianthrenylene, 1,4-thianthrenylene, 2,9-thianthrenylene, 1,9-thianthrenylene, 2,6-thianthrenylene, 1,6-thianthrenylene, wherein the aforementioned monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or can be substituted with one or two R, Ar (having a group).

[0079] Examples of specific subgroups (6a) are moieties X or X, respectively. a and part A are as defined in any one of rows 1 to 288 of Table A below (X a In each case, X is -OH or -OR x (derived from X in formula (Ia) by replacing the group with an oxo (—O—) unit), compounds of formula (Ia) and structural units of formula (IIa).

[0080] [Table 1-1]

[0081] [Table 1-2]

[0082] [Table 1-3]

[0083] [Table 1-4]

[0084] [Table 1-5]

[0085] [Table 1-6]

[0086] [Table 1-7]

[0087] Among the compounds of formula (Ia) listed in Table A, the following compounds of formula (Ia) are particularly preferred: - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene-4,1-phenylene)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene-3,1-phenylene)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene-2,1-phenylene)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-4,1-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-5,1-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-7,2-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-6,2-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-1,3-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-3,1-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-3,2-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-2,1-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenenaphthalene-1,2-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-4',4-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-4',3-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-3',3-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-3,4'-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-2',2-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-2,4'-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-2,3'-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenedibenzo[b,d]thien-8,2-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenedibenzo[b,d]thien-6,4-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenethianthrene-8,2-diyl)]dimethanol - [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylenethianthrene-9,1-diyl)]dimethanol - 4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]dibenzoic acid - 3,3'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]dibenzoic acid - 2,2'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]dibenzoic acid - 4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylic acid) - 5,5'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylic acid) - 7,7'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylic acid) - 6,6'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylic acid) - 3,3'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylic acid) - 2,2'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylic acid) - 1,1'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylic acid) - 4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylic acid) - 3,3'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylic acid) - 4',4''-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-4-carboxylic acid) - 4',4''-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-3-carboxylic acid) - 3',3''-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-3-carboxylic acid) - 3',3''-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-4-carboxylic acid) - 8,8'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(dibenzo[b,d]thiophene-2-carboxylic acid) - 6,6'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(dibenzo[b,d]thiophene-4-carboxylic acid) - 8,8'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(thianthrene-2-carboxylic acid) - 9,9'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(thianthrene-1-carboxylic acid) - Dimethyl 4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]dibenzoate - Dimethyl 3,3'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]dibenzoate - Dimethyl 2,2'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]dibenzoate - Dimethyl 4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 5,5'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 7,7'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylate) - Dimethyl 6,6'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylate) - Dimethyl 3,3'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylate) - Dimethyl 2,2'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 1,1'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylate) - Dimethyl 4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-2-carboxylate) - Dimethyl 3,3'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 4',4"-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-4-carboxylate) - Dimethyl 4',4"-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-3-carboxylate) - Dimethyl 3',3"-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-3-carboxylate) - Dimethyl 3',3"-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di([1,1'-biphenyl]-4-carboxylate) - Dimethyl 8,8'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(dibenzo[b,d]thiophene-2-carboxylate) - Dimethyl 6,6'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(dibenzo[b,d]thiophene-4-carboxylate) - Dimethyl 8,8'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(thianthrene-2-carboxylate) - Dimethyl 9,9'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]di(thianthrene-1-carboxylate)

[0088] In particular subgroup (7a) of groups (7), (7.2), (3′) and (4′) of embodiments, in formula (I), variables p and q are both 1 and X 1 and X 2 The groups have the same meaning, and A 1 and A 2 The groups have the same meaning, and R 1 and R 2 When the groups have the same meaning, the compound of formula (I) is a compound of formula (Ib):

[0089] [ka] (wherein X is the same X 1 and X 2 A represents the same A 1 and A 2 represents a group, and R 0 is the same R 1 and R 2 represents a group, and X 1 , X2 , A 1 , A 2 , R 1 and R 2 have the meanings defined herein, particularly those mentioned herein as preferred).

[0090] In this subgroup (7a) of the groups (7), (7.2), (3′) and (4′) of embodiments, the structural unit of formula (II) is a structural unit of formula (IIb):

[0091] [ka] (wherein # represents a point of attachment to an adjacent structural unit, and X a are the same X 1a and X 2a A represents the same A 1 and A 2 represents a group, and R 0 is the same R 1 and R 2 represents a group, and the variable X 1a , X 2a , A 1 , A 2 , R 1 and R 2 have the meanings defined herein, particularly those mentioned as preferred).

[0092] Preferably, the moiety X of formula (Ib) and the moiety X of formula (IIb) a is defined as either embodiment group (1), embodiment group (2) or embodiment group (3). Thus, the moiety X of formula (Ia) is herein defined as, in particular, —CHOH (i.e., hydroxymethyl) and —C(O)OR x (R x is hydrogen or C1-C4-alkyl), in particular selected from —CH2OH, —C(O)OH, —C(O)OCH3 and —C(O)OCH2CH3, specifically selected from —CH2OH, —C(O)OH and —C(O)OCH3. Thus, the moiety X of formula (IIa) ais herein selected from the group consisting of —CHO— and —C(O)O—.

[0093] Also preferred are compounds of formula (Ib) and structural units of formula (IIb) in which the moiety A is defined as one of the embodiments (4), (4.1), (4.2), (4.3) and (4.4). More preferably, the moiety X of formula (Ib) and formula (IIb) is defined as the embodiment (4.4). Thus, moiety A of formula (Ib) and (IIb) may here in particular be 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,4-naphthylene, 1,5-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 2,3-naphthylene, 1,8-naphthylene, 1,7-naphthylene, 2,8-naphthylene, 1,6-naphthylene, 2,5-naphthylene, 2,4-naphthylene, 1,3-naphthylene, 2,1-naphthylene, 1,2-naphthylene, 4,4′-biphenylylene, 3, 4'-biphenylylene, 3,3'-biphenylylene, 4,3'-biphenylylene, 2,2'-biphenylylene, 4,2'-biphenylylene, 3,2'-biphenylylene, 2,4'-biphenylylene, 2,3'-biphenylylene, 3,6-9H-fluorenylene, 1,6-9H-fluorenylene, 2,6-9H-fluorenylene, 4,6-9H-fluorenylene, 1,3-9H-fluorenylene, 4,3-9H-fluorenylene, 2,3-9H-fluorenylene, 3,8-9H-fluorenylene Fluorenylene, 1,8-9H-fluorenylene, 2,8-9H-fluorenylene, 4,8-9H-fluorenylene, 3,1-9H-fluorenylene, 4,1-9H-fluorenylene, 2,1-9H-fluorenylene, 3,2-9H-fluorenylene, 1,2-9H-fluorenylene, 2,4-9H-fluorenylene, 4,7-9H-fluorenylene, 1,7-9H-fluorenylene, 2,7-9H-fluorenylene, 3,7-9H-fluorenylene, 3,5-9H-fluorenylene , 4,5-9H-fluorenylene, 2,5-9H-fluorenylene, 1,5-9H-fluorenylene, 1,4-9H-fluorenylene, 2,4-9H-fluorenylene, 3,4-9H-fluorenylene, 2,8-dibenzo[b,d]thienylene, 4,6-dibenzo[b,d]thienylene, 2,9-dibenzo[b,d]thienylene, 1,2-dibenzo[b,d]thienylene, 2,4-dibenzo[b,d]thienylene, 3,6-dibenzo[b,d]thienylene, 4,8-dibenzo[b,d]thienylene, 2,6-dibenzo[b,d]thienylene, 3,2-dibenzo[b,d]thienylene, 3,8-dibenzo[b,d]thienylene, 1,6-dibenzo[b,d]thienylene, 1,4-dibenzo[b,d]thienylene, 3,4-dibenzo[b,d]thienylene, 4,2-dibenzo[b,d]thienylene, 2,8-dibenzo[b,d]furanylene, 4, 6-dibenzo[b,d]furanylene, 2,9-dibenzo[b,d]furanylene, 1,2-dibenzo[b,d]furanylene, 2,4-dibenzo[b,d]furanylene, 3,6-dibenzo[b,d]furanylene, 4,8-dibenzo[b,d]furanylene, 2,6-dibenzo[b,d]furanylene, 3,2-dibenzo[b,d]furanylene, 3,8-dibenzo[b,d] and 1,6-dibenzo[b,d]furanylene, 1,4-dibenzo[b,d]furanylene, 3,4-dibenzo[b,d]furanylene, 4,2-dibenzo[b,d]furanylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,8-thianthrenylene, 1,7-thianthrenylene, 1,3-thianthrenylene, 2,3-thianthrenylene, 1,2-thianthrenylene, 2,1-thianthrenylene, 2,4-thianthrenylene, 1,4-thianthrenylene, 2,9-thianthrenylene, 1,9-thianthrenylene, 2,6-thianthrenylene, 1,6-thianthrenylene, wherein the aforementioned monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or can be substituted with one or two R, Ar (having a group).

[0094] R 0 Also preferred are compounds of formula (Ib) and structural units of formula (IIb) in which the radicals are defined as one or more of the embodiments groups (5), (5.1) and (5'). More preferably, R of formula (Ib) and formula (IIb) 0 The group is defined as in embodiment group (5.1). Thus, R in formula (Ib) and (IIb) 0The radicals here are in particular selected from the group consisting of fluorine, CN, methyl, methoxy, phenyl, naphthyl, such as 1-naphthyl or 2-naphthyl, and phenanthrenyl, such as 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl or 9-phenanthrenyl, in particular from the group consisting of fluorine, phenyl or naphthyl, such as 1-naphthyl or 2-naphthyl.

[0095] Examples of specific subgroups (7a) are moieties X or X, respectively. a , parts A and R 0 The combination of groups is as defined in any one of rows 1 to 42 of Table B below (X a In each case, X is -OH or -OR x (Ib) and (IIb) are structural units derived from X of formula (Ib) by replacing the group with an oxo (—O—) unit.

[0096] [Table 2]

[0097] Among the compounds of formula (Ib) listed in Table B, the following compounds of formula (Ib) are particularly preferred: - [(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-4,1-phenylene)]dimethanol - [(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-3,1-phenylene)]dimethanol - [(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylenenaphthalene-4,1-diyl)]dimethanol - [(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylenenaphthalene-5,1-diyl)]dimethanol - [(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylenenaphthalene-6,2-diyl)]dimethanol - [(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-4,1-phenylene)]dimethanol - [(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-3,1-phenylene)]dimethanol - [(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylenenaphthalene-4,1-diyl)]dimethanol - [(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylenenaphthalene-5,1-diyl)]dimethanol - [(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylenenaphthalene-6,2-diyl)]dimethanol - Dimethyl 4,4'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]dibenzoate - Dimethyl 3,3'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]dibenzoate - Dimethyl 4,4'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 5,5'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 6,6'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]di(naphthalene-2-carboxylate) - Dimethyl 4,4'-[(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]dibenzoate - Dimethyl 3,3'-[(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]dibenzoate - Dimethyl 4,4'-[(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 5,5'-[(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]di(naphthalene-1-carboxylate) - Dimethyl 6,6'-[(6,6'-bis(naphthalen-2-yl)[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene)]di(naphthalene-2-carboxylate)

[0098] Compounds of formula (Ia) can be prepared by the process shown in Reaction Scheme 1 below, where X and A are X 1 and X 2 or A 1 and A 2 In particular, X can be prepared according to the formula (I), where X has one of the meanings defined hereinabove for —CHOH or —C(O)OR x (R x is typically C1-C4-alkyl and A is a monocyclic or polycyclic (hetaryl)arylene).

[0099] [ka]

[0100] 1,1'-bi-2-naphthol of formula (1) is reacted with about 2 to 2.5 molar equivalents of a compound of formula (2) (where Z is a suitable leaving group such as chloride, bromide, iodide, tosylate, or mesitylate, particularly chloride or bromide) in the presence of a base, for example, an oxobase such as an alkali carbonate or alkali hydride, particularly an alkali carbonate such as potassium carbonate, to give a compound of formula (Ia). Suitable solvents for this reaction are polar aprotic organic solvents, such as acetone.

[0101] Compounds of formula (Ib) can be prepared by using, as the starting compound, the correspondingly substituted 1,1′-bi-2-naphthol of formula (3) (wherein R 0 has one of the meanings, particularly one of the preferred meanings, defined hereinabove. Such compounds of formula (3) can in turn be prepared in a similar manner to the process for preparing compounds of formula (Ia) shown above in Reaction Scheme 1, by using R 0 When is an optionally substituted phenyl, naphthyl, phenanthrenyl or triphenylenyl group, it can be prepared according to the process shown in Reaction Scheme 2 below.

[0102] [ka]

[0103] In step i) of the process according to Scheme 2, 1,1'-bi-2-naphthol of formula (1) is brominated to selectively produce 6,6'-dibromo-1,1'-bi-2-naphthol of formula (4). Bromination can be easily achieved by mixing 1,1'-bi-2-naphthol (1) with a suitable brominating reagent at low temperature in a polar aprotic solvent inert to bromination. Suitable brominating agents are, in particular, elemental bromine. Suitable polar aprotic solvents for step i) include aliphatic halogenated hydrocarbon compounds such as dichloromethane or dichloroethane, esters such as isopropyl acetate or ethyl acetate, and mixtures thereof. Suitable reaction temperatures for the bromination of 1,1'-bi-2-naphthol with bromine are typically in the range of -100 to 10 °C, particularly in the range of -100 to -30 °C, or alternatively, in the range of -10 to 10 °C. Further details can be found in Bunzen et al. J. Am. Chem. Soc., 2009, 131(10), 3621-3630. Alternatively, N-bromosuccinimide can be used as the brominating agent. In this case, the reaction temperature is usually higher than in the case of bromination with elemental bromine, for example, 0 to 50°C. In this case, suitable solvents include, in addition to aliphatic halogenated hydrocarbons, aliphatic ketones having 3 to 6 carbon atoms, such as acetone or methyl ethyl ketone, ethers having 4 to 6 carbon atoms, such as tetrahydrofuran, dioxane, diethyl ether, and cyclopentyl methyl ether, as well as other solvents, such as acetonitrile, dimethylformamide, chloroform, methylene chloride, and dichloroethane, as well as mixtures thereof with aliphatic halogenated hydrocarbons.

[0104] As a further alternative, 6,6′-dibromo-1,1′-binaphthol of formula (4) can also be synthesized by copper(II)-catalyzed oxidative coupling of 6-bromo-2-naphthol, for example, according to the procedure described in H. Egami et al., J. Am. Chem. Soc. 2009, 13 (17), 6082-83.

[0105] In step ii) of Scheme 2, a compound of formula (4) is reacted with an arylboronic acid compound of formula (5) R 0 -B(OH)2(5) (In the formula, R 0is as defined above), or an ester or anhydride of (5), in particular a C1-C4-alkyl ester of (5), in the presence of a transition metal catalyst, in particular a palladium catalyst. Often, step ii) is carried out under the conditions of the so-called "Suzuki coupling" (e.g., A. Suzuki et al., Chem. Rev. 1995, 95, 2457-2483; N. Zhe et al., J. Med. Chem. 2005, 48 (5), 1569-1609; Young et al., J. Med. Chem. 2004, 47 (6), 1547-1552; C. Slee et al., Bioorg. Med. Chem. Lett. 2001, 9, 3243-3253; T. Zhang et al., Tetrahedron Lett., 52 (2011), 311-313; S. Bourrain et al., Synlett. 5 (2004), 795-798; B. Li et al., Europ. J. Org. Chem. 2011 3932-3937). Suitable transition metal catalysts are, in particular, palladium compounds having at least one palladium atom and at least one trisubstituted phosphine ligand. Examples of palladium catalysts are tetrakis(triphenylphosphine)palladium, tetrakis(tritolylphosphine)palladium, and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)). Often, palladium catalysts are prepared in situ from a suitable palladium precursor and a suitable phosphine ligand. Suitable palladium precursors are palladium compounds such as tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) or palladium(II) acetate (Pd(OAc)2).Suitable phosphine ligands are in particular tri(substituted)phosphines, for example triarylphosphines such as triphenylphosphine, tritolylphosphine or 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (BINAP), tri(cyclo)alkylphosphines such as tris-n-butylphosphine, tris(tert-butyl)phosphine or tris(cyclohexylphosphine), or dicyclohexyl-(2',4',6'-tri-isopropyl-1,1'-biphenyl-2-yl)-phosphane (X-Phos). The reaction is usually carried out in the presence of a base, in particular an oxobase such as an alkali alkoxide, alkali hydroxide, alkali carbonate or alkaline earth carbonate, for example sodium ethoxide, sodium tert-butoxide, lithium hydroxide, sodium carbonate or potassium carbonate. Often, the reaction according to step ii) of scheme 2 is carried out in an organic solvent or a mixture thereof with water. When the reaction is carried out in a mixture of an organic solvent and water, the reaction mixture can be monophasic or biphasic. Suitable organic solvents include, but are not limited to, aromatic hydrocarbons such as toluene, anisole, or xylene; acyclic and cyclic ethers such as methyl tert-butyl ether, diisopropyl ether, dioxane, or tetrahydrofuran; and aliphatic alcohols having 1 to 4 carbon atoms such as methanol, ethanol, or isopropanol, and mixtures thereof. The reaction according to step ii) of Scheme 2 is typically carried out at a temperature ranging from 50 to 150°C.

