Oligomeric binaphthyl compounds and thermoplastic resins

Abstract

The present invention relates to oligomeric binaphthyl compounds of formula (I) which have advantageous optical and mechanical properties and are suitable as monomers for the preparation of thermoplastic resins, such as polycarbonate resins, which can be used in the manufacture of optical elements. [Formula 1] TIFF2025515401000090.tif4273, X 1 and X 2 is hydrogen, -Alk 1 -OH, -CH2-A 2 -CH2-OH, -Alk 2 -C(O)OR x , -CH2-A 2 -C(O)OR x and -C(O)-A 2 -C(O)OR x (R x is independently selected from the group consisting of hydrogen, phenyl, benzyl and C1-C4-alkyl; Y 1 and Y 2 -CH2-, -CHAr Y - and -CH(CHAr Y )-independently selected from; A 1 is, for example, a single bond, -CH2-, -CHAr A -, -CH(CHAr A )-, -C(CHAr A )2-, the moiety of formula (A) is a monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members or a monocyclic or polycyclic hetaryl having a total of 5 to 26 ring atoms, or the moiety -Y of formula (I) is 1 -A 1 -Y 2 - is -CH2- or -CHAr Y -, n is 1, 2 or 3; m, p, q and r are independently 0, 1 or 2; R 1 , R 2 , R 3 and R 4 is halogen, C2-C3-alkynyl, CN, R, OR, CH s R' 3-s , NR2, C(O)R, and CH=CHR″; R 1 , R2 , R 3 or R 4 If two or more of 1 , R 2 , R 3 or R 4 may be the same or different, and s is 0, 1, or 2 for each occurrence.

Description

[Technical field]

[0001] The present invention relates to oligomeric binaphthyl compounds which have advantageous optical and mechanical properties and are suitable as monomers for the preparation of thermoplastic resins, such as polycarbonate resins, which can be used in the manufacture of optical elements. [Background technology]

[0002] Optical elements such as optical lenses made of optical resins instead of optical glass have the advantage that they can be mass-produced by injection molding. Recently, optical resins, especially transparent polycarbonate resins, are frequently used in the manufacture of camera lenses. In this regard, resins with a higher refractive index are highly desirable because they reduce the size and weight of the final product. Usually, when an optical material with a higher refractive index is used, a lens element with the same refractive power can be realized with a surface with a smaller curvature, and the amount of aberration generated by this surface can be reduced. As a result, weight reduction can be achieved by reducing the number of lenses, reducing the decentering sensitivity of the lens, and / or reducing the lens thickness.

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

[0004] [ka]

[0005] During the ceremony, Y is C 1 -C 4 -alkanediyl, particularly 1,2-ethanediyl. In terms of high refractive index, low Abbe number, high transparency, low birefringence and glass transition temperature suitable for injection molding, polycarbonate resins are said to have advantageous optical properties.

[0006] Copolycarbonates of monomers of formula (A) and 10,10-bis(4-hydroxyphenyl)anthrone monomers and their use for producing optical lenses are described in US Patent Application Publication No. 2016 / 0319069.

[0007] WO 2019 / 043060 describes a thermoplastic resin for producing an optical material, the thermoplastic resin comprising a polymerized compound of formula (B).

[0008] [ka]

[0009] During the ceremony, X is, for example, C 2 -C 4 -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.

[0010] However, as observed by the inventors of the present application, despite their multiple advantages, binaphthyl-derived monomers such as those of formula A and formula B above suffer from the drawback of forming a significant proportion of undesirable cyclic oligomers when used as monomers in the manufacture of thermoplastic resins, such as the manufacture of polyesters and polycarbonates. These cyclic oligomers can impair molecular weight build-up and / or impair the product properties of the resin, such as reduced mechanical strength, low glass transition temperature and / or optical properties. Unfortunately, these cyclic components can hardly be removed from the resin in an efficient manner. To reduce the formation of such cyclic compounds, it is typically necessary to polymerize a binaphthyl-containing monomer with a relatively large amount of comonomer.

[0011] Without wishing to be bound by theory, it is believed that the reason for the increased cyclic compound formation when using these monomers is related to these flexible linker units (see moieties -Y-OH and -X-OH in Formula A and Formula B) in combination with the spatial proximity of the 1 and 1' positions of the naphthyl residues to which they are attached. Summary of the Invention

[0012] 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 manufacture of thermoplastic resins, particularly polycarbonates, will result 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 properties and / or improved mechanical properties.

[0013] 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 thermoplastics, in particular for producing polyesters, in particular for producing polycarbonates.

[0014] [ka]

[0015] During the ceremony, X 1 and X 2 is hydrogen, -Alk 1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x , -CH 2 -A 2 -C(O)OR x and -C(O)-A 2 -C(O)OR x (R x is hydrogen, phenyl, benzyl and C 1 -C 4-alkyl); Y 1 and Y 2 -CH 2 -,-CHAr Y - and -CH(CH 2 Ar Y )-independently selected from; A 1 is a single bond, -CH 2 -,-CHAr A -, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -, the moiety of formula (A), monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetaryl having a total of 5 to 26 ring atoms, in which 1, 2, 3 or 4 of these ring atoms of the hetaryl are selected from nitrogen, sulfur and oxygen, and the remaining ring atoms of the hetaryl are carbon atoms. The monocyclic or polycyclic arylene and the monocyclic or polycyclic hetaryl are unsubstituted or have 1, 2, 3 or 4 R Ar a group having a aryl group;

[0016] [ka]

[0017] During the ceremony, Q is a single bond, O, C=O, or CH 2 , S or SO 2 represents; R 5a , R 5b are each independently hydrogen, fluorine, CN, R, OR, CH k R' 3-k , N.R. 2 , C(O)R and C(O)NH 2 (wherein k is 0, 1 or 2); * is Y 1 Or Y 2 represents the attachment point to; Alternatively, the moiety -Y of formula (I) 1 -A1 -Y 2 -HA-CH 2 -or- CHAr Y - may be n is 1, 2 or 3; R 1 , R 2 , R 3 and R 4 is a halogen, C 2 -C 3 -Alkynyl, CN, R, OR, CH s R' 3-s , N.R. 2 R is independently selected from the group consisting of C(O)R and CH=CHR″; 1 , R 2 , R 3 or R 4 If two or more of 1 , R 2 , R 3 or R 4 may be the same or different, and s, for each occurrence, is 0, 1 or 2; m, p, q and r are independently 0, 1 or 2; A 2 is selected from the group consisting of phenylene, naphthylene, and biphenylylene; Alk 1 is C 2 -C 4 -alkanediyl; Alk 2 is C 1 -C 4 -alkanediyl; Ar Y and Ar A is selected from the group consisting of monocyclic or polycyclic aryl having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetaryl having a total of 5 to 26 ring atoms, in which 1, 2, 3 or 4 of these ring atoms are selected from nitrogen, sulfur and oxygen, and the remaining hetaryl ring atoms are carbon atoms; Ar Y and Ar A is unsubstituted or 1, 2 or 3 R Ar is substituted with a group; R ArR, OR, CH t R' 3-t , N.R. 2 and CH=CHR″, wherein R is connected to the same aryl(hetaryl) or arylene(hetaryl) group. Ar when more than one occurs, they may be the same or different, and t, at each occurrence, is 0, 1, or 2; R is C 1 -C 4 - selected from the group consisting of 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 phenyl, OCH 3 , C.H. 3 , N(CH 3 ) 2 and C(O)CH 3 is selected from the group consisting of:

[0018] X 1 and X 2 Both are hydrogen or -CH 2 CH 2 -OH and Y 1 and Y 2 But both are CH 2 And A 1 is a single bond or CH 2 and n is 1, X 1 and X 2 are both hydrogen, and Y 1 and Y 2 But both are CH 2m, p, q and r are all 0; A 1The compounds of formula (I) are novel except for those compounds of formula (I) in which R is 1,2-phenylene, 1,3-phenylene, 1,6-pyrenylene, 4,4'-biphenylylene, 2,6-pyridinylene, 4,4''-meta-terphenylylene, 2,5-[1,3,4]-thiadiazolylene, 2,5-[1,3,4]-oxadiazolylene, 2,5-thienediyl-bis(4,1-phenylenemethylene), 9,9-diethyl-2,7-9H-fluorenylene, 10-methyl-3,7-phenothiazinylene or 10-ethyl-3,7-phenothiazinylene. These compounds are described in AR Abreu et al., Terahedron 2010, 66(3), 743-749;SC Jha et al., Syn-thetic Communications 2003, 33(6), 1005-1009;F. De Jong et al., Journal of the Chemical Society, Chemical Communications 1975, 14, 551-553;EP Kyba et al., Journal of Organic Chemistry 1977, 42(26), 4173-4184;DE 2414188 A1;AR Abreu et al., Journal of Molecular Catalysis A; Chemical 2010, 325(1-2), 91-97;G. Gao et al., European Journal of Organic Chemistry 2011, 2011(26), 5039-5046; German Patent Application No. 2539324; JP 2015-129266; H. Egami et al., Journal of the American Chemical Society 2018, 140(8), 2785-2788; F. Peixoto et al., Current Organic Synthesis 2014, 11(2), 301-309;AR Abreu et al., Chemistry Letters 2013, 42(1), 37-39;GW Gokel et al., Journal of the Chemical Society, Chemical Communications 1975, (11), 444-446;K. Takaishi et al., Journal of the Ameri-can Chemical Society 2020, 142(4), 1774-1779;HK Matsui et al., Bulletin of the Chemical Society of Japan 2000, 73(4), 991-997;K. Ogura, Tetrahedron Let-ters 1999, 40(51), 9065-9068;P. Rajakumar et al., Supramolecular Chemistry 2009, 21(8), 674-680;R. Kanagalatha et al., Asian Journal of Chemistry 2015, 27(12), 4373-4378;R. Sebastian et al. al., Journal of Heterocyclic Chemistry 2016, 53(3), 993-996; A. Thirunarayanan et al., RSC Advances 2014, 4(45), 23433-23439; and P. Rajakumar et al., Tetrahedron 2001, 57(48), 9749-9754. .

[0019] Thus, the second aspect relates to compounds of formula (I) which are novel, i.e. X 1 , X 2 , Y 1 , Y 2 and Ar 1 The combinations are as follows: X 1 and X 2 Both are hydrogen or -CH 2 CH 2 -OH and Y 1 and Y 2 But both are CH 2 And A 1 is a single bond or CH2 That is, Except for compounds of formula (I), And also n, m, p, q, r, X 1 , X 2 , Y 1 , Y 2 and Ar 1 The combinations are as follows: n is 1 and X 1 and X 2 are both hydrogen, and Y 1 and Y 2 But both are CH 2 m, p, q and r are all 0; A 1 is 1,2-phenylene, 1,3-phenylene, 1,6-pyrenylene, 4,4'-biphenylylene, 2,6-pyridinylene, 4,4''-meta-terphenylylene, 2,5-[1,3,4]-thiadiazolylene, 2,5-[1,3,4]-oxadiazolylene, 2,5-thienediyl-bis(4,1-phenylenemethylene), 9,9-diethyl-2,7-9H-fluorenylene, 10-methyl-3,7-phenothiazinylene or 10-ethyl-3,7-phenothiazinylene; relates to compounds of formula (I) excluding compounds of formula (I).

[0020] The third aspect relates to a thermoplastic resin containing polymerized units of the compound of formula (I), that is, a thermoplastic resin containing structural units represented by the following formula (III).

[0021] [ka]

[0022] During the ceremony, # represents the point of attachment to the adjacent structural unit; and X 1a and X 2a are, respectively, X 1 Or X 2 is hydrogen, by replacing the hydrogen with a single bond, or by 1 Or X 2 If is not hydrogen, then X1 Or X 2 -OH group or -OR x The X group of formula (I) is replaced with an oxo (-O-) unit. 1 Or X 2 Derived from, and X 1 , X 2 , Y 1 , Y 2 , A 1 , R 1 , R 2 , R 3 , R 4 , n, m, p, q and r are as defined above.

[0023] The invention further relates to an optical element made from a thermoplastic resin as defined above, in particular a polyester, especially a polycarbonate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0024] Compounds of formula (I) may have axial asymmetry due to restricted rotation of the bonds between the naphthalene units, and therefore compounds of formula (I) may have at least 2 (n+1) The compound may be present in the form of one of two stereoisomers or in the form of any mixture of these stereoisomers (n being a variable as shown in formula (I)). Specific examples of these mixtures include those having at least two n The present invention relates to the pure stereoisomers of the compounds of formula (I) as well as to any mixture of stereoisomers, including racemic and non-racemic mixtures of the two respective stereoisomers which together constitute the enantiomeric pair.

[0025] In the present invention, the term "C 1 -C 4 The term "alkanediyl group" is also referred to as an "alkylene group having 1, 2, 3 or 4 carbon atoms" and refers to a divalent saturated aliphatic hydrocarbon group having 1, 2, 3 or 4 carbon atoms. 1 -C 4 Examples of -alkanediyls are in particular methylene groups (CH 2 ), 1,2-ethanediyl (CH2 CH 2 ), 1,3-propanediyl (CH 2 CH 2 CH 2 ) and 1,4-butanediyl (CH 2 CH 2 CH 2 CH 2 ), but also branched chain 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.

[0026] In the present invention, the term "monocyclic aryl" refers in particular to a monovalent aromatic monocyclic group such as phenyl.

[0027] In the present invention, the term "monocyclic hetaryl" refers to a monovalent heteroaromatic monocyclic group, i.e., a heteroaromatic monocyclic ring attached to the remainder of the molecule by a single covalent bond. The ring atoms are part of a conjugated π-electron system, and the heteroaromatic monocyclic ring has 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 hetero 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.

[0028] In the present 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 remainder of the molecule by a single covalent bond. Polycyclic arenes are: (i) aromatic polycyclic hydrocarbons (i.e., fully unsaturated polycyclic hydrocarbons in which each carbon atom is part of a conjugated pi-electron system); (ii) polycyclic hydrocarbons 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 which are covalently bonded to each other or directly fused to each other and / or to a saturated or unsaturated 4-10 membered monocyclic or bicyclic hydrocarbon ring.

[0029] Monocyclic or polycyclic aryls have 6 to 26, often 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, in particular 6 to 20 carbon atoms, in particular 6, 10, 12, 13, 14, 16, 17 or 18 carbon atoms. Polycyclic aryls typically have 10 to 26, in particular 10 to 20 carbon atoms, in particular 10, 12, 13, 14, 16, 17 or 18 carbon atoms as ring atoms.

[0030] In the present specification, examples of polycyclic aryls having 2, 3 or 4 phenyl rings bonded to each other via single bonds include biphenylyl and terphenylyl. Examples of polycyclic aryls having 2, 3 or 4 phenyl rings directly fused to each other include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, triphenylenyl, chrysenyl and benzo[c]phenanthrenyl. Examples of polycyclic aryls having 2, 3 or 4 phenyl rings fused to a saturated or unsaturated 4-10 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 ... Examples of fluoranthrenyl include 9,10-dihydro-9,10[1',2']-benzenoanthracenyl, dibenzo[a,e][8]annulenyl, 9,9'-spirobi[9H-fluoren]yl, and spiro[1H-cyclobuta[de]naphthalene-1,9'-[9H]fluoren]yl.

[0031] Examples of the 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, and biphenylyl. 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']benzoanthracenyl, 9,9'-spirobi-9H-fluorenyl, and spiro[1H-cyclobuta[de]naphthalene-1,9'-[9H]fluorenyl]yl.

[0032] In the present invention, the term "monocyclic or polycyclic hetaryl" denotes a monovalent heteroaromatic monocyclic group or a monovalent heteroaromatic polycyclic group as defined herein, i.e., a polycyclic hetaryl group attached to the remainder 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 heteroaromatic monocycles as defined above, the aromatic rings of the polycyclic hetarene being covalently bonded to each other and / or directly fused to each other and / or fused to a saturated or unsaturated 4-10 membered monocyclic or bicyclic hydrocarbon ring; or (ii) the polycyclic hetaranes are at least one saturated or partially or completely unsaturated 5-, 6-, 7- or 8-membered heterocycle having one, two or three 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, dioxine, dithiin, dioxepin, dithiepin, dioxo-xine ... Heterocyclic polyhetaranes have at least one aromatic ring, e.g., 1, 2, 3, 4 or 5 aromatic rings selected from heterocyclic, dithiocyanine, and phenyl and heteroaromatic monocycles as defined above, at least one of which is directly fused to a saturated or partially unsaturated 5-8 membered heterocycle, and the aromatic rings of polycyclic hetarenes are bonded to each other by covalent bonds or are directly fused to each other and / or to a saturated or unsaturated 4-10 membered monocyclic or bicyclic hydrocarbon ring.

[0033] Monocyclic or polycyclic hetaryls have 5 to 26, often 5 to 24, especially 5 to 20 ring atoms, including 1, 2, 3 or 4 atoms selected from nitrogen, sulfur and oxygen atoms, the remaining ring atoms being carbon atoms. Polycyclic hetaryls generally have 9 to 26, often 9 to 24, especially 9 to 20 ring atoms, including 1, 2, 3 or 4 atoms selected from nitrogen, sulfur and oxygen atoms, the remaining ring atoms being carbon atoms.

[0034] Examples of polycyclic hetaryl include, but are not limited to, 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, phenthiazinyl, benzo[b][1,5]naphthyridinyl, cinnolinyl, 1,5-naphthyridinyl, 1,8-naphthyridinyl, phenylpyrrolyl, naphthylpyrrolyl, dipyridyl, phenylpyridyl, naphthylpyridyl, pyrido[4,3-b]indolyl aryl, pyrido[3,2-b]indolyl, 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, ben zo[b]naphtho[1,2-d]furanyl, 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]thio-pyranyl, 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-benzodithiynyl, naphtho[1,2-b][1,4]dithiynyl, 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, 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-hi]indolyl, benzo[g]quinoxalinyl, benzo[f]quinoxalinyl, and benzo[h]isoquinolinyl.

[0035] In the present invention, the term "monocyclic arylene" refers specifically to a divalent aromatic monocyclic group such as phenylene.

[0036] In the present 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 are part of a conjugated π-electron system, and the heteroaromatic monocyclic ring has 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 hetero 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.

[0037] In 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 linked to the two remaining parts of the molecule by two single covalent bonds. Polycyclic arenes are: (i) aromatic polycyclic hydrocarbons (i.e., fully unsaturated polycyclic hydrocarbons in which each carbon atom is part of a conjugated pi-electron system); (ii) polycyclic hydrocarbons 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 which are covalently bonded to each other or directly fused to each other and / or to a saturated or unsaturated 4-10 membered monocyclic or bicyclic hydrocarbon ring.

[0038] Monocyclic or polycyclic arylenes have 6 to 26, often 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, in particular 6 to 20 carbon atoms, in particular 6, 10, 12, 13, 14, 16, 17 or 18 carbon atoms. Polycyclic arylenes typically have 10 to 26, in particular 10 to 20 carbon atoms, in particular 10, 12, 13, 14, 16, 17 or 18 carbon atoms as ring atoms.

[0039] In this specification, examples of polycyclic arylenes having 2, 3 or 4 phenyl rings bonded to each other via single bonds include biphenylylene and terphenylylene. Examples of polycyclic arylenes having 2, 3 or 4 phenyl rings directly fused to each other include 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 4-10 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-tetrahydro Examples include phenanthrenylene, cyclopenta[fg]acenaphthylenylene, phenalenylene, fluoranthenylene, benzo[k]fluoranthenylene, perylenylene, 9,10-dihydro-9,10[1',2']-benzenoanthracenylene, dibenzo[a,e][8]annulenylene, 9,9'-spirobi[9H-fluoren]ylene, and spiro[1H-cyclobuta[de]naphthalene-1,9'-[9H]fluoren]ylene.

[0040] Examples of the monocyclic or polycyclic arylene 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, 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 anthracenylene, 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.

[0041] In the present invention, the term "monocyclic or polycyclic hetarylene" denotes a divalent heteroaromatic monocyclic group or a divalent heteroaromatic polycyclic group as defined herein, i.e., a polycyclic hetarene linked 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 heteroaromatic monocycles as defined above, the aromatic rings of the polycyclic hetarene being covalently bonded to each other and / or directly fused to each other and / or fused to a saturated or unsaturated 4-10 membered monocyclic or bicyclic hydrocarbon ring; or (ii) the polycyclic hetaranes are at least one saturated or partially or completely unsaturated 5-, 6-, 7- or 8-membered heterocycle having one, two or three 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, dioxine, dithiin, dioxepin, dithiepin, dioxo-xine ... Heterocyclic polyhetaranes have at least one aromatic ring, e.g., 1, 2, 3, 4 or 5 aromatic rings selected from heterocyclic, dithiocyanine, and phenyl and heteroaromatic monocycles as defined above, at least one of which is directly fused to a saturated or partially unsaturated 5-8 membered heterocycle, and the aromatic rings of polycyclic hetarenes are bonded to each other by covalent bonds or are directly fused to each other and / or to a saturated or unsaturated 4-10 membered monocyclic or bicyclic hydrocarbon ring.

[0042] Monocyclic or polycyclic hetaryl rings have 5 to 26, often 5 to 24, especially 5 to 20 ring atoms, including 1, 2, 3 or 4 atoms selected from nitrogen, sulfur and oxygen, the remaining ring atoms being carbon atoms. Polycyclic hetaryl rings generally have 9 to 26, often 9 to 24, especially 9 to 20 ring atoms, including 1, 2, 3 or 4 atoms selected from nitrogen, sulfur and oxygen, the remaining ring atoms being carbon atoms.

[0043] Examples of polycyclic hetarylenes include, but are not limited to, 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, thianthrenylene, indolylene (=1H-indolylene), Isoindolylene (=2H-isoindolylene), carbazolylene, indolizinylene, benzopyrazolylene, benzimidazolylene, benzoxazolylene, benzothiazolylene, 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, naphthyridinylene, Tylpyrrolylene, 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' ]bisthienylene, 1,4-benzodithienylene, naphtho[1,2-b][1,4]dithienylene, naphtho[2,3-b][1,4]dithienylene, 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]thiopyranylene, 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, Examples of the quinolylene include furo[2,3-g]quinolinylene, 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.

[0044] In the present invention, the suffix "-ylene" means, as is customary in the art, that the respective hetarene (arene) moiety is in its diradical form. Thus, the suffix "-ylene", e.g., phenylene or 1,4-phenylene, is used herein synonymously with the suffix "-diyl", e.g., phendiyl or phen-1,4-diyl.

[0045] In 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.

[0046] In the present invention, the term "optical element" refers to an element that is transparent to visible light and manipulates light rays, especially by refraction. Optical elements include, but are not limited to, prisms, lenses, optical films and combinations thereof, especially camera lenses and eyeglass lenses.

[0047] The following statements concerning preferred embodiments of the variables (substituents) of the compounds of formula (I) and of the structural units of formula (II) are valid on their own and, preferably, in combination with one another.

[0048] Furthermore, the following explanations regarding preferred embodiments of the variables are valid for compounds of formula (I) and structural units of formula (II) and, where applicable, for the uses according to the invention, on their own and preferably in combination with one another.

[0049] In formula (I) and similarly in formula (II), the variable X 1 , X 2 , Y 1 , Y 2 , R 1 , R 2 , R 3 , R 4 , A 1 , n, m, p, q and r, alone or preferably in any combination, preferably have the following meanings:

[0050] Hydrogen, -Alk1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x and -CH 2 -A 2 -C(O)OR x The variable X of formula (I) is independently selected from 1 and X 2 , therefore, -Alk 1 -O-, -CH 2 -A 2 -CH 2 -O-, -Alk 2 -C(O)O- and -CH 2 -A 2 Variable X of formula (II) is independently selected from -C(O)O- 1a and X 2a (Alk 1 , -Alk 2 , A 2 and R x has the meanings defined herein, in particular the preferred meanings).

[0051] In a preferred group (1) of embodiments, the variable X of formula (I) 1 and X 2 -Alk 1 -OH and -CH 2 -A 2 -CH 2 —OH, and therefore the variable X of formula (II) 1a and X 2a -Alk 1 -O- and -CH 2 -A 2 -CH 2 -O- is selected independently (Alk 1 is preferably 1,2-ethanediyl (CH 2 -CH 2 ), 1,3-propanediyl or 1,4-butanediyl, etc. 2 -C 4 -alkanediyl, in particular 1,2-ethanediyl, A 2is preferably selected from 1,4-phenylene, 1,3-phenylene, 2,6-naphthylene, 1,4-naphthylene, 1,5-naphthylene and 4,4'-biphenylylene). In this context, the variable X of formula (I) 1 and X 2 or the variable X of formula (II) 1a and X 2a are also preferably identical to each other.

