Polycyclic aromatic compound, optical material, optical element, and optical apparatus

Abstract

Disclosed is a polycyclic aromatic compound which is a monomer or dimer of a structural unit represented by formula (1), and which is a homodimer or a heterodimer in the case of a dimer. In formula (1), the A ring, the B ring, the C ring, and the D ring each independently represent a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; each R independently represents a hydrogen atom, an alkyl, or the like, and two adjacent R may be bonded to each other to form a ring; Em represents a divalent group in which m E's are connected in series, with one bonding site being bonded to a ring constituent element of the B ring, and the other bonding site being bonded to a ring constituent element of the C ring; each E independently represents an alkylene or the like; m represents an integer that satisfies 5 ≥ m ≥ 1; at least one hydrogen atom in the structural unit represented by formula (1) may be substituted with cyano, a halogen atom, or a deuterium atom; and in the case of a dimer, one of the rings in one structural unit and one of the rings in the other structural unit are bonded to each other by a single bond.

Description

Polycyclic aromatic compounds, optical materials, optical elements and optical equipment

[0001] The present invention relates to a polycyclic aromatic compound having a high refractive index. The present invention also relates to an optical element, an optical material, and an optical instrument using the polycyclic aromatic compound.

[0002] In recent years, there has been an increasing demand for materials with high refractive indexes in the development of optical lenses, holographic optics, image capture optics, spatial light modulators, projection optics, diffractive optics, electromagnetic energy absorption optics, combiner optics, transmission control mirrors, reflective displays, composite materials, color sensors, multispectral filters, and image sensing.

[0003] Materials with high refractive indices are used in the field of optical devices to achieve weight reduction, space saving, and a wide viewing angle. They are also used in the field of multispectral filters to minimize chromatic aberration, reduce lens weight, and achieve diffraction efficiency and direction control. Materials with high refractive indices also have a variety of other effects in various fields. For example, Patent Document 1 discloses a thermoplastic resin that can adjust the balance of high refractive index, high heat resistance, and low birefringence by using a polycyclic aromatic compound with a specific structure.

[0004] International Publication No. 2023 / 074471

[0005] As described above, various materials have been developed for use in numerous optical components. However, in order to increase the options for optical materials, there is a demand for the development of materials made of compounds different from conventional ones. In particular, there is a demand for materials with higher refractive indexes. An object of the present invention is to provide a novel compound having a high refractive index.

[0006] As a result of extensive research, the present inventors have found that the above problems can be solved by using a polycyclic aromatic compound having a specific structure, and have completed the present invention.

[0007] That is, the gist of the present invention is as follows: Item 1. A polycyclic aromatic compound which is a monomer or dimer of a structural unit represented by the following formula (1), and in the case of a dimer, is a homodimer or heterodimer; In the formula (1), ring A, ring B, ring C, and ring D each independently represent a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl, and two adjacent Rs may be bonded to each other to form a ring; E ｍ represents a divalent group in which m E's are bonded in series, one bond being bonded to a ring-constituting element of ring B and the other bond being bonded to a ring-constituting element of ring C; each E is independently a substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene; m is an integer satisfying 5≧m≧1; at least one hydrogen atom in the structural unit represented by formula (1) may be substituted with cyano, a halogen atom, or a deuterium atom; when the polycyclic aromatic compound is a dimer of the structural units, ring A, ring B, ring C, or ring D in one structural unit is bonded to ring A, ring B, ring C, or ring D in the other structural unit by a single bond.

[0008] Item 2. The polycyclic aromatic compound according to Item 1, wherein in the formula (1), ring A, ring B, ring C, and ring D are each independently a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a naphthalene ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, a benzofuran ring, a benzothiophene ring, or an indole ring, and each E is independently phenylene, naphthalenylene, phenanthrenylene, pyrenylene, dibenzofuranylene, or dibenzothiophenylene.

[0009] Item 3. The polycyclic aromatic compound according to Item 1, which is represented by formula (1-1): In the formula (1-1), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚmay be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, one of Z in each structure is a carbon atom, and the carbon atom has a bond to F; R is each independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene.

[0010] Item 4. The polycyclic aromatic compound according to Item 3, wherein F is 1,3-phenylene.

[0011] Item 5. The polycyclic aromatic compound according to Item 3, which is represented by any one of the following formulas:

[0012]

[0013] Item 6. The polycyclic aromatic compound according to Item 1, represented by formula (1-2): In formula (1-2), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, either one of Z in each structure is a carbon atom, and said carbon atom has a bond to F; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene, dibenzofuranylene, or dibenzothiophenylene.

[0014] Item 7. The polycyclic aromatic compound according to Item 6, which is represented by any one of the following formulas:

[0015] Item 8. The polycyclic aromatic compound according to Item 1, which is represented by formula (1-3): In formula (1-3), each Z is independently ═N— or ═C(—R Ｚ)- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, either one of Z in each structure is a carbon atom, and said carbon atom has a bond to F; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene.

[0016] Item 9. The polycyclic aromatic compound according to Item 8, which is represented by any one of the following formulas:

[0017] Item 10. The polycyclic aromatic compound according to Item 1, represented by formula (1-4): In formula (1-4), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, either one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; H ｎ represents a divalent group in which n H's are bonded in series; and n is an integer satisfying the condition 2≧n≧0.

[0018] Item 11. The polycyclic aromatic compound according to Item 10, represented by any one of the following formulas:

[0019] Item 12. The polycyclic aromatic compound according to Item 1, represented by formula (1-5): In formula (1-5), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; n is an integer of 2≧n≧0.

[0020] Item 13. The polycyclic aromatic compound according to Item 12, represented by any one of the following formulas:

[0021] Item 14. The compound according to item 1, which is represented by formula (1-6): In formula (1-6), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚmay be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; n is an integer of 2≧n≧0.

[0022] Item 15. The polycyclic aromatic compound according to Item 14, represented by any one of the following formulas:

[0023] Item 16. An optical material comprising the polycyclic aromatic compound according to any one of items 1 to 15.

[0024] Item 17. An optical element comprising the optical material according to Item 16.

[0025] Item 18. An optical instrument having the optical element according to Item 17.

[0026] According to the present invention, a novel compound having a high refractive index can be provided.

[0027] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "to" refers to a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In this specification, "hydrogen" in the description of a structural formula refers to a "hydrogen atom (H)." Similarly, "carbon atom (C)" may be referred to as "carbon." In this specification, the term "adjacent groups" refers to two groups each bonded to one atom, or two groups each bonded to two adjacent atoms in a structural formula (two atoms directly bonded by a covalent bond). In this specification, the expression "A or B" can be interpreted as "at least one selected from the group consisting of A and B." Although multiple embodiments are described in this specification, various conditions in each embodiment may be applied to each other to the extent applicable.

[0028] In this specification, "Me" represents methyl, "Ph" represents phenyl, "Np" represents naphthalenyl, "DBF" represents dibenzofuranyl, "DBT" represents dibenzothiophenyl, "Tf" represents trifluoromethanesulfonyl, and "D" represents a deuterium atom.

[0029] <Explanation of Rings and Substituents> First, details of rings, substituents, etc. used in this specification will be explained below.

[0030] As used herein, the "aryl ring" includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms.

[0031] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring or an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, or an anthracene ring, a fused tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, or a chrysene ring, or a fused pentacyclic perylene ring or a pentacene ring. The fluorene ring, benzofluorene ring, or indene ring also includes a structure in which a fluorene ring, a benzofluorene ring, or a cyclopentane ring is spiro-bonded, respectively. The fluorene ring, benzofluorene ring, and indene ring also include rings in which two of the two hydrogen atoms of the methylene in the structure are replaced by alkyl such as methyl as a first substituent described below, thereby forming a dimethylfluorene ring, a dimethylbenzofluorene ring, a dimethylindene ring, or the like.