[0106] Compounds of formula (Ib) can then be prepared as described above, similar to the process shown in Scheme 1, by using compounds of formula (3) as starting compounds in a process according to the following Reaction Scheme 3, where R 0 , X and A are R 1 and R 2 , X 1 and X 2 or A 1 and A 2 and R have one of the meanings defined hereinabove). In particular, R0 is a phenyl, naphthyl, phenanthrenyl or triphenylenyl group, which is unsubstituted or substituted with one or two groups typically selected from phenyl, OCH3 and CH3, and X is -CH2OH or -C(O)OR x (R x is typically C1-C4-alkyl), and A is A 1 and A 2 The aryl group is a monocyclic or polycyclic (hetaryl)arylene as defined above.

[0107] [ka]

[0108] The conversion of a 6,6'-substituted 1,1'-bi-2-naphthol of formula (3) with about 2 to 2.5 molar equivalents of a compound of formula (2) to give a compound of formula (Ib), as shown in Scheme 3, can be carried out under substantially the same reaction conditions as the reaction described above in the context of Scheme 1.

[0109] Compounds of formula (I), in particular the different moieties A 1 and A 2 and / or even different X 1 and X 2 Compounds of formula (I) bearing groups can be prepared in two steps, for example, according to the process shown in Reaction Scheme 4 below, where p, q, R 1 , R 2 , X 1 , X 2 , A 1 and A 2 is as defined hereinabove). However, the process according to Scheme 4 is also applicable when p and q are both 0, 1 or 2 and the substituent R 1 and R 2 are particularly suitable for preparing compounds of formula (I) in which, when present, have the same meaning and are attached to the corresponding position of each naphthyl unit.

[0110] [ka]

[0111] In reaction step i) of the process according to Scheme 4, an optionally substituted 1,1'-bi-2-naphthol of formula (6), such as a compound of formula (1) or (3), is reacted with about 0.7 to 1.1 molar equivalents of a compound of formula (2a), where Z is a suitable leaving group such as chloride, bromide, iodide, tosylate, or mesitylate, particularly chloride or bromide. The monoetherified product of formula (7) obtained in step i) is then subjected to further etherification in step ii) with about 1.0 to 1.5 molar equivalents of a compound of formula (2b), where Z is as defined above, to obtain the intended product of formula (I). Alternatively, both reaction steps i) and ii) can be carried out under substantially similar reaction conditions as those described above in connection with Scheme 1.

[0112] A 1 and A 2 Compounds of formula (I) where p and q are the same or different biphenylylene moieties can be prepared in two, three or four steps, for example, similar to the process shown in Reaction Scheme 5 below. The process according to Scheme 5 and similar processes are also suitable for compounds where p and q are both 0, 1 or 2 and the substituent R 1 and R 2 When present, they have the same meaning and are attached to the corresponding positions of each naphthyl unit. Reaction Scheme 5 is particularly suitable for preparing compounds (I) in which p=q=0 and X 1 and X 2 are both -CH2OH, and A 1 is 3,4'-biphenylylene, and A 2 The preparation of compound (I) in which is 3,3'-biphenylylene is exemplified.

[0113] [ka]

[0114] In reaction step i) of the process according to Scheme 5, 1,1'-bi-2-naphthol (1) is reacted with about 0.7 to 1.1 molar equivalents of a bromide of formula (8a) (where Z is a suitable leaving group such as chloride, bromide, iodide, tosylate, or mesitylate, particularly chloride or bromide). The monoetherified product of formula (9) obtained in step i) is then subjected to further etherification in step ii) with about 1.0 to 1.5 molar equivalents of a compound of formula (8b) (where Z is as defined above) to obtain a dibromide of formula (10). The above reaction steps i) and ii) can be carried out under reaction conditions substantially similar to those described above in connection with Scheme 1. Dibromide (10) is then reacted with about 2 molar equivalents of a phenylboronic acid compound of formula (11) in which p and q are both 0 and X is 0, similar to coupling step ii) described above in connection with the process of Scheme 2. 1 and X 2 are both -CH2OH, and A 1 is 3,4'-biphenylylene, and A 2 Compound (12), which is a compound of formula (I) in which is 3,3'-biphenylylene, can be obtained.

[0115] A 1 and A 2 has the same meaning, e.g., 3,4'-biphenylylene, and therefore p=q=0 and X 1 =X 2 = -CH2OH, A 1 =A 2 Compounds of formula (12'), which are compounds of formula (I) where .gtoreq.3,4'-biphenylylene, can be prepared via modified step i) of Scheme 5 in which 1,1'-bi-2-naphthol (1) is reacted with about 2 molar equivalents of bromide of formula (8a), followed by reaction step iii) of Scheme 5.

[0116] X 1 and X 2has a different meaning, therefore, p=q=0, and X 1 is, for example, -C(O)OCH3, and X 2 is, for example, -C(O)OH, and A 1 is 4,3'-biphenylylene, and A 2 Compounds of formula (12"), which are compounds of formula (I) in which R is 3,3'-biphenylylene, can also be prepared using a variant of the process according to Scheme 5. Specifically, compound (9) obtained in step i) of the process of Scheme 5 is reacted, analogously to step iii), with about 1 molar equivalent of compound (11') (compound (11) in which its -CHOH group has been replaced by a -C(O)OCH group). The intermediate product thus obtained is then reacted with compound (8b) according to step ii) of Scheme 5. Finally, the bromide obtained is reacted, analogously to step iii), with about 1 molar equivalent of compound (11") (compound (11) in which its -CHOH group has been replaced by a -C(O)OH group).

[0117] A 1 and A 2 and the variables p, q, and R 1 , R 2 , X 1 and X 2 Compounds of formula (I), wherein A has the meaning defined herein, may also be prepared by the process described in the context of Reaction Scheme 5 above, except that A 1 and A 2 (hetaryl)arylene groups, in which the bond between the two (hetaryl)arylene moieties is a C—C bond, can typically be prepared in two, three, or four reaction steps.

[0118] The transformations shown in Schemes 1-5 can be achieved by the reactions described above in the context of these schemes, or obvious variations of these reactions, or alternatively by procedures well established in preparative organic chemistry, or combinations thereof.

[0119] Additional compounds of formula (I) can be prepared by using obvious variations of the above reactions and combinations thereof with procedures well established in preparative organic chemistry.

[0120] The reaction mixtures obtained in the individual steps of the synthesis for preparing the compounds described in Reaction Schemes 1, 2, 3, 4, and 5 above are usually worked up in a conventional manner, for example by mixing with water, separating the phases, and purifying the crude product, if appropriate, by washing, treating with an adsorbent such as activated carbon, chromatography, or crystallization. In some cases, intermediates are obtained in the form of colorless or light brownish viscous oils and are stripped of volatile substances or purified under reduced pressure and at moderate to high temperatures. If the intermediates are obtained as solids, purification can be achieved by recrystallization or washing procedures such as slurry washing.

[0121] The starting compounds used in the syntheses shown in Schemes 1, 2, 3, 4 and 5 above to prepare compounds of formula (I) are either commercially available or can be prepared by methods known in the art.

[0122] As mentioned above, the compounds of the present invention can be obtained with high purity (meaning that the product does not contain a significant amount of organic impurities other than the compound of formula (I) except for volatile substances).Usually, the purity of the compound of formula (I) is at least 95%, particularly at least 98%, particularly at least 99%, based on non-volatile organic matter, i.e., the product contains at most 5%, particularly at most 2%, particularly at most 1% of non-volatile impurities other than the compound of formula (I).

[0123] In this context, it should be mentioned that mixtures of different compounds of formula (I) are also useful as they can serve as monomer compositions for preparing useful thermoplastic resins, such as polycarbonate resins comprising different structural units of formula (II) derived from said different monomers of formula (I).Thus, mixtures of different compounds of formula (I) and the corresponding thermoplastic resins comprising different structural units of formula (II) are also part of the present invention.

[0124] The term "volatiles" refers to the amount of 5 Non-volatile organic compounds refer to organic compounds having a boiling point of less than 200°C at standard pressure. Consequently, non-volatile organic compounds are understood to mean compounds having a boiling point of more than 200°C at standard pressure.

[0125] A particular advantage of the present invention is that the compounds of formula (I) and their solvates can often be obtained in crystalline form.In crystalline form, the compounds of formula (I) can exist in pure form or in the form of a solvate with water or an organic solvent.Therefore, a particular aspect of the present invention relates to the compounds of formula (I) that exist essentially in crystalline form.In particular, the present invention relates to the crystalline form in which the compounds of formula (I) exist without solvent, and to the crystalline solvates of the compounds of formula (I) that incorporate solvent.

[0126] A particular advantage of the present invention is that compounds of formula (I) and their solvates can often be easily crystallized from conventional organic solvents. This allows for efficient purification of the compounds of formula (I). Suitable organic solvents for crystallizing compounds of formula (I) or their solvates include, but are not limited to, aromatic hydrocarbons such as toluene or xylene; aliphatic ketones, particularly ketones having 3 to 6 carbon atoms such as acetone, methyl ethyl ketone, methyl isopropyl ketone, or diethyl ketone; aliphatic and alicyclic ethers such as diethyl ether, dipropyl ether, methyl isobutyl ether, methyl tert-butyl ether, ethyl tert-butyl ether, dioxane, or tetrahydrofuran; aliphatic-aromatic ethers such as anisole; aliphatic alcohols having 1 to 4 carbon atoms such as methanol, ethanol, or isopropanol; and aliphatic esters such as ethyl acetate, as well as mixtures thereof. It may be beneficial to filter the dissolved crude preparation of the compound of formula (I) through, for example, celite prior to the crystallization step, in order to remove any solid components that may be present in the crude preparation.

[0127] Furthermore, impurities, particularly colour-forming impurities and heavy metals, which may be present in crude preparations of the compound of formula (I), may be removed at any stage of the purification process, for example before the filtration or crystallisation step, by standard procedures such as treatment with adsorbents, e.g. activated carbon.

[0128] Alternatively, the compounds of formula (I) and their solvates can be obtained in purified form by using other simple and efficient methods for purifying the raw products of these compounds, such as slurry washing the raw solids obtained immediately after the conversion to prepare the compounds of formula (I). Slurry washing is typically carried out at ambient temperature or at elevated temperatures, usually about 30-90°C, especially 40-80°C. Suitable organic solvents here are in principle the same as those listed above as being suitable for crystallizing the compounds of formula (I), including the aromatic hydrocarbons, aliphatic ketones and aliphatic ethers mentioned above, such as toluene, methyl ethyl ketone and methyl tert-butyl ether.

[0129] Therefore, the compounds of formula (I) used in the preparation of thermoplastic polymers, particularly polycarbonates, as defined herein can be easily prepared and obtained in high yield and high purity. In particular, the compounds of formula (I) can be obtained in a crystalline form that allows for efficient purification to the extent required in the preparation of optical resins. In particular, these compounds can be obtained with a purity that provides a high refractive index and also low haze, which are particularly important for use in the preparation of optical resins for making optical devices. In conclusion, the compounds of formula (I) are particularly useful as monomers in the preparation of optical resins.

[0130] Those skilled in the art will readily understand that the formula (I) of the monomer used corresponds to the formula (II) of the structural unit contained in the thermoplastic resin. Similarly, the formulas (Ia) and (Ib) of the monomer used, respectively, correspond to the formulas (IIa) and (IIb) of the structural unit contained in the thermoplastic resin, respectively.

[0131] Those skilled in the art will also readily understand that the structural units of formula (II), (IIa), and (IIb) are repeating units in the polymer chain of a thermoplastic resin.The thermoplastic resin may have structural units other than the structural units of formula (II), (IIa), and (IIb), respectively.In a preferred embodiment, these additional structural units are derived from an aromatic monomer of formula (IV) to produce a structural unit of formula (V): HO-R z -A 3 -R z -OH (IV) #-OR z -A 3 -R z -O-# (V) (In the formula, # represents the point of attachment to the adjacent structural unit; A 3 is a polycyclic group having at least two benzene rings (which may be joined by W and / or may be directly fused to each other and / or may be fused to a non-benzene-based carbocyclic ring and / or may be fused to two non-benzene-based carbocyclic rings connected via a linker L), and A 3 is unsubstituted or contains 1, 2 or 3 R aa Group(R aa is substituted with halogen, C1-C6-alkyl, C5-C6-cycloalkyl, phenyl, naphthyl, 1,2-dihydroacenaphthylenyl, phenanthrenyl, pyrenyl, triphenylenyl, benzo[b]furanyl, dibenzo[b,d]furanyl, benzo[b]thienyl, dibenzo[b,d]thienyl and thianthrenyl; W is selected from the group consisting of a single bond, O, C=O, S, S(O), SO2, CH2, CH-Ar, CAr2, CH(CH3), C(CH3)2 and a group of formula (A'):

[0132] [ka] (In the formula, Q' represents a single bond, O, C=O or CH2; R 7a , R 7b are independently hydrogen, fluorine, CN, R, OR, CH v R' 3-v , NR2, C(O)R and C(O)NH2 (wherein R and R' are as defined hereinabove and v is 0, 1 or 2); * denotes the point of attachment to the benzene ring); L is selected from a single bond, C1-C4-alkylene, C4-C7-cycloalkylene, C4-C7-cycloalkylenedimethylene, phenylenedimethylene, and L is unsubstituted or has one or two R L Group(R L is substituted with C1-C4-alkyl, halogen, C1-C4-haloalkyl, C4-C7-cycloalkyl and phenyl), Ar is selected from the group consisting of monocyclic or polycyclic aryl having 6 to 26 carbon atoms as ring atoms and monocyclic or polycyclic hetaryl having a total of 5 to 26 ring atoms, wherein 1, 2, 3, or 4 of the ring atoms of the hetaryl are selected from nitrogen, sulfur, and oxygen, and the remainder of the ring atoms of the hetaryl are carbon atoms, and Ar is unsubstituted or substituted with 1, 2, or 3 R ab Group(R ab is substituted with (selected from the group consisting of halogen, phenyl and C1-C4-alkyl); R z is a single bond, Alk 3 , O-Alk 4 -, O-Alk 4 -[O-Alk 4 -] w - or O-Alk 5 -C(O)-(O is A 3 ) and w is an integer from 1 to 10; Alk 3 is C1-C4-alkanediyl; Alk 4 is C2-C4-alkanediyl; Alk 5 is C1-C4-alkanediyl).

[0133] R in formula (IV) z O-Alk 5 When it is -C(O), an ester of the monomer of formula (IV) can be used instead, in particular a C1-C4-alkyl ester.

[0134] In the context of formulas (IV) and (V), A 3 is in particular any polycyclic group having at least two benzene or naphthalene rings (the benzene rings are fused with two non-benzene-based carbocyclic rings linked by W or via a linker L, W being in particular selected from the group consisting of a single bond, S, S(O), SO2, C(CH3)2 and an A' group, and L being a single bond or C1-C4-alkylene).

[0135] In the context of formulas (IV) and (V), R z is especially O-Alk 4 -(Alk 4 is especially a straight-chain alkanediyl having 2 to 4 carbon atoms), especially O—CH2CH2.

[0136] Among the monomers of formula (IV), the monomers of general formulae (IV-1) to (IV-8) are preferred:

[0137] [ka] (In the formula, a and b are 0, 1, 2 or 3, in particular 0 or 1; a' and b' are 0, 1, 2 or 3, in particular 0 or 1; c and d are 0, 1, 2, 3, 4 or 5, in particular 0 or 1; e and f are 0, 1, 2, 3, 4 or 5, in particular 0 or 1; W' is S, S(O), SO2, O, a single bond, CH2, CH(CH3), C(CH3)2, in particular S, S(O), SO2 or C(CH3)2; R z , R aa , R ab , R 7a , R 7b and L is as defined for formula (IV), and R z is in particular selected from a single bond, CH2 and OCH2CH2).