[0052] Thus, in a particularly preferred subgroup (1.1) of embodiments, the variable X of formula (I) 1 and X 2 is selected from 2-hydroxyethyl (i.e. 2-(HO)-ethyl), hydroxymethyl-phenyl-methyl (i.e. HO-methyl-phenyl-methyl), hydroxymethyl-naphthyl-methyl and hydroxymethyl-biphenylyl-methyl, in particular from 2-hydroxyethyl, 4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, 4-(hydroxymethyl)-1-naphthyl)methyl, (5-(hydroxymethyl)-1-naphthyl)methyl, (6-(hydroxymethyl)-2-naphthyl)methyl and 4'-(hydroxymethyl)-1,1'-biphenylyl-4-methyl, in particular from 2-hydroxyethyl, 4-(hydroxymethyl)phenyl)methyl and (3-(hydroxymethyl)phenyl)methyl. Correspondingly, in a particularly preferred group (1.1) of this embodiment, the variable X of formula (II) 1a and X 2a is selected from 2(-O)-ethyl, -O-methyl-phenyl-methyl and -O-methyl-naphthyl-methyl, in particular from 2(-O)-ethyl, (4(-O-methyl)phenyl)methyl, (3(-O-methyl)phenyl)methyl, (4(-O-methyl)-1-naphthyl)methyl, (5(-O-methyl)-1-naphthyl)methyl, (6(-O-methyl)-2-naphthyl)methyl and 4'(-O-methyl)-1,1'-biphenylyl-4-methyl, in particular from 2(-O)-ethyl, (4(-O-methyl)phenyl)methyl and (3(-O-methyl)phenyl)methyl, (4(-O-methyl)-1-naphthyl)methyl.

[0053] In a particular subgroup (1′) of embodiments, the variable X of formula (I) 1 and X 2 have the same meaning, and similarly, the variable X in formula (II) 1a and X 2a have the same meaning and are selected from the meanings defined in groups (1) and (1.1) of the embodiments.

[0054] In another group (2) of embodiments, the variable X of formulas (I) and (II) 1 and X 2 are both hydrogen, and therefore the variable X in formula (II) 1a and X 2a Both are single bonds.

[0055] In a preferred group (3) of embodiments, the variable X of formula (I) 1 and X 2 -Alk 2 -C(O)OR x and -CH 2 -A 2 -C(O)OR x and thus the variable X of formula (II) is independently selected from 1a and X 2a -Alk 2 -C(O)O- and -CH 2 -A 2 -C(O)O- (Alk 2 is preferably methylene or 1,2-ethanediyl (CH 2 -CH 2 ) and other linear C 1 -C 4 -alkanediyl, in particular methylene; A 2 is preferably selected from 1,4-phenylene, 1,3-phenylene, 2,6-naphthylene, 1,5-naphthylene and 1,4-naphthylene, R x is preferably hydrogen or C 1 -C 4 -alkyl, in particular methyl). In this context, the variable X 1 and X 2 or variable part X1a and X 2a are also preferably identical to each other.

[0056] Thus, in a particularly preferred subgroup (3.1) of embodiments, the variable X of formula (I) 1 and X 2 is methoxycarbonyl-methyl (i.e., CH 3 OC(O)-methyl), methoxycarbonyl-phenyl-methyl (i.e., CH 3 OC(O)-phenyl-methyl) and methoxycarbonyl-naphthyl-methyl, in particular from methoxycarbonyl-methyl, (4-(methoxycarbonyl)phenyl)methyl, (3-(methoxycarbonyl)phenyl)methyl, (4-(methoxycarbonyl)-1-naphthyl)methyl, (5-(methoxycarbonyl)-1-naphthyl)methyl and (6-(methoxycarbonyl)-2-naphthyl)methyl, in particular from methoxycarbonyl-methyl, (4-(methoxycarbonyl)phenyl)methyl and (3-(methoxycarbonyl)phenyl)methyl. Correspondingly, in a particularly preferred group (3.1) of this embodiment, the variable X of formula (II) is 1a and X 2a is selected from -OC(O)-methyl, -OC(O)-phenyl-methyl and -OC(O)-naphthyl-methyl, in particular from -OC(O)-methyl, (4(-OC(O)-phenyl)methyl, (3(-OC(O)-phenyl)methyl, (4-(-OC(O)-)-1-naphthyl)methyl, (5-(-OC(O)-)-1-naphthyl)methyl and (6-(-OC(O)-)-2-naphthyl)methyl, in particular from -OC(O)-methyl, (4(-OC(O)-phenyl)methyl and (3(-OC(O)-phenyl)methyl.

[0057] In a particular subgroup (3') of embodiments, the variable X of formula (I) 1 and X 2 have the same meaning, and similarly, the variable X in formula (II) 1a and X 2a have the same meaning and are selected from the meanings defined in groups (3) and (3.1) of the embodiments.

[0058] In a preferred group of embodiments (4), which is a combination of groups (1.1), (2) and (3.1), the variable X of formula (I) is 1 and X 2 from hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, hydroxymethyl-phenyl-methyl, hydroxymethyl-naphthyl-methyl, hydroxymethyl-biphenylyl-methyl, methoxycarbonyl-phenyl-methyl and methoxycarbonyl-naphthyl-methyl, in particular hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, (4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, (4-(hydroxymethyl)-1-naphthyl)methyl, (5-(hydroxymethyl)-1-naphthyl)methyl, (6-(hydroxymethyl)-2-naphthyl)methyl, 4'-(hydroxymethyl)-1,1'-biphenylyl-4-methyl, (4-(hydroxymethyl)-1,1'-biphenylyl-4-methyl, Correspondingly, in a preferred group (4) of this embodiment, the variable X of formula (II) is selected from among hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, (4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, (4-(methoxycarbonyl)-1-naphthyl)methyl, (5-(methoxycarbonyl)-1-naphthyl)methyl and (6-(methoxycarbonyl)-2-naphthyl)methyl, in particular from hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, (4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, (4-(methoxycarbonyl)phenyl)methyl and (3-(methoxycarbonyl)phenyl)methyl. 1a and X 2afrom the single bond, 2(-O)-ethyl, -OC(O)-methyl, -O-methyl-phenyl-methyl, -O-methyl-naphthyl-methyl, -OC(O)-phenyl-methyl and -OC(O)-naphthyl-methyl, in particular the single bond, 2(-O)-ethyl, -OC(O)-methyl, (4(-O-methyl)phenyl)methyl, (3(-O-methyl)phenyl)methyl, (4(-O-methyl)-1-naphthyl)methyl, (5(-O-methyl)-1-naphthyl)methyl, (6(-O-methyl)-2-naphthyl)methyl, (4(-OC(O)-phenyl)methyl, (3-(-OC(O) (-OC(O)-phenyl)methyl, (4-(-OC(O)-)-1-naphthyl)methyl, (5-(-OC(O)-)-1-naphthyl)methyl and (6-(methoxycarbonyl)-2-naphthyl)methyl, in particular from a single bond, 2(-O)-ethyl, -OC(O)-methyl, (4(-O-methyl)phenyl)methyl, (3(-O-methyl)phenyl)methyl, 4(-OC(O)-phenyl)methyl and (3-(-OC(O)-phenyl)methyl, in particular from a single bond, 2(-O)-ethyl, (4(-O-methyl)phenyl)methyl and (3(-O-methyl)phenyl)methyl.

[0059] In a particular subgroup (4') of embodiments, the variable X of formula (I) 1 and X 2 have the same meaning, and similarly, the variable X in formula (II) 1a and X 2a have the same meaning and are selected from the meanings defined in group (4) of embodiments.

[0060] Single bond, -CH 2 -,-CHAr A -, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -, monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetaryl having 5 to 26 atoms as ring members, in particular a single bond, -CH 2 -, -C(CH 2 ArA ) 2 -, monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetaryl having 5 to 26 atoms as ring members (monocyclic or polycyclic arylene and monocyclic or polycyclic hetaryl are unsubstituted or have 1, 2, 3 or 4 R Ar group, A , monocyclic or polycyclic arylene, monocyclic or polycyclic hetaryl, and R Ar has the meanings defined herein, in particular the meanings given herein as preferred. 1 is preferred.

[0061] In a preferred group (5) of embodiments, variable A of formulas (I) and (II) 1 is a single bond, -CH 2 -,-CHAr A -, -CH(CH 2 Ar A )- and -C(CH 2 Ar A ) 2 -, preferably a single bond, -CH 2 -, -CH(CH 2 Ar A )- and -C(CH 2 Ar A ) 2 -, especially -CH 2 - and -C(CH 2 Ar A ) 2 -, in particular -C(CH 2 Ar A ) 2 -(Ar Ahas one of the meanings defined herein, in particular the meanings described herein as preferred, in particular selected from phenyl, naphth-1-yl, naphth-2-yl, fluoren-2-yl, fluoren-9-yl, phenanthren-9-yl, dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl, dibenzo[b,d]thien-4-yl, dibenzo[b,d]furan-2-yl, dibenzo[b,d]furan-3-yl or dibenzo[b,d]furan-4-yl, thianthren-1-yl, thianthren-2-yl, oxantren-1-yl, oxantren-2-yl, 9H-xanthan-9-yl and 9H-thioxanthan-9-yl).

[0062] In a preferred subgroup (5.1) of embodiments, variable A of formula (I) and (II) 1 -C(CH 2 Ar A ) 2 -(Ar A is selected from phenyl, naphth-1-yl, naphth-2-yl and phenanthren-9-yl.

[0063] In a preferred group (6) of embodiments, variable A of formula (I) 1 are selected from the group consisting of monocyclic or polycyclic arylene having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetaryl having 5 to 26 atoms as ring members, in particular monocyclic or polycyclic aryl having 6 to 22, in particular 6 to 18, carbon atoms as ring members and monocyclic or polycyclic hetaryl having a total of 5 to 26 atoms as ring members, in particular polycyclic hetaryl having a total of 9 to 26 atoms as ring members, in which 1, 2, 3 or 4 of these atoms are nitrogen, oxygen or sulfur atoms, preferably 1, 2 or 3, for example 1 or 2 of these atoms are oxygen or sulfur atoms and the remaining of these atoms are carbon atoms (monocyclic or polycyclic aryl and monocyclic or polycyclic hetaryl are unsubstituted or have 1, 2, 3 or 4, in particular 1 or 2, R Ar group, R Arhas one of the meanings defined herein, particularly one of the meanings described as being preferred).

[0064] In a more preferred subgroup (6.1) of embodiments, A 1are phenylene, naphthylene, 1,2-dihydroacenaphthylene, biphenylylene, 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, dibenzo[1,4]dioxynylene, 2H-naphtho[1,8-d,e][1,3]dioxynylene, phenoxathiinylene, dinaphtho[1,8-d,e][1,3]dioxynylene, [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-benzodithienylene, naphtho[1,2-b][1,4]dithienylene, naphtho[2,3-b][1,4]dithienylene, 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]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, wherein the monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or are substituted with one or two R, Ar It has a group.

[0065] In a particularly preferred subgroup (6.2) of embodiments, A 1 is selected from phenylene, naphthylene, thienylene, furanylene, benzo[b]thienylene, benzo[b]furanylene, dibenzo[b,d]thienylene, dibenzo[b,d]furanylene, biphenylylene, 9H-fluorenylene, oxanthrene, phenoxathiynylene, thianthrenylene, 9H-xanthrene and 9H-thioxanthrene, wherein the monocyclic or polycyclic aryl and monocyclic and polycyclic hetaryl are unsubstituted or have one or two R Ar It has a group.

[0066] In a particularly preferred subgroup (6.3) of embodiments, A 1is selected from phenylene, naphthylene, dibenzo[b,d]thienylene, biphenylylene, 9H-fluorenylene, oxanthrene, phenoxathiynylene, thianthrenylene, 9H-xanthrene and 9H-thioxanthrene, in particular 1,4-phenylene, 1,2-phenylene, 1,3-phenylene, 2,3-naphthylene, 2,7 -naphthylene, 2,6-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,8-naphthylene, 4,6-dibenzo[b,d]thienylene, 2,8-dibenzo[b,d]thienylene, 3,7-dibenzo[b,d]thienylene, 3,3'-biphenylylene, 4,4'-biphenylylene, 9,9-9H-fluorenylene, 2,7-9H-fluorenylene, fluorenylene, 2,7-oxanthrene, 2,8-oxanthrene, 1,4-oxanthrene, 2,3-oxanthrene, 1,6-oxanthrene, 1,9-oxanthrene, 1,4-phenoxathiinylene, 3,7-phenoxathiinylene, 2,8-phenoxathiinylene, 3,8-phenoxathiinylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,4-thianthrenylene, 2,3-thianthrenylene, 1,6-thianthrenylene, 1,9-thianthrenylene, 9,9-9H-xanthrene and 9,9-9H-thioxanthrene, wherein the monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or have one or two R Ar It has a group.

[0067] A preferred subgroup (6') of the embodiment group (6) is 1 Among the compounds of the embodiment group (6') of the present invention, Y 1 Group and Y 2 Base is A 1 Preferred are compounds in which the phenylene ring is linked at the para position. These compounds are also referred to as para isomers of embodiment group (6'). Mixtures of the para isomers of the compounds of formula (I) of embodiment group (6') with the corresponding meta or ortho isomers are also preferred. Among the compounds of embodiment group (6'), A1 Compounds of formula (I) in which A is 1,4-phenylene and 1 Particularly preferred are mixtures thereof with one or both of its isomers, wherein is 1,2-phenylene or 1,3-phenylene.

[0068] In a particularly preferred subgroup (6.4) of embodiments, A 1 are 1,4-phenylene, 1,2-phenylene, 1,3-phenylene, 2,3-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,8-naphthylene, 4,6-dibenzo[b,d]thienylene, 2,8-dibenzo[b,d]thienylene, 3,3'-biphenylylene, 4,4'-biphenylylene, 9,9-9H-fluorenylene , 2,7-9H-fluorenylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,4-thianthrenylene, 2,3-thianthrenylene, 1,6-thianthrenylene, 1,9-thianthrenylene, 9,9-9H-xanthrene and 9,9-9H-thioxanthrene, wherein the monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or have one or two R Ar It has a group and is particularly unsubstituted.

[0069] -CH 2 -,-CHAr Y - and -CH(CH 2 Ar Y )-(Ar Yhas one of the meanings defined herein, in particular the meanings described herein as preferred, and is in particular selected from phenyl, naphth-1-yl, naphth-2-yl, fluoren-2-yl, fluoren-9-yl, phenanthren-9-yl, dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl, dibenzo[b,d]thien-4-yl, dibenzo[b,d]furan-2-yl, dibenzo[b,d]furan-3-yl or dibenzo[b,d]furan-4-yl, thianthren-1-yl, thianthren-2-yl, oxantren-1-yl, oxantren-2-yl, 9H-xanthan-9-yl and 9H-thioxanthan-9-yl, more in particular selected from phenyl, naphth-1-yl, naphth-2-yl and phenanthren-9-yl 1 and Y 2 As used herein, the variable Y 1 and Y 2 are particularly preferably identical to each other.

[0070] In a particular group (7) of embodiments, the variable Y of formulas (I) and (II) 1 and Y 2 Both are -CH 2 -It is.

[0071] In a particularly preferred subgroup (7′) of embodiment group (7), the variable moiety A 1 has the meaning given in one embodiment group (6), preferably in embodiment group (6.1), more preferably in embodiment group (6.2), in particular in embodiment group (6.3), in particular in embodiment group (6.4).

[0072] In alternative group (8) of embodiments, the moiety -Y of formula (I) and (II) 1 -A 1 -Y 2 -HA-CH 2 -or- CHAr Y -(Ar Yhas one of the meanings defined herein, in particular the meanings described herein as preferred).

[0073] In a preferred subgroup (8.1) of embodiments, the moiety -Y of formula (I) and (II) 1 -A 1 -Y 2 -HA-CH 2 -It is.

[0074] Preferably, the variable n in formulae (I) and (II) is 1 or 2.

[0075] In a particular group (9) of embodiments, variable n in formulae (I) and (II) is 1.

[0076] If present, the substituent R in formulae (I) and (II) 1 , R 2 , R 3 and R 4 has one of the meanings defined herein, in particular the meanings described herein as preferred. 1 , R 2 , R 3 and R 4 Preferably, when present, they all have the same meaning. 1 , R 2 , R 3 and R 4 are also preferred herein, if present, attached to the corresponding positions of their respective naphthyl units.

[0077] The variables m, p, q and r in formulae (I) and (II) are preferably 0, 1 or 2, more preferably 0 or 1 and in particular all have the same meaning.

[0078] In a particularly preferred group (10) of embodiments, the variables m, p, q and r in formulae (I) and (II) are all 0.

[0079] A person skilled in the art will recognize that in formulas (I) and (II), X given in one or more of groups (1), (1.1) and (1′) of embodiments 1 and X 2 means A according to one of the groups (5) and (5.1) of embodiments or according to one of the groups (6), (6.1), (6.2), (6.3) and (6.4) of embodiments. 1 The meaning of Y according to group (7) of the embodiment 1 and Y 2 It will be readily understood that the meaning of X given in embodiment group (2) in formulas (I) and (II) can be combined with the meaning of n according to embodiment group (9) and also with the meanings of m, p, q and r according to embodiment group (10). 1 and X 2 means A according to one of the groups (5) and (5.1) of embodiments or according to one of the groups (6), (6.1), (6.2), (6.3) and (6.4) of embodiments. 1 The meaning of Y according to group (7) of the embodiment 1 and Y 2 It will be understood that the meaning of n according to group (9) of the embodiment and also the meanings of m, p, q and r according to group (10) of the embodiment may be combined. A person skilled in the art will also understand that in formulas (I) and (II), the X given in one or more of groups (3), (3.1) and (3′) of the embodiment may be combined with the meaning of n according to group (9) of the embodiment and also with the meanings of m, p, q and r according to group (10). 1 and X 2 means A according to one of the groups (5) and (5.1) of embodiments or according to one of the groups (6), (6.1), (6.2), (6.3) and (6.4) of embodiments. 1 The meaning of Y according to group (7) of the embodiment 1 and Y 2 It will be understood that the meaning of n according to group (9) of the embodiment and also the meanings of m, p, q and r according to group (10) of the embodiment may be combined. Also, a person skilled in the art will understand that in formulas (I) and (II), the X given in one of groups (4) and (4') of the embodiment may be combined with the meaning of n according to group (9) of the embodiment and also with the meanings of m, p, q and r according to group (10) of the embodiment. 1 and X 2means A according to one of the groups (5) and (5.1) of embodiments or according to one of the groups (6), (6.1), (6.2), (6.3) and (6.4) of embodiments. 1 The meaning of Y according to group (7) of the embodiment 1 and Y 2 with the meaning of n according to group (9) of embodiments, and also with the meanings of m, p, q and r according to group (10) of embodiments.

[0080] Furthermore, the skilled person will also understand that in formulas (I) and (II), X according to one or more of the groups of embodiments (1), (1.1) and (1′), or according to the group of embodiments (2), or according to one or more of the groups of embodiments (3), (3.1) and (3′), or according to one of the groups (4) and (4′) 1 and X 2 The meaning of -Y is according to one of the groups (8) and (8.1) of the embodiments. 1 -A 1 -Y 2 It will be understood that the meaning of - may be combined with the meaning of n according to group (9) of embodiments and also with the meanings of m, p, q and r according to group (10) of embodiments.

[0081] In addition, unless otherwise specified, the variable Ar Y , Ar A , Q, R 1 , R 2 , R 3 , R 4 , R 5a , R 5b , R Ar , R, R', R'' and R''', either alone or preferably together with each other and the variable X 1 , X 1 , A 1 , A 2 , n, m, p, q, r, R x , Alk 1 and Alk 2 In combination with the meanings and preferred meanings of the formula (I) have the following meanings:

[0082] Ar Yand Ar A are preferably, independently of each other, monocyclic or polycyclic aryl having 6 to 18 carbon atoms as ring atoms and polycyclic hetaryl having a total of 9 to 16 ring atoms (one or two of these ring atoms of the hetaryl are sulfur atoms or oxygen atoms, and the remaining hetaryls are carbon atoms). The monocyclic or polycyclic aryl and polycyclic hetaryl are unsubstituted or substituted with one or two R Ar Group (R Ar has one of the meanings defined herein, in particular one of the meanings described as preferred, wherein unsubstituted Ar Y and Ar A The group is preferred.

[0083] More preferably, Ar Y and Ar Ais phenyl, naphthyl such as naphth-1-yl or naphth-2-yl, fluorenyl such as fluoren-1-yl, fluoren-2-yl, fluoren-3-yl, fluoren-4-yl or fluoren-9-yl, 11H-benzo[a]fluorenyl such as 11H-benzo[a]fluoren-7-yl, 11H-benzo[b]fluorenyl such as 11H-benzo[b]fluoren-1-yl, 7H-benzo[c]fluorenyl such as 7H-benzo[c]fluoren-5-yl or 7H-benzo[c]fluoren-10-yl, phenanthren-1-yl, phenanthren-2-yl, phenanthrenyl such as phenanthren-2-yl, phenanthren-3-yl, phenanthren-4-yl or phenanthren-9-yl; biphenylyl such as biphenyl-4-yl, biphenyl-3-yl or biphenyl-2-yl; benzo[c]phenanthrenyl such as benzo[c]phenanthren-1-yl, benzo[c]phenanthren-2-yl, benzo[c]phenanthren-3-yl, benzo[c]phenanthren-4-yl, benzo[c]phenanthren-5-yl or benzo[c]phenanthren-6-yl; pyren-1-yl, pyren-2-yl or pyrenyl such as pyren-4-yl; chrysenyl such as chrysen-1-yl, chrysen-2-yl, chrysen-3-yl, chrysen-4-yl, chrysen-5-yl, or chrysen-6-yl; triphenylenyl such as triphenylen-1-yl or triphenylen-2-yl; benzo[b]thienyl such as benzo[b]thien-2-yl, benzo[b]thien-3-yl, benzo[b]thien-4-yl, benzo[b]thien-5-yl, benzo[b]thien-6-yl, or benzo[b]thien-7-yl; dibenzo[b,d]thien-1-yl, dibenzo[b,d]thien-1-yl, dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl, benzo[b]thien-4-yl, benzo[b]thien-5-yl, benzo[b]thien-6-yl, or benzo[b]thien-7-yl; dibenzo[b,d]thienyl such as dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl or dibenzo[b,d]thien-4-yl; dibenzo[b,d]furanyl such as dibenzo[b,d]furan-1-yl, dibenzo[b,d]furan-2-yl, dibenzo[b,d]furan-3-yl or dibenzo[b,d]furan-4-yl; naphtho[1,2-b]thienyl such as naphtho[1,2-b]thien-5-yl; naphtho[2,3-b]thien-3-yl, naphtho[2,3-b]thien-4-yl or naphtho[2,3-b]thien-9-yl.3-b]thienyl, naphtho[2,1-b]thienyl such as naphtho[2,1-b]thien-2-yl or naphtho[2,1-b]thien-5-yl, thianthrenyl such as thianthren-1-yl or thianthren-2-yl, oxanthreneyl such as oxanthrene-1-yl or oxanthrene-2-yl, phenoxathiin-1-yl, phenoxathiin-2-yl, phenoxathiin-3-yl or phenoxathiinyl, such as phenoxathiin-4-yl; 9H-xanthyl, such as 9H-xant-1-yl, 9H-xant-2-yl, 9H-xant-3-yl or 9H-xant-9-yl; and 9H-thioxanthyl, such as 9H-thioxant-1-yl, 9H-thioxant-2-yl, 9H-thioxant-3-yl or 9H-thioxant-9-yl.