[0032] As used herein, examples of the "heteroaryl ring" include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, still more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Furthermore, examples of the "heteroaryl ring" include heterocyclic rings containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, boron, selenium, phosphorus, and tellurium.

[0033] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazan ring), a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, and a thiophene ring. , a benzothiophene ring, a dibenzothiophene ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a dibenzoindolocarbazole ring, a naphthobenzofuran ring, a dioxin ring, a dihydroacridine ring, a xanthene ring, a thioxanthene ring, a dibenzodioxin ring, a dioxaboranaphthoanthracene ring (such as a 5,9-dioxa-13b-bora-13bH-naphtho[3,2,1-de]anthracene ring), a benzoselenophene ring, a dibenzofuran ...benzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzofuran ring, a dibenzo Examples of the dihydroacridine ring include a phenylene ring, a dibenzoselenophene ring, an azacarbazole ring, an azadibenzothiophene ring, an azadibenzofuran ring, an azadibenzoselenophene ring, an azatriphenylene ring, an imidazoimidazole ring, an indoloindole ring, a benzofurocarbazole ring, a benzothienocarbazole ring, an indenocarbazole ring, a selenophenocarbazole ring, a spiro[fluorene-9,9'-xanthene] ring, and a spirobi[silafluorene] ring. Furthermore, the dihydroacridine ring, the xanthene ring, and the thioxanthene ring are also preferably dimethyldihydroacridine ring, dimethylxanthene ring, or dimethylthioxanthene ring in which two of the two hydrogen atoms of the methylene in the ring structure are each replaced by an alkyl such as methyl as the first substituent described below.In addition, bicyclic rings such as bipyridine ring, phenylpyridine ring, or pyridylphenyl ring, and tricyclic rings such as terpyridyl ring, bispyridylphenyl ring, or pyridylbiphenyl ring are also included as "heteroaryl rings." The "heteroaryl ring" also includes a pyran ring.

[0034] In this specification, "substituted or unsubstituted" means that a group may or may not have a substituent. When referring to a "substituent," the type of the substituent is not particularly limited, but unless otherwise specified, it may be any group selected from the substituent group Z described below. For example, when a group that is "substituted or unsubstituted" is substituted, it may be substituted with at least one group selected from the substituent group Z.

[0035] In this specification, a substituent may be substituted with a further substituent. For example, a specific substituent may be described as "substituted or unsubstituted." This means that the specific substituent is substituted with at least one further substituent, or is not substituted. In the same sense, the term "optionally substituted" may also be used. In this specification, the specific substituent may be referred to as a "first substituent," and the further substituent may be referred to as a "second substituent."

[0036] In this specification, the substituent group Z includes: aryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl group, substituted silyl, cyano, and halogen atom; heteroaryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl group, substituted silyl, cyano, and halogen atom; alkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, hydroxyl group, substituted silyl, cyano, and halogen atom; cycloalkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl group, substituted silyl, cyano, and halogen atom; alkoxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, hydroxyl group, substituted silyl, cyano, and halogen atom; aryloxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl group, substituted silyl, cyano, and halogen atom; The aryl, which is the second substituent in each group of the substituent group Z, may be further substituted with an aryl, heteroaryl, alkyl, cycloalkyl, substituted silyl, cyano, or halogen atom, and similarly, the heteroaryl, which is the second substituent, may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, substituted silyl, cyano, or halogen atom.

[0037] In this specification, "aryl" refers to, for example, an aryl having 6 to 30 carbon atoms, and preferably an aryl having 6 to 20 carbon atoms, an aryl having 6 to 16 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aryl having 6 to 10 carbon atoms.

[0038] Specific examples of "aryl" include monovalent groups obtained by removing one hydrogen atom from the above-mentioned "aryl ring." For example, phenyl is a monocyclic ring system; biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl) is a bicyclic ring system; naphthyl (1-naphthyl or 2-naphthyl) is a fused bicyclic ring system; terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl-4-yl) is a tricyclic ring system; acenaphthylene-(1-, 3-, 4-, or 5-) is a fused tricyclic ring system. -)yl, fluoren-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, or 9-)yl; the tetracyclic ring systems quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl fused tetracyclic ring systems such as triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl; or fused pentacyclic ring systems such as perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl. Other examples include monovalent groups of spirofluorene.

[0039] The aryl as the second substituent also includes a structure in which the aryl is substituted with at least one group selected from the group consisting of aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are the groups described below), and cycloalkyl such as cyclohexyl or adamantyl (specific examples are the groups described below). One example is a group in which the hydrogen atom at position 9 of fluorenyl as the second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl.

[0040] The "arylene" is, for example, an arylene having 6 to 30 carbon atoms, and preferably an arylene having 6 to 20 carbon atoms, an arylene having 6 to 16 carbon atoms, an arylene having 6 to 12 carbon atoms, or an arylene having 6 to 10 carbon atoms. Specific examples of the "arylene" include a divalent group obtained by removing one hydrogen atom from the above-mentioned "aryl" (monovalent group).

[0041] The "heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. The "heteroaryl" contains, in addition to carbon, one or more, preferably 1 to 5, heteroatoms selected from oxygen, sulfur, nitrogen, and the like as ring-constituting atoms.

[0042] Specific examples of the "heteroaryl" include monovalent groups obtained by removing one hydrogen atom from the above-mentioned "heteroaryl ring". For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, １ H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, １H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, a monovalent group of a benzophospholeoxide ring, a monovalent group of a dibenzophospholeoxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, dibenzoindolocarbazolyl, imidazolinyl, or oxazolinyl. Other examples include a monovalent group of spiro[fluorene-9,9'-xanthene], a monovalent group of spirobi[silafluorene], and a monovalent group of benzoselenophene.

[0043] The heteroaryl as the second substituent also includes a structure in which the heteroaryl is substituted with at least one group selected from the group consisting of aryl such as phenyl (specific examples are listed above), alkyl such as methyl (specific examples are listed below), and cycloalkyl such as cyclohexyl or adamantyl (specific examples are listed below). One example is a group in which the hydrogen atom at position 9 of the carbazolyl as the second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl. Furthermore, the heteroaryl as the second substituent also includes groups in which a nitrogen-containing heteroaryl such as pyridyl, pyrimidinyl, triazinyl, or carbazolyl is further substituted with phenyl, biphenylyl, or the like.

[0044] The "heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, and preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms. The "heteroarylene" is, for example, a divalent group such as a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. Specific examples of the "heteroarylene" include divalent groups obtained by removing one hydrogen atom from the above-mentioned "heteroaryl" (monovalent group).

[0045] The "alkyl" may be either straight-chain or branched-chain, for example, a straight-chain alkyl having 1 to 24 carbon atoms or a branched-chain alkyl having 3 to 24 carbon atoms, and preferably an alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms), an alkyl having 1 to 5 carbon atoms (branched-chain alkyl having 3 to 5 carbon atoms), an alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms), etc.

[0046] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1 -methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylhexyl Examples of the alkyl group include methylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0047] A specific "hydroxyl-substituted alkyl" is, for example, -CH ２ —OH, —C ２ H ４ —OH, —C ３ H ６ -OH or -C ４ H ８ -OH and the like.

[0048] An "alkylene" is a divalent group obtained by removing any hydrogen from an "alkyl", such as methylene, ethylene, or propylene.

[0049] For "alkenyl," the above explanation of "alkyl" can be referred to, and it is a group in which a C-C single bond in the structure of "alkyl" is replaced with a C=C double bond, and also includes groups in which not only one but two or more single bonds are replaced with double bonds (also called alkadiene-yl or alkatriene-yl).

[0050] "Alkenylene" is a divalent group obtained by removing any hydrogen from "alkenyl", and examples include vinylene.