[0138] Among the monomers of formula (IV), R z and R aa is as defined herein, and R z Particularly preferred are monomers of the general formulae (IV-11) to (IV-22), in which is in particular selected from a single bond, CH and O—CHCH, in particular O—CHCH:

[0139] [ka]

[0140] Examples of the compounds of formulas (IV-11) to (IV-22) include 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-isopropylphenyl)fluorene, 9,9-bis(4-hydroxy-3-tert.-butylphenyl)fluorene, 9,9-bis(4-hydroxy-3-cyclohexylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, and 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene. fluorene (BPEF), 9,9-bis(4-(2-hydroxyethoxy)-3-methylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-isopropylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-tert.-butylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-cyclohexylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene (BPPEF), 9,9-bis(6-hydroxy-2-naphthyl)fluorene 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene, also known as 9,9-bis(6-(2-hydroxyethoxy)naphthalen-2-yl)fluorene (BNEF) or 6,6'-(9-fluorenylidene)bis(2-naphthyloxyethanol) (NOLE), 10,10-bis(4-hydroxyphenyl)anthracen-9-one, 10,10-bis(4-(2-hydroxyethoxy)phenyl)anthracen-9-one, 4,4'-dihydroxytetraphenylmethane, 4,4'-di-(2-hydroxyethoxy) )-Tetraphenylmethane, 3,3'-diphenyl-4,4'-dihydroxy-tetraphenylmethane, di-(6-hydroxy-2-naphthyl)-diphenylmethane, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-diphenyl-phenyl]-1-methyl-ethyl]-2,6-diphenyl-phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3-phenyl-phenyl]-1-methyl-ethyl]-2,6-diphenyl-phenoxy]ethanol, 9,9'-dihydroxymethyl-9,9'-difluorene, 2,2,2'-[1,1'-binaphthalene-2,2'-diylbis(oxy)]diethanol, also known as 2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl or 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), 2,2'-bis(1-hydroxymethoxy)-1,1'-binaphthyl, 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthyl, 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthyl, 2,2'-bis(2-hydroxyethoxy)-6,6'-di Phenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-di(naphthalen-1-yl)-1,1'-binaphthalene, 2,2'-bis(2-hydroxymethoxy)-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxymethoxy)-6,6'-di(naphthalen-1-yl)-1,1'-binaphthalene, 2,2'-bis(2-hydroxypropoxy)-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxypropoxy)-6,6'-di(naphthalen 2,2'-bis(2-hydroxyethoxy)-6,6'-di(naphthalen-2-yl)-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-di(9-phenanthryl)-1,1'-binaphthalene, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(naphthalen-1-yl)-phenyl]-1-methyl-ethyl]-2,6-di(naphthalen-1-yl)-phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5 -di(naphthalen-2-yl)-phenyl]-1-methyl-ethyl]-2,6-di(naphthalen-2-yl)-phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(phenanthren-9-yl)-phenyl]-1-methylethyl]-2,6-di(phenanthren-9-yl)-phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(1,2-dibenzo[b,d]thien-4-yl)-phenyl]-1-methyl-ethyl]-2,6-di(1,2-dibenzo[b,d]thien-4-yl)-phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)-phenyl]-1-methyl-ethyl]-2,6-di(thianthren-1-yl)-phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(naphthalen-1-yl)phenyl]sulfonyl-2,6-di(naphthalen-1-yl)-phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(naphthalen-2-yl)phenyl]sulfonyl-2,6-di(naphthalen-2-yl)-phenoxy]ethanol ]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(phenanthrene-9-yl)phenyl]sulfonyl-2,6-di(phenanthrene-9-yl)-phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)phenyl]sulfonyl-2,6-di(thianthren-1-yl)phenoxy]ethanol, and 2-[4-[4-(2-hydroxyethoxy)-3,5-di(dibenzo[b,d]thien-4-yl)phenyl]sulfonyl-2,6-dibenzo[b,d]thien-4-yl)phenoxy]ethanol.

[0141] Among the monomers of general formula (IV) or formulas (IV-1) to (IV-8), the monomers of formulas (IV-1), (IV-2), (IV-3) and (IV-8) are particularly preferred, and the monomers of formulas (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-21) and (IV-22) are even more preferred, and 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl (BNE or BHBNA), 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl ... naphthyl (DPBHBNA), 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (BPEF), 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene (BNEF), 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene (BPPEF), 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(phenanthren-9-yl)-phenyl]-1-methylethyl]-2,6-di(phenanthren-9-yl)-phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(1,2-dibenzo[b,d]thien-4-yl)-phenyl]-1-methyl-ethyl]-2,6-di(1,2-dibenzo[b,d]thien-4-yl)-phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)-phenyl]-1-methyl-ethyl]-2,6-di(thianthren-1-yl)-phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(phenoxy) Particularly preferred are 2-[4-[4-(2-hydroxyethoxy)-3,5-di(dibenzo[b,d]thien-4-yl)phenyl]sulfonyl-2,6-di(phenantren-9-yl)-phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)phenyl]sulfonyl-2,6-di(thianthren-1-yl)phenoxy]ethanol and 2-[4-[4-(2-hydroxyethoxy)-3,5-di(dibenzo[b,d]thien-4-yl)phenyl]sulfonyl-2,6-dibenzo[b,d]thien-4-yl)phenoxy]ethanol.

[0142] Therefore, among the structural units of formula (V) that can be contained in the thermoplastic resin, structural units of general formulae (V-1) to (V-8) are preferred:

[0143] [ka] (In the formula, a and b are 0, 1, 2 or 3, in particular 0 or 1; a' and b' are 0, 1, 2 or 3, in particular 0 or 1; c and d are 0, 1, 2, 3, 4 or 5, in particular 0 or 1; e and f are 0, 1, 2, 3, 4 or 5, in particular 0 or 1; W' is S, S(O), SO2, O, a single bond, CH2, CH(CH3), C(CH3)2, in particular S, S(O), SO2 or C(CH3)2; R z , R aa , R ab , R 7a , R 7b and L is as defined for formula (V), and R z is in particular selected from a single bond, CH2 and OCH2CH2).

[0144] R z and R aa is as defined herein, and R z Particularly preferred are structural units of the general formulae (V-11) to (V-22), in which is in particular selected from a single bond, CH and O—CHCH, in particular O—CHCH:

[0145] [ka]

[0146] Among the structural units of formulae (V-1) to (V-8), structural units of formulae (V-1), (V-2), (V-3) and (V-8) are particularly preferred. Among the structural units of formulae (V-11) to (V-22), structural units of formulae (V-11), (V-12), (V-13), (V-14), (V-15), (V-21) and (V-22) are particularly preferred, such as 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl (BNE or BHBNA), 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthyl (DPBHBNA), 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (BPEF ), 9,9-bis(6-(2-hydroxyethoxy)naphthalen-2-yl)fluorene (BNEF), 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene (BPPEF), 2-[4-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)phenyl]sulfonyl-2,6-di(thianthren-1-yl)phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(phenanthrene-9-yl)phenyl]sulfonyl sulfonyl-2,6-di(phenanthren-9-yl)-phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(dibenzo[b,d]thien-4-yl)phenyl]sulfonyl-2,6-dibenzo[b,d]thien-4-yl)phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(phenanthren-9-yl)-phenyl]-1-methylethyl]-2,6-di(phenanthren-9-yl)-phenoxy]ethanol, Particularly preferred are structural units derived from -[4-[1-[4-(2-hydroxyethoxy)-3,5-di(1,2-dibenzo[b,d]thien-4-yl)-phenyl]-1-methyl-ethyl]-2,6-di(1,2-dibenzo[b,d]thien-4-yl)-phenoxy]ethanol and 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)-phenyl]-1-methyl-ethyl]-2,6-di(thianthren-1-yl)-phenoxy]ethanol.

[0147] In a particularly preferred group of embodiments, the thermoplastic resin of the present invention comprises at least one structural unit of formula (IIa) or (IIb) and at least one structural unit selected from the group consisting of structural units of formula (V-11), structural units of formula (V-12), structural units of formula (V-13), structural units of formula (V-14), structural units of formula (V-15), structural units of formula (V-21), and structural units of formula (V-22). In this particular group of embodiments, in the structural units of formulas (V-11), (V-12), (V-13), (V-14), (V-15), (V-21), and (V-22), R z Thermoplastic resins in which the group is O-CH2CH2 are preferred.

[0148] In this particular preferred group of thermoplastic resins of the embodiment, it is preferred that the total molar ratio of structural units of formula (IIa) or (IIb) is in the range of 1 to 99 mol %, preferably in the range of 10 to 99 mol %, more preferably in the range of 15 to 97 mol %, and even more preferably in the range of 25 to 95 mol % of the total amount of structural units of formula (II) and formula (V).

[0149] Compounds of formula (IV), (IV-1), (IV-2), (IV-3), (IV-4), (IV-5), (IV-6), (IV-7), (IV-8), (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-16), (IV-17), (IV-18), (IV-19), (IV-20), (IV-21) and (IV-22) are known or can be prepared analogously to known methods.

[0150] For example, the compound of formula (IV-8) can be prepared by various synthesis methods disclosed in, for example, JP 2014-227387 A, JP 2014-227388 A, JP 2015-168658 A, and JP 2015-187098 A. For example, 1,1'-binaphthol may be reacted with ethylene glycol monotosylate; alternatively, 1,1'-binaphthol may be reacted with alkylene oxide, halogenoalkanol, or alkylene carbonate; alternatively, 1,1'-binaphthol may be reacted with ethylene carbonate. Thereby, R z -OH is O-Alk 4 -OH or O-Alk 4 -[O-Alk 4 -] w The compound of formula (IV-8) is obtained, where -OH.

[0151] For example, the compound of formula (IV-2) can be prepared by various synthetic methods disclosed in, for example, Japanese Patent No. 5442800 and Japanese Patent Application Laid-Open No. 2014-028806. Examples include: (a) reacting fluorene with hydroxynaphthalene in the presence of hydrochloride gas and mercapto-carboxylic acid; (b) 9-fluorene is reacted with hydroxynaphthalene in the presence of an acid catalyst (and an alkyl mercaptan); (c) reacting fluorene with hydroxynaphthalene in the presence of hydrochloride and thiols (such as mercapto-carboxylic acids); (d) Reacting fluorene with hydroxynaphthalene in the presence of sulfuric acid and thiols (such as mercapto-carboxylic acids), followed by crystallization of the product from a crystallization solvent consisting of a hydrocarbon and a polar solvent, to form bisnaphtholfluorene; etc. Thereby, R z A compound of formula (IV-2) in which is a single bond can be obtained.

[0152] R z O-Alk 4 - or O-Alk4 -[O-Alk 4 -] w - can be obtained by reaction with an alkylene oxide or a haloalkanol to give R z can be prepared from a compound of formula (IV) where R z When 9,9-bis(hydroxynaphthyl)fluorene of formula (IV-2), in which R is a single bond, is reacted with an alkylene oxide or a haloalkanol, R z O-Alk 4 - or O-Alk 4 -[O-Alk 4 -] w For example, 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene can be prepared by reacting 9,9-bis[6-(2-hydroxynaphthyl]fluorene with 2-chloroethanol under alkaline conditions.

[0153] The monomers of formula (I) and (IV) used to prepare thermoplastic resins may contain certain impurities resulting from their preparation, for example comonomer (IV) may contain, for example, O-Alk 4 It may contain hydroxy compounds with OH groups instead of -OH groups, or O-Alk 4 - group instead of O-Alk 4 -[O-Alk 4 ] w - group. The total amount of such impurity compounds is preferably 5000 ppm or less, more preferably 3000 ppm or less, even more preferably 2000 ppm or less, and particularly preferably 1000 ppm or less. The total content of impurities in the monomers used to prepare the thermoplastic resin is preferably 4000 ppm or less, particularly 1500 ppm or less, and more preferably 1000 ppm or less. In particular, at least one R zThe total amount of dihydroxy compounds having a carbon number of the -OH group different from that of formula (IV) is preferably 3000 ppm or less, more preferably 1500 ppm or less, even more preferably 1000 ppm or less, and particularly preferably 500 ppm or less; the main component of the monomer is the dihydroxy compound represented by formula (IV). z The total content of dihydroxy compounds having a carbon number in the -OH group different from that of formula (IV) is more preferably 1000 ppm or less, more preferably 500 ppm or less.Similarly, the amount of impurities in the monomer of formula (I) is in the range given for the monomer of formula (IV).

[0154] Suitable thermoplastic resins for preparing optical devices such as lenses are in particular polycarbonates, polyester carbonates and polyesters. Preferred thermoplastic resins for preparing optical devices such as lenses are in particular polycarbonates.

[0155] Structurally, the polycarbonates comprise at least one structural unit of formula (II), (IIa) and (IIb), respectively, and optionally structural units derived from diol monomers different from the monomer compounds of formula (I), such as structural units of formula (V): #-OR z -A 3 -R z -O-# (V) (In the formula, #, R z and A 3 is as defined hereinabove), and Structural units of formula (III-1) resulting from carbonate-forming components:

[0156] [ka] wherein each # represents a point of attachment to the adjacent structural unit, i.e., the O at the point of attachment of the structural unit of formula (II) and, if present, the O at the point of attachment of the structural unit of formula (V); The present invention is characterized by having the following.

[0157] The polyesters are structurally characterized by having at least one structural unit of formula (II), (IIa) and (IIb), respectively, and optionally a structural unit derived from a diol monomer different from the monomer compound of formula (I), such as a structural unit of formula V. X in formula (II) 1a and X 2a or X in formula (IIa) and (IIb) a When is selected from -CHO-, the polyester may have structural units derived from one or more dicarboxylic acids, for example of formula (III-2) in the case of benzenedicarboxylic acid, of formula (III-3) in the case of naphthalenecarboxylic acid, of formula (III-4) in the case of oxalic acid, and of formula (III-5) in the case of malonic acid:

[0158] [ka]

[0159] In formulas (III-2) to (III-5), each variable # represents the point of attachment to the adjacent structural unit, i.e., the O of the point of attachment of the structural unit of formula (II) and, if present, the O of the point of attachment of the structural unit of formula (V).

[0160] The polyester carbonates are structurally characterized by having at least one structural unit of formula (II), (IIa) and (IIb), respectively, structural units optionally derived from a diol monomer different from the monomer compound of formula (I), such as structural units of formula (V), structural units of formula (III-1) resulting from a carbonate-forming component, and structural units derived from dicarboxylic acids, such as formula (III-2) in the case of benzenedicarboxylic acid, formula (III-3) in the case of naphthalenecarboxylic acid, formula (III-4) in the case of oxalic acid, and formula (III-5) in the case of malonic acid.

[0161] A particular group of embodiments relates to thermoplastic copolymer resins, in particular polycarbonates, polyestercarbonates and polyesters having both structural units of formula (II) and one or more structural units of formula (V), i.e. resins, in particular polycarbonates, polyestercarbonates and polyesters that can be obtained by reacting at least one monomer of formula (I) with one or more monomers of formula (IV). In this case, the molar ratio of the monomers of formula (I) to the monomers of formula (IV), and likewise the molar ratio of the structural units of formula (II) to the structural units of formula (V), is in the range of 1:99 to 99:1, in particular in the range of 10:90 to 99:1, in particular in the range of 30:70 to 97:3 or in the range of 10:90 to 99:1, in particular in the range of 15:85 to 97:3, more preferably in the range of 20:80 to 96:4 or in the range of 25:75 to 96:4, in particular in the range of 25:75 to 90:10 or in the range of 27:73 to 96:4 or in the range of 27:73 to 99:1, even more preferably in the range of 25:75 to 85:15 or in the range of 27:73 to 90:10, in particular in the range of 25:75 to 70:30 or in the range of 30:70 to 80:20 or in the range of 35:65 to 70:30. Therefore, the molar ratio of the structural unit of formula (II) is usually 1 to 99 mol%, particularly 10 to 99 mol%, more preferably 15 to 97 mol% or 5 to 99 mol%, particularly 10 to 97 mol% or 17 to 97 mol%, even more preferably 17 to 90 mol%, specifically 20 to 80 mol% or 25 to 70 mol%, based on the total molar amount of the structural units of formula (II) and formula (V). Therefore, the molar ratio of the structural unit of formula (V) is usually 1 to 99 mol%, particularly 1 to 90 mol%, more preferably 3 to 85 mol% or 1 to 95 mol%, particularly 3 to 90 mol% or 3 to 83 mol%, even more preferably 10 to 83 mol%, specifically 20 to 80 mol% or 30 to 75 mol%, based on the total molar amount of the structural units of formula (II) and formula (V).

[0162] A particular group of embodiments relates to thermoplastic copolymer resins, in particular polycarbonates, polyestercarbonates and polyesters having both structural units of formula (II) and one or more structural units of formula (V-14) or (V-15), i.e., resins, in particular polycarbonates, polyestercarbonates and polyesters obtainable by reacting at least one monomer of formula (I) with one or more monomers of formula (IV-14) or (IV-15), in which the molar ratio of the monomer of formula (I) to the monomers of formulae (IV-14) and (IV-15), and likewise the molar ratio of the structural units of formula (II) to the structural units of formulae (V-14) and (V-15), is in the range of 50:50 to 99:1, in particular in the range of 70:30 to 98:2, in particular in the range of 80:20 to 97:3.

[0163] Another specific group of embodiments relates to thermoplastic copolymer resins, in particular polycarbonates, polyestercarbonates and polyesters having both structural units of formula (II) and one or more structural units of formula (V-11), (V-12), (V-13), (V-21) or (V-22), i.e. resins, in particular polycarbonates, polyestercarbonates and polyesters obtainable by reacting at least one monomer of formula (I) with one or more monomers of formula (IV-11), (IV-12), (IV-13), (IV-21) or (IV-22). In this case, the molar ratio of the monomer of formula (I) to the monomer of formulae (IV-11), (IV-12), (IV-13), (IV-21) and (IV-22) and similarly the molar ratio of the structural unit of formula (II) to the structural units of formulae (V-11), (V-12), (V-13), (V-21) and (V-22) is in the range of 30:70 to 90:10, in particular in the range of 40:60 to 85:15, in particular in the range of 50:50 to 80:20.

[0164] The thermoplastic copolymer resin of the present invention, such as a polycarbonate resin, can have any one of a random copolymer structure, a block copolymer structure, and an alternating copolymer structure. The thermoplastic resin of the present invention does not necessarily contain all of the structural unit (II) and one or more different structural units (V) in the same polymer molecule. That is, the thermoplastic copolymer resin of the present invention may be a blend resin, as long as each of the above structures is contained in one of multiple polymer molecules. For example, a thermoplastic resin containing all of the structural units (II) and (V) may be a copolymer containing all of the structural units (II) and (V), a mixture of a homopolymer or copolymer containing at least one structural unit (II) and a homopolymer or copolymer containing at least one structural unit (V), a blend resin of a copolymer containing at least one structural unit (II) and a first structural unit (V) and a copolymer containing at least one structural unit (II) and at least one other structural unit (V) different from the first structural unit (V), etc.