[0084] Even more preferably, Ar Y and Ar Aare phenyl, naphthyl, fluorenyl, phenanthrenyl, dibenzo[b,d]furanyl, dibenzo[b,d]thienyl, thianthrenyl, oxanthrenyl, phenoxathiinyl, 9H-xanthyl and 9H-thioxanthyl, e.g. phenyl, naphth-1-yl, naphth-2-yl, fluoren-2-yl, fluoren-3-yl, fluoren-9-yl, phenanthren-1-yl, phenanthren-2-yl, phenanthren-3-yl, phenanthren-4-yl, phenanthren-9-yl, dibenzo[b,d]thien-1-yl, dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl, dibenzo[b,d]thien-4-yl, dibenzo[b,d]thien-4-yl, dibenzo[b,d]thien-5-yl, dibenzo[b,d]thien-6-yl, dibenzo[b,d]thien-7-yl, dibenzo[b,d]thien-8-yl, dibenzo[b,d]thien-9-yl, dibenzo[b,d]thien-1-yl, dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl, dibenzo[b,d]thien-4 ...1-yl, dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl, dibenzo[b,d]th and independently selected from benzo[b,d]furan-1-yl, dibenzo[b,d]furan-2-yl, dibenzo[b,d]furan-3-yl or dibenzo[b,d]furan-4-yl, thianthren-1-yl, thianthren-2-yl, oxantren-1-yl, oxantren-2-yl, phenoxathiin-1-yl, phenoxathiin-2-yl, phenoxathiin-3-yl, phenoxathiin-4-yl, 9H-xant-1-yl, 9H-xant-2-yl, 9H-xant-3-yl, 9H-xant-9-yl, 9H-thioxant-1-yl, 9H-thioxant-2-yl, 9H-thioxant-3-yl and 9H-thioxant-9-yl.

[0085] In particular, Ar Y and Ar A is independently selected from phenyl, naphth-1-yl, naphth-2-yl, fluoren-2-yl, fluoren-9-yl, phenanthren-9-yl, dibenzo[b,d]thien-2-yl, dibenzo[b,d]thien-3-yl, dibenzo[b,d]thien-4-yl, dibenzo[b,d]furan-2-yl, dibenzo[b,d]furan-3-yl or dibenzo[b,d]furan-4-yl, thianthren-1-yl, thianthren-2-yl, oxantren-1-yl, oxantren-2-yl, 9H-xanthan-9-yl and 9H-thioxanthan-9-yl.

[0086] In particular, Ar Y and ArA is independently selected from phenyl, naphth-1-yl, naphth-2-yl, and phenanthren-9-yl.

[0087] Q is preferably a single bond, S, O, or SO 2 , in particular a single bond, S and O, in particular a single bond.

[0088] R 1 , R 2 , R 3 and R 4 are preferably, independently of one another, halogen, C 2 -C 3 -Alkynyl, CN, R, OR and CH t R' 3-t and more preferably selected from the group consisting of fluorine, CN, R and OR, where t is 1 or 2, in particular 2, and the variables R and R' each have one of the meanings, in particular the preferred meanings, defined herein. In particular, R 1 , R 2 , R 3 and R 4 The groups are independently selected from the group consisting of fluorine, CN, methyl, methoxy, phenyl, naphthyl and phenanthrenyl, in particular from the group consisting of fluorine, phenyl or naphthyl.

[0089] R 5a and R 5b are preferably, independently of one another, hydrogen, fluorine, CN, R, OR and CH k R' 3-k and more preferably selected from the group consisting of hydrogen, fluorine, CN, R and OR, where k is 1 or 2, in particular 2, and the variables R and R' each have one of the meanings defined herein, in particular the preferred meanings. In particular, R 5a and R 5b The groups are independently selected from the group consisting of hydrogen, fluorine, CN, methyl, methoxy, phenyl, naphthyl and phenanthrenyl, in particular from the group consisting of hydrogen, fluorine, phenyl or naphthyl.

[0090] R Aris preferably R, OR and CH t R' 3-t and more preferably selected 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 radicals are selected from the group consisting of methyl, methoxy, phenyl, naphthyl, phenanthrenyl and triphenylenyl, in particular phenyl, naphthyl or phenanthrenyl.

[0091] R is preferably selected from the group consisting of methyl, ethyl, phenyl, naphthyl, phenanthrenyl and triphenylenyl and is unsubstituted or substituted with one, two or three identical or different R'" groups, where R'" independently at each occurrence has one of the meanings defined herein, in particular the preferred meanings. More preferably, R is selected from the group consisting of phenyl, naphthyl and phenanthrenyl and is unsubstituted.

[0092] R' is preferably selected from the group consisting of phenyl, naphthyl, phenanthrenyl and triphenylenyl and is unsubstituted or substituted with one, two or three identical or different R'" groups, where R'" has, independently at each occurrence, one of the meanings defined herein, in particular the preferred meanings. More preferably, R' is selected from the group consisting of phenyl, naphthyl and phenanthrenyl and is unsubstituted.

[0093] R" is preferably selected from the group consisting of hydrogen, methyl, phenyl and naphthyl, which are unsubstituted or substituted with 1, 2 or 3, especially 1 or 2, identical or different R'" groups, where R'" independently at each occurrence has one of the meanings defined herein, especially the preferred meanings. More preferably, R" is unsubstituted phenyl or unsubstituted naphthyl.

[0094] R''' is preferably phenyl, OCH 3 and C.H. 3 is selected from the group consisting of:

[0095] In formula (I), Y 1 Group and Y 2 Both groups are -CH 2 -, the variable n is 1, the variables m, p, q and r are all 0, and X 1 Group and X 2 In a particular subgroup (7a) of the groups (7), (9) and (10) of embodiments in which the radicals have the same meaning, the compound of formula (I) is a compound of formula (Ia):

[0096] [ka]

[0097] In the formula, X is the same X 1 Group and X 2 represents a group, and A 1 , X 2 and X 2 have the meanings defined herein, in particular those stated as being preferred.

[0098] In subgroup (7a) of groups (7), (9) and (10) of embodiments, the structural unit of formula (II) is a structural unit of formula (IIa):

[0099] [ka]

[0100] In the formula, # represents a point of attachment to an adjacent structural unit, and X a are the same X 1a Group and X 2a represents a group, and variable A 1 , X 1a and X 2a have the meanings defined herein, in particular those stated as being preferred.

[0101] Preferably, the moiety X of formula (Ia) and the moiety X of formula (IIa) ais defined as one of the groups (1) and (1.1) of embodiments, as one of the groups (2) of embodiments or as one of the groups (3) and (3.1) of embodiments. More preferably, the moiety X of formula (Ia) and the moiety X of formula (IIa) are a is defined as in embodiment group (1.1), embodiment group (2) or embodiment group (3.1). The moiety X of formula (Ia) is therefore particularly represented here as hydrogen, 2-hydroxyethyl (i.e. 2-(HO)-ethyl), 4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, (4-(hydroxymethyl)-1-naphthyl)methyl, (5-(hydroxymethyl)-1-naphthyl)methyl, (6-(hydroxymethyl)-2-naphthyl)methyl, 4'-(hydroxymethyl)-1,1'-biphenylyl-4-methyl, methoxycarbonyl-methyl, (4-(methoxycarbonyl)phenyl)methyl, (3-(methoxycarbonyl)phenyl)methyl, (4-(methoxycarbonyl)phenyl)methyl, The moiety X of formula (IIa) is therefore preferably selected from the group consisting of hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, (4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, (4-(methoxycarbonyl)phenyl)methyl and (3-(methoxycarbonyl)phenyl)methyl, in particular hydrogen, 2-hydroxyethyl, (4-(hydroxymethyl)phenyl)methyl and (3-(hydroxymethyl)phenyl)methyl. Thus, the moiety X of formula (IIa) is preferably selected from the group consisting of hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, (4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl and (6-(methoxycarbonyl)-2-naphthyl)methyl. ais here in particular a single bond, 2(-O)-ethyl, (4(-O-methyl)phenyl)methyl, (3(-O-methyl)phenyl)methyl, (4(-O-methyl)-1-naphthyl)methyl, (5(-O-methyl)-1-naphthyl)methyl, (6(-O-methyl)-2-naphthyl)methyl, 4'(-O-methyl)-1,1'-biphenylyl-4-methyl, -OC(O)-methyl, (4(-OC(O)-phenyl)methyl, (3(-OC(O)-phenyl)methyl, (4-(-OC(O)-)-1-naphthyl)methyl, ( It is selected from the group consisting of 5-(-OC(O)-)-1-naphthyl)methyl and (6-(-OC(O)-)-2-naphthyl)methyl, in particular selected from a single bond, 2(-O)-ethyl, -OC(O)-methyl, (4(-O-methyl)phenyl)methyl, (3(-O-methyl)phenyl)methyl, 4(-OC(O)-phenyl)methyl and (3-(-OC(O)-phenyl)methyl, in particular selected from a single bond, 2(-O)-ethyl, (4(-O-methyl)phenyl)methyl and (3(-O-methyl)phenyl)methyl.

[0102] Preferred are compounds of formula (Ia) and structural units of formula (IIa) in which the moiety A 1is as defined in one of the groups of embodiments (5) and (5.1) or as defined in one of the groups of embodiments (6), (6.1), (6.2), (6.3) and (6.4). More preferably, the moiety X of formula (Ia) and formula (IIa) is as defined in the group of embodiments (5.1) or as defined in the group of embodiments (6.4). The moiety X of formula (Ia) is therefore particularly represented here by bisphenylmethanediyl, bis(naphth-1-yl)methanediyl, bis(naphth-2-yl)methanediyl, bis(phenanthren-9-yl)methanediyl, 1,4-phenylene, 1,2-phenylene, 1,3-phenylene, 2,3-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,8-naphthylene, 4,6-dibenzo[b,d] thienylene, 2,8-dibenzo[b,d]thienylene, 3,3'-biphenylylene, 4,4'-biphenylylene, 9,9-9H-fluorenylene, 2,7-9H-fluorenylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,4-thianthrenylene, 2,3-thianthrenylene, 1,6-thianthrenylene, 1,9-thianthrenylene, 9,9-9H-xanthrene and 9,9-9H-thioxanthrene.

[0103] Examples of specific subgroups (7a) are compounds of formula (Ia) and structural units of formula (IIa): a and variable part A 1 The combinations are as defined in any one of rows 1 to 266 of Table A below. a by replacing the hydrogen with a single bond when X is hydrogen, or by replacing X with -OH or -OR when X is not hydrogen. x It is derived from X of formula (Ia) by substituting a group with an oxo (-O-) unit, where X has one of the meanings defined herein, in particular one of the meanings described herein as being preferred.

[0104] [Table 1-1]

[0105]

Table 1-2

[0106]

Table 1-3

[0107]

Table 1-4

[0108]

Table 1-5

[0109]

Table 1-6

[0110]

Table 1-7

[0111]

Table 1-8

[0112]

Table 1-9

[0113]

Table 1-10

[0114]

Table 1-11

[0115] Among the compounds of formula (Ia) shown in Table A, particularly preferred are those in which the moiety X in the formula (Ia) is 2-hydroxyethyl (i.e. 2-HO-ethyl), and therefore in the structural unit of formula (IIa), the moiety X a is 2(-O)-ethyl. That is, particularly preferred is the following compound of formula (Ia): - 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[1,2-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[1,3-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[[1,1'-biphenyl]-4,4'-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[[1,1'-biphenyl]-3,3'-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[naphthalene-2,3-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[naphthalene-2,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[naphthalene-2,6-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[naphthalene-1,4-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[naphthalene-1,5-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[naphthalene-1,8-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[dibenzo[b,d]thien-4,6-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[dibenzo[b,d]thien-2,8-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[dibenzo[b,d]thien-3,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[thianthrene-2,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[thianthrene-2,8-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[thianthrene-1,4-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[thianthrene-2,3-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[thianthrene-1,6-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[thianthrene-1,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[9H-fluorene-9,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[9H-xanthene-9,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[9H-thioxanthene-9,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[9H-fluorene-2,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) - 2,2'-[{2,2-bis[(naphthalene-1-yl)methyl]propane-1,3-diyl}bis(oxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol)

[0116] Among the compounds of formula (Ia) shown in Table A, particularly preferred are those compounds of formula (Ia) in which the moiety X is (4-(hydroxymethyl)phenyl)methyl, and therefore in the structural unit of formula (IIa) the moiety X a is (4(-O-methyl)phenyl)methyl. That is, particularly preferred is the following compound of formula (Ia): - [1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [1,3-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [1,2-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [[1,1'-biphenyl]-4,4'-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [[1,1'-biphenyl]-3,3'-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Naphthalene-2,3-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Naphthalene-2,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Naphthalene-2,6-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Naphthalene-1,4-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Naphthalene-1,5-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Naphthalene-1,8-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Dibenzo[b,d]thien-4,6-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Dibenzo[b,d]thien-2,8-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Dibenzo[b,d]thien-3,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Thianthrene-2,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Thianthrene-2,8-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Thianthrene-1,4-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Thianthrene-2,3-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [thianthrene-1,6-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [Thianthrene-1,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [9H-fluorene-9,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [9H-fluorene-2,7-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [9H-Xanthene-9,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol - [9H-thioxanthene-9,9-diylbis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol

[0117] In formula (I), the moiety -Y 1 -A 1 -Y 2 -Ga-CH 2 -, the variable n is 1, the variables m, p, q and r are all 0, and X 1 Group and X 2In a particular subgroup (8.1a) of the groups (8.1), (9) and (10) of embodiments in which the radicals have the same meaning, the compounds of formula (I) are compounds of formula (Ib):

[0118] [ka]

[0119] In the formula, X is the same X 1 Group and X 2 Represents the group (X 1 and X 2 have the meanings defined herein, in particular those stated as being preferred).

[0120] In subgroup (8.1a) of groups (8.1), (9) and (10) of embodiments, the structural unit of formula (II) is a structural unit of formula (IIb):

[0121] [ka]

[0122] In the formula, # represents a point of attachment to an adjacent structural unit, and X a are the same X 1a Group and X 2a represents a group, and the variable X 1a and X 2a have the meanings defined herein, in particular those stated as being preferred.

[0123] Preferably, the moiety X of formula (Ib) and the moiety X of formula (IIb) a is defined as one of the groups (1) and (1.1) of embodiments, as one of the groups (2) of embodiments or as one of the groups (3) and (3.1) of embodiments. More preferably, the moiety X of formula (Ib) and the moiety X of formula (IIb) are a is defined as in embodiment group (1.1), embodiment group (2) or embodiment group (3.1). In particular, the moiety X of formula (Ib) and the moiety X of formula (IIb) ais defined as in group (1.1) of embodiments. Thus, the moiety X of formula (Ia) here is in particular selected from the group consisting of 2-hydroxyethyl (i.e. 2-(HO)-ethyl), (4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, (4-(hydroxymethyl)-1-naphthyl)methyl, (6-(hydroxymethyl)-2-naphthyl)methyl, 4'-(hydroxymethyl)-1,1'-biphenylyl-4-methyl, in particular both being 2-hydroxyethyl.

[0124] Thus, particularly preferred are those compounds of formula (Ib) in which both moieties X are 2-hydroxyethyl. Similarly, particularly preferred are those compounds of formula (IIb) in which both moieties X are a is 2(-O)-ethyl. That is, among the compounds of formula (Ib), a particularly preferred one is the compound 2,2'-[methylenebis(oxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol).

[0125] A compound of formula (Ia) 1 is a monocyclic or polycyclic arylene(hetaryl) moiety as defined herein, is preferably prepared in a manner similar to that shown in Reaction Scheme 1 below, where Ar represents said monocyclic or polycyclic arylene(hetaryl) moiety.

[0126] [ka]

[0127] 1,1'-bi-2-naphthol of formula (3) is reacted with a compound of formula (4) (wherein Z is a suitable leaving group such as a chloride, bromide, iodide, tosylate or mesitylate group) in the presence of a base, for example an oxobase such as an alkali carbonate such as potassium carbonate, to give a compound of formula (Ia) (wherein A 1 is a monocyclic or polycyclic arylene (hetaryl) moiety Ar) to obtain compound (5).

[0128] The compounds of formula (Ia) herein, wherein X is hydrogen and A 1 is the moiety -CH(CH 2 Ar A )- or -C(CH 2 Ar A ) 2 -) can be prepared, for example, by methods similar to those shown in Reaction Scheme 2 below.

[0129] [ka]

[0130] 1,1'-bi-2-naphthol of formula (3) is reacted in the presence of a base, for example an oxobase such as an alkali carbonate, for example potassium carbonate, to give a compound of formula (6), a is hydrogen or -CH 2 Ar A The resulting compound (7) is reacted with a compound of formula (Ia) (wherein A is a group) to obtain a compound of formula (7). 1 is the moiety -CH(CH 2 Ar A )- or -C(CH 2 Ar A ) 2 - and X is hydrogen. Suitable solvents for this reaction are polar aprotic organic solvents such as acetone.

[0131] A compound of formula (Ia) 1 is a single bond or -CH 2 -), and compounds of formula (I) 1 and X 2 are both hydrogen, and the moiety -Y 1 -A 1 -Y 2 -HA-CH 2-), i.e. compounds of formula (Ib) where X is hydrogen, can be prepared, for example, by a method similar to that shown in Reaction Scheme 3 below.

[0132] [ka]

[0133] The 1,1'-bi-2-naphthol of formula (3) is converted in the presence of a base, for example an oxobase such as an alkali carbonate or an alkali hydride, in particular an alkali hydride such as sodium hydride, to a compound of formula (8), 2 -, -CH 2 CH 2 -or-CH 2 CH 2 CH 2 -) to obtain a compound of formula (9). The obtained compound (9) is reacted with a compound of formula (Ia) or (Ib) (wherein X group is hydrogen and A of (Ia) is -). 1 is a single bond or the moiety -CH 2 Suitable solvents for this reaction are polar aprotic organic solvents such as, for example, dimethylformamide or, when an alkali carbonate is used as the base, for example, acetone.

[0134] A compound of formula (Ia) or (Ib) 1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x or -CH 2 -A 2 -C(O)OR x and moiety A of formula (Ia) 1 is a single bond, Ar, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -or-CH 2- (Ar is as defined in Scheme 1 above) can be prepared, for example, from compounds of formula (5), (7) or (9) above in a manner similar to that shown in Reaction Scheme 4 below.

[0135] [ka]

[0136] Compounds of formula (5), (7) or (9) can be converted to compounds of formula (10) in the presence of a base, for example an oxobase such as an alkali carbonate, to give compounds of formula (10), where Z is a suitable leaving group such as a chloride, bromide, iodide, tosylate or mesitylate group, and L is -Alk 1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x or -CH 2 -A 2 -C(O)OR x to give compound (11), where V is the moiety -CH 2 -Ar-CH 2 , -CH 2 -CH(CH 2 Ar A )-CH 2 -, -CH 2 -C(CH 2 Ar A ) 2 -CH 2 -, -CH 2 -, -CH 2 CH 2 -or-CH 2 CH 2 CH 2 -(Ar is as defined in Scheme 1 above). Thus, V is -CH 2 -, compound (11) is a compound (Ib) of the invention, in which X has one of the meanings given above for the L group, or a compound (Ia), in which the unit -Y 1 -A 1 -Y 2 -HA-CH 2-has one of the meanings given above for the unit V, which is different from -, and the X group has one of the meanings given above for the group L. Suitable solvents for the reaction of scheme 4 are polar aprotic organic solvents, such as, for example, dimethylformamide.

[0137] When the L group of the compound of formula (11) is hydroxyethyl, the transformation shown in Scheme 4 above is preferably carried out using 2-chloro-ethanol, or ethylene carbonate or ethylene oxide, especially ethylene carbonate, in place of the compound of formula (10). Such transformations using 2-chloro-ethanol, ethylene carbonate or ethylene oxide are carried out in the presence of a base, for example an oxobase such as an alkali carbonate, for example potassium carbonate.

[0138] As a preferred alternative to the transformations shown in Schemes 2 to 4 above, compounds of formula (Ia) or (Ib) 1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x or -CH 2 -A 2 -C(O)OR x , especially hydrogen, -Alk 1 -OH or -Alk 2 -C(O)OR x and moiety A of formula (Ia) 1 is a single bond, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -or-CH 2 -) can also be prepared, for example, by a method similar to the three or four step method shown in Reaction Scheme 5 below.

[0139] [ka]

[0140] In step a) of the process, only one of the two hydroxyl groups of the 1,1'-bi-2-naphthol of formula (3) is protected by introducing a protecting group, preferably an aryl-methyl group, in particular a benzyl group. The arylmethyl group, in particular a benzyl group, can be introduced by procedures well established in the art, for example by reacting the 1,1'-bi-naphthol (3) with typically 0.5 to 1.5 molar equivalents of benzyl bromide or benzyl chloride in the presence of a suitable base, such as an alkali metal carbonate, for example potassium carbonate, or an alkali metal hydride, for example sodium hydride. In this way, the monoprotected derivative of formula (12), in which PG is a suitable protecting group, such as a benzyl group, is obtained. In the following step b), the monoprotected 1,1′-bi-2-naphthol derivative (12) is converted in the presence of a base, for example an oxobase such as an alkali metal carbonate, for example potassium carbonate, or an alkali metal hydride, for example sodium hydride, to a compound of formula (13), in which Z is a suitable leaving group, for example a bromide, iodide, tosylate or mesitylate group and V′ is the moiety —CH 2 -CH(CH 2 Ar A )-CH 2 -, -CH 2 -C(CH 2 Ar A ) 2 -CH 2 -, -CH 2 -, -CH 2 CH 2 -or-CH 2 CH 2 CH 2 -) to give a compound of formula (14). In the subsequent step c), when the protecting group to be removed is benzyl, compound (14) can be deprotected to the corresponding diol of formula (15) using well-established procedures, such as catalytic hydrogenation. The resulting diol (15) can be reacted with a compound of formula (Ia) or (Ib) (wherein X is hydrogen and the moiety A of formula (Ia) is substituted with a phenyl group, such as phenyl, to give a compound of formula (15). 1 is a single bond, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -or-CH2 In optional step d), diol (15) is reacted with a compound of formula (Ia) or (Ib) where X is Alk instead of hydrogen. 1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x or -CH 2 -A 2 -C(O)OR x Especially -Alk 1 -OH or -Alk 2 -C(O)OR x or -CH 2 -A 2 -C(O)OR x Obviously, the conversion of diol (15) to compound (15') can be carried out, for example, by converting diol (15) into a compound of formula (10'), where Z has the same meaning as described for compound (10) and L' is -Alk 1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x or -CH 2 -A 2 -C(O)OR x , especially -Alk 1 -OH or -Alk 2 -C(O)OR x This reaction sequence can be achieved by reacting compounds of formula (Ia) and (Ib) (wherein X is hydrogen, -Alk 1 -OH or -Alk 2 -C(O)OR x and moiety A of formula (Ia) 1 is a single bond, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -or-CH 2 - is particularly useful for generating

[0141] As a further preferred alternative to the transformations shown in Schemes 2 to 4 above, compounds of formula (Ia) or (Ib) 2 -A 2 -CH 2 -OH or -CH 2 -A 2 -C(O)OR x and moiety A of formula (Ia) 1 is a single bond, Ar, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -or-CH 2 -, especially single bond, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -or-CH 2 - (wherein Ar is as defined in Scheme 1 above) can also be prepared, for example, by a method similar to the two-step method shown in Reaction Scheme 6 below.