[0051] For "alkynyl", the above explanation of "alkyl" can be referred to, and it is a group in which a C-C single bond in the "alkyl" structure is replaced with a C≡C triple bond, and also includes groups in which not only one but two or more single bonds are replaced with triple bonds (also called alkadiyn-yl or alkatriyn-yl).

[0052] The "cycloalkyl" is, for example, a cycloalkyl having 3 to 24 carbon atoms, and preferably a cycloalkyl having 3 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, a cycloalkyl having 5 to 8 carbon atoms, a cycloalkyl having 5 to 6 carbon atoms, or a cycloalkyl having 5 carbon atoms.

[0053] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituted derivatives thereof having 1 to 5 carbon atoms or 1 to 4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0054] "Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, and preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, or cycloalkylene having 5 carbon atoms. Specific examples of "cycloalkylene" include a structure obtained by removing one hydrogen atom from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

[0055] "Cycloalkenyl" refers to a group having a structure in which at least one pair of single bonds between two carbon atoms in the above-mentioned "cycloalkyl" is replaced with a double bond (for example, -CH ２ -CH ２ Examples of the aryl group include 1-cyclohexenyl, 1-cyclopentenyl, and the like, which are groups in which - is replaced by -CH=CH- and do not fall under the category of aryl.

[0056] "Alkoxy" is a group represented by "Alk-O- (Alk is alkyl)", and the above explanation of "alkyl" can be cited for details of the alkyl.

[0057] A specific example of an "alkoxy substituted with a hydroxyl group" is, for example, -O-CH ２ —OH, —O—C ２ H ４ —OH, —O—C ３ H ６ —OH, or —O—C ４ H ８ -OH and the like.

[0058] "Aryloxy" is a group represented by "Ar-O- (Ar is aryl)", and the above explanation of "aryl" can be cited for details of the aryl.

[0059] The "substituted silyl" is, for example, a silyl substituted with at least one of aryl, alkyl, and cycloalkyl, and is preferably triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0060] "Triarylsilyl" is a silyl group substituted with three aryl groups, and the above description of "aryl" can be cited for details of this aryl. Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

[0061] "Trialkylsilyl" is a silyl group substituted with three alkyl groups, and the details of this alkyl can be found in the above description of "alkyl". Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

[0062] "Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups. For details of this cycloalkyl, refer to the explanation of "cycloalkyl" above. Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

[0063] "Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0064] "Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0065] The "halogen atom" is a fluorine atom, chlorine atom, bromine atom or iodine atom, preferably a fluorine atom, chlorine atom or bromine atom, more preferably a fluorine atom or chlorine atom, and even more preferably a fluorine atom.

[0066] When cyano or halogen atoms are substituted, it is also preferred that all or part of the hydrogen atoms in the aryl or heteroaryl in the structure are substituted with cyano or halogen atoms.

[0067] [When two groups bonded to the same atom are bonded to each other] In this specification, when it is said that two groups (also referred to as "two adjacent groups") bonded to the same atom may be bonded to each other to form a ring, they may be bonded to each other by a single bond or a linking group (collectively referred to as a linking group), and examples of the linking group include -CH ２ -CH ２ --, --CHR １ -CHR １ -, -CR １ ２ -CR １ ２ -, -CH=CH-, -CR １ =CR １-, -C≡C-, -N(-R １ )-, -O-, -S-, -C(-R １ ) ２ -, -Si(-R １ ) ２ - or -Se-, for example, the following structure: １ -CHR １ -R １ , -CR １ ２ -CR １ ２ -R １ , -CR １ =CR １ -R １ , -N(-R １ )-R １ , -C(-R １ ) ２ -R １ , and -Si(-R １ ) ２ -R １ are each independently a hydrogen atom, an aryl which may be substituted with an alkyl or cycloalkyl, a heteroaryl which may be substituted with an alkyl or cycloalkyl, an alkyl which may be substituted with a cycloalkyl, an alkenyl which may be substituted with an alkyl or cycloalkyl, an alkynyl which may be substituted with an alkyl or cycloalkyl, or a cycloalkyl which may be substituted with an alkyl or cycloalkyl. １ They may be bonded together to form a ring, forming a cycloalkylene, arylene, or heteroarylene.

[0068]

[0069] The bonding group may be a single bond or a linking group such as -CR １ =CR １ -, -N(-R １ )-, -O-, -S-, -C(-R １ ) ２ -, -Si(-R １ ) ２ - or -Se- is preferred, and a single bond or -CR as a linking group is preferred. １=CR １ -, -N(-R １ )-, -O-, -S-, or -C(-R １ ) ２ - is more preferred, a single bond or -CR as a linking group １ =CR １ -, -N(-R １ )-, --O-, or --S-- is more preferred, and a single bond is most preferred.

[0070] The two R １ The positions at which the are bonded are not particularly limited as long as they are positions at which bonding is possible, but they are preferably bonded at the positions closest to each other. For example, when the two groups are phenyl, they are preferably bonded at positions ortho (2-position) relative to the bonding position (1-position) of "C" or "Si" in the phenyl (see the structural formula above).

[0071] [Stereoisomers, etc.] The polycyclic aromatic compounds described below may exist as enantiomers or diastereomers depending on the type of substituents, etc., but regardless of the structural formula described, any pure stereoisomer, any mixture of stereoisomers, racemate, etc. are all intended to be encompassed within the scope of the present invention.

[0072] <Polycyclic aromatic compound> As a result of extensive research, the present inventors have found that a polycyclic aromatic compound having a structure in which two fluorene skeletons are bonded via a linking group containing an arylene or the like has a high refractive index.

[0073] A polycyclic aromatic compound according to one embodiment of the present invention (hereinafter also referred to simply as a "polycyclic aromatic compound") is a monomer or dimer of a structural unit represented by the following formula (1) in which the above-mentioned aromatic rings (aryl rings or heteroaryl rings) are linked together and which has a fluorene skeleton. When the compound is a dimer, it is a homodimer or a heterodimer.

[0074]

[0075] When the polycyclic aromatic compound is a dimer of the above structural units, the ring A, ring B, ring C, or ring D in one structural unit is bonded to the ring A, ring B, ring C, or ring D in the other structural unit via a single bond. Note that the dimer in the above polycyclic aromatic compound refers to a dimer linked by a chemical bond such as a covalent bond, but an embodiment linked by a physical bond such as a hydrogen bond or intermolecular force is treated as if there were two monomers.

[0076] The structural unit represented by formula (1) is an E ｍ is bonded to a hydrogen atom bonded to a ring-constituting element of either the aryl ring or the heteroaryl ring in ring B of the structure represented by formula (1), and the other is bonded to a hydrogen atom bonded to a ring-constituting element of either the aryl ring or the heteroaryl ring in ring C of the structure represented by formula (1).