[0165] Thermoplastic polycarbonates can be obtained by polycondensation of a diol component with a carbonate-forming component. Similarly, thermoplastic polyesters and polyestercarbonates can be obtained by polycondensation of a diol component with a dicarboxylic acid or an ester-forming derivative thereof and, optionally, a carbonate-forming component.

[0166] Specifically, the thermoplastic resin (polycarbonate resin) can be prepared by the following method.

[0167] The method for preparing the thermoplastic resins of the present invention, such as polycarbonate resins, comprises a process of melt polycondensation of a dihydroxy component corresponding to the structural unit described above with a carbonic acid diester. According to the present invention, the dihydroxy compound comprises at least one dihydroxy compound represented by formula (I), particularly formula (Ia) or (Ib), respectively, as defined herein. In addition to the compound of formula (I), the dihydroxy compound may also comprise one or more dihydroxy compounds represented by formula (IV), preferably formulas (IV-1) to (IV-8), particularly formulas (IV-11) to (IV-22), and particularly formulas (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-21), or (IV-22).

[0168] As is apparent from the above, polycarbonate resins can be formed by reacting a dihydroxy component with a carbonate precursor, such as a carbonic acid diester (the dihydroxy component comprising at least one compound represented by formula (I), (Ia), and (Ib), respectively, or a combination of at least one compound represented by formula (I), (Ia), and (Ib), respectively, with at least one compound represented by formula (IV), (IV-1), (IV-2), (IV-3), (IV-4), (IV-5), (IV-6), (IV-7), (IV-8), (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-16), (IV-17), (IV-18), (IV-19), (IV-20), (IV-21), or (IV-22)). Specifically, polycarbonate resins can be formed by a melt polycondensation process in which a compound represented by formula (I), (Ia), and (Ib), or a combination thereof with at least one compound of formula (IV), (IV-1), (IV-2), (IV-3), (IV-4), (IV-5), (IV-6), (IV-7), (IV-8), (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-16), (IV-17), (IV-18), (IV-19), (IV-20), (IV-21), or (IV-22), is reacted with a carbonate precursor, such as a carbonate diester, in the presence of a basic compound catalyst, a transesterification catalyst, or a mixture thereof, or in the absence of a catalyst.

[0169] Thermoplastic resins (or polymers) other than polycarbonate resins, such as polyester carbonates and polyesters, can be obtained by using, as a material (or monomer), a dihydroxy compound represented by formula (I), (Ia) and (Ib), respectively, or a combination thereof with at least one compound represented by formula (IV), (IV-1), (IV-2), (IV-3), (IV-4), (IV-5), (IV-6), (IV-7), (IV-8), (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-16), (IV-17), (IV-18), (IV-19), (IV-20), (IV-21) or (IV-22).

[0170] As previously mentioned, the monomers of formula (I) and likewise the comonomers of formula (IV) used to prepare the thermoplastic resin may contain impurities resulting from their preparation.

[0171] For example, R z O-Alk 4 - or O-Alk 4 -[O-Alk 4 -] w The monomers of formula (IV-1) and (IV-2) are O-Alk 4 - or O-Alk 4 -[O-Alk 4 -] w - Instead of both R z is a single bond, or R z may include dihydroxy compounds in which one of the groups is a single bond.

[0172] At least one R z O-Alk 4 - or O-Alk 4 -[O-Alk 4 -] wThe total amount of such dihydroxy compounds of formula (IV-1) or (IV-2) different from - is preferably 3000 ppm or less, more preferably 1500 ppm or less, even more preferably 1000 ppm or less, and particularly preferably 500 ppm or less; the main component in the monomer is the dihydroxy compound represented by formula (IV-1) or (IV-2). The total content of dihydroxy compounds in which at least one of the values ​​of a and b or c and d is different from formula (IV-1) or (IV-2) is further preferably 300 ppm or less, more preferably 200 ppm or less.

[0173] The polycarbonate resins can be obtained by reacting, as dihydroxy component, a monomeric compound of formula (I), or a combination of at least one monomeric compound of formula (I), particularly at least one monomer (I) mentioned herein as being preferred, with one or more monomeric compounds of formula (IV), particularly formula (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-21) or (IV-22), with a carbonate precursor, such as a carbonic acid diester.

[0174] However, in the polymerization process for producing polycarbonate resins, some compounds of formula (I) and (IV) contain a terminal -R z The OH groups may be converted to impurities in which one or both are replaced with different groups, such as vinyl end groups represented by -OCH=CH2. The amount of such impurities is generally small, so the polymer product formed can be used as a polycarbonate resin without any purification process.

[0175] The thermoplastic resin of the present invention may also contain trace amounts of impurities, for example, as an excess content of the thermoplastic resin composition or as part of the polymer backbone of the thermoplastic resin. Examples of such impurities include phenols, unreacted carbonic acid diesters, and monomers formed during the process for forming the thermoplastic resin. The total amount of impurities in the thermoplastic resin may be 5,000 ppm or less, or 2,000 ppm or less. The total amount of impurities in the thermoplastic resin is preferably 1,000 ppm or less, more preferably 500 ppm or less, even more preferably 200 ppm or less, and particularly preferably 100 ppm or less.

[0176] The total amount of phenols as impurities in the thermoplastic resin may be 3000 ppm or less, or 2000 ppm or less, preferably 1000 ppm or less, more preferably 800 ppm or less, even more preferably 500 ppm or less, and particularly preferably 300 ppm or less.

[0177] The total amount of carbonate diesters as impurities in the thermoplastic resin is preferably 1000 ppm or less, more preferably 500 ppm or less, even more preferably 100 ppm or less, and particularly preferably 50 ppm or less.

[0178] The total amount of unreacted monomers as impurities in the thermoplastic resin is preferably 3000 ppm or less, more preferably 2000 ppm or less, even more preferably 1000 ppm or less, and particularly preferably 500 ppm or less.

[0179] The lower limit of the total amount of these impurities is not critical, but may be 0.1 ppm or 1.0 ppm.

[0180] The total amount of residual heavy metals, such as palladium, as impurities in the thermoplastic resin is preferably 50 ppm or less, more preferably 10 ppm or less. The amount of residual palladium can be reduced by standard procedures such as treatment with adsorbents, such as activated carbon.

[0181] Resins with targeted characteristics can be formed by adjusting the amounts of phenol and diester carbonate. The amounts of phenol, diester carbonate, and monomer can be suitably adjusted by adjusting the polycondensation conditions, the operating conditions of the device used for polymerization, or the conditions for extrusion molding after the polycondensation process.

[0182] The weight-average molecular weight (Mw) of the thermoplastic resin of the present invention, as determined by GPC (gel permeation chromatography), is preferably in the range of 5,000 to 100,000 daltons, more preferably 10,000 to 80,000 daltons, particularly 10,000 to 50,000 daltons, and especially 15,000 to 50,000 daltons. GPC measurements can be calibrated using polystyrene standards. The Mw of the thermoplastic resin of the present invention, determined in this manner, is also referred to herein as the "weight-average molecular weight in terms of polystyrene." The number-average molecular weight (Mn) of the thermoplastic resin of the present invention is preferably in the range of 3,000 to 30,000, more preferably 5,000 to 25,000, and especially 7,000 to 20,000. The viscosity-average molecular weight (Mv) of the thermoplastic resin of the present invention is preferably in the range of 8,000 to 28,000, more preferably 9,000 to 22,000, and even more preferably 10,000 to 18,000.

[0183] The molecular weight distribution (Mw / Mn) of the thermoplastic resin according to the present invention is preferably 1.5 to 9.0, more preferably 1.8 to 7.0, and even more preferably 2.0 to 4.0.

[0184] When a thermoplastic resin has a weight average molecular weight (Mw) value within the above-mentioned appropriate range, molded articles made from the thermoplastic resin have high strength. Furthermore, such a thermoplastic resin having an appropriate Mw value is advantageous for molding due to its excellent fluidity.

[0185] The thermoplastic resin may contain low-molecular-weight compounds. Preferably, the thermoplastic resin contains 9 wt. % or less, particularly 7 wt. % or less, particularly 5 wt. % or less, or 0.01 wt. % or more, particularly 0.1 wt. % or more, particularly 1 wt. % or more, based on the total weight of the thermoplastic resin; for example, 0.1 to 9 wt. %, particularly 0.1 to 7 wt. %, particularly 0.1 to 5 wt. %, specifically 0.5 to 5 wt. %, 1 to 5 wt. %, 1 to 4 wt. %, or 1 to 3 wt. % of low-molecular-weight compounds having a molecular weight of less than 1000. When such low-molecular-weight compounds are present in the thermoplastic resin in amounts within the above ranges, the mechanical strength of molded articles made from such thermoplastic resins is generally increased, especially compared with molded articles made from thermoplastic resins containing higher amounts of low-molecular-weight compounds. Furthermore, thermoplastic resins according to this embodiment containing 9 wt. % or less, particularly 7 wt. % or less, particularly 5 wt. % of low-molecular-weight compounds having a molecular weight of less than 1000 tend not to undergo, or only slightly undergo, precipitation of low-molecular-weight compounds, also known as bleed-out, during molding processes such as injection molding. In contrast, molding of thermoplastic resins containing higher amounts of low molecular weight compounds can involve a significant degree of bleed-out.

[0186] In particular, the thermoplastic resin of the present invention, such as the polycarbonate resin described above, has a high refractive index (n D or n d) and is therefore suitable for preparing optical lenses. The refractive index values ​​referred to herein are those of a 0.1 mm thick film, as measured by an Abbe refractometer according to the method of JIS-K-7142. The refractive index of the thermoplastic resin of the present invention, particularly the polycarbonate resin of the present invention, at 23°C and a wavelength of 589 nm, when the resin contains structural unit (II), is often 1.640 or higher, preferably 1.650 or higher, more preferably 1.660 or higher, even more preferably 1.670 or higher, even more preferably 1.680 or higher, and particularly 1.690 or higher, for example, 1.700 or higher. For example, the refractive index of a copolycarbonate resin according to the present invention containing structural unit (II) and structural unit (V) is preferably 1.640 to 1.700, 1.650 to 1.750, or 1.660 to 1.800, more preferably 1.670 to 1.800, and even more preferably 1.680 to 1.800.

[0187] The Abbe number (v) of the thermoplastic resin of the present invention, particularly the polycarbonate resin of the present invention, is preferably no greater than 24, more preferably no greater than 22, and even more preferably no greater than 20. The Abbe number can be calculated using the following formula based on the refractive index at wavelengths of 487 nm, 589 nm, and 656 nm at 23° C.: v=(n D -1) / (n F -n C ) n D : Refractive index at wavelength 589 nm n C : Refractive index at wavelength 656 nm n F : Refractive index at wavelength 486 nm

[0188] Considering that the polycarbonate resin of the present invention can be used for injection molding, the glass transition temperature (Tg) of the thermoplastic resin, particularly the polycarbonate resin of the present invention, is often in the range of 90 to 185°C, preferably 90 to 180°C, more preferably 100 to 170°C, and particularly 110 to 160°C. Regarding molding flowability and molding heat resistance, the lower limit of Tg is preferably 130°C, more preferably 135°C, and the upper limit of Tg is preferably 180°C, more preferably 170°C. A glass transition temperature (Tg) in the range given above provides a significant usable temperature range and avoids the risk of the resin's melting temperature being too high, which could result in unnecessary decomposition or discoloration. Furthermore, it enables the preparation of molds with high surface accuracy. The values ​​given for the glass transition temperature refer to values ​​measured by differential scanning calorimetry (DSC) using a 10°C / min heating program according to the JIS K7121-1987 protocol.

[0189] The absolute value of the orientation birefringence of the thermoplastic resin of the present invention, particularly the polycarbonate resin of the present invention, is preferably 0 to 1 × 10 -2 range, more preferably 0 to 5 × 10 -3 and more preferably in the range of 0 to 2 × 10 -3 In particular, the range of 0 to 1 × 10 -3 The range is 0 to 0.4 × 10 -3 is in the range.

[0190] The optical molded article, for example, an optical element, produced by using the polycarbonate resin of the present invention preferably has a total light transmittance of 85% or more, more preferably 87% or more, and particularly preferably 88% or more. The total light transmittance of preferably 85% or more is as good as that provided by bisphenol A polycarbonate resin, etc.

[0191] The thermoplastic resin of the present invention has high moist heat resistance. Moist heat resistance can be evaluated by performing a "PCT test" (pressure cooker test) on a molded article, such as an optical element, manufactured using the thermoplastic resin and then measuring the total luminous transmittance of the molded article after the PCT test. In the PCT test, an injection-molded article with a diameter of 50 mm and a thickness of 3 mm is first held for 20 hours under conditions of 120°C, 0.2 MPa, 100% RH, and 20 hours using a PC305S III tester manufactured by Hirayama Seisakusho. The injection-molded article sample is then removed from the device, and the total luminous transmittance is measured using a Nippon Denshoku Industries SE2000 spectroscopic parallax analyzer according to the method of JIS-K-7361-1.

[0192] The thermoplastic resin according to the present invention has a total light transmittance after a PCT test of 60% or more, preferably 70% or more, more preferably 75% or more, even more preferably 80% or more, and particularly preferably 85% or more. As long as the total light transmittance is 60% or more, the thermoplastic resin is considered to have higher moist heat resistance than conventional thermoplastic resins.

[0193] The thermoplastic resin according to the present invention preferably has a b value, which indicates hue, of not more than 5. The smaller the b value, the weaker the yellowness and the better the hue.

[0194] According to the present invention, the diol component used in the preparation of the polycarbonate or polyester may further comprise one or more diol monomers different from the monomer compound of formula (I), for example, one or more monomers of formula (IV).

[0195] Suitable diol monomers other than the monomer compounds of formula (I) are those conventionally used in the preparation of polycarbonates, such as, for example: aliphatic diols, such as ethylene glycol, propanediol, butanediol, pentanediol and hexanediol; Examples of diols include alicyclic diols, such as tricyclo[5.2.1.02,6]decanedimethanol, cyclohexane-1,4-dimethanol, decalin-2,6-dimethanol, norbornane dimethanol, pentacyclopentadecanedimethanol, cyclopentane-1,3-dimethanol, spiroglycol, 1,4:3,6-dianhydro-D-sorbitol, 1,4:3,6-dianhydro-D-mannitol and 1,4:3,6-dianhydro-L-iditol; and aromatic diols, in particular aromatic diols of formula (IV), such as bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)ether, bis(4-hydroxyphenyl)sulfoxide, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxyphenyl)ketone, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-tert-butylphenyl)propane, 2,2-bis(4-hydroxy-3- methylphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, bis(4-hydroxyphenyl)diphenylmethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, α,ω-bis[2-(p-hydroxyphenyl)ethyl]polydimethylsiloxane, α,ω-bis[3-(o-hydroxyphenyl)propyl]polydimethylsiloxane, 4,4'-[1,3-phenylenebis(4-hydroxyphenyl)propyl]polydimethylsiloxane Bis(1-methylethylidene)hydroxyphenyl]-1-phenylethane, 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-tert-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene, 9,9-bis(4-hydroxy-3-phenyl)fluorene, phenylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethyl)phenyl)fluorene, 9,9-bis(4-(2-hydroxyethyl)-3-phenylphenyl)fluorene, 9,9-bis(6-hydroxy-2-naphthyl)fluorene, 9,9-bis(6-(2-hydroxyethyl)-2-naphthyl)fluorene, 10,10-bis(4-hydroxyphenyl)anthracen-9-one, 10,10-bis(4-(2-hydroxyethyl)phenyl)anthracen-9-one, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)phenyl]sulfonyl-2,6-di(thianthren-1-yl)phenoxy]ethanol, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(dibenzo[b,d]thien-4-yl)phenyl]sulfonyl-2,6-dibenzo[b,d]thien-4-yl)phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(fu [phenanthrene-9-yl)-phenyl]-1-methylethyl]-2,6-di(phenanthrene-9-yl)-phenoxy]ethanol and 2,2'-[1,1'-binaphthalene-2,2'-diylbis(oxy)]diethanol, also known as 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl or 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE).

[0196] Preferably, the diol component comprises, in addition to the monomer of formula (I), at least one monomer of formula (IV). In particular, the combined amount of the monomers of formulas (I) and (IV) contributes to the diol component by at least 90 wt% based on the total weight of the diol component, or at least 90 mol% based on the total molar amount of the diol monomers of the diol component. In particular, the diol component comprises, in addition to the monomer of formula (I), at least one monomer selected from the monomers of formulas (IV-11) to (IV-22). More particularly, the diol component comprises, in addition to the monomer of formula (I), at least one monomer selected from the monomers of formulas (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-21), and (IV-22). In particular, the diol component may be, in addition to the monomer of formula (I), 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl, 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthyl, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, 2-[4-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)phenyl]sulfonyl-2,6-di(thianthren-1-yl)phenoxy]ethanol, 2-[4- The monomer comprises at least one monomer selected from [4-(2-hydroxyethoxy)-3,5-di(dibenzo[b,d]thien-4-yl)phenyl]sulfonyl-2,6-dibenzo[b,d]thien-4-yl)phenoxy]ethanol, 2-[4-[1-[4-(2-hydroxyethoxy)-3,5-di(phenanthren-9-yl)-phenyl]-1-methylethyl]-2,6-di(phenanthren-9-yl)-phenoxy]ethanol, and 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene, and combinations thereof.