[0142] [ka]

[0143] In step a) of the process, 1,1'-bi-2-naphthol of formula (3) is reacted in the presence of a base, for example an oxobase such as an alkali metal carbonate, for example potassium carbonate, with typically 0.5 to 1.5 molar equivalents of a compound of formula (10″), where Z is a suitable leaving group such as chloride, bromide, iodide, tosylate or mesitylate group and L″ is —CH 2 -A 2 -CH 2 -OH or -CH 2 -A 2 -C(O)OR xA suitable solvent for this reaction step is preferably selected from polar aprotic organic solvents such as, for example, dimethylformamide. In step b), compound (16) is reacted with a compound of formula (13'), where Z is a suitable leaving group such as a chloride, bromide, iodide, tosylate or mesitylate group and V'' is a moiety -CH, in the presence of a base, for example an oxobase such as an alkali carbonate such as potassium carbonate, to give a compound of formula (13'), where Z is a suitable leaving group such as a chloride, bromide, iodide, tosylate or mesitylate group and V'' is a moiety -CH 2 -Ar-CH 2 -, -CH 2 -CH(CH 2 Ar A )-CH 2 -, -CH 2 -C(CH 2 Ar A ) 2 -CH 2 -, -CH 2 -, -CH 2 CH 2 -or-CH 2 CH 2 CH 2 -, especially the moiety -CH 2 -CH(CH 2 Ar A )-CH 2 -, -CH 2 -C(CH 2 Ar A ) 2 -CH 2 -, -CH 2 -, -CH 2 CH 2 -or-CH 2 CH 2 CH 2 -). Suitable solvents for this reaction step are polar aprotic organic solvents such as acetone. The compound of formula (17) obtained by this reaction is particularly suitable for the case where X is -CH 2 -A 2 -CH 2 -OH or -CH 2 -A 2 -C(O)OR x The desired compound of formula (Ia) or (Ib) is characterized in that: 2 -A2 -CH 2 -OH or -CH 2 -A 2 -C(O)OR x In formula (Ia), the moiety A 1 is a single bond, -CH(CH 2 Ar A )-, -C(CH 2 Ar A ) 2 -or-CH 2 - is particularly useful for generating

[0144] As an alternative to the transformations depicted in Schemes 1-6 above, compounds of formula (Ia) or (Ib) where X is different from hydrogen can also be prepared in a similar manner to the four-step process depicted, for example, in Reaction Scheme 7 below.

[0145] [ka]

[0146] In step a) of the process, 1,1'-bi-2-naphthol of formula (3) is mono-protected by introducing a suitable protecting group PG' selected from hydroxyl protecting groups established in the art, such as 2-tetrahydropyranyl, benzyl, diphenylmethyl, trityl, allyl, propargyl or tert-butyloxycarbonyl (Boc), to obtain a compound of formula (18). As will be clear to the skilled artisan, the PG' group should be selected so as to be compatible with the subsequent reactions. For example, in step d), variable A of compound of formula (20) is 1When is the moiety Ar, as defined in Scheme 1 above, PG' should preferably be different from benzyl. The introduction of the protecting group PG′ in step a) and its removal in step c) to give the alcohol of formula (19) can be carried out analogously to the respective procedures established in the art (see, for example, EP 0915073; T. Song et al., Advanced Synthesis & Catalysis 2014, 356(8), 1708-1718; C. Dong et al., Catalysis Science & Technology 2015, 5(10), 4755-4759; L. Jin et al., Tetrahedron: Asymmetry 2008, 19(16), 1947-1953; AR Abreu et al., Tet-rahedron 2010, 66(3), 743-749; Y. Wang et al., Journal of the American Chemi-cal Society 2012, 134(7), 3342-3345;H. Hocke et al., Tetrahedron 2003, 59(5), 619-630;G. Ma et al., Angewandte Chemie, International Edition 2014, 53(44), 11818-11821;M. Nuruzzaman et al., Synlett 2008, 2, 207-212; and SC Jha et al., Synthetic Organic Chemistry 2003, 33:6, 1005-1009). -Alk 1 -OH, -CH 2 -A 2 -CH 2 -OH, -Alk 2 -C(O)OR x or -CH 2 -A 2 -C(O)OR x The intermediate step b) of the process for introducing the L" group, which is, for example, can be carried out analogously to the reaction of Scheme 4 above. The desired product of formula (20) (wherein the moiety V" is -CH 2-Ar-CH 2 -, -CH 2 -CH(CH 2 Ar A )-CH 2 -, -CH 2 -C(CH 2 Ar A ) 2 -CH 2 -, -CH 2 -, -CH 2 CH 2 -or-CH 2 CH 2 CH 2 The final step d) leading to -) can be carried out analogously to any one of the reactions of step b) of schemes 1 to 3 and schemes 5 and 6, for example.

[0147] The above reactions according to schemes 1-7, especially schemes 1-4, can also be applied to prepare compounds of formula (I) where the variable n is different from 1, i.e., 2 or 3, or to prepare mixtures of compounds of formula (I) differing only by the value of the variable n. As will be clear to the skilled person, by suitable adaptation of the reaction conditions of the reactions of schemes 1-7, especially 1-3, above, it is typically possible to shift these reactions to compounds of formula (I) where n is 2 or 3. This can be achieved, for example, by suitably increasing the quantitative ratio of the compounds of formulae (4), (6) and (8), respectively, to 1,1'-bi-2-naphthol (3) used in the reactions of schemes 1-3.

[0148] Compounds of formula (I) in which the naphthyl moiety is a substituent R 1 , R 2 , R 3 and / or R 4 has at least R 1 and R 2 are R 3 and R 4 When the 1,1'-bi-2-naphthol (3) used in the reactions of Schemes 1 to 7 is the same as R 1 (=R 3) and possibly also R 2 (=R 4 ) with a correspondingly substituted 1,1'-bi-2-naphthol derivative.

[0149] The transformations shown in Schemes 1-7 can be accomplished by the reactions described above in connection with these schemes, or by obvious modifications of these reactions, or alternatively by procedures or combinations thereof that are well established in preparative organic chemistry.

[0150] Additional compounds of formula (I) may be prepared using obvious modifications of the above reactions and combinations thereof with procedures well established in preparative organic chemistry.

[0151] The reaction mixture obtained in each step of the synthesis for preparing the compounds of the above reaction schemes 1, 2, 3, 4, 5, 6 and 7 is usually treated by conventional methods, such as mixing with water, separating the phases, and purifying the crude product by washing, chromatography or crystallization, if necessary. In some cases, the intermediate is in the form of a colorless or light brown viscous oil, and the volatile components are removed or purified at moderately elevated temperatures under reduced pressure. If the intermediate is obtained as a solid, purification can be achieved by recrystallization or washing procedures such as slurry washing.

[0152] The starting compounds used in the syntheses shown in Schemes 1, 2, 3, 4, 5, 6 and 7 above to prepare compounds of formula (I) are either commercially available or can be prepared by methods known in the art.

[0153] As mentioned above, the compound of the present invention can be obtained with high purity.This means that the product obtained does not contain significant amounts of organic impurities other than volatile substances that are different from the compound of formula (I).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.That is, 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).

[0154] The term "volatile substances" refers to substances at standard atmospheric pressure (10 5 Non-volatile organics are therefore understood to mean compounds having a boiling point above 200° C. at standard atmospheric pressure.

[0155] Particularly advantageously, the compounds of formula (I), as well as 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 solvates with water or organic solvent. Thus, 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 forms in which the compounds of formula (I) exist without solvent and to the crystalline solvates (crystals containing incorporated solvent) of the compounds of formula (I).

[0156] Particularly advantageously, the compounds of formula (I), as well as their solvates, can often be easily crystallized by conventional organic solvents. This allows for efficient purification of the compounds of formula (I). Suitable organic solvents for the crystallization of the compounds of formula (I) or their solvates include, but are not limited to, aromatic hydrocarbons such as toluene or xylene; aliphatic ketones, in particular ketones having 3 to 6 carbon atoms, such as acetone, methyl ethyl ketone, methyl isopropyl ketone or diethyl ketone; aliphatic and cycloaliphatic 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; and aliphatic alcohols having 1 to 4 carbon atoms, such as methanol, ethanol or isopropanol, as well as mixtures thereof. It may be beneficial to subject the dissolved crude preparation of the compound of formula (I) to a filtration, for example through celite, before the crystallization step, in order to remove any solid components that may be present in the crude preparation.

[0157] Furthermore, impurities, in particular colour-forming impurities, which may be present in the crude preparation of the compound of formula (I), may be removed at any stage of the purification process, for example prior to the filtration or crystallisation steps, by standard procedures such as treatment with an adsorbent, e.g. activated carbon.

[0158] Alternatively, the compounds of formula (I), as well as their solvates, can be obtained in purified form by using other simple and efficient methods for purifying the crude products of these compounds. For example, slurry washing, in particular of the crude solid obtained immediately after conversion to produce the compounds of formula (I). Slurry washing is generally carried out at room temperature or at elevated temperatures, usually about 30-90°C, in particular 40-80°C. Suitable organic solvents here are in principle the same as those listed above as suitable for the crystallization of the compounds of formula (I). For example, in particular the aromatic hydrocarbons, aliphatic ketones and aliphatic ethers mentioned above, such as toluene, methyl ethyl ketone and methyl tert-butyl ether.

[0159] Therefore, the compounds of formula (I) used for the manufacture of thermoplastic polymers, particularly polycarbonates, as defined herein, can be easily prepared and obtained with high yield and high purity, respectively. In particular, the compounds of formula (I) can be obtained in crystalline form, and therefore can be efficiently purified to the degree required for the manufacture of optical resins. In particular, these compounds can be obtained with a purity that provides high refractive index and low haze. This is particularly important for use in the manufacture of optical resins to manufacture optical elements. In conclusion, the compounds of formula (I) are particularly useful as monomers in the manufacture of optical resins.

[0160] Those skilled in the art will readily understand that the monomer of formula (I) used corresponds to the structural unit of formula (II) contained in the thermoplastic resin. Similarly, the monomers of formulas (Ia) and (Ib) used correspond to the structural units of formulas (IIa) and (IIb), respectively, contained in the thermoplastic resin.

[0161] Those skilled in the art will also appreciate that the structural units of formulae (II), (IIa) and (IIb) are repeat units in the polymer chain of a thermoplastic resin.

[0162] In addition to the structural units of each of the formulae (II), (IIa) and (IIb), the thermoplastic resin may have structural units different therefrom. In a preferred embodiment, these further structural units are derived from aromatic monomers of formula (IV) and result in structural units of formula (V): H.O.R. z -A 3 -R z -OH (IV) #-OR z -A 3 -R z -O-# (V) During the ceremony, # 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 linked 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 linked via a linker L; A 3 is unsubstituted or 1, 2 or 3 R aa Group (R aa is 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, SO 2 , C.H. 2 , CH-Ar, CAr 2 , CH(CH 3 ), C(CH 3 ) 2and groups of formula (A'),

[0163] [ka]

[0164] During the ceremony, Q' is a single bond, O, C=O or CH 2 represents; R 7a , R 7b are each independently hydrogen, fluorine, CN, R, OR, 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; L is unsubstituted or selected from 1 or 2 R L Group (R L is C 1 -C 4 -Alkyl, halogen, C 1 -C 4 -Haloalkyl, C 4 -C 7 -substituted with -(selected from the group consisting of 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, in which 1, 2, 3 or 4 of the hetaryl ring atoms are selected from nitrogen, sulfur and oxygen, and the remaining hetaryl ring atoms are carbon atoms, and Ar is unsubstituted or substituted with 1, 2 or 3 R ab Group (R ab is halogen, phenyl and C 1-C 4 -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 (bonded to); w is an integer from 1 to 10; Alk 3 is C 1 -C 4 -alkanediyl; Alk 4 is C 2 -C 4 -alkanediyl; and Alk 5 is C 1 -C 4 -Alkanediyl.

[0165] R in formula (IV) z O-Alk 5 -C(O), the ester, in particular the C of the monomer of formula (IV) 1 -C 4 -Alkyl esters can be used instead.

[0166] In formulas (IV) and (V), A 3 is in particular a polycyclic group having two benzene or naphthalene rings, the benzene rings being connected to W or fused to two non-benzene carbocyclic rings connected via a linker L (W is in particular a single bond, S, S(O), SO 2 , C(CH 3 ) 2 and A′ groups, and L is a single bond or C 1 -C 4 -alkylene).

[0167] In formulas (IV) and (V), R z In particular, O-Alk4 -Alk 4 is in particular a straight-chain alkanediyl having 2 to 4 carbon atoms, in particular O-CH 2 CH 2 It is.

[0168] Among the monomers of formula (IV), preferred are the monomers of general formulae (IV-1) to (IV-8).

[0169] [ka]

[0170] During the ceremony, 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 ), C(CH 3 ) 2 , especially S, S(O), and SO 2 or C(CH 3 ) 2 and; R z , R aa , R ab , R 7a , R 7b and L is as defined in formula (IV), R z is, in particular, a single bond, CH 2 and OCH 2 CH 2 is selected from.

[0171] Among the monomers of formula (IV), particularly preferred are those represented by the general formulae (IV-11) to (IV-22) (wherein R z and R aa is as defined herein, and R z is a single bond, especially CH2 and O-CH 2 CH 2 In particular, O-CH 2 CH 2 is a monomer of:

[0172] [ka]

[0173] [ka]

[0174] Examples of the compounds of formulae (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, 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-methylphenyl)fluorene (BPEF), 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 Phenylmethane, 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'-[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), 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'-diphenyl-1, 1'-Binaphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-di(naphthalene-1-yl)-1,1'-binaphthalene, 2,2'-bis(2-hydroxymethoxy)-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxymethoxy)-6,6'-di(naphthalene-1-yl)-1,1'-binaphthalene, 2,2'-bis(2-hydroxypropoxy)-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxypropoxy)-6,6'-di(naphthalene-1-yl) 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-methyl-ethyl]-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 2-[4-[4-(2-hydroxyethoxy)-3,5-di(phenanthren-9-yl)phenyl]sulfonyl-2,6-di(phenanthren-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.

[0175] Among the monomers of general formula (IV) or formulae (IV-1) to (IV-8), particularly preferred are the monomers of formulae (IV-1), (IV-2), (IV-3) and (IV-8), further more preferred are the monomers of formulae (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-21) and (IV-22), and particularly preferred are 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)-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)-fluorene 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(phenanthren-9-yl)phenyl]sulfonyl-2,6-di(phenanthren-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.

[0176] Therefore, among the structural units of formula (V) that can be contained in the thermoplastic resin, the structural units of general formulae (V-1) to (V-8) are preferred.

[0177] [ka]

[0178] During the ceremony, 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 ), C(CH 3 ) 2 , especially S, S(O), and SO 2 or C(CH 3 ) 2 and; R z , R aa , R ab , R 7a , R 7b and L is as defined in formula (V), R z is, in particular, a single bond, CH 2 and OCH 2 CH 2 is selected from.

[0179] Particularly preferred structural units are those represented by the general formulae (V-11) to (V-22) (wherein R z and R aa is as defined herein, and R z is a single bond, especially CH 2 and O-CH 2 CH 2 In particular, O-CH 2 CH 2 ) is a structural unit.

[0180]

change

[0181]

change

[0182] Among the structural units of the formulae (V-1) to (V-8), the structural units of the formulae (V-1), (V-2), (V-3) and (V-8) are preferred. Among the structural units of the formulae (V-11) to (V-22), the structural units of the formulae (V-11), (V-12), (V-13), (V-14), (V-15), (V-21) and (V-22) are particularly preferred, and ... )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-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(phenanthren-9-yl)-phenyl]-1-methylethyl]-2,6-di(phenanthren-9-yl)-phenoxy] It is a structural unit derived from 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 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.

[0183] 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, the following thermoplastic resins, i.e., structural units of formula (V-11), formula (V-12), formula (V-13), formula (V-14), formula (V-15), formula (V-21) and formula (V-22), are selected from the group consisting of structural units of formula (V-11), formula (V-12), formula (V-13), formula (V-14), formula (V-15), formula (V-21) and formula (V-22), in which R z The group is O-CH 2 CH 2 It is preferred that:

[0184] In this particular preferred group of thermoplastic resins of the embodiment, the total molar ratio of structural units of formula (IIa) or (IIb) in the total molar amount of structural units of formula (II) and formula (V) is preferably in the range of 1 to 99 mol%, preferably in the range of 5 to 98 mol%, more preferably in the range of 10 to 97 mol%, and even more preferably in the range of 20 to 95 mol%.

[0185] 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 by methods analogous to known methods.

[0186] For example, the compound of formula (IV-8) can be produced by various synthesis methods, as described in, for example, JP 2014-227387 A, JP 2014-227388 A, JP 2015-168658 A, and JP 2015-187098 A. For example, the compound can be produced by a method of reacting 1,1'-binaphthol with ethylene glycol monotosylate, a method of reacting 1,1'-binaphthol with alkylene oxide, halogenoalkanol, or alkylene carbonate, a method of reacting 1,1'-binaphthol with ethylene carbonate, or the like. As a result, R z -OH is O-Alk 2 -Or O-Alk 2 -[Alk 2 -]p-, a compound of formula (IV-8) can be prepared.

[0187] For example, the compound of formula (IV-2) can be produced by various synthesis methods, as described in, for example, Japanese Patent Publication No. 5442800 and Japanese Patent Publication No. 2014-028806. Specific examples of the synthesis methods include (a) a method of reacting fluorenes with hydroxynaphthalenes in the presence of hydrogen chloride gas and mercaptocarboxylic acid, (b) a method of reacting 9-fluorene with hydroxynaphthalenes in the presence of an acid catalyst (and alkyl mercaptan), (c) a method of reacting fluorenes with hydroxynaphthalenes in the presence of hydrochloric acid and thiols (mercaptocarboxylic acid, etc.), and (d) a method of reacting fluorenes with hydroxynaphthalenes in the presence of sulfuric acid and thiols (mercaptocarboxylic acid, etc.), and crystallizing the fluorenes with a crystallization solvent composed of a hydrocarbon and a polar solvent to produce bisnaphtholfluorene, to obtain 9,9-bis(hydroxynaphthyl)fluorenes, etc. Includes:

[0188] As a result, R z Compounds of formula (IV-2) in which is a single bond can be prepared.

[0189] R z O-Alk 2 -Or O-Alk 2-[O-Alk 2 -] p The compound of formula (IV) is R z It can be produced by reacting a compound of formula (IV) in which R is a single bond with an alkylene oxide or a haloalkanol. z By reacting alkylene oxides or haloalkanols with 9,9-bis(hydroxynaphthyl)fluorenes of formula (IV-2) in which R is a single bond, z O-Alk 2 -Or O-Alk 2 -[Alk 2 -] p For example, 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene may be obtained by reacting 9,9-bis[6-(2-hydroxynaphthyl]fluorene with 2-chloroethanol under alkaline conditions.

[0190] The monomers of formula (I) and the comonomers of formula (IV) used to prepare the thermoplastic resins may contain certain impurities resulting from their preparation, e.g., O-Alk 1 It may contain hydroxy compounds having OH groups instead of -OH groups, or O-Alk 1 -Alk instead of - group 1 -[O-Alk 1 -] o - groups or, instead of a mixture of oligomers with different values ​​of n, only one oligomer monomer with n=1, 2 or 3 is intended, which may contain unwanted oligomers in addition to the intended oligomers. The total amount of such impurities 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 contained in the monomers used to produce the thermoplastic resin is desirably 4000 ppm or less, particularly desirably 1500 ppm or less, and more desirably 1000 ppm or less. In particular, formula (I) refers to X 1 Or X 2The total amount of dihydroxy compounds having at least one carbon number different in the group 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 in the monomer mainly composed of the dihydroxy compound represented by formula (I). 1 Or X 2 The total content of dihydroxy compounds having at least one different carbon number value in at least one of the groups is preferably 1000 ppm or less, more preferably 500 ppm or less.Similarly, the content of impurities in the comonomer of formula (IV) is within the above-mentioned ranges given for the monomer of formula (I).

[0191] It should be noted again that mixtures of compounds of formula (I) with different values ​​of the variable n are also part of the present invention. Such mixtures, like the individual compounds of formula (I), are well suited as monomers for producing thermoplastic resins with advantageous properties. Thus, to produce the thermoplastic resins of the present invention, monomers of formula (I) with n=1, monomers of formula (I) with n=2, monomers of formula (I) with n=3, or any mixture of these compounds may be used.

[0192] Suitable thermoplastic resins for the production of optical elements such as lenses are in particular polycarbonates, polyester carbonates and polyesters. Suitable thermoplastic resins for the production of optical elements such as lenses are in particular polycarbonates.

[0193] Said polycarbonates are structurally characterized by having at least one structural unit of formula (II), (IIa) and (IIb), respectively, optionally derived from a diol monomer different from the monomer compound of formula (I), for example a structural unit of formula (V): #-OR z -A 3 -R z -O-# (V) (In the formula, #, R z and A 3is as defined herein above); and structural units of formula (III-1) derived from carbonate moieties.

[0194] [ka]

[0195] In the formula, each # represents a point of attachment to an adjacent structural unit, i.e., the point of attachment of the structural unit of formula (II) to O, and, if present, the point of attachment of the structural unit of formula (V) to O.

[0196] Said polyesters are structurally characterized by having at least one structural unit of formula (II), (IIa) and (IIb), respectively, optionally derived from a diol monomer different from the monomer compound of formula (I), for example a structural unit of formula V. X in formula (II), (IIa) and (IIb) 1a and X 2a is a single bond, -Alk 1 -O- and -CH 2 -A 2 -CH 2 When selected from -O-, 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, 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:

[0197] [ka]

[0198] In formulae (III-2) to (III-5), each variable # represents the point of attachment to the adjacent structural unit, i.e., the point of attachment of the structural unit of formula (II) to O, and, if present, the point of attachment of the structural unit of formula (V) to O.

[0199] Said polyester carbonates are structurally characterized by having at least one structural unit of formula (II), (IIa) and (IIb), and optionally a structural unit derived from a diol monomer different from the monomer compound of formula (I). For example, the structural unit of formula (V), the structural unit of formula (III-1) derived from a carbonate-forming component and the structural unit derived from a dicarboxylic acid. For example, the structural unit of formula (III-2) in the case of benzenedicarboxylic acid, the structural unit of formula (III-3) in the case of naphthalenecarboxylic acid, the structural unit of formula (III-4) in the case of oxalic acid and the structural unit of formula (III-5) in the case of malonic acid.

[0200] A particular group of embodiments relates to thermoplastic copolymer resins, in particular polycarbonates, polyestercarbonates and polyesters, which contain both structural units of formula (II) and one or more structural units of formula (V), for example resins, in particular polycarbonate resins, polyestercarbonates resins and polyester resins obtained by reacting at least one monomer of formula (I) with one or more monomers of formula (IV), in which the molar ratio of the monomer of formula (I) to the monomer of formula (IV) and the analogous 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 20:80 to 98:2, 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 98:2, 15:85 to 90:10, 15:85 to 80:20 or 15:85 to 70:30, more preferably Preferably, it is within the range of 20:80 to 97:3 or 20:80 to 85:15, or within the range of 25:75 to 97:3, 25:75 to 85:15 or 25:75 to 80:20, in particular within the range of 27:73 to 75:25, 27:73 to 80:20, 27:73 to 97:3 or within the range of 27:73 to 99:1, and even more preferably within the range of 27:73 to 90:10, in particular within the range of 30:70 to 80:20 or within 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 20 to 98 mol%, based on the total molar amount of the structural units of formulae (II) and (V), more preferably within the range of 30 to 97 mol% or within the range of 10 to 99 mol%, particularly within the range of 20 to 97 mol% or within the range of 27 to 97 mol%, and even more preferably within the range of 27 to 90 mol%, particularly within the range of 30 to 80 mol% or within the range of 35 to 70 mol%.Therefore, the molar ratio of the structural unit of formula (V) is usually 1 to 99 mol%, particularly 2 to 80 mol%, more preferably 3 to 70 mol% or 1 to 90 mol%, particularly 2 to 85 mol% or 3 to 80 mol%, and even more preferably 10 to 73 mol%, particularly 20 to 70 mol% or 30 to 65 mol%, based on the total molar amount of the structural units of formula (II) and formula (V). The above molar ratio can also be applied to the molar ratio of the structural unit of formula (II) to the total structural units of the thermoplastic copolymer resin.

[0201] A particular group of embodiments relates to thermoplastic copolymer resins, in particular polycarbonates, polyestercarbonates and polyesters, both of which have structural units of formula (II) and one or more structural units of formula (V-14) or (V-15), i.e. resins obtainable by reacting at least one monomer of formula (I) with one or more monomers of formula (IV-14) or (IV-15). In this case, the molar ratio of the monomer of formula (I) to the monomers of formula (IV) and formula (IV-15), and the molar ratio of the analogous structural units of formula (II) to the structural units of formula (V-14) and formula (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. The above molar ratios also apply to the molar ratio of the structural units of formula (II) to the total structural units of the thermoplastic copolymer resin.

[0202] Another particular group of embodiments relates to thermoplastic copolymer resins, in particular polycarbonates, polyestercarbonates and polyesters, both having 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 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 particular polycarbonates, polyestercarbonates and polyesters. 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 (I-22), and the molar ratio of the structural unit of formula (II) similar thereto to the structural unit of formulae (V-11), (V-12), (V-13), (V-21) and (V-22) are within the range of 10:90 to 90:10, 15:85 to 80:20, 20:80 to 70:30, 25:75 to 80:20, 30:70 to 90:10 or 30:70 to 80:20, particularly within the range of 35:65 to 75:25, 35:65 to 70:30, 40:60 to 85:15 or 40:60 to 80:20, particularly within the range of 50:50 to 80:20. The above molar ratios can also be applied to the molar ratios between the structural unit of formula (II) and all structural units of the thermoplastic copolymer resin.