[0077] [Explanation of Ring Structure] E in the above formula (1) ｍ The structure on the left side and the structure on the right side are separated and shown in the following formula (1A): In formula (1A), "A," "B," "C," and "D" in the circles are symbols indicating the ring structures represented by the respective circles, and ring A, ring B, ring C, and ring D are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0078]

[0079] Each of the rings A, B, C, and D in formula (1A) has a bond to two adjacent elements (preferably carbon) on the aryl or heteroaryl ring in the structure, and the entire structure on the left side of formula (1A) forms a monovalent group, and the entire structure on the right side of formula (1A) forms a monovalent group. The bond from ring B in the left structure of formula (1A) and the bond from ring C in the right structure of formula (1A) form a divalent E ｍand form a bond. Among the rings A, B, C, and D, the rings having the above-mentioned two bonded elements as ring constituent elements are preferably five- or six-membered rings, more preferably six-membered rings. This ring may be further fused with another ring. Examples of six-membered rings include a benzene ring, a pyridine ring, a pyrazine ring, or a pyrimidine ring. Examples of six-membered rings further fused with another ring include a naphthalene ring, a quinoline ring, a benzofuran ring, a benzothiophene ring, an indole ring, a benzoselenophene ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, or a dibenzoselenophene ring. Examples of five-membered rings include a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, or a selenophene ring. Examples of five-membered rings further fused with another ring include a benzofuran ring, a benzothiophene ring, an indole ring, or a benzoselenophene ring. The aryl ring or heteroaryl ring in ring A, ring B, ring C, and ring D is preferably a benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, naphthalene ring, quinoline ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, furan ring, thiophene ring, pyrrole ring, thiazole ring, benzofuran ring, benzothiophene ring, or indole ring, more preferably a benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, naphthalene ring, quinoline ring, benzofuran ring, benzothiophene ring, or benzoselenophene ring, still more preferably a benzene ring, pyridine ring, naphthalene ring, or quinoline ring, and still more preferably a benzene ring or naphthalene ring.

[0080] In the substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in the A ring, B ring, C ring, and D ring of the structure represented by formula (1A), the substituent when "substituted or unsubstituted (substituted or unsubstituted)" is referred to is not particularly limited, but examples thereof include aryl (which may be substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), heteroaryl (which may be substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), alkyl (which may be substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), halogen atom, or cyano, and halogen atom or cyano is preferred.When there are multiple substituents, the multiple substituents may be the same or different from each other.

[0081] It is preferable that ring A, ring B, ring C, and ring D are each independently a benzene ring or a naphthalene ring which may be substituted with a halogen atom or cyano, and more preferably an unsubstituted benzene ring or a naphthalene ring.

[0082] R is each independently a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl, preferably a hydrogen atom; an alkyl; a cycloalkyl; an aryl that may be substituted with an alkyl or cycloalkyl; or a heteroaryl that may be substituted with an alkyl or cycloalkyl, and two adjacent Rs may be bonded to each other to form a ring.R is more preferably a phenyl, an embodiment in which two adjacent Rs are both phenyl and bonded to each other, or a methyl.In addition, in this specification, alkyl groups are not considered as substituents of alkyl groups.

[0083] Specific examples of the partial structure represented by formula (1A) (the left-side structure and the right-side structure in formula (1A)) are each independently represented by the following formulas (1A-1) and (1A-2). In formula (1A-1), the left-side ring of the five-membered ring to which R is bonded may be either ring A or ring B of formula (1A); when the left-side ring is ring A, the right-side ring becomes ring B, and when the left-side ring is ring B, the right-side ring becomes ring A. Similarly, in formula (1A-2), the left-side ring of the five-membered ring to which R is bonded may be either ring C or ring D of formula (1A); when the left-side ring is ring C, the right-side ring becomes ring D, and when the left-side ring is ring D, the right-side ring becomes ring C. As the two structures of formula (1A), the structure of formula (1A-1) may be applied to both, the structure of formula (1A-2) may be applied to both, or both of formula (1A-1) and formula (1A-2) may be applied.

[0084]

[0085] In formulas (1A-1) and (1A-2), each Z is independently -N= or -C(-R Ｚ )=, and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, provided that any one of Z in each fluorene skeleton is E ｍ The conditions for R described above can be similarly applied to each R independently, and unsubstituted aryl, unsubstituted heteroaryl, or unsubstituted alkyl is preferable, phenyl, pyridyl, an embodiment in which two adjacent Rs are both bonded to each other via phenyl, methyl, or ethyl is more preferable, and phenyl, an embodiment in which two adjacent Rs are both bonded to each other via phenyl, or methyl is even more preferable.

[0086] [E ｍ ] E ｍrepresents a divalent group in which m E's are bonded in series, one bond being bonded to a ring-constituting element of ring B and the other bond being bonded to a ring-constituting element of ring C. m is an integer of 1 or more and 5 or less (5≧m≧1). When m is an integer of 2 or more and 5 or less (5≧m≧2), the multiple E's may be the same or different.

[0087] Each E is independently a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene. In the arylene and heteroarylene of E, it is preferable that both of the two bonds are on the same monocyclic ring or the same fused ring, and it is more preferable that both are on the same monocyclic ring. The substituent when referring to "substituted or unsubstituted" is not particularly limited, but includes aryl (which may be substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), heteroaryl (which may be substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), alkyl (which may be substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), halogen atom, cyano, etc. When there are multiple substituents, the multiple substituents may be the same or different from each other. It is preferable that the arylene and heteroarylene of E are unsubstituted.

[0088] Examples of E include phenylene, naphthalenylene, phenanthrenylene, pyrenylene, dibenzofuranylene, and dibenzothiophenylene, preferably phenylene, naphthalenylene, dibenzofuranylene, and dibenzothiophenylene, and more preferably 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,5-naphthalenylene, 2,6-naphthalenylene, 2,8-dibenzofuranylene, and 2,8-dibenzothiophenylene.

[0089] E ｍ Preferred examples of the above include structures represented by any of the following formulas:

[0090]

[0091]

[0092]

[0093] [Substitution with Cyano, Halogen Atom, or Deuterium Atom] At least one hydrogen atom in the structural unit represented by formula (1) may be substituted with a cyano, halogen atom, or deuterium atom.

[0094] For example, in the structural unit represented by formula (1), the A ring, the B ring, the C ring, the D ring, and the E ring are ｍ In the structural unit represented by formula (1), hydrogen atoms in the aryl ring or heteroaryl ring and in the substituents thereof may be replaced by cyano, halogen atoms, or deuterium atoms, and among these, embodiments in which all or part of the hydrogen atoms in the aryl and / or heteroaryl are replaced by cyano, halogen atoms, or deuterium atoms are preferred. From the viewpoint of durability, it is also preferred that all or part of the hydrogen atoms in the structural unit represented by formula (1) are deuterated.

[0095] [Specific Examples of Polycyclic Aromatic Compounds] Examples of polycyclic aromatic compounds include compounds represented by the following formula (1-1): The conditions for the structure of formula (1-1) can be similarly applied to the corresponding conditions for the structure of formula (1) above, to the extent applicable.

[0096]

[0097] In formula (1-1), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, one of Z in each structure is a carbon atom, and the carbon atom has a bond to F; R is each independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene.

[0098] F in formula (1-1) is preferably 1,3-phenylene.

[0099] Examples of the polycyclic aromatic compound represented by formula (1-1) include compounds represented by any of the following structural formulas.

[0100]

[0101]

[0102] Examples of polycyclic aromatic compounds include compounds represented by the following formula (1-2): The conditions for the structure of formula (1-2) can be similarly applied to the corresponding conditions for the structure of formula (1) above, to the extent applicable.

[0103]

[0104] In formula (1-2), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, either one of Z in each structure is a carbon atom, and said carbon atom has a bond to F; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene, dibenzofuranylene, or dibenzothiophenylene.

[0105] Examples of the polycyclic aromatic compound represented by formula (1-2) include compounds represented by any of the following structural formulas:

[0106]

[0107] An example of the polycyclic aromatic compound is a compound represented by the following formula (1-3): The conditions for the structure of formula (1-3) can be similarly applied to the corresponding conditions for the structure of formula (1) above, to the extent applicable.

[0108]

[0109] In formula (1-3), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, either one of Z in each structure is a carbon atom, and said carbon atom has a bond to F; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene.

[0110] Examples of the polycyclic aromatic compound represented by formula (1-3) include compounds represented by any of the following structural formulas:

[0111] An example of the polycyclic aromatic compound is a compound represented by the following formula (1-4): The conditions for the structure of formula (1-4) can be similarly applied to the corresponding conditions for the structure of formula (1) above, to the extent applicable.