[0197] Often the relative amount of monomeric compounds of formula (I), based on the total weight of the diol components, is at least 1% by weight, preferably at least 10% by weight or at least 25% by weight, in particular at least 15% by weight or at least 20% by weight, in particular at least 15% by weight or at least 25% by weight, preferably in the range of 1 to 99% by weight or in the range of 10 to 98% by weight, in particular in the range of 15 to 98% by weight or in the range of 20 to 98% by weight or in the range of 25 to 98% by weight or in the range of 25 to 97% by weight, in particular in the range of 10 to 96% by weight or in the range of 15 to 95% by weight or in the range of 25 to 95% by weight or in the range of 25 to 93% by weight, but may be as high as 100% by weight.

[0198] Often the relative molar amount of the monomeric compounds of formula (I), based on the total molar amount of the diol components, is at least 1 mol%, preferably at least 10 mol% or at least 25 mol%, in particular at least 15 mol% or at least 20 mol%, in particular at least 15 mol% or at least 25 mol%, preferably in the range of 1 to 99 mol% or 10 to 98 mol% or 15 to 98 mol% or 20 to 98 mol%, in particular 10 to 96 mol% or 15 to 95 mol% or 25 to 95 mol% or 25 to 93 mol%, in particular 15 to 90 mol% or 20 to 90 mol% or 25 to 90 mol% or 30 to 90 mol%, but may be as high as 100 mol%.

[0199] As a result, the relative molar amount of the monomeric compounds of formula (IV), based on the total molar amount of the diol components, does not exceed 99 mol% or 90 mol% or 75 mol%, in particular does not exceed 85 mol% or 80 mol%, in particular does not exceed 85 mol% or 75 mol%, preferably in the range of 1 to 99 mol% or 2 to 90 mol% or 2 to 85 mol% or 3 to 75 mol%, in particular 4 to 90 mol% or 5 to 85 mol% or 5 to 75 mol% or 7 to 75 mol%, in particular 10 to 85 mol% or 10 to 80 mol% or 10 to 75 mol% or 10 to 70 mol%, but may be as high as 99.9 mol%.

[0200] Often, the total molar amount of the monomers of formula (I) and formula (IV) is at least 80 mol %, particularly at least 90 mol %, and especially at least 95 mol % or up to 100 mol %, based on the total molar amount of the diol monomers in the diol component.

[0201] Examples of further preferred aromatic dihydroxy compounds that may be used in addition to the monomer of formula (I) and optionally the monomer of formula (IV) include, but are not limited to, bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, bisphenol Z, and the like.

[0202] To adjust molecular weight and melt viscosity, the monomers forming the thermoplastic polymer may also contain monofunctional compounds, such as monofunctional alcohols in the case of polycarbonates, and monofunctional alcohols or monofunctional carboxylic acids in the case of polyesters. Suitable monoalcohols include butanol, hexanol, and octanol. Suitable monocarboxylic acids include, for example, benzoic acid, propionic acid, and butyric acid. To increase molecular weight and melt viscosity, the monomers forming the thermoplastic polymer may also contain polyfunctional compounds, such as polyfunctional alcohols with three or more hydroxyl groups in the case of polycarbonates, or polyfunctional alcohols with three or more hydroxyl groups or polyfunctional carboxylic acids with three or more carboxyl groups in the case of polyesters. Suitable polyfunctional alcohols include, for example, glycerin, trimethylolpropane, pentaerythritol, and 1,3,5-trihydroxypentane. Suitable polyfunctional carboxylic acids with three or more carboxyl groups include trimellitic acid and pyromellitic acid. The total amount of these compounds often does not exceed 10 mol% based on the molar amount of the diol component.

[0203] Suitable carbonate-forming monomers are those commonly used as carbonate-forming monomers in the preparation of polycarbonates, including, but not limited to, phosgene, diphosgene, and carbonic acid diesters such as diethyl carbonate, diphenyl carbonate, di-p-tolyl carbonate, phenyl-p-tolyl carbonate, di-p-chlorophenyl carbonate, and dinaphthyl carbonate. Among these, diphenyl carbonate is particularly preferred. The carbonate-forming monomer is often used in a ratio of 0.97 to 1.20 mol, more preferably 0.98 to 1.10 mol, per mol of the total dihydroxy compounds.

[0204] Suitable dicarboxylic acids include, but are not limited to: aliphatic dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid; alicyclic dicarboxylic acids, such as tricyclo[5.2.1.02,6]decanedicarboxylic acid, cyclohexane-1,4-dicarboxylic acid, decalin-2,6-dicarboxylic acid, and norbornanedicarboxylic acid; and aromatic dicarboxylic acids, such as benzenedicarboxylic acids, in particular phthalic acid, isophthalic acid, 2-methylterephthalic acid or terephthalic acid, and naphthalene dicarboxylic acids, in particular naphthalene-1,3-dicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-1,5-dicarboxylic acid, naphthalene-1,6-dicarboxylic acid, naphthalene-1,7-dicarboxylic acid, naphthalene-2,5-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, 2-[9-(carboxymethyl)fluoren-9-yl]acetic acid (formula DC1), 2-[9-(carboxymethyl)fluoren-9-yl]propionic acid (formula DC2), 2,2′-bis(carboxymethyloxy)-1,1′-binaphthyl (formula DC3) and naphthalene-2,7-dicarboxylic acid.

[0205] [ka]

[0206] Suitable ester-forming derivatives of dicarboxylic acids include, but are not limited to, dialkyl esters, diphenyl esters, and ditolyl esters.

[0207] In the case of polyesters, the ester-forming monomers are often used in a ratio of 0.97 to 1.20 mol, more preferably 0.98 to 1.10 mol, per 1 mol of the total dihydroxy compounds.

[0208] The polycarbonates of the present invention can be prepared by reacting a diol component comprising a monomer of Formula (I) and optionally an additional diol monomer, such as a monomer of Formula (IV), with carbonate-forming monomers, similar to the preparation of known polycarbonates, as described, for example, in U.S. Pat. No. 9,360,593, U.S. Patent Application Publication No. 2016 / 0319069, and U.S. Patent Application Publication No. 2017 / 0276837, the entire contents of which are incorporated by reference.

[0209] The polyesters of the present invention can be prepared by reacting a diol component comprising a monomer of formula (I) and optionally an additional diol monomer, such as a monomer of formula (IV), with a dicarboxylic acid or an ester-forming derivative thereof, similar to the preparation of known polyesters as described, for example, in U.S. Patent Application Publication No. 2017 / 044311 and the references cited therein, which are incorporated by reference in their entirety.

[0210] The polyestercarbonates of the present invention can be prepared by reacting a diol component comprising a monomer of formula (I) and optionally a further diol monomer such as a monomer of formula (IV), a carbonate-forming monomer and a dicarboxylic acid or an ester-forming derivative thereof, similar to the preparation of known polyestercarbonates described in the art.

[0211] Polycarbonates, polyesters and polyestercarbonates are usually prepared by reacting the monomers of the diol component with carbonate-forming monomers and / or ester-forming monomers, i.e., dicarboxylic acids or their ester-forming derivatives, in the presence of an esterification catalyst, particularly in the presence of a transesterification catalyst when carbonate-forming monomers or ester-forming derivatives of polycarboxylic acids are used.

[0212] Suitable transesterification catalysts are basic compounds, including, but not limited to, alkali metal compounds, alkaline earth metal compounds, nitrogen-containing compounds, etc. Similarly, suitable transesterification catalysts are acidic compounds, including, but not limited to, Lewis acid compounds of polyvalent metals, including, but not limited to, compounds of zinc, tin, titanium, zirconium, lead, etc.

[0213] Examples of suitable alkali metal compounds include alkali metal salts of organic acids such as acetic acid, stearic acid, benzoic acid, or phenylphosphoric acid, alkali metal phenolates, alkali metal oxides, alkali metal carbonates, alkali metal borohydrides, alkali metal hydrogencarbonates, alkali metal phosphates, alkali metal hydrogenphosphates, alkali metal hydroxides, alkali metal hydrides, alkali metal alkoxides, and the like. Specific examples thereof include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cerium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium borophenoxide, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, and disodium phenylphosphate; disodium, dipotassium, dicesium, and dilithium salts of bisphenol A; and sodium, potassium, cesium, and lithium salts of phenol.

[0214] Examples of alkaline earth metal compounds include alkaline earth metal salts of organic acids such as acetic acid, stearic acid, benzoic acid, or phenylphosphoric acid, alkaline earth metal phenolates, alkaline earth metal oxides, alkaline earth metal carbonates, alkali metal borohydrides, alkaline earth metal bicarbonates, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal alkoxides, etc. Specific examples thereof include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium bicarbonate, calcium bicarbonate, strontium bicarbonate, barium bicarbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenylphosphate, etc.

[0215] Examples of nitrogen-containing compounds include quaternary ammonium hydroxides, their salts, and amines. Specific examples include quaternary ammonium hydroxides containing alkyl or aryl groups, such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide; tertiary amines, such as triphenylamine, dimethylbenzylamine, and triphenylamine; secondary amines, such as diethylamine and dibutylamine; primary amines, such as propylamine and butylamine; imidazoles, such as 2-methylimidazole, 2-phenylimidazole, and benzimidazole; and bases or basic salts, such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, and tetraphenylammonium tetraphenylborate.

[0216] Preferred examples of transesterification catalysts include salts of polyvalent metals such as zinc, tin, titanium, zirconium, and lead, particularly chlorides, alkoxides, alkanoates, benzoates, and acetylacetonates. These may be used independently or in combination of two or more. Specific examples of such transesterification catalysts include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin(II) chloride, tin(IV) chloride, tin(II) acetate, tin(IV) acetate, dibutyltin laurate, dibutyltin oxide, dibutyltin methoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead(II) acetate, and lead(IV) acetate.

[0217] The transesterification catalyst is often used in an amount of 10 moles per mole of the total dihydroxy compounds. -9 ~10 -3 mol, preferably 10 -7 ~10 -4 Used in molar ratios.

[0218] Polycarbonates, polyesters, and polyestercarbonates are often prepared by melt polycondensation, in which the monomers are reacted in the absence of an additional inert solvent. During the reaction, the reaction mixture is heated at ambient or reduced pressure to remove by-products formed in the transesterification reaction.

[0219] The melt polycondensation reaction preferably involves charging monomers and a catalyst into a reactor and subjecting the reaction mixture to conditions that allow reaction between the monomers and the formation of by-products. It has been found to be advantageous for the by-products to be present in the polycondensation reaction for at least some time. However, to drive the polycondensation reaction toward the product side, it is beneficial to remove at least a portion of the formed by-products during the polycondensation reaction or, preferably, at the end of the polycondensation reaction. To allow the by-products to remain in the reaction mixture, the pressure may be controlled by closing the reactor or increasing or decreasing the pressure. The reaction time for this step is 20 to 240 minutes, preferably 40 to 180 minutes, and particularly preferably 60 to 150 minutes. In this step, if the by-products are removed by distillation immediately after their formation, the final thermoplastic resin will have a low content of high-molecular-weight resin molecules. In contrast, if the by-products are allowed to remain in the reactor for a certain period of time, the final thermoplastic resin will have a high content of high-molecular-weight resin molecules.

[0220] The melt polycondensation reaction may be carried out continuously or batchwise. The reactor that can be used for the reaction may be a vertical type including an anchor-type impeller, Maxblend (registered trademark) impeller, helical ribbon impeller, etc., a horizontal type including a paddle impeller, lattice impeller, spectacle impeller, etc., or an extruder type including a screw. In consideration of the viscosity of the polymerization product, a reactor including a combination of such reactors can be preferably used.

[0221] In some methods for producing thermoplastic resins such as polycarbonate resins, catalysts may be removed or deactivated after the polymerization reaction to maintain thermal and hydrolytic stability. A preferred method for deactivating a catalyst is the addition of an acidic substance. Specific examples of acidic substances include esters such as butyl benzoate; aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate; phosphoric acids such as phosphorous acid, phosphoric acid, and phosphonic acid; phosphite esters such as triphenyl phosphite, monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di-n-butyl phosphite, di-n-hexyl phosphite, dioctyl phosphite, and monooctyl phosphite; triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, dioctyl phosphate, and phosphate. Examples of suitable deactivators include phosphate esters such as monooctyl phosphate; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, and dibutylphosphonic acid; phosphonic acid esters such as diethyl phenylphosphonate; phosphines such as triphenylphosphine and bis(diphenylphosphino)ethane; boric acids such as boric acid and phenylboric acid; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate; organic halides such as stearic acid chloride, benzoyl chloride, and p-toluenesulfonic acid chloride; alkylsulfonic acids such as dimethylsulfonic acid; and organic halides such as benzyl chloride. These deactivators are often used in an amount of 0.01 to 50 mol, preferably 0.3 to 20 mol, relative to the catalyst. After deactivating the catalyst, a step of removing low-boiling compounds from the polymer by distillation may be performed. The distillation is preferably carried out under reduced pressure, for example, at a pressure of 0.1 to 1 mmHg, and at a temperature of 200 to 350°C. For this step, horizontal devices containing stirring blades with high surface renewal capacity, such as paddle blades, lattice blades, spectacle blades, or thin film evaporators are preferably used.

[0222] It is desirable for thermoplastic resins such as polycarbonate resins to have an extremely low amount of foreign matter. Therefore, the molten product is preferably filtered to remove solids from the melt. The mesh of the filter is preferably 5 μm or less, more preferably 1 μm or less. The produced polymer is preferably filtered through a polymer filter. The mesh of the polymer filter is preferably 100 μm or less, more preferably 30 μm or less. Needless to say, the step of sampling the resin pellets must be carried out in a low-dust environment. The dust environment is preferably class 6 or less, more preferably class 5 or less.

[0223] Thermoplastic resins can be molded by any conventional molding procedure for producing optical elements. Suitable molding procedures include, but are not limited to, injection molding, compression molding, casting, rolling, extrusion, drawing, etc.

[0224] While the thermoplastic resin of the present invention can be molded in this manner, it is also possible to mold a resin composition containing at least one thermoplastic resin of the present invention and at least one additive and / or additional resin. Suitable additives include antioxidants, processing stabilizers, light stabilizers, polymerized metal deactivators, flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, mold release agents, UV absorbers, plasticizers, compatibilizers, etc. Suitable additional resins include, for example, other polycarbonate resins, polyestercarbonate resins, polyester resins, polyamides, polyacetals, etc. that do not contain the repeating unit of formula (I).

[0225] Examples of antioxidants include triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 3,9-bis(2, 6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)benzofuran-2(3H)-one, 5,7-di-tert-butyl-3-(1,2dimethylphenyl)benzofuran-2(3H)-one, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, N,N-hexamethylenebis(3,5-di-tert-butyl) Examples include, but are not limited to, t-butyl-4-hydroxy-hydrocinnamide, 3,5-di-tert-butyl-4-hydroxy-benzylphosphonate-diethyl ester, tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, and 3,9-bis{1,1-dimethyl-2-[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]ethyl}-2,4,8,10-tetraoxaspiro(5,5)undecane. , 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)benzofuran-2(3H)-one, and 5,7-di-tert-butyl-3-(1,2 dimethylphenyl)benzofuran-2(3H)-one are more preferred. The content of the antioxidant in the thermoplastic resin is preferably 0.001 to 0.3 parts by weight based on 100 parts by weight of the thermoplastic resin.

[0226] Examples of processing stabilizers include, but are not limited to, phosphorus-based processing stabilizers, sulfur-based processing stabilizers, etc. Examples of phosphorus-based processing stabilizers include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid, esters thereof, etc. Specific examples of these include triphenyl phosphite, tris(nonylphenyl)phosphite, tris(2,4-di-tert-butylphenyl)phosphite, tris(2,6-di-tert-butylphenyl)phosphite, tridecyl phosphite, trioctyl phosphite, trioctadecyl phosphite, didecyl monophenyl phosphite, dioctyl monophenyl phosphite, diisopropyl monophenyl phosphite, monobutyl diphenyl phosphite, monodecyl diphenyl phosphite, monooctyl diphenyl phosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, 2,2-methylenebis(4,6-di-tert-butylphenyl)octyl phosphite, bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, diphenyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, tributyl phosphate, triethyl phosphate, trimethyl phosphate, triphenyl phosphate, diphenyl monoorthoxenyl phosphate, dibutyl phosphate, dioctyl phosphate, diisopropyl phosphate, dimethyl benzene phosphonate, diethyl benzene phosphonate, dipropyl benzene phosphonate, tetrakis(2,4-di-t-butylphenyl)-4,4'-biphenylene diphosphonite, tetrakis(2,4-di-t-butylphenyl)-4,3'-biphenylene diphosphonite, tetrakis(2,4-di-t-butylphenyl)-3,3'-biphenylene diphosphonite, bis(2,4-di-tert-butylphenyl)-4-phenyl-phenylphosphonite, bis(2,4-di-tert-butylphenyl)-3-phenyl-phenylphosphonite, and the like. The content of the phosphorus-based processing stabilizer in the thermoplastic resin composition is preferably 0.001 to 0.2 parts by weight based on 100 parts by weight of the thermoplastic resin.