[0203] The thermoplastic copolymer resin of the present invention, such as a polycarbonate resin, may have any of a random copolymer structure, a block copolymer structure, and an alternating copolymer structure. In the thermoplastic resin of the present invention, the above-mentioned structural unit (II) and one or more different structural units (V) may not all be contained in the same polymer molecule. That is, if the above-mentioned structure is contained in each of a plurality of polymer molecules, the thermoplastic copolymer resin of the present invention may be a blend resin. For example, the thermoplastic resin containing both the above-mentioned structural unit (II) and the structural unit (V) may be a copolymer containing both the structural unit (II) and the structural unit (V), or 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), or 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 second structural unit (V) other than the first structural unit (V).

[0204] Thermoplastic polycarbonates can be obtained by polycondensation of a diol component with a carbonate-forming component.Similarly, thermoplastic polyesters and thermoplastic polyester carbonates can be obtained by polycondensation of a diol component with a dicarboxylic acid or an ester-forming derivative thereof, and an optional carbonate-forming component.

[0205] Specifically, the thermoplastic resin (polycarbonate resin) can be produced by the following method.

[0206] The method for producing a thermoplastic resin such as a polycarbonate resin of the present invention includes a step of melt polycondensing a dihydroxy component corresponding to the above-mentioned structural unit and a carbonate diester. The dihydroxy compound in the present invention includes at least one dihydroxy compound represented by formula (I), particularly a dihydroxy compound represented by formula (Ia) or (Ib), as each is defined herein. In addition to the compound of formula (I), the dihydroxy compound may include one or more dihydroxy compounds represented by formula (IV), preferably (IV-1) to (IV-8), particularly formula (IV-11) to (IV-22), particularly formula (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-21) or (IV-22).

[0207] As is clear from the above, a dihydroxy component containing a compound represented by each of the above formulas (I), (Ia) and (Ib), or a combination of at least one compound represented by formulas (I), (Ia) and (Ib) and 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) can be reacted with a carbonate precursor such as a carbonate diester to produce a polycarbonate resin. Specifically, a polycarbonate resin can be produced by reacting compounds represented by formulas (I), (Ia) and (Ib), or a combination of these with at least one compound represented by formulas (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), and a carbonate precursor such as a carbonic acid diester in the presence of a basic compound catalyst, an ester exchange catalyst or a mixed catalyst consisting of both, or in the absence of a catalyst, by a melt polycondensation method.

[0208] Thermoplastic resins (or polymers) other than polycarbonate resins, such as polyester carbonate resins and polyester resins, can be obtained by using dihydroxy compounds represented by formulas (I), (Ia) and (Ib), respectively, or combinations of these 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) as raw materials (monomers).

[0209] As mentioned above, the monomers of formula (I) and the comonomers of formula (IV) used to produce the thermoplastic resin may contain impurities that may arise from the production of those monomers.

[0210] For example, R z O-Alk 2 Or O-Alk 2 -[O-Alk 2 -] p The monomers of formulae (IV-1) and (IV-2) are O-Alk 2 -Or O-Alk 2 -[O-Alk 2 -] p - Instead of R z are single bonds, or R z may include a dihydroxy compound in which one of the radicals is a single bond.

[0211] In formula (IV-1) or (IV-2), R z At least one of them is O-Alk 4 -Or O-Alk 4 -[O-Alk 4 -] pThe total amount of such dihydroxy compounds different from - in the monomer mainly composed of a dihydroxy compound represented by formula (IV-1) or (IV-2) 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 total amount 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 more preferably 300 ppm or less, more preferably 200 ppm or less.

[0212] The polycarbonate resins can be obtained by reacting a carbonate precursor, such as a diester carbonate, with a monomeric compound of formula (I) or by reacting a combination of at least one monomeric compound of formula (I), in particular at least one monomer (I) described herein as being preferred, as a dihydroxy component, and one or more monomeric compounds of formula (IV), in particular the monomeric compounds of formula (IV-11), (IV-12), (IV-13), (IV-14), (IV-15), (IV-21) or (IV-22).

[0213] However, in the polymerization process for producing polycarbonate resins, some of the compounds of formulae (I) and (IV) have a terminal -X 1 , -X 2 or -R z Either or both of the OH groups may be replaced with a different group, e.g., -OCH=CH 2 The amount of such impurities is usually small, and the produced polymer can be used as a polycarbonate resin without purification.

[0214] The thermoplastic resin of the present invention may also contain some amount of impurities, such as excess amounts of the thermoplastic resin composition or part of the polymer backbone of the thermoplastic resin. Examples of such impurities include phenols, unreacted diester carbonates and monomers resulting from the manufacturing process of the thermoplastic resin. The total amount of impurities in the thermoplastic resin may be 5000 ppm or less, or 2000 ppm. The total amount of impurities in the thermoplastic resin is preferably 1000 ppm or less, more preferably 500 ppm or less, even more preferably 200 ppm or less, and particularly preferably 100 ppm or less.

[0215] The total amount of phenol as an impurity in the thermoplastic resin may be 3000 ppm or less, or 2000 ppm or less. The total amount of phenol as an impurity in the thermoplastic resin is 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. The total amount of carbonate diesters as impurities in the thermoplastic resin is preferably 1000 ppm or less, more preferably 500 ppm or less, further preferably 100 ppm or less, and particularly preferably 50 ppm or less. 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. The lower limit for the total amount of these impurities is not critical but could be as low as 0.1 ppm or 1.0 ppm.

[0216] The total amount of residual heavy metals, e.g. 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, e.g. activated carbon.

[0217] By adjusting the amounts of phenol and dicarbonate, a resin having properties according to the purpose can be obtained. The amounts of phenol, dicarbonate, and monomer can be appropriately adjusted by changing the polycondensation conditions and the operating conditions of the apparatus used in the polymerization. The amounts can also be adjusted by the conditions of extrusion molding after polycondensation.

[0218] The weight average molecular weight (Mw) of the thermoplastic resin of the present invention is preferably 5,000 to 100,000 daltons, more preferably 10,000 to 80,000 daltons or 20,000 to 650,000 daltons, particularly 10,000 to 50,000 daltons or 20,000 to 40,000 daltons, as determined by GPC (gel permeation chromatography). The GPC measurement value can be calibrated using a polystyrene standard. The Mw of the thermoplastic resin of the present invention thus determined is also referred to herein as the "polystyrene converted weight average molecular weight". The number average molecular weight (Mn) of the thermoplastic resin of the present invention is preferably 3,000 to 30,000, more preferably 5,000 to 25,000, particularly 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.

[0219] The molecular weight distribution (Mw / Mn) of the thermoplastic resin of the present invention is preferably from 1.5 to 9.0, more preferably from 1.8 to 7.0, and further preferably from 2.0 to 4.0.

[0220] If the weight average molecular weight (Mw) of the thermoplastic resin is within the above-mentioned appropriate range, the molded article produced from the thermoplastic resin has sufficient strength. Furthermore, a thermoplastic resin having an appropriate weight average molecular weight (Mw) has an advantage in molding due to its high fluidity.

[0221] Preferably, the thermoplastic resin contains 9% by weight or less, particularly 7% by weight or less, particularly 5% by weight or less, for example 0.1 to 9% by weight, particularly 0.1 to 7% by weight, particularly 0.1 to 5% by weight, of low molecular weight compounds having a molecular weight of less than 1000, based on the total weight of the thermoplastic resin. When such low molecular weight compounds are present in the thermoplastic resin in an amount within the above range, the mechanical strength of a molded body made from such a thermoplastic resin is generally increased, especially compared to a molded body made from a thermoplastic resin containing a higher amount of low molecular weight compounds. Furthermore, the thermoplastic resin of this embodiment containing 9% by weight or less, particularly 7% by weight or less, particularly 5% by weight, of low molecular weight compounds having a molecular weight of less than 1000 is not susceptible to or only slightly susceptible to precipitation of low molecular weight compounds, also known as bleed-out, during a molding process such as an injection molding process. In contrast, molding of a thermoplastic resin containing a higher amount of low molecular weight compounds may involve a large amount of bleed-out. It is also preferred that the thermoplastic resin contains, based on the total weight of the thermoplastic resin, 0.1% by weight or more, particularly 0.3% by weight or more or 0.5% by weight or more, particularly 1.0% by weight or more, for example 0.5 to 9% by weight, particularly 1 to 9% by weight or 1 to 7% by weight, particularly 1 to 5% by weight of a low molecular weight compound having a molecular weight of less than 1000.

[0222] 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 therefore suitable for optical lenses. The refractive index values ​​described herein can be measured for a 0.1 mm thick film using an Abbe refractometer according to the method of JIS-K-7142. The refractive index at 23°C and a wavelength of 589 nm of the thermoplastic resin of the present invention, particularly the polycarbonate resin of the present invention, when the resin contains the structural unit (II), is often 1.630 or more, preferably 1.640 or more, more preferably 1.650 or more, even more preferably 1.660 or more, particularly 1.665 or more, 1.670 or more, 1.675 or more, or 1.680 or more, particularly 1.685 or more. For example, the refractive index of the copolycarbonate resin containing the structural unit (II) and the structural unit (V) of the present invention is preferably 1.640 to 1.730, preferably 1.650 to 1.730, even more preferably 1.660 to 1.730.

[0223] The Abbe number (ν or νd) of the thermoplastic resin of the present invention, particularly the polycarbonate resin of the present invention, is preferably 24 or less, or 23 or less, more preferably 22 or less, or 21 or less, and even more preferably 20 or less, or 19 or less. The Abbe number can be calculated from the refractive indexes at wavelengths of 487 nm, 589 nm, and 656 nm at 23° C. using the following formula: ν=(nD-1) / (nF-nC) nD: Refractive index at a wavelength of 589 nm nC: Refractive index at a wavelength of 656 nm nF: Refractive index at a wavelength of 486 nm

[0224] Considering that the polycarbonate can be used for injection molding, the glass transition temperature (Tg) of the thermoplastic resin of the present invention, particularly the polycarbonate resin of the present invention, is often in the range of 90 to 185 ° C, preferably in the range of 90 to 180 ° C, more preferably in the range of 100 to 170 ° C or 110 to 170 ° C, particularly in the range of 110 to 160 ° C, 120 to 165 ° C, or 130 to 160 ° C. From the viewpoint of 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. According to the Tg in the above range, a sufficient use temperature range is given, and the possibility that the melting temperature of the resin becomes high and the resin is likely to decompose or discolor. Furthermore, it enables the production of molded products with strict surface accuracy. The values ​​given for the glass transition temperature refer to values ​​measured by differential scanning calorimetry (DSC) using a heating program of 10° C. / min according to the JIS K7121-1987 protocol.

[0225] In a preferred group (11) of embodiments, the absolute value of the orientation birefringence of the thermoplastic resin is preferably 0 to 1 × 10 -2 More preferably, it is in the range of 0 to 5×10 -3 More preferably, the range is 0 to 2×10 -3 In particular, the range is 0 to 1 × 10 -3 In particular, the range is 0 to 0.4 × 10 -3 The range is.

[0226] The optical molded article such as an optical member obtained 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. If the total light transmittance is 85% or more, it is comparable to that of bisphenol A type polycarbonate resin.

[0227] The thermoplastic resin of the present invention has high moisture resistance and heat resistance. The moisture and heat resistance can be evaluated by performing a "PCT test" (pressure cooker test) on a molded article such as an optical member obtained using the thermoplastic resin, and measuring the total light transmittance of the molded article after the PCT test. In the PCT test, first, an injection molded article having a diameter of 50 mm and a thickness of 3 mm is held for 20 hours under the conditions of 120°C, 0.2 MPa, 100% RH, and 20 hours by PC-305-S III manufactured by Hirayama Seisakusho. Then, the sample of the injection molded article is removed from the device, and the total light transmittance is measured by the method of JIS-K-7361-1 using a spectrophotometer SE2000 manufactured by Nippon Denshoku Kogyo Co., Ltd.

[0228] The thermoplastic resin of the present invention has a total light transmittance after 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. If the total light transmittance is 60% or more, it can be said to have higher moist heat resistance than conventional thermoplastic resins.

[0229] The b value, which indicates the hue of the thermoplastic resin of the present invention, is preferably not more than 5. The smaller the b value, the weaker the yellowness, and the better the hue.

[0230] According to the present invention, the diol component used to prepare the polycarbonate or polyester may further comprise one or more diol monomers different from the monomeric compound of formula (I), such as one or more monomers of formula (IV).

[0231] Suitable diol monomers other than the monomeric compounds of formula (I) are customarily used in the preparation of polycarbonates, for example: aliphatic diols, such as ethylene glycol, propanediol, butanediol, pentanediol and hexanediol; 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, may also be mentioned as examples of diols; and aromatic diols, in particular aromatic diols of the formula (IV), such as, for example, 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-t-butylphenyl)propane, 2 ,2-bis(4-hydroxy-3-methylphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxy-phenyl)cyclohexane, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, bis(4-hydroxy-phenyl)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(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-isopropylphenyl]fluorene, hydroxyethoxy)-3-cyclohexylphenyl]fluorene, 9,9-bis(4-hydroxy-3-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 2,2'-[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).

[0232] The diol component preferably contains at least one monomer of formula (IV) in addition to the monomer of formula (I). In particular, the total amount of the monomers of formula (I) and formula (IV) contributes to the diol component by being at least 90% by weight 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 contains at least one monomer selected from the monomers of formulas (IV-11) to (IV-22) in addition to the monomer of formula (I). Furthermore, the diol component contains 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 addition to the monomer of formula (I). In particular, in addition to the monomers 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-[4-(2-hydroxyethoxy)-3,5-di(thianthren-1-yl)phenyl]sulfonyl-2,6-di(thianthren-1-yl)phenoxy]ethanol, The diol component includes at least one monomer selected from the group consisting of 2-[4-[1-[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.

[0233] Often the relative amount of monomeric compounds of formula (I) will be at least 1% by weight, preferably at least 10% by weight or at least 30% by weight, in particular at least 15% by weight or at least 20% by weight, and in particular at least 25% by weight or at least 30% by weight, preferably in the range 1-99% by weight or 10-98% by weight, in particular in the range 20-98% by weight, 25-98% by weight, 30-98% by weight or 30-97% by weight, in particular in the range 15-96% by weight, 20-95% by weight, 30-95% by weight or 30-93% by weight, but may be as high as up to 100% by weight, based on the total weight of the diol component.

[0234] Frequently, the relative molar amount of 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 30 mol%, in particular at least 15 mol% or at least 20 mol%, in particular at least 25 mol% or at least 30 mol%, preferably in the range from 1 to 99 mol% or in the range from 10 to 98 mol% or in the range from 20 to 98 mol% or in the range from 25 to 98 mol%, in particular in the range from 15 to 96 mol% or in the range from 20 to 95 mol% or in the range from 30 to 95 mol% or in the range from 30 to 93 mol%, in particular in the range from 20 to 90 mol% or in the range from 25 to 90 mol% or in the range from 30 to 90 mol% or in the range from 32 to 90 mol% or in the range from 35 to 90 mol%, but may be as high as up to 100 mol%.

[0235] As a result, the relative molar amount of monomeric compounds of formula (IV), based on the total molar amount of the diol components, does not exceed 99 mol% or 90 mol% or 70 mol%, in particular does not exceed 85 mol% or 80 mol%, in particular does not exceed 75 mol% or 70 mol%, preferably in the range from 1 to 99 mol% or in the range from 2 to 90 mol% or in the range from 2 to 80 mol% or in the range from 2 to 75 mol%, in particular in the range from 4 to 85 mol% or in the range from 5 to 80 mol% or in the range from 5 to 70 mol% or in the range from 7 to 70 mol%, in particular in the range from 10 to 80 mol% or in the range from 10 to 75 mol% or in the range from 10 to 70 mol% or in the range from 10 to 68 mol% or in the range from 10 to 65 mol%, but may be as high as up to 99.9 mol%.

[0236] Frequently, the total molar amount of monomers of formula (I) and monomers of formula (IV) is at least 80 mol %, in particular at least 90 mol %, and in particular at least 95 mol % or even up to 100 mol %, based on the total molar amount of diol monomers of the diol component.

[0237] 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, and bisphenol Z.

[0238] To adjust the molecular weight and melt viscosity, the monomers forming the thermoplastic polymer may contain a monofunctional compound (monofunctional alcohol in the case of polycarbonate, monofunctional alcohol or monofunctional carboxylic acid in the case of polyester). Suitable monoalcohols are butanol, hexanol and octanol. Suitable monocarboxylic acids include, for example, benzoic acid, propionic acid and butyric acid. To increase the molecular weight and melt viscosity, the monomers forming the thermoplastic polymer may contain a polyfunctional compound (polyfunctional alcohol having three or more hydroxyl groups in the case of polycarbonate, polyfunctional alcohol having three or more hydroxyl groups or polyfunctional carboxylic acid having three or more carboxyl groups in the case of polyester). Suitable polyfunctional alcohols include, for example, glycerin, trimethylolpropane, pentaerythritol and 1,3,5-trihydroxypentane. Suitable polyfunctional carboxylic acids having three or more carboxyl groups are, for example, trimellitic acid and pyromellitic acid. The total amount of these compounds is often not more than 10 mol% based on the molar amount of the diol component.

[0239] Suitable carbonate-forming monomers are those conventionally used as carbonate-forming monomers in the production of polycarbonates, including, but not limited to, phosgene, diphosgene and diester carbonates, 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 of dihydroxy compounds.

[0240] Suitable dicarboxylic acids include, but are not limited to, the following: - aliphatic dicarboxylic acids, for example, 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.

[0241] [ka]

[0242] Suitable ester forming derivatives of dicarboxylic acids include, but are not limited to, dialkyl esters, diphenyl esters, and ditolyl esters.

[0243] In polyesters, the ester-forming monomers are often used in a ratio ranging from 0.97 to 1.20 mol, more preferably from 0.98 to 1.10 mol, per mol of the total of the dihydroxy compounds.

[0244] The polyestercarbonates of the present invention can be prepared by reacting a diol component comprising a monomer of formula (I) and, optionally, a diol monomer, such as a monomer of formula (IV), with carbonate-forming monomers, similar to the preparation of known polycarbonates, for example, as described 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, which are incorporated herein by reference in their entirety.

[0245] The polyesters of the present invention can be prepared by reacting a diol component comprising a monomer of formula (I) and, optionally, a 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, for example, as described in U.S. Patent Application Publication No. 2017 / 044311, which is incorporated by reference in its entirety, and the references cited therein.

[0246] The polyestercarbonates of the present invention can be prepared by reacting a diol component comprising a monomer of formula (I) and, optionally, a diol monomer such as a monomer of formula (IV) with a carbonate-forming monomer and a dicarboxylic acid or an ester-forming derivative thereof in a manner similar to that used for preparing polyestercarbonates as known in the art.

[0247] Polycarbonates, polyesters and polyestercarbonates are usually produced by reacting a monomer of a diol component with a carbonate-forming monomer and / or an ester-forming monomer, such as a dicarboxylic acid or an ester-forming derivative thereof, in the presence of an esterification catalyst, and particularly, when a carbonate-forming monomer or an ester-forming derivative of a polycarboxylic acid is used, by reacting them in the presence of an ester exchange catalyst.

[0248] Suitable transesterification catalysts are specifically, but not limited to, basic compounds including alkali metal compounds, alkaline earth metal compounds, nitrogen-containing compounds, etc. Similarly, suitable transesterification catalysts are specifically, but not limited to, acidic compounds including Lewis acid compounds of polyvalent metals including compounds of zinc, tin, titanium, zirconium, lead, etc.

[0249] Suitable examples of the alkali metal compound include alkali metal salts of organic acids such as acetic acid, stearic acid, benzoic acid, and 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, and alkali metal alkoxides. 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, cesium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium phenylborohydride, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, disodium phenylphosphate, the disodium, dipotassium, or dicesium salt of bisphenol A, the sodium, potassium, cesium, or lithium salt of phenol, and the like.

[0250] Examples of the alkaline earth metal compound include alkaline earth metal salts of organic acids such as acetic acid, stearic acid, benzoic acid, and phenylphosphoric acid, alkaline earth metal phenolates, alkaline earth metal oxides, alkaline earth metal carbonates, alkaline earth metal borohydrides, alkaline earth metal hydrogen carbonates, alkaline earth metal hydroxides, alkaline earth metal hydrides, and alkaline earth metal alkoxides. Specific examples thereof include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogen carbonate, calcium hydrogen carbonate, strontium hydrogen carbonate, barium hydrogen carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, and magnesium phenylphosphate.

[0251] Examples of the nitrogen-containing compound include quaternary ammonium hydroxides and their salts, amines, etc. Specifically, quaternary ammonium hydroxides having an alkyl group, an aryl group, etc., such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide; tertiary amines such as triethylamine, 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; or bases or basic salts such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, and tetraphenylammonium tetraphenylborate, etc., are used.

[0252] Suitable examples of the transesterification catalyst include salts of polyvalent metals such as zinc, tin, titanium, zirconium, and lead, and in particular, chlorides, alkoxides, alkanoates, benzoates, acetylacetonates, and the like. They 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 dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead(II) acetate, lead(IV) acetate, and the like.

[0253] These transesterification catalysts are used in a ratio of 10 to 1 mole of dihydroxy compounds. -9 ~10 -3 In terms of mole ratio, preferably 10 -7 ~10 -4 Often used as a molar ratio.

[0254] Polycarbonates, polyesters and polyestercarbonates are often produced by melt polycondensation processes, in which the monomers are reacted without the presence of additional inert solvents, during which the by-products resulting from the transesterification reaction are removed by heating the reaction mixture at atmospheric pressure or under reduced pressure.

[0255] The melt polycondensation reaction preferably involves charging the monomers and catalyst into a reaction vessel and subjecting the reaction mixture to conditions under which the monomers react to produce by-products. It has been found to be advantageous for the by-product residues to remain in the melt polycondensation reaction system for some time. However, in order to drive the melt polycondensation reaction towards the product, it is preferred to remove at least a portion of the by-products produced during the melt polycondensation reaction or, preferably, at the end of the melt polycondensation reaction. To allow the by-products in the reaction mixture, the pressure can be controlled by blocking, depressurizing or pressurizing the reactor. The reaction time for this step is from 20 to 240 minutes, preferably from 40 to 180 minutes, and particularly preferably from 60 to 150 minutes. In this case, if the by-products are distilled off immediately after production, the final thermoplastic resin will have a low content of high molecular weight resin molecules. However, if the by-products are allowed to remain in the reaction vessel for a certain period of time, the final thermoplastic resin will have a high content of high molecular weight resin molecules.

[0256] The melt polycondensation reaction may be carried out continuously or batchwise. The reaction apparatus used for the reaction may be a vertical type equipped with an anchor-type impeller, a Maxblend (registered trademark) impeller, a helical ribbon-type impeller, or the like, a horizontal type equipped with a paddle impeller, a lattice impeller, a spectacle impeller, or the like, or an extruder type equipped with a screw. In addition, it is preferable to use a reaction apparatus that is an appropriate combination of these reaction apparatuses, taking into consideration the viscosity of the polymer.

[0257] In the method for producing a thermoplastic resin used in the present invention, such as a polycarbonate resin, the catalyst may be removed or deactivated after the polymerization reaction is completed in order to maintain thermal stability and hydrolytic stability. A method of deactivating the catalyst by adding a known acidic substance can be preferably carried out. Specific examples of the acidic substance 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, phosphoric acid 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, and esters such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, and dioctyl phosphate. Phosphates such as phosphate esters, monooctyl phosphate, etc.; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, dibutylphosphonic acid, etc.; phosphonic acid esters such as diethyl phenylphosphonate, etc.; phosphines such as triphenylphosphine, bis(diphenylphosphino)ethane, etc.; boric acid, phenylboric acid, etc.; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate, etc.; organic halides such as stearic acid chloride, benzoyl chloride, p-toluenesulfonic acid chloride, etc.; alkyl sulfuric acid such as dimethyl sulfate, etc.; organic halides such as benzyl chloride, etc. are preferably used. These deactivators are often used in an amount of 0.01 to 50 times by mole, preferably 0.3 to 20 times by mole, based on the amount of the catalyst. After the catalyst deactivation, a step of volatilizing and removing low boiling point compounds in the polymer at a pressure of 0.1 to 1 mmHg and a temperature of 200 to 350°C may be provided. In this step, a horizontal apparatus equipped with stirring blades with excellent surface renewal capability, such as paddle blades, lattice blades, or spectacle blades, or a thin film evaporator is preferably used.