[0112]

[0113] In formula (1-4), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚmay be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R are independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; H ｎ represents a divalent group in which n H's are bonded in series; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; and n is an integer satisfying 2≧n≧0.

[0114] Examples of the polycyclic aromatic compound represented by formula (1-4) include compounds represented by any of the following structural formulas:

[0115]

[0116]

[0117] An example of the polycyclic aromatic compound is a compound represented by the following formula (1-5): The conditions for the structure of formula (1-5) can be similarly applied to the corresponding conditions for the structure of formula (1) above, to the extent applicable.

[0118]

[0119] In formula (1-5), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚmay be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; n is an integer of 2≧n≧0.

[0120] Examples of the polycyclic aromatic compound represented by formula (1-5) include compounds represented by any of the following structural formulas:

[0121]

[0122] An example of the polycyclic aromatic compound is a compound represented by the following formula (1-6): The conditions for the structure of formula (1-6) can be similarly applied to the corresponding conditions for the structure of formula (1) above, to the extent applicable.

[0123]

[0124] In formula (1-6), each Z is independently ═N— or ═C(—R Ｚ )- and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚmay be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; n is an integer of 2≧n≧0.

[0125] Examples of the polycyclic aromatic compound represented by formula (1-6) include compounds represented by any of the following structural formulas:

[0126]

[0127] When the polycyclic aromatic compound is a dimer, the polycyclic aromatic compound can also be represented by the following formulas (2-1) to (2-6), for example.

[0128]

[0129] In the above formulas (2-1) to (2-6), the A' ring, the B' ring, the C' ring, and the D' ring can be respectively subject to the same conditions as those for the A ring, the B ring, the C ring, and the D ring in this specification, and these may be the same as each other (homodimer) or different from each other (heterodimer). In this specification, a heterodimer refers to a heterodimer in which all structural units satisfy the structure of formula (1), but the A ring, the B ring, the C ring, the D ring, R, and E ring are different from each other (heterodimer). ｍand the skeleton of the ring constituting each ring structure is the same for ring A, ring B, ring C, and ring D, and ring A', ring B', ring C', and ring D', respectively, but at least one of the substituents R and R' that each ring structure may have is different. Note that, for example, in formula (2-1) and formula (2-2), the bond connecting the two structural units is a single bond connecting ring D and ring A' and a single bond connecting ring D and ring D', respectively, but may also be a single bond connecting ring A and ring C' or a single bond connecting ring C and ring C', etc. Furthermore, the same conditions as for R in this specification can be applied to each R' independently. Furthermore, E ｍ ' is the E ｍ Therefore, the following conditions can be applied to ring A, ring B, ring C, ring D, R, and E. ｍ These descriptions are given for the A' ring, B' ring, C' ring, D' ring, R', and E' ring. ｍ The embodiment of the dimer is not particularly limited, but from the viewpoint of ease of synthesis, it is preferably the above formula (2-1) or formula (2-2), from the viewpoint of easier suppression of crystallization, it is preferably the above formula (2-3) or formula (2-4), and from the viewpoint of even easier suppression of crystallization, it is preferably the above formula (2-5) or formula (2-6).

[0130] In particular, the compound of general formula (1-1) is preferably a compound represented by any one of the following formulas:

[0131]

[0132]

[0133]

[0134]

[0135] In particular, the compound of general formula (1-2) is preferably a compound represented by any one of the following formulas:

[0136]

[0137]

[0138]

[0139]

[0140] In particular, the compound of general formula (1-3) is preferably a compound represented by any one of the following formulas:

[0141] A preferred embodiment of the general formula (1-3) is a compound represented by the following formula (1-3-a) or (1-3-b).

[0142]

[0143] In the above formulas (1-3-a) and (1-3-b), Aa is a divalent group selected from the groups shown below, and the bonding sites Xa and Xb of the fluorene are each selected from the groups shown below.

[0144]

[0145]

[0146] Specific combinations of Aa, Xa, and Xb in the above formulas are shown in Tables 1-1 to 1-5 below.

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] In particular, the compound of general formula (1-4) is preferably a compound represented by any one of the following formulas:

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] In particular, the compound of general formula (1-5) is preferably a compound represented by any one of the following formulas:

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] In particular, the compound of general formula (1-6) is preferably a compound represented by any one of the following formulas:

[0231] A preferred embodiment of the general formula (1-6) is a compound represented by the following formula (1-6-a):

[0232]

[0233] In the above formula (1-6-a), A １ , A ２ , A ３ is a divalent group selected from the groups shown below, and the bonding sites Xa and Xb of the fluorene are each selected from the groups shown below.

[0234]

[0235]

[0236]

[0237] Specific combinations of A1, A2, A3, Xa, and Xb in the above formulas are shown in Tables 2-1 to 2-6 below.

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] Among the compounds represented by the above formulae, more preferred compounds are those represented by any of the following formulae.

[0245] Compounds represented by formula (1-1) Preferably, formula 1-1-4, formula 1-1-5, formula 1-1-6, formula 1-1-11, formula 1-1-12, formula 1-1-17, formula 1-1-18, formula 1-1-19, formula 1-1-25, formula 1-1-26, formula 1-1-30, formula 1-1-34, formula 1-1-35, and formula 1-1-36.

[0246] Compounds represented by formula (1-2) Preferably, formula 1-2-4, formula 1-2-5, formula 1-2-7, formula 1-2-8, formula 1-2-12, formula 1-2-13, formula 1-2-27, and formula 1-2-28.

[0247] Compounds represented by formula (1-3) Preferably, formula 1-3-7, formula 1-3-62, formula 1-3-65, and formula 1-3-114.

[0248] Compounds represented by formula (1-4) Preferably, formula 1-4-2, formula 1-4-28, formula 1-4-42, formula 1-4-62, formula 1-4-95, formula 1-4-162, formula 1-4-188, formula 1-4-282, formula 1-4-345, formula 1-4-348, formula 1-4-349, formula 1-4-350, formula 1-4-352, formula 1-4-360, formula 1-4-367, and formula 1-4-371.

[0249] Compounds represented by formula (1-5) Preferably, formula 1-5-6, formula 1-5-48, formula 1-5-131, formula 1-5-165, formula 1-5-244, formula 1-5-321, formula 1-5-323, and formula 1-5-331.

[0250] Compounds represented by formula (1-6) Preferably, formula 1-6-69 and formula 1-6-135.

[0251] <Method for Producing Polycyclic Aromatic Compound> The polycyclic aromatic compound described above is not particularly limited, and can be produced by utilizing a known synthesis method such as the Suzuki coupling reaction. The Suzuki coupling reaction is a method of coupling an aromatic halide or triflate with an aromatic boronic acid or an aromatic boronic acid ester using a palladium catalyst in the presence of a base. Specific examples of reaction routes for obtaining polycyclic aromatic compounds using this method are as follows (Schemes 1 to 3). Note that the following reaction routes are reaction routes for obtaining a polycyclic aromatic compound consisting of only one structural unit represented by the above formula (1). In addition, R in each scheme １ ~R ４ is the same as above, TfO is triflate, and Pin is pinacol. In addition, the sum of n of Ln and o of Lo in (Scheme 3) (n+o) is m.

[0252]

[0253] Specific examples of palladium catalysts that can be used in this reaction include Pd(PPh ３ ) ４ , PdCl ２ (PPh ３ ) ２ , Pd(OAc) ２ , tris(dibenzylideneacetone)dipalladium(0), tris(dibenzylideneacetone)dipalladium(0) chloroform complex, bis(dibenzylideneacetone)palladium(0), etc. In order to promote the reaction, a phosphine compound may be added to these palladium compounds in some cases. Specific examples of the phosphine compound include tri(t-butyl)phosphine, tricyclohexylphosphine, 1-(N,N-dimethylaminomethyl)-2-(di-t-butylphosphino)ferrocene, 1-(N,N-dibutylaminomethyl)-2-(di-t-butylphosphino)ferrocene, 1-(methoxymethyl)-2-(di-t-butylphosphino)ferrocene, 1,1′-bis(di-t-butylphosphino)ferrocene, 2,2′-bis(di-t-butylphosphino)-1,1′-binaphthyl, and 2-methoxy-2′-(di-t-butylphosphino)-1,1′-binaphthyl.