[0227] Examples of sulfur-based processing stabilizers include, but are not limited to, pentaerythritol-tetrakis(3-laurylthiopropionate), pentaerythritol-tetrakis(3-myristylthiopropionate), pentaerythritol-tetrakis(3-stearylthiopropionate), dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, etc. The content of the sulfur-based processing stabilizer in the thermoplastic resin composition is preferably 0.001 to 0.2 parts by weight per 100 parts by weight of the thermoplastic resin.

[0228] A preferred release agent contains at least 90% by weight of an ester of alcohol and fatty acid. Specific examples of the ester of alcohol and fatty acid include an ester of monohydric alcohol and fatty acid, and a partial or full ester of polyhydric alcohol and fatty acid. A preferred example of the ester of alcohol and fatty acid is an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms. A preferred example of a partial or full ester of a polyhydric alcohol and fatty acid is a partial or full ester of a polyhydric alcohol having 2 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms. Specific examples of the ester of monohydric alcohol and fatty acid include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, isopropyl palmitate, etc. Specific examples of partial or full esters of polyhydric alcohols and fatty acids include stearic acid monoglyceride, stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid monoglyceride, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, and dipentaerythritol full or partial esters such as dipentaerythritol hexastearate. The content of the release agent in the resin composition is preferably 0.005 to 2.0 parts by weight, more preferably 0.01 to 0.6 parts by weight, and even more preferably 0.02 to 0.5 parts by weight, per 100 parts by weight of the thermoplastic resin.

[0229] Preferred UV absorbers are selected from the group consisting of benzotriazole-based UV absorbers, benzophenone-based UV absorbers, triazine-based UV absorbers, cyclic iminoester-based UV absorbers, and cyanoacrylate-based UV absorbers. That is, the following UV absorbers may be used independently or in combination of two or more.

[0230] Examples of the benzotriazole-based ultraviolet absorber include 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-3,5-dicumylphenyl)phenylbenzotriazole, 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2N-benzotriazol-2-yl)phenol)], 2-(2-hydroxy-3,5-di-tert-butylphenyl)benzotriazole, 2-(2-hydroxy-3,5-di-tert-butylphenyl)benzotriazole, 2-(2-hydroxy-3,5-di-tert-amylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-butylphenyl)benzotriazole, 2-(2-hydroxy-4-octoxyphenyl)benzotriazole, 2,2'-methylenebis(4-cumyl-6-benzotriazolephenyl), 2,2'-p-phenylenebis(1,3-benzoxazin-4-one), 2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidomethyl)-5-methylphenyl]benzotriazole, and the like.

[0231] Examples of benzophenone-based ultraviolet absorbers include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid hydrate, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5-sodiumsulfoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2-hydroxy-4-n-dodecyloxybenzophenone, and 2-hydroxy-4-methoxy-2'-carboxybenzophenone.

[0232] Examples of triazine-based ultraviolet absorbers include 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-([(hexyl)oxy]-phenol, 2-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-([(octyl)oxy]-phenol, and the like.

[0233] Examples of cyclic iminoester-based ultraviolet absorbers include 2,2'-bis(3,1-benzoxazin-4-one), 2,2'-p-phenylenebis(3,1-benzoxazin-4-one), 2,2'-m-phenylenebis(3,1-benzoxazin-4-one), 2,2'-(4,4'diphenylene)bis(3,1-benzoxazin-4-one), 2,2'-(2,6-naphthalene)bis(3,1-benzoxazin-4-one), oxazin-4-one), 2,2'-(1,5-naphthalene)bis(3,1-benzoxazin-4-one), 2,2'-(2-methyl-p-phenylene)bis(3,1-benzoxazin-4-one), 2,2'-(2-nitro-p-phenylene)bis(3,1-benzoxazin-4-one), 2,2'-(2-chloro-p-phenylene)bis(3,1-benzoxazin-4-one), and the like.

[0234] Examples of cyanoacrylate ultraviolet absorbers include 1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis(((2-cyano-3,3-diphenylacryloyl)oxy)methyl)propane and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl)oxy]benzene.

[0235] The content of the ultraviolet absorber in the resin composition is preferably 0.01 to 3.0 parts by weight, more preferably 0.02 to 1.0 part by weight, and even more preferably 0.05 to 0.8 parts by weight, relative to 100 parts by weight of the thermoplastic resin. If the ultraviolet absorber is contained within such a content range, it can provide the thermoplastic resin with sufficient weather resistance depending on the application.

[0236] As described above, the thermoplastic polymer resins, particularly polycarbonate resins, comprising repeating units of formulas (II), (IIa) and (IIb), respectively, described herein provide the thermoplastic resins with high transparency and high refractive index, and are therefore suitable for preparing optical devices requiring high transparency and high refractive index. More precisely, the thermoplastic polycarbonates having structural units of formulas (II), (IIa) and (IIb), respectively, are characterized by a high refractive index, preferably at least 1.640, more preferably at least 1.660, and particularly at least 1.670.

[0237] The contribution of the monomers of formula (I), (Ia) and (Ib) to the refractive index of thermoplastic resin, especially polycarbonate resin, depends on the refractive index of said monomer and the relative amount of said monomer in thermoplastic resin.Generally, the higher the refractive index of the monomer contained in thermoplastic resin, the higher the refractive index of the resulting thermoplastic resin.In addition, the refractive index of the thermoplastic resin that comprises the structural unit of formula (II) can be calculated from the refractive index of the monomer used to prepare the thermoplastic resin (the refractive index of the monomer can be determined by refractometer measurement or by calculation from scratch using, for example, computer software ACD / ChemSketch 2012 (Advanced Chemistry Development, Inc.)).

[0238] In the case of thermoplastic copolymer resins, the refractive index of a thermoplastic resin, in particular a polycarbonate resin, can be calculated from the refractive index of the homopolymers of the respective monomers forming the copolymer resin by the so-called "Fox equation" as follows: 1 / n D =x1 / n D1 +x2 / n D2 +....x n / n Dn (In the formula, n D are the refractive indices of the copolymer, and x1, x2, ....x n is the mass fraction of monomers 1, 2, ....n in the copolymer, and n D1 , n D2 ,...n Dn is the refractive index of a homopolymer synthesized from only one monomer at a time (x1, x2, ....n). For polycarbonate, x1, x2, ....x n is the mass fraction of OH monomers 1, 2, ....n based on the total amount of OH monomers. It is clear that the higher the refractive index of the homopolymer, the higher the refractive index of the copolymer.

[0239] The refractive index of the thermoplastic resin can be determined directly or indirectly. In the case of direct determination, the refractive index of the thermoplastic resin, n Dis measured at a wavelength of 589 nm using an Abbe refractometer according to protocol JIS-K-7142, applying a 0.1 mm film of the thermoplastic resin. In the case of the refractive index of the homopolycarbonate of the compound of formula (I), the refractive index can also be determined indirectly. For this purpose, copolycarbonates of each monomer of formula (I) with 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene and diphenyl carbonate are prepared according to the protocol of Example 1 in column 48 of U.S. Pat. No. 9,360,593, and the refractive index of the copolycarbonate, n D is measured at a wavelength of 589 nm using an Abbe refractometer, applying a 0.1 mm film of the copolycarbonate, according to protocol JIS-K-7142. The refractive index n D From the above, the refractive index of the homopolycarbonate of each monomer was calculated using the Fox formula and the known refractive index of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (n D (589 nm) = 1.639).

[0240] The compounds of formula (I) can be obtained in a purity that provides a low Yellowness Index, YI, determined according to ASTM E313, which can be equally important for use in the preparation of optical resins.

[0241] More precisely, the Yellowness Index YI of the compounds of formula (I), determined according to ASTM E313, preferably does not exceed 100, more preferably 50, even more preferably 20, in particular 10 or 5.

[0242] The thermoplastic resin according to the present invention has a high refractive index and a low Abbe number. The thermoplastic resin according to the present invention can be used to produce transparent conductive substrates that can be used in liquid crystal displays, organic electroluminescence displays, solar cells, and the like. Similarly, the thermoplastic resin according to the present invention can be used as a structural material for optical components such as optical disks, liquid crystal panels, optical cards, optical sheets, optical fibers, connectors, vapor-deposited plastic reflectors, and displays; or as an optical device suitable for functional material applications.

[0243] Thus, the thermoplastic resins of the present invention can be used to form molded articles such as optical devices. Optical devices include optical lenses and optical films. Specific examples of optical devices include lenses, films, mirrors, filters, prisms, etc. These optical devices can be formed by any manufacturing process, such as injection molding, compression molding, injection-compression molding, extrusion, or solution casting.

[0244] Due to their excellent moldability and high heat resistance, the thermoplastic resins of the present invention are highly suitable for the production of optical lenses requiring injection molding. For molding, the thermoplastic resins of the present invention, such as polycarbonate resins, can be used as mixtures with other thermoplastic resins, such as different polycarbonate resins, polyestercarbonate resins, polyester resins, and other resins.

[0245] Furthermore, the thermoplastic resin of the present invention can be mixed with additives for forming optical devices. The additives for forming optical devices can include those described above. Examples of additives include antioxidants, processing stabilizers, light stabilizers, polymerized metal deactivators, flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, mold release agents, UV absorbers, plasticizers, and compatibilizers.

[0246] As is clear from the above, another aspect of the present invention relates to an optical device made from a thermoplastic resin as defined above, which comprises structural units of formula (II) and optionally formula (V). With regard to the preferred meanings and preferred embodiments of the structural units of formula (II) and formula (V), reference is made to the above statements.

[0247] Optical devices made from optical resins containing repeating units of formula (II) and optionally repeating units of formula (V) as defined herein are typically optical lenses, such as automobile headlamp lenses, Fresnel lenses, fθ lenses for laser printers, camera lenses, eyeglass lenses, and rear-projection TV projection lenses, CD-ROM pickup lenses, as well as optical molded articles such as optical disks, optical elements for image display media, optical films, film substrates, optical filters or prisms, liquid crystal panels, optical cards, optical sheets, optical fibers, optical connectors, and vapor-deposited plastic reflectors. Optical lenses and optical films are particularly preferred. Optical resins containing repeating units of formula (II) and optionally repeating units of formula (V) are also useful for producing transparent conductive substrates suitable for use in optical devices as structural or functional components of transparent conductive substrates for liquid crystal displays, organic electroluminescent displays, solar cells, and the like.

[0248] Optical lenses made from the thermoplastic resins of the present invention have a high refractive index, a low Abbe number, and low birefringence, and are highly resistant to humidity and heat. Therefore, the optical lenses can be used in fields where expensive glass lenses with high refractive indices are commonly used, such as telescopes, binoculars, and TV projectors. It is preferable that the optical lenses be used in the form of aspherical lenses. Spherical aberration can be substantially eliminated with a single aspherical lens. Therefore, it is not necessary to use multiple spherical lenses to eliminate spherical aberration. This reduces the weight and manufacturing costs of devices containing spherical aberration. Among various types of optical lenses, aspherical lenses are particularly useful as camera lenses. The present invention easily provides aspherical lenses with a high refractive index and low birefringence, which are technically difficult to manufacture by processing glass.

[0249] The optical lenses of the present invention can be formed, for example, by injection molding, compression molding, injection-compression molding, or casting a resin of repeating units of formula (II) and optionally repeating units of formula (V), as defined herein.

[0250] The optical lens of the present invention is characterized by small optical distortion. Optical lenses containing conventional optical resins have large optical distortion. Although it is not impossible to reduce the value of optical distortion by adjusting molding conditions, the range of conditions is very narrow, making molding extremely difficult. The resin having the repeating unit of formula (II) and optionally the repeating unit of formula (V) defined in this specification has extremely small optical distortion caused by the orientation of the resin and small molding distortion, so that excellent optical elements can be obtained without strictly setting molding conditions.

[0251] To produce the optical lens of the present invention by injection molding, it is preferable to mold the lens at a cylinder temperature of 260°C to 320°C and a mold temperature of 100°C to 140°C.

[0252] The optical lens of the present invention can be advantageously used as an aspherical lens if necessary. Because a single aspherical lens can substantially eliminate spherical aberration, it is not necessary to eliminate spherical aberration by combining spherical lenses, thereby reducing weight and manufacturing costs. Therefore, among optical lenses, aspherical lenses are particularly useful as camera lenses.

[0253] Resins having repeating units of formula (II) and optionally repeating units of formula (V) as defined herein have high moldability and are therefore particularly useful as materials for thin, small, and complex-shaped optical lenses. The lens size is such that the thickness at the center is 0.05 to 3.0 mm, preferably 0.05 to 2.0 mm, and more preferably 0.1 to 2.0 mm. The lens diameter is 1.0 to 20.0 mm, preferably 1.0 to 10.0 mm, and more preferably 3.0 to 10.0 mm. The lens is preferably a meniscus lens with one convex surface and the other concave surface.

[0254] The surface of the optical lens of the present invention may have a coating layer such as an anti-reflection layer or a hard coat layer, if necessary. The anti-reflection layer may be a single layer or multiple layers, and may be composed of an organic material or an inorganic material, but is preferably composed of an inorganic material. Examples of inorganic materials include oxides and fluorides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesium oxide, and magnesium fluoride.

[0255] The optical lenses of the present invention may be formed by any method such as metal forming, cutting, polishing, laser machining, electrical discharge machining or deburring, with metal forming being preferred.

[0256] Optical films produced using the thermoplastic resin of the present invention have high transparency and heat resistance, and are therefore suitable for use as liquid crystal substrate films, optical memory cards, etc. To prevent foreign matter from being incorporated into the optical film as much as possible, molding must be carried out in a low-dust environment. The dust environment is preferably class 6 or less, more preferably class 5 or less.

[0257] The following examples serve as further illustration of the present invention.

[0258] 1. Abbreviation: mp: melting point eq.: molar equivalent THF: tetrahydrofuran TBME: tert-butyl methyl ether MeOH: Methanol THF: tetrahydrofuran K2CO3: Potassium carbonate KI: Potassium iodide NaHCO3: Sodium bicarbonate NaOH: Sodium hydroxide NH4Cl: Ammonium chloride Na2SO4: Sodium sulfate HCl: Hydrochloric acid TLC: Thin Layer Chromatography n D : Refractive index

[0259] 2. Preparation of Monomers of Formula (I) 2.1 Analysis of the monomer of formula (I): 1 H-NMR spectra were determined at 23 °C using an 80 MHz NMR spectrometer (Magritek Spinsolve 80).

[0260] The melting points of the compounds were determined by BUchi Melting Point B-545.

[0261] 2.2 Preparation example: [Example 1] [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene-4,1-phenylene)]dimethanol (compound of formula (Ia) where X = -CHOH and A = 1,4-phenylene; compound 1 of Table A)

[0262] [ka] Racemic 1,1'-bi-2-naphthol (40 g, 140 mmol, 1.00 molar equivalent), 4-chloromethylbenzyl alcohol (50.32 g, 321 mmol, 2.3 molar equivalent), and K2CO3 (57.92 g, 419 mmol, 3 molar equivalent) were mixed with acetone (500 mL). KI (2.3 g, 13.9 mmol, 0.1 molar equivalent) was added to the mixture, which was then stirred at 60 °C until TLC control (cyclohexane / ethyl acetate 1:1) showed complete conversion. The reaction mixture was hot filtered through celite to remove inorganic salts, and then the solvent was completely removed under reduced pressure. The crude product thus obtained was recrystallized from toluene / ethyl acetate (100 mL / 7.5 mL). The resulting crystals were recrystallized again from toluene / ethyl acetate (100 mL / 7.5 mL) (before the crystallization began, the solution was treated with activated carbon (5 g, Norit DX Ultra)) to give the title compound as a white solid (52.7 g, 100 mmol, 71% yield) with a chemical purity of 98.3%. Melting point = 138~140℃. 1 H-NMR (80 MHz, CDCl3, ppm): δ = 8.03-7.74 (m, 4H), 7.50-7.11 (m, 8H), 7.09-6.78 (s, 8H), 5.04 (s, 4H), 4.51 (d, J = 4.5 Hz, 4H), 1.95 (t, J = 4.5 Hz, 2H).

[0263] [Example 2] Dimethyl 4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]dibenzoate (compound of formula (Ia) where X = -C(O)OCH3 and A = 1,4-phenylene; compound 193 in Table A)

[0264] [ka] Racemic 1,1'-bi-2-naphthol (11 g, 38.4 mmol, 1.00 molar equivalents), methyl-(4-chloromethyl)benzoate (16.2 g, 87.7 mmol, 2.3 molar equivalents), and K2CO3 (15.93 g, 115 mmol, 3 molar equivalents) were mixed with acetone (300 mL). The mixture was stirred at 60 °C until TLC control (cyclohexane / ethyl acetate 2:1) indicated complete conversion. The reaction mixture was filtered through celite to remove inorganic salts, and then the solvent was removed under reduced pressure. The crude product was recrystallized from ethyl acetate to give the title compound as a white solid (8.9 g, 15.3 mmol, 39.8% yield) with a chemical purity of 96.2%. Melting point = 164~166℃. 1 H-NMR (80 MHz, CDCl3, ppm): δ = 8.05-7.62 (m, 8H), 7.51-7.12 (m, 8H), 6.94 (d, J = 8.2 Hz, 4H), 5.07 (s, 4H), 3.86 (s, 6H).