[0258] In thermoplastic resins such as polycarbonate resins, it is desirable to minimize the content of foreign matter, and therefore filtration of the melt and filtration of solid matter from the melt are preferably carried out. The mesh of the filter is preferably 5 μm or less, more preferably 1 μm or less. Furthermore, filtration of the produced polymer with a polymer filter is preferably carried out. The mesh of the polymer filter is preferably 100 μm or less, more preferably 30 μm or less. Furthermore, the process of collecting resin pellets must be carried out in a low-dust environment, preferably class 6 or less, more preferably class 5 or less.

[0259] The thermoplastic resins may be molded by any conventional molding procedure for producing optical components. Suitable molding procedures include, but are not limited to, injection molding, compression molding, casting, rolling, extrusion, stretching, and the like.

[0260] While the thermoplastic resin of the present invention can be molded as described above, it is also possible to mold a resin composition that further comprises at least one thermoplastic resin of the present invention and at least one additive and / or further thermoplastic 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 further resins, i.e., other polycarbonate resins, polyester carbonate resins, polyester resins, polyamides, polyacetals, etc., include those that do not contain the repeating unit of formula (I).

[0261] 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 ... ,7-di-tert-butyl-3-(1,2-dimethylphenyl)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-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. Among these, 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 part by weight based on 100 parts by weight of the thermoplastic resin.

[0262] Examples of the processing stabilizer include, but are not limited to, phosphorus-based processing stabilizers, sulfur-based processing stabilizers, etc. Phosphorus-based processing stabilizers include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid, and esters thereof. Specifically, 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-butyl phenyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, tributyl phosphate, triethyl phosphate, trimethyl phosphate, triphenyl phosphate, diphenyl monoorthoxenyl phosphate, dibutyl phosphate, dioctyl phosphate, diisopropyl phosphate, dimethyl benzenephosphonate, diethyl benzenephosphonate, dipropyl benzenephosphonate, 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, and bis(2,4-di-tert-butylphenyl)-3-phenyl-phenylphosphonite. The content of the phosphorus-based process 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.

[0263] 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 relative to 100 parts by weight of the thermoplastic resin.

[0264] As an example of the release agent, it is preferable that 90% by weight or more of the release agent is composed of an ester of alcohol and a fatty acid. Specific examples of the ester of alcohol and a fatty acid include an ester of a monohydric alcohol and a fatty acid, and a partial ester or a full ester of a polyhydric alcohol and a fatty acid. As the ester of alcohol and a fatty acid, an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms is preferable. In addition, as a partial ester or a full ester of a polyhydric alcohol and a fatty acid, a partial ester or a full ester of a polyhydric alcohol having 2 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms is preferable. Specific examples of the ester of a monohydric alcohol and a fatty acid include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, isopropyl palmitate, etc. Examples of the partial or full ester of polyhydric alcohol and fatty acid 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 hexastearate. The content of the release agent in these resin compositions is preferably in the range of 0.005 to 2.0 parts by weight, more preferably in the range of 0.01 to 0.6 parts by weight, and even more preferably in the range of 0.02 to 0.5 parts by weight, relative to 100 parts by weight of the thermoplastic resin.

[0265] Examples of the ultraviolet absorbent include at least one ultraviolet absorbent selected from the group consisting of benzotriazole ultraviolet absorbents, benzophenone ultraviolet absorbents, triazine ultraviolet absorbents, cyclic iminoester ultraviolet absorbents, and cyanoacrylate ultraviolet absorbents. That is, the ultraviolet absorbents listed below may be used alone or in combination of two or more.

[0266] Examples of benzotriazole-based ultraviolet absorbers 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.

[0267] 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-sodium sulfoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2-hydroxy-4-n-dodecyloxybenzophenone, and 2-hydroxy-4-methoxy-2'-carboxybenzophenone.

[0268] 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.

[0269] Examples of cyclic imino ester-based ultraviolet absorbers include 2,2'-bis(3,1-benzoxazine-4-one), 2,2'-p-phenylenebis(3,1-benzoxazine-4-one), 2,2'-m-phenylenebis(3,1-benzoxazine-4-one), 2,2'-(4,4'-diphenylene)bis(3,1-benzoxazine-4-one), 2,2'-(2,6-naphthalene)bis(3,1-benzoxazine-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), and 2,2'-(2-chloro-p-phenylene)bis(3,1-benzoxazin-4-one).

[0270] 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.

[0271] 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 parts by weight, and further preferably 0.05 to 0.8 parts by weight, based on 100 parts by weight of the thermoplastic resin. If the content is within this range, it is possible to impart sufficient weather resistance to the thermoplastic resin depending on the application.

[0272] As mentioned above, the thermoplastic polymer resin, especially the polycarbonate resin containing the repeating units of each of the formulae (II), (IIa) and (IIb) described herein, provides the thermoplastic resin with high transparency and high refractive index. Therefore, it is suitable for manufacturing optical elements that require high transparency and high refractive index. More specifically, the thermoplastic polycarbonate having the structural units of each of the formulae (II), (IIa) and (IIb) is characterized by having a high refractive index, preferably at least 1.640, more preferably at least 1.660, especially at least 1.670.

[0273] The contribution of each monomer of formula (I), (Ia) and (Ib) to the refractive index of a thermoplastic resin, particularly a polycarbonate resin, depends on the refractive index of said monomer and the relative amount of said monomer in the thermoplastic resin. In general, the higher the refractive index of the monomer contained in the thermoplastic resin, the higher the refractive index of the resulting thermoplastic resin. Alternatively, the refractive index of a thermoplastic resin containing a structural unit of formula (II) can be calculated from the refractive index of the monomer used to prepare the thermoplastic resin (either from the refractive index of the monomer or from scratch, for example, using computer software ACD / ChemSketch 2012 (Advanced Chemistry Development, Inc.)).

[0274] In the case of a thermoplastic copolymer resin, the refractive index of the thermoplastic resin, particularly a polycarbonate resin, can be calculated from the refractive index of the homopolymer of each monomer forming the copolymer resin using the so-called "Fox formula" below. 1 / n D =x 1 / n D1 +x 2 / n D2 +....x n / n Dn , In the formula, n D is the refractive index of the copolymer, and x 1 , x 2 , x n are the mass fractions 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 type of monomer, 1, 2, …, n, at a time. In the case of polycarbonate, x 1 , x 2 , x n is the mass fraction of OH monomers 1, 2, …n based on the total amount of OH monomers. It is clear that a higher refractive index of the homopolymer leads to a higher refractive index of the copolymer.

[0275] The refractive index of a thermoplastic resin can be measured directly or indirectly. In a direct measurement, the refractive index of the thermoplastic resin, n D is measured at a wavelength of 589 nm, using an Abbe refractometer, applying a 0.1 mm film of the thermoplastic resin, according to the protocol of JIS-K-7142. In the case of the refractive index of the homopolycarbonate of the compound of formula (I), the refractive index can also be measured indirectly. For this, 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 then the refractive index n of the copolycarbonate is measured. Dis measured at a wavelength of 589 nm using an Abbe refractometer according to the protocol of JIS-K-7142, applying a 0.1 mm film of the copolycarbonate. The refractive index n D From the above, the refractive index of the homopolycarbonate of each monomer is calculated by the Fox formula and the refractive index of the known 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (n D (589 nm) = 1.639) can be applied to the calculation.

[0276] The compounds of formula (I) can be obtained in a purity that gives a low yellowness index YI (measured according to ASTM E313), which can be important for use in the manufacture of optical resins.

[0277] More particularly, the Yellowness Index YI of the compounds of formula (I), measured according to ASTM E313, preferably does not exceed 100, more preferably 50, even more preferably 20, in particular 10 or 5.

[0278] The thermoplastic resin of the present invention has a high refractive index and a low Abbe number. The thermoplastic resin of the present invention can be advantageously used to manufacture transparent conductive substrates and the like used in liquid crystal displays, organic EL displays, solar cells, and the like. Furthermore, the thermoplastic resin of the present invention can be advantageously used as an optical element suitable for structural or functional material applications of optical components such as optical disks, liquid crystal panels, optical cards, optical sheets, optical fibers, connectors, evaporated plastic reflectors, and displays.

[0279] Therefore, the thermoplastic resin of the present invention can be used to manufacture molded articles such as optical elements. Optical elements include optical lenses and optical films. Specific examples of optical elements include lenses, films, mirrors, filters, prisms, etc. These optical elements are molded by any manufacturing method such as injection molding, compression molding, injection compression molding, extrusion molding, solution casting, etc.

[0280] Due to its excellent moldability and heat resistance, the thermoplastic resin of the present invention is particularly suitable for the manufacture of optical lenses that require injection molding. During molding, the thermoplastic resin such as the polycarbonate resin of the present invention can be mixed with other thermoplastic resins such as other polycarbonate resins, polyester carbonate resins, polyester resins, etc.

[0281] Furthermore, the thermoplastic resin of the present invention may be mixed with additives for forming optical elements. The additives for forming optical elements may be the above-mentioned ones. The additives may include antioxidants, processing stabilizers, light stabilizers, polymerized metal deactivators, flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, release agents, ultraviolet absorbers, plasticizers, compatibilizers, etc.

[0282] As is clear from the above description, another aspect of the present invention relates to an optical element manufactured from the above thermoplastic resin comprising a structural unit of formula (II) and optionally a structural unit of 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 description.

[0283] Optical elements produced from optical resins containing repeating units of formula (II) and optionally repeating units of formula (V) as defined herein are usually optical lenses, such as automobile headlamp lenses, Fresnel lenses, fθ lenses for laser printers, camera lenses, lenses for glasses and projection lenses for rear projection televisions, pickup lenses for CD-ROMs (optical disks), as well as optical disks; optical members for image display media; optical films; film substrates; optical filters; prisms, or optical molded products such as liquid crystal panels, optical cards, optical sheets, optical fibers, optical connectors, and evaporated plastic reflectors. Particularly preferred here are optical lenses and optical films. Optical resins containing repeating units of formula (II) and optionally repeating units of formula (V) are also useful for producing transparent conductive substrates usable in optical elements suitable as structural or functional members of transparent conductive substrates for liquid crystal displays, organic EL displays, solar cells, and the like.

[0284] The optical lens manufactured using the thermoplastic resin of the present invention has a high refractive index, a low Abbe number, low birefringence, and high resistance to moist heat. Therefore, the optical lens can be used in fields where expensive high refractive index glass lenses have been used in the past, such as telescopes, binoculars, and television projectors, and is extremely useful. The optical lens is preferably used in the form of an aspherical lens as necessary. Since an aspherical lens can substantially reduce spherical aberration to zero with a single lens, it is not necessary to remove spherical aberration by combining multiple spherical lenses, and it is possible to reduce weight and production costs. Therefore, the aspherical lens is particularly useful as a camera lens among optical lenses. According to the present invention, a high refractive index, low birefringence aspherical lens, which is technically difficult to process with a glass lens, can be obtained more easily.

[0285] The optical lenses of the present invention can be produced, for example, by injection molding, compression molding, injection compression molding, or co-molding of a resin of repeating units of formula (II) and, optionally, repeating units of formula (V) as defined herein.

[0286] The optical lens of the present invention is characterized by small optical distortion. Conventional optical lenses containing optical resins have large optical distortion. Although it is not impossible to reduce the value of optical distortion by changing molding conditions, the condition range is very narrow, and molding is very difficult. The resin having the repeating unit of formula (II) defined in this specification and the repeating unit of formula (V) optionally has very small optical distortion caused by the orientation of the resin, and small molding distortion, so that excellent optical members can be obtained without strictly setting molding conditions.

[0287] To produce the optical lens of the present invention by injection molding, it is preferable to carry out molding at a cylinder temperature of 260°C to 320°C and a mold temperature of 100°C to 140°C.

[0288] The optical lens of the present invention can be advantageously used as an aspherical lens as necessary. Since a single aspherical lens can substantially eliminate spherical aberration, it is not necessary to combine spherical lenses to eliminate spherical aberration, which can reduce weight and manufacturing costs. Therefore, among optical lenses, aspherical lenses are particularly useful as camera lenses.

[0289] Resins having the repeating unit of formula (II) and optionally the repeating unit of formula (V) as defined herein have good moldability and are particularly useful as materials for thin, small, and complex-shaped optical lenses. The lens size is 0.05-3.0 mm, preferably 0.05-2.0 mm, and more preferably 0.1-2.0 mm, in terms of thickness at the center of the lens. The lens diameter is 1.0-20.0 mm, preferably 1.0-10.0 mm, and more preferably 3.0-10.0 mm. Preferably, the lens is a meniscus lens with one surface convex and the other surface concave.

[0290] 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 a multilayer, 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.

[0291] The optical lens of the present invention can be formed by any method such as metal forming, cutting, polishing, laser processing, electric discharge processing, deburring, etc. Metal forming is preferred.

[0292] The optical film produced using the thermoplastic resin of the present invention has excellent transparency and heat resistance, and is therefore suitable for use as a film for liquid crystal substrates, optical memory cards, etc. It goes without saying that the molding environment must be a low-dust environment in order to prevent foreign matter from being mixed into the optical film as much as possible. The dust environment is preferably class 6 or less, more preferably class 5 or less.

[0293] The following examples serve to further illustrate the invention. EXAMPLES

[0294] 1. Abbreviation: mp: melting point eq.: Molar equivalent DMF: Dimethylformamide HCl: Hydrochloric acid K 2 CO 3 : Potassium carbonate KI: Potassium iodide KOH: Potassium hydroxide MTBE: Methyl tert-butyl ether NaCl: Sodium chloride Na 2 SO 4 : Sodium sulfate NaHCO 3 :Sodium bicarbonate NH 4 Cl: Ammonium chloride THF: tetrahydrofuran TLC: Thin Layer Chromatography n D : Refractive index ν: Abbe number Mw: molecular weight Tg: Glass transition temperature CLWC: Content of low molecular weight compounds GPC: Gel Permeation Chromatography BPEF: 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluoride BNEF: 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene BNE: 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl DPC: Diphenyl carbonate

[0295] 2. Preparation of Monomers of Formula (I) 2.1 Analysis for monomers of formula (I): 1 H-NMR spectra were recorded on an 80 MHz NMR spectrometer (Magritek Spinsolve 80) at 23 °C. Unless otherwise stated, the solvent was CDCl 3 It was decided.

[0296] The melting points of the compounds were measured using a Büchi Melting Point B-545.

[0297] 2.2 Preparation example: Example 1a: 2',2''-[1,4-phenylenebis(methyleneoxy)]di([1,1'-binaphthalen]-2-ol) (DBNABHP) (X=hydrogen and A 1 = 1,4-phenylene; Compound 1 of Table A)

[0298] [ka] rac.1,1'-bi-2-naphthol (111 g, 388 mmol, 2.05 equiv.) in acetone (1.20 kg) and K 2 CO 3 (152 g, 1.10 mol, 5.8 equiv.) was added dropwise to a solution of 1,4-bis(bromomethyl)benzene (50.0 g, 189 mmol, 1.0 equiv.) in acetone (1.00 kg) at 60° C. The reaction mixture was stirred at 60° C. until a TLC control (cyclohexane / ethyl acetate 2:1) showed complete conversion.

[0299] The reaction was quenched by the addition of water (1.00 kg) and the acetone was removed under reduced pressure. Dichloromethane (500 g) was added to the residue and the aqueous phase was acidified (pH=4-5) by the addition of 10% hydrochloric acid. The phases were separated and the organic phase was then washed with water (200 g) followed by saturated aqueous NaCl (200 g) and sodium hydroxide. 2 SO 4 The extract was dried at rt and the solvent was completely removed under reduced pressure.

[0300] The crude product was recrystallized twice from toluene and washed with pentane to give the title compound as a white solid (52.0 g, 77.1 mmol, yield: 41%, chemical purity: 99.3%). mp=170~200°C. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.11-7.71 (m, 8H), 7.53-6.93 (m, 16H), 6.83 (s, 4H), 4.98 (s, 4H), 4.87 (s, 2H) ppm.

[0301] Example 1b: 2',2''-[1,4-phenylenebis(methyleneoxy)]di([1,1'-binaphthalen]-2-ol) (DBNABHP) (X=hydrogen and A 1 = 1,4-phenylene; Compound 1 of Table A)

[0302] [ka] rac.1,1'-bi-2-naphthol (288 g, 1.01 mol, 2.2 equiv.) in acetone (1.6 kg), K 2 CO 3 To a mixture of (139 g, 1.01 mol, 2.2 equiv.) and KI (15.2 g, 91.4 mmol, 0.2 equiv.) was added dropwise a solution of para-α,α'-dichloroxylene (80.0 g, 457 mmol, 1.0 equiv.) in acetone (400 g) at 60° C. over 8 h. The reaction mixture was stirred at 60° C. until a TLC control (cyclohexane / ethyl acetate 2:1) showed complete conversion (approximately 18 h).

[0303] After complete conversion, 2 L of acetone was removed under reduced pressure. Then, water (1 kg) and toluene (1 kg) were added to the reaction mixture and the remaining acetone was removed under reduced pressure. 10% hydrochloric acid was added to acidify the residue (pH=4-5). The phases were separated at 60° C. and the aqueous phase was extracted with toluene (500 g). The combined organic phase was washed with water (500 g) and diluted with Na 2 SO 4 The mixture was dried at 40° C. and the solution was concentrated to a residual mass of 1 g. The mixture was cooled to room temperature and stirred for approximately 2 hours. The suspension was diluted with toluene (300 g) and the crystals formed were filtered off and washed with pentane to give the crude product as a slightly yellow solid. The crude product was recrystallized twice from toluene to give the title compound as a white solid (184 g, 273 mmol, yield: 60%, chemical purity: 99.3%). mp=170~200℃. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.11-7.71 (m, 8H), 7.53-6.93 (m, 16H), 6.83 (s, 4H), 4.98 (s, 4H), 4.87 (s, 2H) ppm.

[0304] Example 2a: 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNABHP) (X=2-hydroxyethyl and A 1 = 1,4-phenylene; compound 25 of Table A)

[0305] [ka] To a solution of di(2'-hydroxy-1,1'-binaphthyl)bishydroxymethylbenzene (34.0 g, 50.4 mmol, 1.0 equiv.) in DMF (280 g), 2 CO 3 (27.9 g, 202 mol, 4.0 equiv) was added and the reaction was heated to 50° C. for 30 min. 2-Chloroethanol (16.2 g, 202 mmol, 4.0 equiv) was added at 50° C. and the reaction was heated to 130° C. until TLC (cyclohexane / ethyl acetate 1:1) showed complete conversion.

[0306] The reaction was cooled to below 100° C., then water (750 g) was added and the mixture was extracted with dichloromethane at room temperature. 2 SO 4 The mixture was dried at rt and the solvent was completely removed under reduced pressure to give the title compound as a white solid (35.0 g, 45.9 mmol, yield: 91%, chemical purity: 97.8%). 1 H NMR (80 MHz, CDCl 3 ): δ = 8.07-7.72 (m, 8H), 7.49-6.99 (m, 16H), 6.62 (s, 4H), 4.89 (m c , 4H), 4.16-3.91 (m, 4H), 3.62-3.32 (m, 4H), 1.95 (apparent dt, J = 6.6, 2.1 Hz, 2H) ppm.

[0307] Example 2b: 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNABHP) (X=2-hydroxyethyl and A 1 = 1,4-phenylene; compound 25 of Table A)

[0308] [ka] Di(2'-hydroxy-1,1'-binaphthyl)bishydroxymethylbenzene (5.0 g, 7.4 mmol, 1.0 equiv.) in toluene (30 g), K 2 CO 3 A mixture of (1.0 g, 7.4 mmol, 1.0 equiv) and KI (0.25 g, 1.5 mmol, 0.2 equiv) was heated to 100° C. A solution of ethylene carbonate (16.2 g, 202 mmol, 4.0 equiv) in toluene (10 g) was added dropwise and the reaction was heated to reflux until TLC (cyclohexane / ethyl acetate 1:1) showed complete conversion.

[0309] The reaction was cooled to 70°C then water (10g) was added and the mixture was stirred for 30 minutes. The aqueous phase was removed and then 10% aqueous citric acid (10g) was added. The mixture was again stirred for 30 minutes, the aqueous phase was removed and 15% aqueous NaOH (10g) was added. The mixture was again stirred for 1 hour and the aqueous phase was removed. Water (10g) was added and the mixture was stirred once more for 30 minutes and the phases were separated. The organic phase was diluted with Na 2 SO 4 After drying at rt and complete removal of the solvent under reduced pressure, the title compound was obtained as a slightly yellow solid (5.1 g, 6.7 mmol, yield: 90%, chemical purity: 93.1%). The compound was further purified by repeated recrystallization from toluene or isobutanol to obtain the product as a white solid with chemical purity >95%. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.07-7.72 (m, 8H), 7.49-6.99 (m, 16H), 6.62 (s, 4H), 4.89 (m c , 4H), 4.16-3.91 (m, 4H), 3.62-3.32 (m, 4H), 1.95 (apparent dt, J = 6.6, 2.1 Hz, 2H) ppm.

[0310] Example 2c: 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNABHP) (X=2-hydroxyethyl and A 1 = 1,4-phenylene; compound 25 of Table A)

[0311] [ka] Di(2'-hydroxy-1,1'-binaphthyl)bishydroxymethylbenzene (10 g, 14.8 mmol, 1.0 equiv.) in toluene (30 g) and DMF (2.5 g), K 2 CO 3 A mixture of (1.0 g, 7.4 mmol, 0.5 equiv) was heated to 100° C. A solution of ethylene carbonate (2.74 g, 31.1 mmol, 2.1 equiv) in toluene (10 g) was added dropwise and the reaction mixture was heated to reflux until TLC (cyclohexane / ethyl acetate 1:1) showed complete conversion.

[0312] The reaction was cooled to 70° C., then methanol (5 g) was added and the mixture was stirred under reflux for 2 hours. Water (20 g) was then added and the mixture was stirred for 30 minutes. The aqueous phase was removed. Activated charcoal (200 mg) was added to the organic phase and the mixture was stirred for 30 minutes. The mixture was filtered through celite at 60° C. to remove the charcoal. The filtrate was concentrated under reduced pressure to remove the methanol and then cooled to room temperature. The crystallized product was isolated by filtration, washed with n-pentane and dried to give the title compound DBHBNABHP (9.2 g; 12 mmol) as white crystals with a chemical purity of 98.1%. mp=120~150℃ 1 H NMR (80 MHz, CDCl 3 ): δ = 8.07-7.72 (m, 8H), 7.49-6.99 (m, 16H), 6.62 (s, 4H), 4.89 (m c , 4H), 4.16-3.91 (m, 4H), 3.62-3.32 (m, 4H), 1.95 (apparent dt, J = 6.6, 2.1 Hz, 2H) ppm.

[0313] Example 3: [1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxymethylene-4,1-phenylene)]dimethanol (DMOBBNABHP) (X = (4-(hydroxymethyl)phenyl)methyl and A1 = 1,4-phenylene; compound 73 of Table A)

[0314] [ka] DBNABHP (70.0 g, 104 mmol, 1.0 equiv.) in acetone (450 g), K 2 CO 3 To a mixture of (29.4 g, 213 mmol, 2.05 equiv.) and KI (1.72 g, 10.4 mmol, 0.1 equiv.) was added 4-chloromethylbenzyl alcohol (33.3 g, 213 mmol, 2.05 equiv.). The mixture was heated to reflux until a TLC control (cyclohexane / ethyl acetate 1:1) showed complete conversion. The reaction mixture was filtered through celite at 40° C. to remove inorganic salts, and then the solvent was completely removed under reduced pressure.