[0254] Specific examples of the base used in this reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, tripotassium phosphate, and potassium fluoride.

[0255] Specific examples of the solvent used in this reaction include benzene, toluene, xylene, N,N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butyl methyl ether, cyclopentyl methyl ether, 1,4-dioxane, methanol, ethanol, isopropyl alcohol, and water. These solvents can be appropriately selected depending on the structures of the aromatic halide, triflate, aromatic boronic acid ester, aromatic boronic acid, and the like to be reacted. The solvents may be used alone or as a mixed solvent.

[0256] In addition, in polycyclic aromatic compounds, R １ and R ２ or R ３ and R ４ Compounds in which M is bonded to form a ring (for example, an aliphatic ring or an aromatic ring) can be produced by referring to the method for producing a benzofluorene compound having a spiro structure described in, for example, JP 2009-184993 A. Paragraph 0055 of this publication describes a method for producing a compound in which a fluorene ring is spiro-bonded to a five-membered benzofluorene ring (Scheme 1c), and by referring to this, the above polycyclic aromatic compound can be produced according to Scheme 4 below. In the following scheme, M is Li, MgCl, MgBr, or MgI.

[0257]

[0258] Polycyclic aromatic compounds also include those in which at least some of the hydrogen atoms are substituted with deuterium atoms, and such compounds can be produced in the same manner as described above by using raw materials in which desired positions are deuterated.

[0259] <Composition> Another embodiment of the present invention is a composition containing the above-described polycyclic aromatic compound. The composition is not particularly limited as long as it contains a polycyclic aromatic compound, and may contain other components depending on the application. The content of the polycyclic aromatic compound in the composition is not particularly limited and can be set appropriately depending on the application. For example, from the viewpoint of ensuring a sufficient refractive index, the content may be 1.0 mass% or more, 10.0 mass% or more, 50.0 mass% or more, or 90.0 mass% or more, or 10.0 mass% or less, 50.0 mass% or less, 90.0 mass% or less, or 99.0 mass% or less.

[0260] The composition may contain a solvent, and the solvent is not particularly limited as long as it can dissolve the components constituting the composition, such as the polycyclic aromatic compound, and examples thereof include alcohol-based solvents, alkylbenzene-based solvents, phenyl ether-based solvents, alkyl ether-based solvents, cyclic ketone-based solvents, aliphatic ketone-based solvents, monocyclic ketone-based solvents, solvents having a diester skeleton, and fluorine-containing solvents. The solvent may be used alone or in combination.

[0261] The composition may contain an antioxidant, a light stabilizer, a heavy metal deactivator, a flame retardant, a lubricant, an antistatic agent, a surfactant, an antibacterial agent, a release agent, an ultraviolet absorber, a plasticizer, a compatibilizer, a bluing agent, or the like.

[0262] The use of the composition is not limited, and it can be used in the same manner as the use of polycyclic aromatic compounds described below.

[0263] <Molded Article> A molded article according to another embodiment of the present invention is a molded article containing the polycyclic aromatic compound described above, or a molded article that is a cured product of the composition described above.

[0264] The use of the molded article is not limited, and it can be used in the same manner as the use of the polycyclic aromatic compounds described below.

[0265] [Uses of Polycyclic Aromatic Compounds] The uses of the polycyclic aromatic compounds described above are not particularly limited, but they can be particularly effectively applied to fields requiring a high refractive index, such as the optical field, electrical field, or semiconductor field. More specifically, they can be effectively applied to optical materials. Another embodiment of the present invention is an optical material containing the polycyclic aromatic compound described above. The form in which the optical material contains a polycyclic aromatic compound is not particularly limited, and the optical material may be composed only of the polycyclic aromatic compound, or the polycyclic aromatic compound may be contained in the optical material together with other components. For example, a composition containing a polycyclic aromatic compound may be used as the optical material, or a cured product containing a polycyclic aromatic compound may be used as the optical material.

[0266] In the field of high refractive index materials, particularly high refractive index resins, halogen-free materials are sometimes required, but depending on the polycyclic aromatic compound according to the above-described embodiment, a halogen-free high refractive index material can be obtained. Furthermore, in the past, in order to obtain a high refractive index product, it was necessary to increase the amount of material and increase the size of the product, but by using the above-described high refractive index polycyclic aromatic compound as a material, it is possible to reduce material costs by reducing the amount of material, and to reduce the size of the product, and ultimately to reduce manufacturing costs by promoting mass production.

[0267] The applications of the optical material are not particularly limited and can be used in various aspects, such as optical elements such as lenses (optical lenses), prisms, mirrors, or diffraction gratings, as described below. Another embodiment of the present invention is an optical element containing the polycyclic aromatic compound described above, and yet another embodiment is an optical instrument having the optical element. Specifically, when used as a lens, the application is not particularly limited, and the lens can be used as an imaging lens, an image capture lens, a projection lens, an electron energy absorbing lens, a high NA objective lens, a collimating lens, or a telecentric lens, and the size is not limited, and the lens can also be used as a microlens. The applications of the optical material will be described in more detail below.

[0268] The optical material is suitable in optical fields such as holographic optics, image capture optics, projection optics, diffractive optics, electromagnetic energy absorption optics, or combiner optics. Specifically, the optical material can be used in optical devices such as AR (Augmented Reality) glasses; AR goggles; imaging devices; displays such as HUDs (Head Up Displays), organic EL displays, or light field displays; optical sensors such as image sensors, in-vehicle sensors, infrared sensors, light sensors, or multispectral sensors; distance measuring devices; spatial light phase modulators; cameras such as digital cameras, smartphone cameras, in-vehicle cameras, or personal computer cameras; beam steering devices; projectors; microscopes; endoscopes; free-space optical communication systems; reflectors for aerial displays; LED encapsulants; photoelectric converters; navigation devices; automotive lighting; or optical devices for laser processing; road signs, anti-reflective films, adhesives used for bonding glass, etc., action recorders, game consoles, drones, autonomous driving assistance sensing, ophthalmic applications, medical imaging for surgical robotics, etc. Furthermore, the polycyclic aromatic compound or a composition containing the polycyclic aromatic compound can also be used as a material for a 3D printer (e.g., a filament for a 3D printer, etc.), and by performing 3D printing using this material, components for each of the above-mentioned products can be formed.

[0269] In AR glasses or AR goggles, polycyclic aromatic compounds can be used in components related to holography, multispectral filtering, optical diffraction, spatial modulation, or electromagnetic energy absorption, specifically, optical waveguides, diffraction gratings, surface structure formation films of optical elements (especially films for forming nanopillars on the surface), sealing layers, buffer layers, or polymer thin films provided for the purpose of absorbing electromagnetic energy. The AR method is not particularly limited, and for example, a waveguide method can be adopted. Furthermore, when used as an optical waveguide, it can be used as a planar waveguide or a curved diffraction waveguide, and these can be embedded in a lens to achieve weight reduction. Furthermore, since diffraction gratings are usually provided in contact with a waveguide, and the refractive index of the waveguide is determined depending on the refractive index of such adjacent components, it is particularly effective to use the above-mentioned polycyclic aromatic compounds in the diffraction grating. On the other hand, since waveguides account for a large volume proportion of the product among components requiring a high refractive index, it is effective to use the above-mentioned polycyclic aromatic compounds in the waveguide. Furthermore, the above-described polycyclic aromatic compounds can be used as waveguides, etc., as described above, but can also be used as a coating material for components such as waveguides, and can compensate for the refractive index characteristics of other components that are coated. Note that the specific use examples in AR glasses, etc., described above can also be similarly applied to devices such as glasses relating to other XR (Cross Reality) technologies, such as VR (Virtual Reality), MR (Mixed Reality), or SR (Substitutional Reality).