[0265] Example 3a 2,2'-bis[(4-bromophenyl)methoxy]-1,1'-binaphthalene

[0266] [ka] To a mixture of racemic 1,1'-bi-2-naphthol (100 g, 349 mmol, 1.00 molar equivalents) and K2CO3 (120.7 g, 873 mmol, 2.5 molar equivalents) in acetone (900 mL) was added 4-bromobenzyl bromide (187.7 g, 751 mmol, 2.15 molar equivalents). The reaction mixture was stirred at 60 °C until TLC control (cyclohexane / ethyl acetate 2:1) indicated complete conversion. The solution was filtered through celite to remove inorganic salts, and then the acetone was removed under reduced pressure. The crude product was recrystallized from ethyl acetate to give the title compound as a white solid (181 g, 289.9 mmol, 83% yield) with a chemical purity of 99.9%. Melting point = 122-124°C. 1 H-NMR (80 MHz, CDCl3, ppm): δ = 8.05-7.78 (m, 4H), 7.49-7.06 (m, 12H), 6.74 (d, J = 8.4 Hz, 4H), 4.96 (s, 4H).

[0267] Example 3b [[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene[1,1'-biphenyl]-4',4-diyl)]dimethanol (compound of formula (Ia) where X = -CHOH and A = 4,4'-biphenylylene; compound 18 of Table A)

[0268] [ka] To a mixture of racemic 2,2'-bis[(4-bromophenyl)methoxy]-1,1'-binaphthalene (25 g, 40 mmol, 1.00 molar equivalent) and [4-(hydroxymethyl)phenyl]boronic acid (18 g, 118.46 mmol, 2.96 molar equivalent) in THF (500 mL) was added aqueous KCO (2 M, 350 mL). A mixture of palladium(II) acetate (90 mg, 0.4 mmol) and tris(orthotolyl)phosphine (488 mg, 1.6 mmol) was then added to the reaction mixture, which was then stirred under reflux until TLC control (cyclohexane / ethyl acetate 1:1) showed complete conversion. After cooling to ambient temperature, the phases were separated, the aqueous phase was extracted with THF (100 mL), and the combined organic phases were washed twice with a mixture of aqueous NaOH (10 wt %, 100 mL), saturated aqueous NH4Cl (20 mL), and aqueous HCl (3 M, 50 mL), and finally saturated aqueous NH4Cl (50 mL). The THF solution was treated with activated carbon (5 g, Norit DX Ultra) and Na2SO4 (50 g) at 55 °C for 1 h, then cooled to ambient temperature and filtered through celite and cellulose. The solvent was removed in vacuo, and the crude product was dissolved in 8 times its weight in THF. It was then precipitated by adding 2 times its volume of cyclohexane. The resulting solid was filtered off by suction filtration and washed twice with 50 mL of a 1:1 mixture of THF and cyclohexane. The product was dried in vacuo to give the title compound as a white solid (21.8 g, 32.1 mmol, 80.3% yield) with a chemical purity of 95.8%. Melting point = 235-240°C (decomposition). 1 H NMR (80 MHz, DMSO-d6, ppm): δ = 8.18-7.84 (m, 4H), 7.74-6.92 (m, 24H), 5.22 (s, 4H), 5.18 (t, J = 5.6 Hz, 2H), 4.50 (d, J = 5.6 Hz, 4H).

[0269] Example 4a [(6,6'-dibromo[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-4,1-phenylene)]dimethanol

[0270] [ka] Racemic 6,6'-dibromo[1,1'-binaphthalene]-2,2'-diol (100 g, 0.225 mol, 1.0 molar equivalent), 4-chloromethylbenzyl alcohol (81.1 g, 0.518 mol, 2.3 molar equivalent), and K2CO3 (93.36 g, 3.0 molar equivalent) were mixed with acetone (1000 mL). KI (0.5 g, 3 mmol, 0.013 molar equivalent) was added to the mixture, and the mixture was stirred at 60 °C until TLC control (cyclohexane / ethyl acetate 1:1) showed complete conversion. The reaction mixture was hot filtered through celite to remove inorganic salts, and then the solvent was completely removed under reduced pressure. The crude product thus obtained was washed twice with 500 mL of TBME and then recrystallized twice from toluene / ethyl acetate (500 mL / 50 mL) to give the title compound as a white solid (137.1 g, 0.177 mol, 78.7% yield) with a chemical purity of 97.6% in the form of a toluene solvate containing 1 molar equivalent of toluene. 1 H NMR (80 MHz, DMSO-d6, ppm): δ = 8.31-6.75 (m, 23H), 5.13 (s, 4H), 5.07 (t, J = 5.6 Hz, 2H), 4.39 (d, J = 5.6 Hz, 4H), 2.30 (s, 3H).

[0271] Example 4b [(6,6'-di-2-naphthyl-[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-4,1-phenylene)]dimethanol (X = -CHOH; A = 1,4-phenylene, R 0 = 2-naphthyl; Compound 8 of Table B)

[0272] [ka] One molar equivalent of toluene (56.69 g, 0.073 mol, 1.0 molar equivalent) and 2-naphthylboronic acid (30.16 g, 0.175 mol, 2.4 molar equivalents) in [(6,6'-dibromo[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-4,1-phenylene)]dimethanol was mixed with 500 mL of THF and 250 mL of 2 molar aqueous K2CO3 solution. To this mixture, palladium(II) acetate (0.2 g, 0.89 mmol, 0.012 molar equivalents) and tris(o-tolyl)phosphine (0.68 g, 2.23 mmol, 0.03 molar equivalents) were added. The reaction mixture was heated to reflux until TLC control (MeOH / water 3:1) indicated complete conversion. The reaction mixture was filtered hot through celite to remove impurities. The organic phase was then separated and washed with 20% (w / w) aqueous NaOH (2 x 100 mL), saturated aqueous NH4Cl (100 mL), 4 molar aqueous HCl (100 mL), and again saturated aqueous NH4Cl (100 mL). The resulting solution was dried over Na2SO4, filtered successively through Celite and cellulose, and then treated with activated carbon (5 g, Norit DX Ultra) at 55 °C for 1 hour. The solution was cooled to ambient temperature and filtered successively through Celite and cellulose, after which the solvent was removed under reduced pressure. The crude product thus obtained was recrystallized from toluene / ethyl acetate (600 mL, 10:1) (before the start of crystallization the solution was treated with activated carbon (5 g, Norit DX Ultra)) and then recrystallized twice from toluene / methanol (91 g and 35 g) to give the title compound as a white solid (20.7 g, 0.027 mol, 36.4% yield) with a chemical purity of 97.6% after drying at 60°C. Melting point: 188~191℃. 1 H NMR (80 MHz, DMSO-d6, ppm): δ = 8.53-7.12 (m, 24H), 7.07 (s, 8H), 5.19 (s, 4H), 5.07 (t, J = 5.6 Hz, 2H), 4.38 (d, J = 5.6 Hz, 4H).

[0273] [Example 5] [(6,6'-diphenyl-[1,1'-binaphthalene]-2,2'-diyl)bis(oxymethylene-4,1-phenylene)]dimethanol (X = -CHOH; A = 1,4-phenylene, R 0 = phenyl; Compound 1 of Table B)

[0274] [ka] 6,6'-Diphenyl[1,1'-binaphthalene]-2,2'-diol (50 g, 0.114 mol, 1.0 molar equivalent), 4-chloromethylbenzyl alcohol (39.28 g, 0.251 mol, 2.2 molar equivalent), and K2CO3 (47.28 g, 3.0 molar equivalent) were mixed with acetone (500 mL). KI (1 g, 6 mmol, 0.05 molar equivalent) was added to the mixture, and the mixture was stirred at 60 °C until TLC control (cyclohexane / ethyl acetate 1:1) showed complete conversion. The reaction mixture was hot filtered through Celite to remove inorganic salts, and then the solvent was completely removed under reduced pressure. The crude product thus obtained was recrystallized from toluene / ethyl acetate (232 mL / 19 mL) (before the crystallization began the solution was treated with activated carbon (4 g Norit DX Ultra)) and then recrystallized once more from toluene / ethyl acetate (174 mL / 14 mL) to give the title compound as a white solid (19.8 g, 0.029 mmol, 25.6% yield) with a chemical purity of 95.4%. Melting point = 170-171°C. 1 H NMR (80 MHz, CDCl3, ppm): δ = 8.17-7.30 (m, 20 H), 6.98 (s, 8H) 5.09 (s, 4H), 4.51 (d, J = 2.8 Hz, 2H), 2.03 (t, J = 2.8 Hz, 2H).

[0275] 2.3 Refractive index n of the monomer of formula (I) D : Table C below lists the refractive indexes of some monomers of formula (I) calculated using the software ACD / ChemSketch 2012 (Advanced Chemistry Development, Inc.). Individual monomers are identified in Table C by their respective registration numbers in Tables A and B. Furthermore, quantum chemical calculations have verified that all monomers included in Table C have no or only a very small absorption range in the visible light range and are therefore essentially colorless.

[0276] [Table 3-1]

[0277] [Table 3-2]

[0278] [Table 3-3]

[0279] 3. Preparation of polycarbonate resin from monomer of formula (I) 3.1 Analysis of resins prepared from monomers of formula (I):

[0280] Refractive index (n D ): Refractive index measurements were performed using specimens obtained by the general procedure for preparing homopolycarbonates described in Section 3.2 below, using a Rudolph Instruments J257 autorefractometer at 23°C and 589 nm.

[0281] Abbe number (v): The Abbe number was determined using the same approximately 3 mm thick sample used in the refractive index measurement method described above. Refractive index values ​​were measured using a Metricon 2010M Prism Coupler at a temperature of 23°C and wavelengths of 486 nm, 589 nm, and 656 nm. The Abbe number was then calculated using the following formula: v=(n D -1) / (n F -n C ) n D : Refractive index at wavelength 589 nm n C : Refractive index at wavelength 656 nm n F : Refractive index at wavelength 486 nm

[0282] Glass transition temperature (Tg): The glass transition temperature was measured by differential scanning calorimetry (DSC) using a 10°C / min heating program according to JIS K7121-1987. Differential scanning calorimetry device: X-DSC7000 manufactured by Hitachi High-Tech Science Corporation.

[0283] molecular weight The molecular weight distribution of the resin molecules, particularly the weight average molecular weight (Mw) of the resin, was measured by gel permeation chromatography (GPC) and calculated using the standard polystyrene conversion method. The following device, column, and measurement conditions were used: GPC device: HLC-8420GPC (Tosoh Corporation); Columns: three TSKgel SuperHM-M (Tosoh Corporation); One guard column, SuperHM-M (Tosoh Corporation), one TSKgel SuperH-RC (manufactured by Tosoh Corporation); Detection device: RI detection Standard polystyrene: PstQuick C (Tosoh Corporation) as a standard polystyrene kit; Eluent: tetrahydrofuran; Eluent flow rate: 0.6 ml / min; Column temperature: 40°C.

[0284] The number average molecular weight (Mn) value can be calculated using a method similar to that used to measure the Mw value described above. The weight average molecular weight (Mw) and number average molecular weight (Mn) converted to polystyrene were calculated using a previously prepared polystyrene standard curve. Specifically, a standard curve was prepared using a standard polystyrene ("PStQuick C" manufactured by Tosoh Corporation) with a known molecular weight. Furthermore, a calibration curve was obtained by plotting the elution time and molecular weight value of each peak based on the measured data of the standard polystyrene and performing a three-dimensional fit. The values ​​for Mw and Mn were calculated based on the following formula: Mw = Σ(Wi × Mi) ÷ Σ(Wi) Mn = Σ(Ni × Mi) ÷ Σ(Wi) In the formula, "i" represents the "i"th division point, "Wi" represents the molecular weight (g) of the polymer at the "i"th division point, "Ni" represents the number of polymer molecules at the "i"th division point, and "Mi" represents the molecular mass at the "i"th division point. The molecular mass (M) represents the value of the molecular mass of polystyrene at the corresponding elution time of the calibration curve.

[0285] Low molecular weight compound (CLWC) content The content of low molecular weight compounds is less than 1000 M by GPC analysis. W The area ratio of compounds with a value of 0.01 represents the area ratio of compounds with a value of 0.01. Therefore, the content of low molecular weight compounds was determined according to the following formula:

[0286]

number

[0287] GPC analysis of low molecular weight compounds is carried out as described above for determining the molecular weight of thermoplastic resins.

[0288] 3.2 Example of preparation of homopolycarbonate: General steps: 1.0 mmol of the monomer of formula (I), 214 mg (1.0 molar equivalent) of diphenyl carbonate, and 11 μl of 0.1 mM aqueous NaHCO3 were thoroughly mixed and then dried at 30 °C and 500 mbar for 30 minutes. Half of this mixture was then transferred to a test tube (diameter: 10 mm, length: 80 mm) and heated in an oil bath at 180-200 °C for 3 hours under a gentle argon flow. An overhead stirrer at a speed of approximately 35 rpm was used for mixing. The heating was then turned off, and the formed polymer was allowed to slowly cool to room temperature in the oil bath. The test tube was cut just above the polymer surface with a tube cutter, and the resulting specimen lens was released by striking the test tube section with a rubber mallet. The homopolycarbonates prepared by this procedure are listed in Table D below, along with their measured refractive indices and Abbe numbers.

[0289] [Table 4]

[0290] 3.3 Preparation example of copolycarbonate resin: [Example 6 (E6)] The materials used were 19.8339 g (0.0452 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF), 10.2092 g (0.0194 mol) of [[1,1′-binaphthalene]-2,2′-diylbis(oxymethylene-4,1-phenylene)]dimethanol obtained in Example 1 (i.e., the compound of formula (Ia) in which X = —CHOH and A = 1,4-phenylene), 14.2581 g (0.0666 mol) of diphenyl carbonate (DPC), and 0.5428 × 10 sodium bicarbonate. -4 g(0.6462×10 -6 The resulting mixture (100 mol) was placed in a 300-milliliter reactor equipped with a stirrer and a distillation device. The reactor was flushed with nitrogen and the internal pressure was set to 101.3 kPa.

[0291] The reactor was immersed in an oil bath at 200°C, and the transesterification reaction was then initiated. Stirring of the mixture was started 5 minutes after the start of the reaction, and 20 minutes later, the pressure was reduced from 101.3 kPa to 26.66 kPa over 10 minutes. During this reduced pressure, the mixture was heated to 210°C. It was then further heated to 220°C 60 minutes after the start of the reaction. From 80 minutes after the start of the reaction, the pressure was reduced to 20.00 kPa over 10 minutes. The reaction mixture was then heated to 240°C, and the pressure was reduced to 0 kPa, after which these conditions were maintained for 30 minutes. Finally, the pressure was increased to 101.3 kPa by introducing nitrogen into the reactor, yielding the desired polycarbonate resin.

[0292] The resulting polycarbonate resin had a refractive index of 1.6487, an Abbe number of 22.09, a Tg of 138° C., and a weight average molecular weight (Mw) of 35,067 in terms of polystyrene. The ratio of the diol compounds and the characteristics of the resulting resin are summarized in Table E below.

[0293] [ka]

[0294] Comparative example 1 (CE1): The process of Example 6 set forth above was repeated, except that the copolycarbonate resin was prepared using the same molar amount of 2,2-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE) as the diol component instead of the monomer of Example 1. The characteristics of the resulting resin are also summarized in Table E below.

[0295] Comparative Example 2 (CE2): The process of Example 6 set forth above was repeated, except that the polycarbonate resin was prepared using only BPEF as the diol component in an amount of 0.0646 mol instead of the mixture of monomers and BPEF in Example 1. The characteristics of the resulting resin are also summarized in Table E below.