[0315] The crude product was recrystallized from a mixture of toluene (200 g) and ethyl acetate (10 g) using activated carbon (2.5 g, Norit DX Ultra) followed by slurry washing with MTBE to give the title compound as a white solid (84.4 g, 92.2 mmol, yield: 89%, chemical purity: 96.9%). mp=92~98℃. 1 H NMR (80 MHz, CDCl 3 , ppm): δ = 8.02-7.77 (m, 8H), 7.48-7.11 (m, 16H), 7.08-6.75 (m, 8H), 6.65 (s, 4H), 4.95 (s, 4H), 4.90 (s, 4H), 4.48 (s, 4H) ppm. 1 H NMR (80 MHz, DMSO-d 6 , ppm): δ = 8.18-7.81 (m, 8H), 7.74-6.82 (m, 24H), 6.74 (s, 4H), 5.05 (s, 4H), 5.04 (s, 4H), 5.04 (t, J = 4.7 Hz, 2H), 4.37 (d, J = 4.7Hz, 4H) ppm.

[0316] Example 4: Di(2'-hydroxy-1,1'-binaphthyl)bishydroxymethyl-2,6-naphthalene (DBNABHN) (X = hydrogen and A 1 = 2,6-naphthylene; compound 6 of Table A)

[0317] [ka] rac.1,1'-bi-2-naphthol (39.2 g, 137 mmol, 2.2 equiv.) in acetone (330 g), K 2 CO 3 To a mixture of (18.9 g, 137 mmol, 2.2 equiv.) and KI (2.06 g, 12.4 mmol, 0.2 equiv.) was added dropwise a solution of 2,6-di(chloromethyl)naphthalene (14.0 g, 62.2 mmol, 1.0 equiv.) in acetone (160 g) at 60° C. The reaction mixture was stirred at 60° C. until a TLC control (cyclohexane / ethyl acetate 2:1) showed complete conversion.

[0318] Water (140 g) and toluene (140 g) were added to the reaction mixture and acetone was removed under reduced pressure. 10% hydrochloric acid was added to acidify the residue (pH=4-5). The phases were separated at 60° C. and the aqueous phase was extracted with toluene (40 g). The combined organic phase was washed with water (70 g) and diluted with Na 2 SO 4 The mixture was dried at 40° C. and the solution was concentrated to a residual mass of 90 g. The mixture was cooled to room temperature and stirred for approximately 2 hours. The formed crystals were filtered off and washed with pentane to give the title compound as a white solid (30.0 g, 41.4 mmol, yield: 67%, chemical purity: 91.5%). The compound can be further purified by repeated crystallization from toluene to give the product with chemical purity >95%. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.07-7.71 (m, 8H), 7.55-6.89 (m, 22H), 5.26-4.89 (m, 6H) ppm.

[0319] Example 5: 2,2'-[1,4-naphthylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNA14BHN) (X = 2-hydroxyethyl and A 1 = 1,4-naphthylene; compound 31 of Table A) Example 5a: 2-[2-Hydroxy-(1,1'-binaphthalene)-2'-oxy]-ethan-1-ol (Building Block 1)

[0320] [ka] rac. 1,1'-bi-2-naphthol (200 g, 692 mmol, 1.0 equiv.) in methyl ethyl ketone (MEK) (930 g) and K 2 CO 3 A mixture of (110 g, 795 mmol, 1.15 equiv) was heated to reflux for 60 min. Then, a solution of 2-bromoethanol (112 g, 899 mmol, 1.3 equiv) in MEK (200 mL) was added slowly and the reaction mixture was stirred at reflux for approximately 7 h.

[0321] The reaction mixture was cooled to room temperature, then toluene (1000 ml) and water (400 ml) were added. The mixture was acidified with aqueous HCl. The phases were separated and the aqueous phase was extracted with toluene. The combined organic phase was washed with water and brine. The organic phase was concentrated under reduced pressure (150 mbar) until MEK was removed by distillation. The mixture was cooled to room temperature. The formed crystals were filtered off to give the title compound as a white solid (80.0 g, 242 mmol, yield: 35%, chemical purity: 83.75%). Repeated slurry washing in THF gave the desired product with chemical purity >99%. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.16-7.75 (m, 4H), 7.56-6.96 (m, 8H), 5.05 (br s, 1H), 4.23-4.03 (m, 2H), 3.71-3.44 (m, 2H), 1.52 (br s, 1H) ppm.

[0322] Example 5b: 1,4-Di(bromomethyl)naphthalene (Building Block 2) Example 5b.1: 1,4-Naphthalene-dimethanol

[0323] [ka] To a mixture of lithium aluminum hydride (12 g, 316 mmol, 3.4 equiv.) in THF (350 g), 1,4-naphthalenedicarboxylic acid (20 g, 92.5 mmol, 1 equiv.) was added portionwise and the mixture was heated to reflux for 16 h until TLC (cyclohexane / ethyl acetate 1:1) showed complete conversion.

[0324] The mixture was cooled to room temperature and 25 g of water was carefully added. 10% (w / w) aqueous HCl was added to adjust the pH to 1.5. Ethyl acetate (200 g) and brine (50 g) were added. The phases were separated and the aqueous phase was extracted with ethyl acetate (100 g). The combined organic phase was washed with water (50 mL), saturated NaHCO 3 Aqueous solution (2 x 50 mL) and saturated NH 4 The organic phase was washed with aqueous Cl (50 mL). 2 SO 4 The mixture was dried at rt and concentrated under reduced pressure to give the title compound (14.3 g, 76.0 mmol, yield: 82%) as a white solid. 1 H NMR (80 MHz, DMSO-d 6 ): δ = 8.25-7.94 (m, 2H), 7.69-7.36 (m, 4H), 5.36-5.16 (m, 2H), 5.03-4.85 (m, 4H) ppm.

[0325] Example 5b.2: 1,4-Di(bromomethyl)naphthalene

[0326] [ka] 1,4-Naphthalene-dimethanol (14 g, 74 mmol, 1 eq.) obtained in Example 5b.1 above was dissolved in THF (250 g) at 0° C. Phosphorus tribromide (44.3 g; 163 mmol; 2.2 eq.) was then added and the mixture was stirred at room temperature for 24 h until TLC (cyclohexane / ethyl acetate 1:1) showed complete conversion.

[0327] The mixture was added with saturated NaHSO 3Aqueous solution (100 mL) was added slowly. To the mixture, dichloromethane (400 mL) and water (220 mL) were added. The phases were separated and the aqueous phase was extracted with dichloromethane (100 mL). The combined organic phase was washed with brine and water. The organic phase was concentrated under reduced pressure. To the remaining residue, methanol (100 g) was added and the mixture was stirred at room temperature for 2 hours. The title compound 1,4-di(bromomethyl)naphthalene was recovered by filtration as a white solid (19.5 g, 62.1 mmol, yield: 83%). 1 H NMR (80 MHz, DMSO-d 6 ): δ = 8.45-8.07 (m, 2H), 7.90-7.48 (m, 4H), 5.21 (s, 4H) ppm.

[0328] Example 5c: 2,2'-[1,4-naphthylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNA14BHN) (X = 2-hydroxyethyl and A 1 = 1,4-naphthylene; compound 31 of Table A)

[0329] [ka] 2-[2-hydroxy-(1,1'-binaphthalene)-2'-oxy]-ethan-1-ol (36.3 g, 110 mmol, 2.1 equivalents, obtained in Example 5a) was dissolved in acetone (300 g). 2 CO 3 (15.2 g, 110 mmol, 2.1 equiv.) was added and the mixture was heated to 60-70° C. Then, a solution of 1,4-di(bromomethyl)naphthalene (16.4 g, 52.3 mmol, 1 equiv., obtained in Example 5b) in acetone (120 g) was added dropwise. The mixture was stirred under reflux for 1 day until TLC (cyclohexane / ethyl acetate 1:1) showed complete conversion.

[0330] To the mixture was added water (300 g) and toluene (300 g). The resulting mixture was concentrated under reduced pressure to remove acetone and then acidified by adding aqueous HCl (16% w / w). The aqueous phase was separated and extracted with dichloromethane. The combined organic phase was concentrated under reduced pressure to a thick suspension which was then stirred at room temperature for 18 hours. The solid product was collected by filtration. The crude product was dissolved in dichloromethane. The resulting solution was washed with water and diluted with Na 2 SO 4 The mixture was dried at rt and concentrated to dryness under reduced pressure to give the title compound (30.0 g, 36.9 mmol, yield: 67%) as a white solid with a chemical purity of 99.7%. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.05-7.67 (m, 8H), 7.62-6.74 (m, 22H), 5.28 (m c , 4H), 4.07-3.77 (m, 4H), 3.59-3.21 (m, 4H), 2.05 (t, J = 5.9 Hz, 2H) ppm.

[0331] Example 6: 2,2'-[1,2-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNAOBHP) (X=2-hydroxyethyl and A 1 = 1,2-phenylene; compound 26 of Table A)

[0332] [ka] 2-[2-hydroxy-(1,1'-binaphthalene)-2'-oxy]-ethan-1-ol (50 g, 151.3 mmol, 2.1 equivalents, obtained in Example 5a) was dissolved in acetone (450 g). 2 CO 3 (20.9 g, 151.3 mmol, 2.1 equiv.) was added and the mixture was heated to 60-70 °C. Then, a solution of 1,2-bis(bromomethyl)benzene (19 g, 72 mmol, 1 equiv.) in acetone (180 g) was added dropwise. The mixture was stirred under reflux for 18 h until TLC (cyclohexane / ethyl acetate 2:1) showed complete conversion.

[0333] To the mixture was added water (450 g) and toluene (450 g). The mixture was concentrated under reduced pressure to remove acetone and then acidified by adding aqueous HCl (16% w / w). The aqueous phase was separated and extracted with toluene (225 g). The combined organic phase was washed with water (225 g) and diluted with Na 2 SO 4 The mixture was dried at rt and concentrated to dryness under reduced pressure. n-Pentane was added to the residue and the mixture was stirred at room temperature for 1 h. The solid was collected by filtration and dried under vacuum at 40° C. to give the title compound (42.5 g, 55.7 mmol, yield: 74%) with a chemical purity of 96.7%. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.06-7.65 (m, 8H), 7.53-6.52 (m, 20H), 4.88-4.34 (m, 4H), 4.17-3.79 (m, 4H), 3.62-3.24 (m, 4H), 2.16-1.49 (m, 2H) ppm.

[0334] Example 7: 2,2'-[1,3-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNAMBHP) (X=2-hydroxyethyl and A 1 = 1,3-phenylene; compound 27 of Table A)

[0335] [ka] 2-[2-hydroxy-(1,1'-binaphthalene)-2'-oxy]-ethan-1-ol (17.4 g, 52.7 mmol, 2.1 equivalents, obtained in Example 5a) was dissolved in acetone (150 g). 2 CO 3 (7.3 g, 52.7 mmol, 2.1 equiv.) was added and the mixture was heated to 60-70 °C. Then, a solution of 1,3-bis(bromomethyl)benzene (6.6 g, 25 mmol, 1 equiv.) in acetone (60 g) was added dropwise. The mixture was stirred under reflux for 18 h until TLC (cyclohexane / ethyl acetate 2:1) showed complete conversion.

[0336] To the mixture was added water (150 g) and toluene (150 g). The mixture was concentrated under reduced pressure to remove acetone and then acidified by adding aqueous HCl (16% w / w). The aqueous phase was separated and extracted with toluene (75 g) at 60° C. The combined organic phase was washed with water (75 g) and diluted with Na 2 SO 4 The residue was recrystallized twice from MTBE and dried at 40° C. under vacuum to give the title compound (13.4 g, 17.5 mmol, yield: 66%, chemical purity: 97.8%) as a white solid. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.05-7.69 (m, 8H), 7.52-6.96 (m, 16H), 6.94-6.22 (m, 4H), 4.76 (m c , 4H), 4.19-3.83 (m, 4H), 3.64-3.27 (m, 4H), 1.95 (apparent dt, J = 6.5, 3.0 Hz, 2H) ppm.

[0337] Example 8a: Dimethyl-2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(acetate) (X = methoxycarbonylmethyl and A 1 = 1,4-phenylene; compound 49 of Table A)

[0338] [ka] 2,2'-[1,4-phenylenebis(methyleneoxy)]di([1,1'-binaphthalen]-2-ol (147 g, 218 mmol, 1.0 equivalent, obtained in Example 1), K 2 CO 3 A mixture of (90 g, 654 mmol, 3 equiv.) and acetone (1500 g) was heated to 50° C. Bromoacetic acid methyl ester (100 g, 654 mmol, 3 equiv.) was added dropwise and the reaction mixture was heated under reflux for approximately 12 h until TLC (cyclohexane / ethyl acetate 2:1) showed complete conversion.

[0339] The reaction mixture was concentrated under reduced pressure to remove most of the acetone. Water (500 g) and ethyl acetate (1000 g) were then added and the mixture was stirred for 30 minutes. The aqueous phase was separated and extracted with ethyl acetate (250 g). The combined organic phase was washed with brine (500 g) and diluted with Na 2 SO 4 The mixture was dried at 40° C. and concentrated to dryness under reduced pressure to give the crude product. n-Pentane was added and the slurry was stirred at room temperature for 1 hour. The crystals that formed were filtered off to give the desired product as an off-white solid in quantitative yield. 1 H NMR (80 MHz, CDCl 3 ): δ = 8.03-7.72 (m, 8H), 7.48-7.02 (m, 16H), 6.75 (s, 4H), 4.97 (s, 4H), 4.44 (s, 4H), 3.52 (s, 6H) ppm.

[0340] Example 8b: 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(acetic acid)

[0341] [ka] A mixture of dimethyl-2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(acetate) (178.4 g, 218 mmol, 1.0 eq., obtained in Example 8a), KOH (133.3 g; 871.6 mmol, 4 eq.), ethanol (424 g) and water (106 g) was heated under reflux for 2 h. After complete conversion, the mixture was cooled to room temperature and acidified by adding dilute aqueous HCl. Water was decanted from the solid formed. Toluene (400 g) was added to the solid and the mixture was heated to reflux for 30 min. The solid was filtered off and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by first stirring in a pentane / MTBE mixture (9:1) for 2 h and then stirring in MTBE under reflux to give the title compound (84.2 g, 106 mmol, yield: 49%, chemical purity: 99.1%) as a white solid. 1 H NMR (80 MHz, CDCl 3): δ = 9.88 (br s, 2H, OH), 8.07-7.53 (m, 8H), 7.48-6.89 (m, 16H), 6.59 (d, J = 3.9 Hz, 4H), 5.03-4.49 (m, 4H), 4.45-4.02 (m, 4H) ppm.

[0342] 2.3 Refractive index n of the monomer of formula (I) D : Table B below lists the refractive index of several monomers of formula (I) calculated using the software ACD / ChemSketch 2012 (Advanced Chemistry Development, Inc.). Individual monomers are identified in Table B by their name and entry number in Table A. Furthermore, all monomers included in Table B have been confirmed by quantum chemical calculations to have no or only slight to negligible absorption in the visible light range and therefore are essentially colorless.

[0343] [Table 2-1]

[0344] [Table 2-2]

[0345] [Table 2-3]

[0346] [Table 2-4]

[0347] [Table 2-5]

[0348] 3. Preparation of thermoplastic resins from monomers of formula (I) 3.1 Analysis of resins prepared from monomers of formula (I): Refractive index (n D ): The refractive index was measured using a 3 mm thick disk-shaped test piece made of polycarbonate resin according to JIS B 7071-2:2018. The measurement was performed at 23°C using the following refractive index measuring device. Refractometer: KPR-3000 manufactured by Shimadzu Corporation

[0349] Abbe number (ν): A disk-shaped test piece with a thickness of 3 mm was used, which was the same as the test piece used in the refractive index measurement. Using a refractive index measuring device, the refractive index values ​​were measured at wavelengths of 486 nm, 589 nm, and 656 nm at temperatures below 23° C. Then, the Abbe number was calculated using the following formula. Refractometer: KPR-3000 manufactured by Shimadzu Corporation ν=(nD-1) / (nF-nC) nD: Refractive index at a wavelength of 589 nm nC: Refractive index at a wavelength of 656 nm nF: Refractive index at a wavelength of 486 nm

[0350] Glass transition temperature (Tg): The glass transition temperature was measured by differential scanning calorimetry (DSC) using a heating program of 10° C. / min according to JIS K7121-1987. Differential scanning calorimetry: X-DSC7000 manufactured by Hitachi High-Tech Science Co., Ltd.

[0351] molecular weight The molecular weight distribution of the resin molecules, in particular the weight average molecular weight (Mw) value of the resin was measured by gel permeation chromatography (GPC) and calculated by the standard polystyrene conversion approach. The following equipment, columns and measurement conditions were used: GPC equipment: HLC-8420GPC (Tosoh Corporation); Columns: 3 TSKgel SuperHM-M (Tosoh Corporation), One guard column, SuperHM-M (Tosoh Corporation), One TSKgel SuperH-RC (manufactured by Tosoh Corporation); Detector: RI detector Standard polystyrene: PstQuick C (Tosoh Corporation) as a standard polystyrene kit; Eluent: tetrahydrofuran; Eluent flow rate: 0.6 ml / min; Column temperature: 40°C.

[0352] The number average molecular weight (Mn) value was calculated using a method similar to that used to measure the Mw value described above. The polystyrene converted weight average molecular weight (Mw) and number average molecular weight (Mn) were calculated from a calibration curve of a standard polystyrene prepared in advance. Specifically, a calibration curve was prepared using a standard polystyrene (manufactured by Tosoh Corporation, "PStQuick C") with a known molecular weight. Furthermore, the elution time and molecular weight value of each peak were plotted from the measured data of the standard polystyrene, and a calibration curve was prepared by approximating the data using a cubic equation. The Mw and Mn values ​​were calculated using the following formula: Mw = Σ(Wi × Mi) ÷ Σ(Wi) Mn = Σ(Ni × Mi) ÷ Σ(Wi) Here, "i" is the "i"th division point, Wi is the molecular weight (g) of the "i"th polymer, "Ni" is the number of molecules of the "i"th polymer, and "Mi" is the mass of the "i"th molecule. The molecular weight (M) is the polystyrene molecular weight value at the same elution time on the calibration curve.

[0353] Low molecular weight compound content (CLWC) The content of low molecular weight compounds represents the area ratio of compounds with Mw values ​​of less than 1000 in GPC analysis. Therefore, the content of low molecular weight compounds was determined based on the following formula:

[0354]

number

[0355] Birefringence The value of Δn (birefringence) was determined as follows: a cast film with a thickness of 0.1 mm was cut into a square with a side of 5.0 cm, and then both ends of the film were fixed with chucks (distance between chucks: 3.0 cm), and stretched 1.5 times at a temperature of Tg+20°C of the polycarbonate resin. The retardation (Re) was measured at 589 nm using an ellipsometer M-220 (JASCO Corporation, Japan), and subsequently calculated according to the following formula: Δn=Re / d Δn: Orientation birefringence Re: phase difference d: Thickness

[0356] The birefringence (Δn) criteria are given in the table below.

[0357] [Table 3]

[0358] 3.2 Example for thermoplastics production: 3.2.1 Polycarbonate resin Example 9 (E9): As raw materials, 21.6375 g (0.0493 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF), 4.4587 g (0.0055 mol) of 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNABHP) obtained in Example 2, 12.0983 g (0.0565 mol) of diphenyl carbonate (DPC), and 0.4606 × 10 -4 g(0.5483×10 -6(mol) of sodium bicarbonate was placed in a 300 mL reactor equipped with a stirrer and a distillation apparatus. The reactor was flushed with nitrogen and the internal pressure was set to 101.3 kPa.

[0359] The reactor was immersed in an oil bath heated to 200°C, and the transesterification reaction was then initiated. Stirring of the reaction mixture was started 5 minutes after the reaction start time. After 20 minutes, the pressure of the reaction mixture was reduced from 101.3 kPa to 26.66 kPa over 10 minutes. During the pressure reduction, the reaction mixture was heated to 210°C. It was then further heated to 220°C at 60 minutes after the reaction start time. From 80 minutes after the reaction start time, the pressure of the reaction mixture was reduced to 20.00 kPa and the reaction mixture was heated to 240°C in 10 minutes. The pressure of the reaction mixture was then reduced to 0 kPa and maintained at this level for 30 minutes.

[0360] Nitrogen gas was introduced into the reactor to return the pressure of the reaction mixture to 101.3 kPa, and finally a polycarbonate resin was obtained.

[0361] The resulting polycarbonate resin had a refractive index of 1.647, an Abbe number of 22.31, and a Tg of 144° C., with a polystyrene converted weight average molecular weight of 34,459. The molar ratios of the diol monomers used are listed in Table D, and the properties of the resulting resin are summarized in Table E.

[0362] Example 10 (E10): 10.4972 g of DBHBNABHP (0.0138 mol), 14.0818 g of BPEF (0.0321 mol), 10.0725 g of DPC (0.047 mol), and 0.7707 × 10 -4 g NaHCO 3 (0.9175×10 -6 Polycarbonate resins were prepared following the same method as used in Example 9, with the only difference being that 100 moles of dimethylformamide were used. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resins are summarized in Table E.

[0363] Example 11 (E11): 16.7174 g of DBHBNABHP (0.0219 mol), 6.4222 g of BPEF (0.0146 mol), 7.9897 g of DPC (0.0373 mol), and 0.6143 × 10 -4 g NaHCO 3 (0.7312×10 -6 Polycarbonate resins were prepared following the same method as used in Example 9, with the only difference being that 100 moles of dimethylformamide were used. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resins are summarized in Table E.

[0364] Examples 12 to 20, 23 to 27, and 29 to 33 (E12 to E20, E23 to E27, and E29 to E33) The polycarbonate resins of these examples were prepared according to the same method used in Example 9, with the only difference being that the amounts and types of monomers and catalysts shown in Tables C1-C4 were used. The molar ratios of the monomers used in each example are listed in Table D, and the properties of the resulting resins are summarized in Table E.

[0365] 3.2.2 Polyester carbonate resin Example 21 (E21): As raw materials, 13.7869 g (0.0181 mol) of 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethane-1-ol) (DBHBNABHP), 16.2236 g (0.301 mol) of 9,9-bis[6-(2-hydroxyethoxy)2-naphthyl]fluorene (NOLE), 9.5057 g (0.0181 mol) of 6,6'-difluorophenyl The mixture was prepared by subjecting the mixture to 100 mL of phenyl-2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl (DPBN), 21.8162 g (0.0542 mol) of 2,2'-[(1,1'-binaphthalene-2,2'-diyl)bis(oxy)]diacetic acid (BINOL-DC), 3.0558 g (0.0143 mol) of diphenyl carbonate (DPC), and the catalyst tris(2,4-pentanedionato)aluminum(III) (0.4701 × 10 -2 g, 0.1449 x 10 -3 mol, also known as Al(acac) 3) and (4-methylbenzyl)phosphonic acid diethyl ester (0.5882 × 10 -2 g, 0.2428 x 10 -3 The mixture (1.2 g / mol) was placed in a 300 ml reactor equipped with a stirrer and a distillation apparatus. The reactor was flushed with nitrogen and the internal pressure was set to 101.3 kPa.

[0366] The reactor was immersed in an oil bath heated to 200° C. and the transesterification reaction was then initiated. Stirring of the reaction mixture was started 5 minutes after the reaction initiation time. After 20 minutes, the pressure of the reaction mixture was reduced from 101.3 kPa to 93.33 kPa over 10 minutes. 10 minutes after the pressure reduction was complete, the reaction mixture was heated to 240° C. for 40 minutes. The pressure of the reaction mixture was then further reduced to 40.00 kPa over 20 minutes.

[0367] Nitrogen gas was introduced into the reactor to return the pressure of the reaction mixture to normal pressure. The trap was then replaced with a new one and the reaction conditions were set as 240° C. and 300 Torr. The reaction mixture was heated to 250° C., and then the pressure of the reaction mixture was reduced to 0 kPa in 60 minutes and maintained at this level for 30 minutes.

[0368] Nitrogen gas was introduced into the reactor to return the pressure of the reaction mixture to 101.3 kPa, and finally a polyester carbonate resin was obtained.

[0369] The resulting polyestercarbonate resin had a refractive index of 1.690, an Abbe number of 17.80, and a Tg of 160° C., with a polystyrene converted weight average molecular weight of 36,654. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resin are summarized in Table E.