[0270] In imaging devices, polycyclic aromatic compounds can be used in components related to imaging, multispectral filtering, image capture, and electromagnetic energy absorption, specifically, lenses (preferably one or more lenses in a five-element lens configuration), components having a core structure or hollow structure for multispectral filtering, and microlenses provided for the purpose of absorbing electromagnetic energy.

[0271] In displays, polycyclic aromatic compounds can be used in components such as photoconductive layers in HUDs; diffraction gratings or anti-reflection coatings provided in HUDs for the purpose of absorbing electromagnetic energy; and retroreflective materials in light field displays.

[0272] In sensors, polycyclic aromatic compounds can be used in, for example, sensor heads; components related to multispectral filtering, specifically optical filters in multispectral sensors; components related to image sensing, specifically interference filters in image sensors or on-board sensors; components related to image capture, specifically lenses; hard mask layers that are photoconductive layers in image sensors; components provided for the purpose of absorbing electromagnetic energy, specifically infrared transmission filters in infrared sensors; and components related to projection, specifically lenses in image sensors. Multispectral sensors are particularly effective when used in applications such as color inspection or quality inspection of camera systems, and incorporating such multispectral sensors into smartphones is also a preferred embodiment.

[0273] In distance measurement devices, polycyclic aromatic compounds can be used in components such as beam splitters; lenses for imaging (preferably one or more lenses in a five-element lens configuration); nanostructures for spatial modulation; or lenses for projection.

[0274] In the spatial light phase modulator, for example, a polycyclic aromatic compound can be used in a member such as a photoconductive layer.

[0275] In cameras, polycyclic aromatic compounds can be used, for example, in components related to multispectral filtering, specifically, photoconductive layers in cameras mounted on smartphones, and in components related to image capture, specifically, lenses in digital cameras.

[0276] In a beam steering device, for example, polycyclic aromatic compounds can be used for components such as nanostructures related to spatial modulation.

[0277] In a projector, for example, polycyclic aromatic compounds can be used in components related to imaging, specifically, components such as lenses (preferably one or more lenses in a five-element lens configuration).

[0278] In a microscope, for example, polycyclic aromatic compounds can be used in components related to imaging, specifically, components such as lenses (preferably one or more lenses in a five-element lens configuration).

[0279] In endoscopes, for example, polycyclic aromatic compounds can be used in components such as holographic lens support structures.

[0280] In a free space optical communication system, for example, polycyclic aromatic compounds can be used in components such as lenses related to projection.

[0281] In reflectors for aerial displays, for example, polycyclic aromatic compounds can be used in components such as retroreflective materials.

[0282] In road signs, polycyclic aromatic compounds can be used in components such as microspheres as a photoconductive layer or microspheres provided for the purpose of absorbing electromagnetic energy. These microspheres can be used in any manner, for example, they can be used in a state where the microspheres are collected in the form of a tape or sheet, or they can be used by being contained in a tape or sheet. When polycyclic aromatic compounds are used in road signs, they can be used, for example, as retroreflective materials.

[0283] In anti-reflection films, for example, polycyclic aromatic compounds can be used in members such as anti-reflection coatings that are provided for the purpose of absorbing electromagnetic energy.

[0284] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0285] <NMR (Nuclear Magnetic Resonance Spectrum)> A 500 MHz NMR measurement device manufactured by JEOL Ltd. was used. １ For H-NMR, the measurement sample was dissolved in a heavy solvent such as deuterated chloroform and the like and then measured.

[0286] <Liquid Chromatography Mass Spectrometry> A liquid chromatography mass spectrometer manufactured by Thermo Fisher Science Inc. was used. The column used was a Mightysil RP-18 GP 100-4.6 (5 μm) manufactured by Kanto Chemical Co., Inc. The sample was dissolved in a solvent such as toluene or chloroform and then measured.

[0287] <Glass Transition Temperature (° C.)> The glass transition temperature (° C.) was measured using a Diamond DSC system scanning calorimeter manufactured by PerkinElmer Co., Ltd.

[0288] <Optical Refractive Index> A sample was dissolved in o-dichlorobenzene (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and the optical refractive index of the solution was measured using an Abbe refractometer (NAR-2T: manufactured by Atago Co., Ltd.) with the D line of a sodium lamp in an environment of 25°C, and the refractive index of the sample was calculated by extrapolation.

[0289] <<Examples>> Synthesis Example (1)

[0290]

[0291] Compound (A-1) (4.00 g) synthesized by the synthesis method described in Korean Patent Registration No. 102284600, compound (A-2) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.93 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.024 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (0.24 g), potassium carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (3.27 g), toluene (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (20.0 ml), and pure water (20.0 ml) were added and heated with stirring for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent of the fraction containing the target substance was distilled off under reduced pressure, yielding the compound represented by formula (1-1-25) (2.80 g).

[0292] １H-NMR (500MHz, DMSO-d6) δ = 7.720 (t, 1H), 7.627 (d, 2H), 7.494 (s, 1H), 7.43 2 (d, 1H), 7.380-7.326 (m, 4H), 7.263-7.068 (m, 26H), 6.939-6.927 (m, 2H).

[0293] Glass transition temperature (Tg) = 148.0°C; refractive index (nD25) = 1.77; Abbe number (νd) = 11.4.

[0294] <<Examples>> Synthesis Example (2)

[0295]

[0296] Compound (A-3) (3.70 g) synthesized by the synthesis method described in Chinese Patent No. 112661714, compound (A-4) (4.37 g) synthesized by the synthesis method described in International Publication No. 2011 / 018951, bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.20 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (0.90 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (3.87 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (40.0 ml), and pure water (40.0 ml) were added and heated and stirred for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 4 / 1 (volume ratio)). The solvent of the fraction containing the target substance was distilled off under reduced pressure, yielding the compound represented by formula (1-4-2) (2.10 g).

[0297] １ H-NMR (500MHz, CDCl ３ ) δ = 8.162-8.151 (m, 2H), 8.042-8.014 (m, 3H), 7.881-7.805 (m, 5H), 7.782-7.767 (m, 2H), 7.747-7 .731 (m, 3H), 7.594 (t, 1H), 7.482-7.459 (m, 2H), 7.388-7.321 (m, 4H), 1.583 (t, 6H), 1.566 (t, 6H).

[0298] Glass transition temperature (Tg) = 106.15°C; refractive index (nD25) = 1.79; Abbe number (νd) = 10.2

[0299] <<Examples>> Synthesis Example (3)

[0300]

[0301] Step 1 Compound (A-5) (manufactured by Tokyo Chemical Industry Co., Ltd.) (5.0 g), Compound (A-6) (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.97 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.26 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (1.22 g), potassium carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (5.22 g), Solmix A-11 (manufactured by Japan Alcohol Sales Co., Ltd.) (25.0 ml), and water (25.0 ml) were added and heated and stirred for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound represented by formula (A-8) (4.72 g).

[0302] Second Step: Compound (A-7) (54.72 g), Compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.79 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (Pd(dppf)Cl ２ ・CH ２ Cl ２ To the mixture were added potassium acetate (KOAc) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.33 g), potassium acetate (KOAc) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (3.23 g), and cyclopentyl methyl ether (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (45.0 ml), followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure, yielding the compound represented by formula (A-9) (3.25 g).