[0296] [ka]

[0297] Table 5

Claims

1. Use of compounds of formula (I) as monomers for producing thermoplastic resins: 【Chemistry 1】 (In the formula, X １ and X ２ is -CH ２ OH and —C(O)OR ｘ are independently selected from R ｘ is hydrogen, phenyl, benzyl and C １ ~C ４ - selected from the group consisting of alkyl; A １ and A ２ represents a monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members and a monocyclic or polycyclic hetarylene having a total of 5 to 26 ring atoms, wherein 1, 2, 3, or 4 of the ring atoms of the hetarylene are selected from nitrogen, sulfur, and oxygen, and the remainder of the ring atoms of the hetarylene are carbon atoms, and the monocyclic or polycyclic arylene and the monocyclic or polycyclic hetarylene are unsubstituted or have 1, 2, 3, or 4 R Ａｒ independently selected from the group consisting of: R １ and R ２ is a halogen, C ２ ~C ３ -Alkynyl, CN, R, OR, CH ｓ R' ３－ｓ , N.R. ２ , C(O)R, and CH=CHR″; and when p+q>1, R １ and R ２ may be the same or different, and s, at each occurrence, is 0, 1, or 2; p and q are independently 0, 1, or 2; R Ａｒ is R, OR, CH ｔ R' ３－ｔ , N.R. ２ and CH=CHR″, R Ａｒ may be the same or different when present more than once on the same (hetaryl)arylene group, and t is 0, 1, or 2 at each occurrence; R is C １ ~C ４ selected from the group consisting of alkyl, phenyl, naphthyl, phenanthrenyl and triphenylenyl, wherein phenyl, naphthyl, phenanthrenyl and triphenylenyl are unsubstituted or substituted with 1, 2, 3 or 4 identical or different R''' groups; R' is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, and triphenylenyl, wherein phenyl, naphthyl, phenanthrenyl, and triphenylenyl are unsubstituted or substituted with 1, 2, 3, or 4 identical or different R''' groups; R" is selected from hydrogen, methyl, phenyl and naphthyl, wherein phenyl and naphthyl are unsubstituted or substituted with 1, 2, 3 or 4 identical or different R'" groups; R''' is phenyl, halogen, OCH ３ , C.H. ３ , N(CH ３ ) ２ and C(O)CH ３ (selected from the group consisting of:

2. A １ and A ２ are both unsubstituted phenylene, p and q are both 0, and X １ and X ２ Both are -CH ２ OH or -C(O)OR ｘ and R ｘ Compounds of formula (I) except for compounds of formula (I) wherein is hydrogen, methyl, or ethyl. 【Chemistry 2】 (In the formula, X １ and X ２ is -CH ２ OH and —C(O)OR ｘ are independently selected from R ｘ is hydrogen, phenyl, benzyl and C １ ~C ４ - selected from the group consisting of alkyl; A １ and A ２ represents a monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members and a monocyclic or polycyclic hetarylene having a total of 5 to 26 ring atoms, wherein 1, 2, 3, or 4 of the ring atoms of the hetarylene are selected from nitrogen, sulfur, and oxygen, and the remainder of the ring atoms of the hetarylene are carbon atoms, and the monocyclic or polycyclic arylene and the monocyclic or polycyclic hetarylene are unsubstituted or have 1, 2, 3, or 4 R Ａｒ independently selected from the group consisting of: R １ and R ２ is a halogen, C ２ ~C ３ -Alkynyl, CN, R, OR, CH ｓ R' ３－ｓ , N.R. ２ , C(O)R, and CH=CHR″; and when p+q>1, R １ and R ２ may be the same or different, and s, at each occurrence, is 0, 1, or 2; p and q are independently 0, 1, or 2; R Ａｒ is R, OR, CH ｔ R' ３－ｔ , N.R. ２ and CH=CHR″, R Ａｒ may be the same or different when present more than once on the same (hetaryl)aryl or (hetarylene)arylene group, and t is 0, 1, or 2 at each occurrence; R is C １ ~C ４ selected from the group consisting of alkyl, phenyl, naphthyl, phenanthrenyl and triphenylenyl, wherein phenyl, naphthyl, phenanthrenyl and triphenylenyl are unsubstituted or substituted with 1, 2, 3 or 4 identical or different R''' groups; R' is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, and triphenylenyl, wherein phenyl, naphthyl, phenanthrenyl, and triphenylenyl are unsubstituted or substituted with 1, 2, 3, or 4 identical or different R''' groups; R" is selected from hydrogen, methyl, phenyl and naphthyl, wherein phenyl and naphthyl are unsubstituted or substituted with 1, 2, 3 or 4 identical or different R'" groups; R''' is phenyl, halogen, OCH ３ , C.H. ３ , N(CH ３ ) ２ and C(O)CH ３ (selected from the group consisting of:

3. X １ and X ２ Both are -CH ２ 3. The use according to claim 1 or the compound according to claim 2, wherein R is OH.

4. X １ and X ２ Both are -C(O)OR ｘ and R ｘ is hydrogen, phenyl, benzyl and C １ ~C ４ - alkyl, in particular selected from the group consisting of hydrogen, methyl and ethyl, in particular hydrogen and methyl.

5. A １ and A ２ 5. The use or compound of claim 1, wherein at least one of comprises a first benzene ring and at least one further ring selected from benzene and 5- and 6-membered heterocyclic rings, wherein the further ring is fused to the first benzene ring or attached to the first benzene ring by a single bond.

6. A １ and A ２ phenylene, naphthylene, 1,2-dihydroacenaphthylene, biphenylylene, 1,1'-oxydiphenylene, 1,1'-thiodiphenylene, 9H-fluorenylene, 11H-benzo[a]fluorenylene, 11H-benzo[b]fluorenylene, 7H-benzo[c]fluorenylene, anthracylene, phenanthrylene, benzo[c]phenanthrylene, pyrenylene, chrysenylene, picenylene, triphenylenylene, furanylene, benzo[b]furanylene, dibenzo[b,d]furanylene, naphtho[1,2-b]furanylene, naphtho[2,3 -b]furanylene, naphtho[2,1-b]furanylene, benzo[b]naphtho[1,2-d]furanylene, benzo[b]naphtho[2,3-d]furanylene, benzo[b]naphtho[2,1-d]furanylene, benzo[1,2-b:4,3-b']difuranylene, benzo[1,2-b:6,5-b']difuranylene, benzo[1,2-b:5,4-b']difuranylene, benzo[1,2-b:4,5-b']difuranylene, 9H-xanthrene, tribenzo[b,d,f]oxepinylene, oxanthrene, 2H-naphtho[1,8-d,e][1,3]difuranylene Xynylene, phenoxathienylene, dinaphtho[2,3-b:2',3'-d]furanylene, oxanthrenylene, benzo[a]oxanthrenylene, benzo[b]oxanthrenylene, thienylene, benzo[b]thienylene, dibenzo[b,d]thienylene, naphtho[1,2-b]thienylene, naphtho[2,3-b]thienylene, naphtho[2,1-b]thienylene, benzo[b]naphtho[1,2-d]thienylene, benzo[b]naphtho[2,3-d]thienylene, benzo[b]naphtho[2,1-d]thienylene, benzo[1,2-b:4,3-b']di Thienylene, benzo[1,2-b:6,5-b']dithienylene, benzo[1,2-b:5,4-b']dithienylene, benzo[1,2-b:4,5-b']dithienylene, 9H-thioxanthrene, 6H-dibenzo[b,d]thiopyranylene, 1,4-benzodithiinylene, naphtho[1,2-b][1,4]dithiinylene, naphtho[2,3-b][1,4]dithiinylene, 9H-10-thia-anthracylene, thianthrenylene, benzo[a]thianthrenylene, benzo[b]thianthrenylene, dibenzo[a,c]thianthrenylene, dibenzo[a,h]thianthrenylene, dibenzo[a,i]thianthrenylene, dibenzo[a,j]thianthrenylene, dibenzo[b,i]thianthrenylene, 2H-naphtho[1,8-b,c]thienylene, dibenzo[b,d]thiepinylene, dibenzo[b,f]thiepinylene, 5H-phenanthro[4,5-b,c,d]thiopyranylene, tribenzo[b,d,f]thiepinylene, 2,5-dihydronaphtho[1,8-b,c:4,5-b',c']dithienylene, 2,6-dihydronaphtho[1,8-b,c:5,4-b',c']dithienylene, The use or compound according to any one of claims 1 to 4, wherein the thienylene is independently selected from the group consisting of tribenzo[a,c,i]thianthrenylene, benzo[b]naphtho[1,8-e,f][1,4]dithiepinylene, dinaphtho[2,3-b:2',3'-d]thienylene, 5H-phenanthro[1,10-b,c]thienylene, 7H-phenanthro[1,10-c,b]thienylene, dibenzo[d,d']benzo[1,2-b:4,5-b']dithienylene and dibenzo[d,d']benzo[1,2-b:5,4-b']dithienylene.

7. A １ and A ２ is independently selected from the group consisting of phenylene, naphthylene, biphenylylene, benzo[b]furanylene, dibenzo[b,d]furanylene, benzo[b]thienylene, dibenzo[b,d]thienylene, 9H-fluorenylene, oxanthrenylene, thianthrenylene, phenoxathienylene, 9H-xanthrene and 9H-thioxanthrene, preferably the group consisting of phenylene, naphthylene, biphenylylene, dibenzo[b,d]thienylene, 9H-fluorenylene, oxanthrenylene, thianthrenylene, phenoxathienylene, 9H-xanthrene and 9H-thioxanthrene, in particular the group consisting of phenylene, naphthylene, biphenylylene, dibenzo[b,d]thienylene and thianthrenylene.

8. A １ and A ２ However, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,4-naphthylene, 1,5-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 1,3-naphthylene, 3,1-naphthylene, 2,3-naphthylene, 1,2-naphthylene, 2,1-naphthylene, 4,4'-biphenylylene, 3,4'-biphenylylene, 3,3'-biphenylylene, 4,3'-biphenylylene 8. The use or compound of claim 7, wherein the aryl group is independently selected from the group consisting of 2,2'-biphenylylene, 4,2'-biphenylylene, 3,2'-biphenylylene, 2,4'-biphenylylene, 2,3'-biphenylylene, 2,8-dibenzo[b,d]thienylene, 4,6-dibenzo[b,d]thienylene, 2,8-thianthrenylene and 1,9-thianthrenylene.

9. A １ and A ２ and have the same meaning.

10. R １ and R ２ is independently selected from the group consisting of fluorine, CN, methyl, methoxy, phenyl, naphthyl and phenanthrenyl, in particular from the group consisting of phenyl and naphthyl.

11. R １ and R ２ and have the same meaning.

12. 12. The use or compound of any one of claims 1 to 11, wherein p and q are both 0.

13. Formula (I) is formula (Ia) (wherein X is X in any one of claims 1 to 4). １ and X ２ and A is as defined in any one of claims 1, 2 and 5 to 9 as A １ and A ２ 13. The use or compound according to any one of claims 1 to 12, wherein the compound is defined as 【Transformation 3】

14. 14. The use or compound according to claim 13, wherein X and A are as defined in row 1 of Table A: Table 1-1 Table 1-2 Table 1-3 Table 1-4 Table 1-5 Table 1-6

15. p and q are both 1, and R １ and R ２ 12. The use or compound of any one of claims 1 to 11, wherein: are attached to the 6- and 6'-positions of the binaphthyl moiety of formula (I), respectively.

16. Formula (I) is formula (Ib) (wherein X is X in any one of claims 1 to 4). １ and X ２ and A is as defined in any one of claims 1, 2 and 5 to 9 as A １ and A ２ is defined as R ０ is defined as R in any one of claims 1, 2, 10 and 11. １ and R ２ 16. The use or compound according to any one of claims 1 to 15, wherein the compound is defined as 【Chemistry 4】

17. X, A and R ０ is as defined in row 1 of Table B. Table 2

18. 18. The use according to any one of claims 1 and 3 to 17, wherein the thermoplastic resin is selected from the group consisting of polycarbonates, polyesters and polyester carbonates.

19. A thermoplastic resin comprising structural units represented by the following formula (II): 【Transformation 5】 (In the formula, # represents the point of attachment to the adjacent structural unit; X １ａ and X ２ａ is X １ or X ２ -OH or -OR ｘ groups with oxo (—O—) moieties, respectively, to form X １ and X ２ Derived from X １ , X ２ , A １ , A ２ , R １ , R ２ , p and q are as defined in any one of claims 1 to 12 and 15).

20. Formula (IIa) (wherein, X ａ is X in claim 19. １ａ and X ２ａ A is defined as in any one of claims 1, 2 and 5 to 9. １ and A ２ 20. The thermoplastic resin of claim 19, wherein the thermoplastic resin is of the formula: 【Transformation 6】

21. Formula (IIb) (wherein, X ａ is X in claim 19. １ａ and X ２ａ A is defined as in any one of claims 1, 2 and 5 to 9. １ and A ２ is defined as R ０ is defined as R in any one of claims 1, 2, 10 and 11. １ and R ２ 20. The thermoplastic resin of claim 19, wherein the thermoplastic resin is of the formula: 【Transformation 7】

22. The structural unit of formula (II) １ａ and X ２ａ are both -CH ２ The thermoplastic resin according to any one of claims 19 to 21, wherein the aryl group is aryl, ... 【Transformation 8】 (In the formula, # represents the point of attachment to the adjacent structural unit).

23. 23. The thermoplastic resin according to any one of claims 19 to 22, wherein the thermoplastic resin is selected from copolycarbonate resins, copolyestercarbonate resins and copolyester resins, which, in addition to the structural units of formula (II), also contain structural units of formula (V): #-O-R ｚ -A ３ -R ｚ -O-#- (V) (In the formula, # represents the point of attachment to the adjacent structural unit; A ３ is a polycyclic group having at least two benzene rings which may be joined by W and / or which may be directly fused to each other and / or which may be fused to a non-benzene-based carbocyclic ring and / or which may be fused to two non-benzene-based carbocyclic rings which are connected via a linker L; A ３ is unsubstituted or contains 1, 2 or 3 R ａａ Group (R ａａ is a halogen, C １ ~C ６ -Alkyl, C ５ ~C ６ -substituted with cycloalkyl, phenyl, naphthyl, 1,2-dihydroacenaphthylenyl, phenanthrenyl, pyrenyl, triphenylenyl, benzo[b]furanyl, dibenzo[b,d]furanyl, benzo[b]thienyl, dibenzo[b,d]thienyl and thianthrenyl; W is a single bond, O, C=O, S, S(O), SO ２ , C.H. ２ , CH-Ar, CAr ２ , CH(CH ３ ), C(CH ３ ) ２ and a group of formula (A'): 【Chemistry 9】 (In the formula, Q' is a single bond, O, C=O, or CH ２ , S or SO ２ represents; R ７ａ , R ７ｂ are each independently hydrogen, fluorine, CN, R, OR, CH ｖ R' ３－ｖ , N.R. ２ , C(O)R and C(O)NH ２ wherein R and R′ are as defined in claim 1 and v is 0, 1 or 2; * represents the point of attachment to the benzene ring); L is a single bond, C １ ~C ４ - alkylene, C ４ ~C ７ -cycloalkylene, C ４ ~C ７ -cycloalkylenedimethylene, phenylenedimethylene, and L is unsubstituted or selected from one or two R Ｌ Group (R Ｌ is C １ ~C ４ -Alkyl, halogen, C １ ~C ４ -haloalkyl, C ４ ~C ７ -substituted with aryl, ... Ar is selected from the group consisting of monocyclic or polycyclic aryl having 6 to 26 carbon atoms as ring atoms and monocyclic or polycyclic hetaryl having a total of 5 to 26 ring atoms, wherein 1, 2, 3, or 4 of the ring atoms of the hetaryl are selected from nitrogen, sulfur, and oxygen, and the remainder of the ring atoms of the hetaryl are carbon atoms; Ar is unsubstituted or contains 1, 2, or 3 R ａｂ Group (R ａｂ is halogen, phenyl and C １ ~C ４ -substituted with (selected from the group consisting of -alkyl); R ｚ is a single bond, Alk ３ , O-Alk ４ -, O-Alk ４ -[O-Alk ４ -] ｗ - or O-Alk ５ -C(O)- (O is A ３ ) and w is an integer from 1 to 10; Alk ３ is C １ ~C ４ -alkanediyl; Alk ４ is C ２ ~C ４ -alkanediyl; Alk ５ is C １ ~C ４ -alkanediyl).

24. The thermoplastic resin according to claim 23, wherein the structural unit of formula V is represented by one of the following formulas V-1 to V-8: 【Chemistry 10】 (In the formula, a and b are 0, 1, 2 or 3, in particular 0 or 1; a' and b' are 0, 1, 2 or 3, in particular 0 or 1; c and d are 0, 1, 2, 3, 4 or 5, in particular 0 or 1; e and f are 0, 1, 2, 3, 4 or 5, in particular 0 or 1; W' is S, S(O), SO ２ , O, single bond, CH ２ , CH(CH ３ ) or C(CH ３ ) ２ , especially S, S(O), SO ２ or C(CH ３ ) ２ and R ｚ , R ａａ , R ａｂ , R ７ａ , R ７ｂ and L is as defined for formula (V).

25. 25. Thermoplastic resin according to claim 23 or 24, wherein the molar ratio of the structural units of formula (II) is 1 to 99 mol %, preferably 10 to 99 mol %, in particular 15 to 97 mol %, based on the total molar amount of the structural units of formula (II) and formula (V), and the molar ratio of the structural units of formula (V) is 1 to 99 mol %, preferably 1 to 90 mol %, in particular 3 to 85 mol %, based on the total molar amount of the structural units of formula (II) and formula (V).

26. 26. The thermoplastic resin of any one of claims 23 to 25, having a refractive index of 1.640 or greater.

27. 27. The thermoplastic resin of any one of claims 23 to 26, having an Abbe number of 24 or less.

28. 28. The thermoplastic resin according to any one of claims 23 to 27, having a glass transition temperature (Tg) of 90 to 185°C.

29. 29. The thermoplastic resin of any one of claims 23 to 28, having a weight average molecular weight of 10,000 to 50,000, as determined by gel permeation chromatography compared to polystyrene standards.

30. 30. The thermoplastic resin of any one of claims 23 to 29, comprising no more than 9 wt% of low molecular weight compounds having a molecular weight of less than 1000, based on the total weight of the thermoplastic resin.

31. 31. The thermoplastic resin of any one of claims 23 to 30, selected from the group consisting of polycarbonates, polyesters, and polyestercarbonates.

32. 32. An optical device made from a thermoplastic resin as defined in any one of claims 19 to 31.

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