[0370] Example 28 (E28): Polyestercarbonate resins were prepared according to the same method used in Example 21, with the only difference being that the amounts and types of monomers and catalysts shown in Tables C1-C4 were used. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resins are summarized in Table E.

[0371] 3.2.3 Polyester resin Example 22 (E22): The raw materials were 3.5226 g (0.0046 mol) of 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethane-1-ol) (DBHBNABHP), 2.4287 g (0.0046 mol) of 6,6'-diphenyl-2,2'bis(2-hydroxyethoxy)-1,1'-binaphthyl (DPBN), 1.0031 g (0.0162 mol) of ethylene glycol (EG), 4.6451 g (0.0115 mol) of 2,2'-[(1,1'-binaphthalene-2,2'-diyl)bis(oxy)]diacetic acid (BINOL-DC), and 0.1267 × 10 -2 g(0.5170×10 -5 mol) of manganese(II) acetate tetrahydrate and 0.1251 × 10 -2 g(0.7100×10 -5 ) of calcium acetate monohydrate was placed in a 50 milliliter reactor equipped with a stirrer and a distillation apparatus. The reactor was flushed with nitrogen.

[0372] The reactor was immersed in an oil bath heated to 100° C. and the transesterification reaction was then initiated. Stirring of the reaction mixture was started 5 minutes after the reaction initiation time. By the time 120 minutes after the reaction initiation time, the reaction mixture was heated to 230° C. and maintained at this level for 290 minutes.

[0373] Next, 0.1498 x 10 -2 g(1.5283×10 -5 mol) of phosphoric acid and 0.4092×10 -2 g(3.9144×10 -5 100 mol) of germanium dioxide was added to the reaction mixture to initiate the polycondensation reaction. The reaction mixture was then heated to 270° C. and the pressure of the reaction mixture was reduced to 0 kPa in 90 minutes and maintained at this level for 120 minutes.

[0374] Nitrogen gas was introduced into the reactor, and the pressure of the reaction mixture was returned to 101.3 kPa to obtain a polyester resin.

[0375] The resulting polyester resin had a refractive index of 1.690, an Abbe number of 17.60, and a Tg of 148° C., with a polystyrene converted weight average molecular weight of 34,544. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resin are summarized in Table E.

[0376] 3.2.4 Comparative examples of polycarbonate resin Comparative example 1 (CE1): 10.2444 g of BNEF (0.019 mol), 19.4593 g of BPEF (0.0444 mol), 13.9877 g of DPC (0.0653 mol), and 0.3838 × 10 -4 g NaHCO 3 (0.4568×10 -6 Polycarbonate resins were prepared following the same method as used in Example 9, with the only difference being that 100 moles of dimethylformamide were used. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resins are summarized in Table E.

[0377] Comparative Example 2 (CE2): 15.2611 g of BNE (0.0408 mol), 11.9149 g of BPEF (0.0272 mol), 14.9882 g of DPC (0.07 mol), and 0.4981 × 10 -4 g NaHCO 3 (0.593×10 -6 Polycarbonate resins were prepared following the same method as used in Example 9, with the only difference being that 100 moles of dimethylformamide were used. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resins are summarized in Table E.

[0378] Comparative Example 3 (CE3): 16.2901 g of BNE (0.0435 mol), 4.7694 g of BPEF (0.0109 mol), 11.8826 g of DPC (0.0555 mol), and 0.4568 × 10 -4 g NaHCO 3 (0.5438×10 -6Polycarbonate resins were prepared following the same method as used in Example 9, with the only difference being that 100 moles of dimethylformamide were used. The molar ratios of the monomers used are listed in Table D, and the properties of the resulting resins are summarized in Table E.

[0379] Tables C1-C4 below summarize the amounts of monomers and catalysts used to prepare the thermoplastic resins of Examples E9-E33 and CE1-CE3. The molar ratios of the monomers used in each example are listed in Table D, and the properties of the resulting resins are summarized in Table E. Table C1: Amounts of Monomers (in grams) Used in Examples 9-33 and CE1-CE3 Table C2: Amounts of monomers (molar basis) used in Examples 9-33 and CE1-CE3 Table C3: Amount of catalyst (in grams) used in Examples 9-33 and CE1-CE3 Table C4: Amount of catalyst (molar basis) used in Examples 9-33 and CE1-CE3 Table D: Molar ratios of monomers used in Examples 9-33 and CE1-CE3 Table E: Properties of thermoplastic resins E9-E33 and CE1-CE3

[0380] [Table 4]

[0381] [Table 5]

[0382] [Table 6]

[0383] [Table 7]

[0384] [Table 8]

[0385]

Table 9

[0386]

change

[0387]

change

Claims

1. Compound of formula (I) 【Chemistry 1】 (In the formula, X １ and X ２ are independently selected from hydrogen, -Alk １ -OH, -CH ２ -A ２ -CH ２ -OH, -Alk ２ -C(O)OR ｘ -CH ２ -A ２ -C(O)OR ｘ and -C(O)-A ２ -C(O)OR ｘ (R ｘ is independently selected from the group consisting of hydrogen, phenyl, benzyl and C １ -C ４ -alkyl); Y １ and Y ２ is, -CH ２ -, -CHAR Ｙ - and CH(CH ２ Ar Ｙ ) - Selected independently of; A １ This is a single bond, -CH ２ -, -CHAR Ａ -, -CH(CH ２ Ar Ａ )-,-C(CH ２ Ar Ａ ) ２ -, part of formula (A), monocyclic or polycyclic arylenes having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetalylenes having a total of 5 to 26 ring member atoms (these ring member atoms of 1, 2, 3 or 4 hetalylenes are selected from nitrogen, sulfur and oxygen, and the remaining ring member atoms of the hetalylenes are carbon atoms. Monocyclic or polycyclic arylenes and monocyclic or polycyclic hetalylenes are unsubstituted or have 1, 2, 3 or 4 R Ａｒ Selected from the group consisting of (having a group); 【Chemistry 2】 During the ceremony, Q is a single bond, O, C=O, CH ２ , S or SO ２ It represents; R ５ａ , R ５ｂ These are, independently of each other, hydrogen, fluorine, CN, R, OR, and CH. ｋ R' ３－ｋ , NR ２ , C(O)R and C(O)NH ２ Selected from the group consisting of (where k is 0, 1, or 2); * is Y １ or Y ２ Represents the connection point to; Alternatively, part Y of equation (I) １ -A １ -Y ２ - is - CH ２ - or -CHAR Ｙ - may be, n is 1, 2, or 3; R １ , R ２ , R ３ and R ４ is hydrogen, halogen, C ２ -C ３ -Alkinyl, CN, R, OR, CH ｓ R' ３－ｓ , NR ２ , independently selected from the group consisting of C(O)R and CH=CHR'', R １ , R ２ , R ３ or R ４ If two or more of these exist, then R １ , R ２ , R ３ or R ４ They may be the same or different, and s is 0, 1, or 2 for each occurrence; m, p, q, and r are independently 0, 1, or 2; A ２ It is selected from the group consisting of phenylene, naphthylene, and biphenylylene; Alk １ C ２ -C ４ - It is Arcanziel; Alk ２ C １ -C ４ - It is Arcanziel; Ar Ｙ and Ar Ａ It is selected from the group consisting of monocyclic or polycyclic aryls having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetalils having a total of 5 to 26 ring member atoms (these ring member atoms of 1, 2, 3, or 4 hetalils are selected from nitrogen, sulfur, and oxygen, and the ring member atoms of the remaining hetalils are carbon atoms), and Ar Ｙ and Ar Ａ is unsubstituted or has 1, 2, 3 or 4 R Ａｒ It is substituted with the base; R Ａｒ R, OR, CH ｔ R' ３－ｔ , NR ２ Selected from the group consisting of and CH=CHR'', with the same aryl (hetalil) or arylene (hetalylene) group R Ａｒ If there are two or more, they may be the same or different, and t is 0, 1, or 2 for each occurrence; R is C １ -C ４ - Selected from the group consisting of alkyl, phenyl, naphthyl, phenantrenyl, and triphenylenyl (phenyl, naphthyl, phenantrenyl, and triphenylenyl are unsubstituted or substituted with one, two, three, or four identical or different R''' groups); R' is selected from the group consisting of phenyl, naphthyl, phenantrenyl, and triphenylenyl (phenyl, naphthyl, phenantrenyl, and triphenylenyl are unsubstituted or substituted with one, two, three, or four identical or different R''' groups); R'' is selected from hydrogen, methyl, phenyl, and naphthyl (phenyl and naphthyl are unsubstituted or substituted with one, two, three, or four identical or different R''' groups); R''' is phenyl, OCH ３ ,CH ３ , N (CH ３ ) ２ and C(O)CH ３ (Selected from the group consisting of) And, X １ and X ２ are both hydrogen or -CH ２ CH ２ -OH, Y １ and Y ２ are both CH ２ and A １ is a single bond or CH ２ except for the compound of formula (I) wherein; and n is 1, X １ and X ２ are both hydrogen, Y １ and Y ２ are both CH ２ and m, p, q and r are all 0, A １ is 1,2-phenylene, 1,3-phenylene, 1,6-pyrenylene, 4,4'-biphenylene, 2,6-pyridinylene, 4,4''-meta-terphenylenylene, 2,5-[1,3,4]-thiadiazolylene, 2,5-[1,3,4]-oxadiazolylene, 2,5-thienediyl-bis(4,1-phenylenemethylene), 9,9-diethyl-2,7-9H-fluorenylene, 10-methyl-3,7-phenothiazinylene or 10-ethyl-3,7-phenothiazinylene, excluding the compound of formula (I).

2. X １ and X ２ ga-Alk １ -OH and -CH ２ -A ２ -CH ２ A compound according to claim 1, selected from -OH.

3. X １ and X ２ The compound according to claim 1 or claim 2, wherein both are hydrogen.

4. X １ and X ２ ga-Alk ２ -C(O)OR ｘ and -CH ２ -A ２ -C(O)OR ｘ A compound according to claim 1 or claim 2, selected from the above.

5. X １ and X ２ The compound according to claim 1 or claim 2, which is selected from hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, hydroxymethyl-phenyl-methyl, hydroxymethyl-naphthyl-methyl, hydroxymethyl-biphenylyl-methyl, methoxycarbonyl-phenyl-methyl and methoxycarbonyl-naphthyl-methyl, particularly hydrogen, 2-hydroxyethyl, methoxycarbonyl-methyl, (4-(hydroxymethyl)phenyl)methyl, (3-(hydroxymethyl)phenyl)methyl, (4-(hydroxymethyl)-1-naphthyl)methyl, (6-(hydroxymethyl)-2-naphthyl)methyl, 4'-(hydroxymethyl)-1,1'-biphenylyl-4-methyl, (4-(methoxycarbonyl)phenyl)methyl, (3-(methoxycarbonyl)phenyl)methyl, (4-(methoxycarbonyl)-1-naphthyl)methyl and (6-(methoxycarbonyl)-2-naphthyl)methyl.

6. X １ and X ２ The compound according to claim 1 or claim 2, wherein the terms have the same meaning.

7. Y １ and Y ２ Both are -CH ２ - The compound according to claim 1 or claim 2.

8. A １ However, the part of formula (A), monocyclic or polycyclic arylene and monocyclic or polycyclic hetalylene (monocyclic or polycyclic arylene and monocyclic or polycyclic hetalylene are unsubstituted or have 1, 2, 3 or 4 R Ａｒ A compound according to claim 1 or claim 2, selected from the group consisting of (having a group).

9. A １ However, phenylene, naphthylene, 1,2-dihydroacenaphthylene, biphenylylene, 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]dioxynylene, 2H-naphtho[1,8-d,e][1,3]dioxynylene, phenoxathinylene, dinaph To[2,3-b:2',3'-d]furanylene, oxantrenylene, benzo[a]oxantrenylene, benzo[b]oxantrenylene, 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']ditienylene, 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-thioxanthiene, 6H-dibenzo[b,d] thiopyranylene, 1,4-benzodithienylene, naphtho[1,2-b][1,4] dithienylene, naphtho[2,3-b][1,4] dithienylene, 9H-10-thiaanthreylene, thianthrenylene, benzo[a] thianthrenylene, benzo[b] thianthrenylene, dibenzo[a,c] thianthrenylene, dibenzo[a,i) Thiantreniylene, dibenzo[a,j] thiantreniylene, dibenzo[b,i] thiantreniylene, 2H-naphtho[1,8-b,c] thienylene, dibenzo[b,d] thiepinylene, dibenzo[b,f] thiepinylene, 5H-phenanthrone[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, tri A compound according to claim 1 or claim 2, selected from the group consisting of benzo[a,c,i]thiantrenylene, benzo[b]naphtho[1,8-e,f][1,4]ditiepinylene, 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']ditienylene, and dibenzo[d,d']benzo[1,2-b:5,4-b']ditienylene.

10. A １ However, phenylene, naphthylene, dibenzo[b,d]thienylene, biphenylylene, 9H-fluorenylene, thiantreylene, 9H-xantylene and 9H-thioxantylene, especially 1,4-phenylene, 1,2-phenylene, 1,3-phenylene, 2,3-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,8-naphthylene, 4,6-dibenzo[b,d]thienylene, and 2,8-dibenzo[b,d]thienylene The compound according to claim 9, selected from the group consisting of 3,7-dibenzo[b,d]thienylene, 3,3'-biphenylylene, 4,4'-biphenylylene, 9,9-9H-fluorenylene, 2,7-9H-fluorenylene, 2,7-thianthrenylene, 2,8-thianthrenylene, 1,4-thianthrenylene, 2,3-thianthrenylene, 1,6-thianthrenylene, 1,9-thianthrenylene, 9,9-9H-xantylene, and 9,9-9H-thioxantylene.

11. A １ However, single bonds, -CH ２ -, -CHAR Ａ -, -CH(CH ２ Ar Ａ )- and -C(CH ２ Ar Ａ ) ２ - is selected from, in particular -C(CH ２ Ar Ａ ) ２ - The compound according to claim 1 or claim 2.

12. -Y in equation (I) １ -A １ -Y ２ -ga-CH ２ - or -CHAR Ｙ - and especially -CH ２ - The compound according to claim 1 or claim 2.

13. R １ , R ２ , R ３ and R ４ The compound according to claim 1 or claim 2, wherein the same meaning is achieved.

14. The compound according to claim 1 or claim 2, wherein m, p, q, and r are all 0.

15. Equation (I) is expressed by equation (Ia), where X is X in claim 1. １ and X ２ The compound according to claim 1 or claim 2, as defined as follows. 【Transformation 3】

16. X and A １ The compound according to claim 15, wherein is 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 Table 1-7 Table 1-8 Table 1-9 Table 1-10 Table 1-11

17. In equation (I), the part -Y １ -A １ -Y ２ -ga-CH ２ - and X １ and X ２ The compound according to claim 12, wherein both are 2-hydroxyethyl, m, p, q and r are all 0, and n is 1.

18. A compound of formula (I) or a mixture thereof, as a monomer for producing a thermoplastic resin. 【Chemistry 4】 (In the formula, X1 and X2 are independently selected from hydrogen, -Alk1-OH, -CH2-A2-CH2-OH, -Alk2-C(O)ORx, -CH2-A2-C(O)ORx, and -C(O)-A2-C(O)ORx (where Rx is selected from the group consisting of hydrogen, phenyl, benzyl, and C1-C4-alkyl); Y1 and Y2 are selected independently from -CH2-, -CHArY-, and -CH(CH2ArY)-; A1 is selected from the group consisting of single bonds, -CH2-, -CHArA-, -CH(CH2ArA)-, -C(CH2ArA)2-, the part of formula (A), monocyclic or polycyclic arylenes having 6 to 26 carbon atoms as ring members, and monocyclic or polycyclic hetalylenes having a total of 5 to 26 ring member atoms (these ring member atoms of 1, 2, 3, or 4 hetalylenes are selected from nitrogen, sulfur, and oxygen, and the remaining ring member atoms of the hetalylenes are carbon atoms. Monocyclic or polycyclic arylenes and monocyclic or polycyclic hetalylenes are unsubstituted or have 1, 2, 3, or 4 RAr groups); 【Transformation 5】 During the ceremony, Q represents a single bond, O, C=O, CH₂, S, or SO₂; R 5a and R 5b are independently selected from the group consisting of hydrogen, fluorine, CN, R, OR, CH k R' 3-k, NR 2, C(O)R, and C(O)NH 2 (where k is 0, 1, or 2); * indicates a connection point to Y1 or Y2; Alternatively, the part of equation (I) -Y1 -A1 -Y2- may be -CH2- or -CHARY-, n is 1, 2, or 3; R1, R2, R3, and R4 are independently selected from the group consisting of halogens, C2-C3-alkynyl, CN, R, OR, CHsR'3-s, NR2, C(O)R, and CH=CHR'', and if two or more of R1, R2, R3, or R4 are present, R1, R2, R3, or R4 may be the same or different, and s is 0, 1, or 2 for each occurrence; m, p, q, and r are independently 0, 1, or 2; A2 is selected from the group consisting of phenylene, naphthylene, and biphenylylene; Alk1 is a C2-C4-alkanediyl; Alk2 is a C1-C4-alkanediyl; ArY and ArA are selected from the group consisting of monocyclic or polycyclic aryls having 6 to 26 carbon atoms as ring members and monocyclic or polycyclic hetalils having a total of 5 to 26 ring member atoms (these ring member atoms of 1, 2, 3, or 4 hetalils are selected from nitrogen, sulfur, and oxygen, and the ring member atoms of the remaining hetalils are carbon atoms), and ArY and ArA are unsubstituted or substituted with 1, 2, or 3 RAr groups; R Ar is selected from the group consisting of R, OR, CH t R' 3-t, NR 2, and CH=CHR'', and may be the same or different if two or more R Ars are present on the same aryl (hetalir) or arylene (hetalirene) group, and t is 0, 1, or 2 for each occurrence; R is selected from the group consisting of C1-C4-alkyl, phenyl, naphthyl, phenantrenyl, and triphenylenyl (phenyl, naphthyl, phenantrenyl, and triphenylenyl are unsubstituted or substituted with one, two, three, or four identical or different R''' groups); R' is selected from the group consisting of phenyl, naphthyl, phenantrenyl, and triphenylenyl (phenyl, naphthyl, phenantrenyl, and triphenylenyl are unsubstituted or substituted with one, two, three, or four identical or different R''' groups); R'' is selected from hydrogen, methyl, phenyl, and naphthyl (phenyl and naphthyl are unsubstituted or substituted with one, two, three, or four identical or different R''' groups); R''' is selected from the group consisting of phenyl, OCH3, CH3, N(CH3)2, and C(O)CH3.

19. A thermoplastic resin containing a structural unit represented by the following formula (II). 【Transformation 6】 (In the formula, # represents a connection point to an adjacent structural unit; and, X １ａ and X ２ａ These are, respectively, X １ Or X ２ If is hydrogen, then by substituting hydrogen with a single bond, or X １ Or X ２ If it is not hydrogen, X １ Or X ２ -OH group or -OR ｘ By substituting the base with an oxo (-O-) unit, X in formula (I) １ or X ２ Induced from, and, X １ , X ２ , Y １ , Y ２ A １ , R １ , R ２ , R ３ , R ４ n, m, p, q, and r are as defined in claim 1.

20. This is the result of equation (IIa), where X ａ In claim 19, X １ａ and X ２ａ The thermoplastic resin according to claim 19, as defined as follows. 【Transformation 7】

21. The structural unit of formula (II) is combined with one of the structures represented by the following formulas (III-1) to (III-5), where X １ａ and X ２ａ It is a single bond, -Alk １ -O- and -CH ２ -A ２ -CH ２ A thermoplastic resin according to claim 19 or 20, selected from -O-. 【Transformation 8】 (In the formula, (# represents a connection point to an adjacent structural unit.)

22. A thermoplastic resin according to claim 19 or 20, which includes structural units of formula (V) in addition to structural units of formula (II), selected from a copolycarbonate resin, a copolyester carbonate resin, and a copolyester resin. #-O-R ｚ -A ３ -R ｚ -O-# (V) (In the formula, # represents a connection point to an adjacent structural unit; A ３ A is a polycyclic group having at least two benzene rings (the benzene rings may be linked by W, and / or directly fused to each other, and / or fused by non-benzene carbon rings, and / or fused by two non-benzene carbon rings linked via a linker L), and A ３ is unsubstituted or has 1, 2, or 3 R ａａ Group (R ａａ is halogen, C １ -C ６ - Alkyl, C ５ -C ６ - Substituted with a molecule selected from the group consisting of cycloalkyl, phenyl, naphthyl, 1,2-dihydroacenaphthirenyl, phenantrenyl, pyrenyl, triphenylenyl, benzo[b]furanyl, dibenzo[b,d]furanyl, benzo[b]thienyl, dibenzo[b,d]thienyl, and thianthrenyl; W represents a single bond, O, C=O, S, SO ２ ,CH ２ , CH-Ar, CAr ２ , CH (CH ３ ), C (CH ３ ) ２ and selected from the group consisting of the bases of formula (A'); 【Chemistry 9】 During the ceremony, Q' represents a single bond, O, C=O, or CH ２ It represents; R ７ａ , R ７ｂ These are hydrogen, fluorine, CN, R, OR, and CH, which are independent of each other. ｖ R' ３－ｖ , NR ２ , C(O)R and C(O)NH ２ Selected from the group consisting of (where R and R' are as defined in claim 1, and v is 0, 1, or 2); * indicates a bond point to the benzene ring; L is a single bond, C １ -C ４ - Alkylene, C ４ -C ７ -Cycloalkylene, C ４ -C ７ - Selected from cycloalkylenedimethylene and phenylenedimethylene, where L is unsubstituted or one or two R Ｌ Group (R Ｌ C １ -C ４ - Alkyl, halogen, C １ -C ４ - Haloalkyl, C ４ -C ７ - Substituted with (selected from the group consisting of cycloalkyl and phenyl); Ar is selected from the group consisting of monocyclic or polycyclic aryls having 6 to 26 carbon atoms as ring member atoms and monocyclic or polycyclic hetalils having a total of 5 to 26 ring member atoms (these ring member atoms of 1, 2, 3, or 4 hetalils are selected from nitrogen, sulfur, and oxygen, and the ring member atoms of the remaining hetalils are carbon atoms), and Ar is unsubstituted or has 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 groups); 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 (It is connected to the other); w is an integer between 1 and 10; Alk ３ C １ -C ４ - It is Arcanziel; Alk ４ C ２ -C ４ - It is Arcanziel; and, Alk ５ C １ -C ４ - It is Arcanziel.

23. The thermoplastic resin according to claim 22, 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, especially 0 or 1; a' and b' are 0, 1, 2, or 3, especially 0 or 1; c and d are 0, 1, 2, 3, 4, or 5, especially 0 or 1; e and f are 0, 1, 2, 3, 4, or 5, especially 0 or 1; W' is S, S(O), SO ２ O, single bond, CH ２ , CH (CH ３ ), 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 defined in equation (V).

24. The thermoplastic resin according to claim 22, wherein the molar ratio of the structural unit of formula (II) is 1 to 99 mol%, preferably 30 to 98 mol%, based on the total molar amount of the structural units of formula (II) and (V), and the molar ratio of the structural unit of formula (V) is 1 to 99 mol%, preferably 2 to 70 mol%, based on the total molar amount of the structural units of formula (II) and (V).

25. 1. A thermoplastic resin according to claim 19 or 20, having a refractive index of 1.630 or higher.

26. A thermoplastic resin according to claim 19 or 20, having an Abbe number of 24 or less.

27. A thermoplastic resin according to claim 19 or 20, having a glass transition temperature (Tg) of 90 to 185°C.

28. The thermoplastic resin according to claim 19 or 20, having a weight-average molecular weight of 10,000 to 50,000 as determined by gel permeation chromatography against a polystyrene standard.

29. The thermoplastic resin according to claim 19 or 20, comprising 7% by weight or less of a low molecular weight compound having a molecular weight of less than 1000, based on the total weight of the thermoplastic resin.

30. The thermoplastic resin according to claim 19 or 20, comprising 1% by weight or more of a low molecular weight compound having a molecular weight of less than 1000, based on the total weight of the thermoplastic resin.

31. The thermoplastic resin according to claim 19 or 20, which is polycarbonate, polyester carbonate, or polyester.

32. An optical element made of a thermoplastic resin according to claim 19 or 20.

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