[0303] Third Step: Compound (A-5) (manufactured by Tokyo Chemical Industry Co., Ltd.) (5.00 g), Compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (3.20 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (Pd(dppf)Cl ２ ・CH ２ Cl ２ To the mixture were added potassium acetate (KOAc) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.31 g), potassium acetate (KOAc) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (3.71 g), and cyclopentyl methyl ether (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (50.0 ml), followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure, yielding the compound represented by formula (A-9) (5.02 g).

[0304] Step 4 Compound (A-9) (5.02 g), compound (A-11) (Tokyo Chemical Industry Co., Ltd.) (2.51 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.23 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (1.09 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (4.67 g), Solmix A-11 (Nippon Alcohol Sales Co., Ltd.) (50.0 ml), and water (50.0 ml) were added and heated and stirred for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound represented by formula (A-12) (4.15 g).

[0305] Fifth Step: Compound (A-12) (4.15 g), trifluoromethanesulfonic anhydride (Tf ２ O) (Tokyo Chemical Industry Co., Ltd.) (3.05 g), pyridine (Fujifilm Wako Pure Chemical Industries, Ltd.) (1.42 g), dichloromethane (CH ２ Cl２ ) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (40.0 ml) was added and the mixture was stirred overnight. After completion of the reaction, pure water and dichloromethane were added and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain the compound represented by formula (A-13) (3.70 g).

[0306] Step 6 Compound (A-9) (1.5 g), compound (A-13) (1.71 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.06 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (0.28 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (1.20 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (15.0 ml), and water (15.0 ml) were added and heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound (1.20 g) represented by formula (1-4-42).

[0307] １ H-NMR (500MHz, CDCl ３ ) δ = 8.226 (s, 1H), 8.019-8.000 (m, 2H), 7.967 (d, 1H), 7.936 (s, 1H), 7.894-7.878 (m, 2H), 7.666-7.635 (m, 2H), 7.547 (d, 1H), 7.460-7.435 (m, 2H), 7.401-7.360 (m, 2H), 7.342-7.040 (m, 28H), 6.941-6.931 (m, 2H).

[0308] Glass transition temperature (Tg) = 158.11°C; refractive index (nD25) = 1.89; Abbe number (νd) = 18.4

[0309] <<Examples>> Synthesis Example (4)

[0310]

[0311] Step 1 Compound (A-6) (manufactured by Tokyo Chemical Industry Co., Ltd.) (20.0 g), Compound (A-11) (manufactured by Tokyo Chemical Industry Co., Ltd.) (14.02 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.69 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (8.67 g), potassium carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (37.18 g), Solmix A-11 (manufactured by Japan Alcohol Sales Co., Ltd.) (200.0 ml), water (200.0 ml) were added and heated and stirred for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound represented by formula (A-14) (11.43 g).

[0312] Second step: Compound (A-14) (11.43 g), trifluoromethanesulfonic anhydride (Tf ２ O) (Tokyo Chemical Industry Co., Ltd.) (19.00 g), pyridine (Fujifilm Wako Pure Chemical Industries, Ltd.) (4.26 g), dichloromethane (CH ２ Cl ２ ) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (250.0 ml) was added and the mixture was stirred overnight. After completion of the reaction, pure water and dichloromethane were added and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain the compound represented by formula (A-15) (3.70 g).

[0313] Third Step: Compound (A-15) (3.00 g), Compound (A-8) (Tokyo Chemical Industry Co., Ltd.) (2.17 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (Pd(dppf)Cl ２ ・CH ２ Cl ２To the mixture were added potassium acetate (KOAc) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.20 g), potassium acetate (KOAc) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (2.28 g), and cyclopentyl methyl ether (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (30.0 ml), followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure, yielding the compound represented by formula (A-16) (2.80 g).

[0314] Step 4 Compound (A-16) (2.80 g), compound (A-17) (Tokyo Chemical Industry Co., Ltd.) (3.03 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.16 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (0.74 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (3.18 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (30.0 ml), and water (30.0 ml) were added and heated and stirred for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound represented by formula (A-18) (2.10 g).

[0315] Fifth Step: Compound (A-18) (2.10 g), Compound (A-8) (Tokyo Chemical Industry Co., Ltd.) (1.16 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (Pd(dppf)Cl ２ ・CH ２ Cl ２To the mixture were added potassium acetate (KOAc) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.21 g), potassium acetate (KOAc) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (1.12 g), and cyclopentyl methyl ether (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (20.0 ml), followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure, yielding the compound represented by formula (A-19) (2.20 g).

[0316] Step 6 Compound (A-19) (1.00 g), compound (A-17) (Tokyo Chemical Industry Co., Ltd.) (0.61 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.03 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (0.15 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (0.64 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (10.0 ml), and water (10.0 ml) were added and heated and stirred for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound (0.80 g) represented by formula (1-4-62).

[0317] １ H-NMR (500MHz, CDCl ３ ) δ = 7.955-7.911 (m, 3H), 7.886-7.781 (m, 9H), 7.754 (d, 1H), 7.647 (d, 1H), 7.719 (s, 1H), 7.647 (d, 1H), 7.577 (d, 1H), 7 .547 (t, 1H), 7.396-7.333 (m, 8H), 7.139-7.080 (m, 7H), 6.980 (s, 1H), 6.812-6.768 (m, 4H), 6.732 (d, 1H), 6.715 (d, 1H).

[0318] Glass transition temperature (Tg) = 191.23°C; refractive index (nD25) = 1.86; Abbe number (νd) = 21.6

[0319] <<Examples>> Synthesis Example (5)

[0320] First Step: Compound (A-20) (19.00 g) synthesized by the synthesis method described in Korean Patent Publication No. 10-2015-0103241, Compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (14.93 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (Pd(dppf)Cl ２ ・CH ２ Cl ２ To the mixture were added potassium acetate (KOAc) (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.29 g), potassium acetate (KOAc) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (17.3 g), and cyclopentyl methyl ether (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (190.0 ml), followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure, yielding the compound represented by formula (A-21) (16.45 g).

[0321] Step 2 Compound (A-21) (4.00 g), compound (A-22) (Tokyo Chemical Industry Co., Ltd.) (3.06 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.22 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (1.05 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (4.48 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (30.0 ml), and water (30.0 ml) were added and heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound represented by formula (A-23) (2.50 g).

[0322] Step 3 Compound (A-21) (7.67 g), compound (A-24) (Tokyo Chemical Industry Co., Ltd.) (5.00 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.43 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (2.00 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (8.58 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (50.0 ml), and water (50.0 ml) were added and heated and stirred for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound represented by formula (A-25) (6.47 g).

[0323] Fourth Step: Compound (A-25) (6.47 g), Compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (4.87 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (Pd(dppf)Cl ２ ・CH ２ Cl ２ To the mixture were added potassium acetate (KOAc) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.22 g), potassium acetate (KOAc) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (4.70 g), and cyclopentyl methyl ether (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (65.0 ml), followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent of the fraction containing the target product was distilled off under reduced pressure, yielding the compound represented by formula (A-26) (7.40 g).

[0324] Step 5 Compound (A-23) (2.00 g), compound (A-26) (2.49 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.) (0.11 g), tetrabutylammonium bromide (TBAB) (Fujifilm Wako Pure Chemical Industries, Ltd.) (0.48 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (2.08 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (25.0 ml), and water (25.0 ml) were added and heated and stirred for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 4 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound (1.15 g) represented by formula (1-5-6).

[0325] Glass transition temperature (Tg) = 159.76°C; refractive index (nD25) = 1.79; Abbe number (νd) = 16.2

[0326] <<Examples>> Synthesis Example (6)

[0327] Compound (A-27) (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.00 g), compound (A-9) (6.39 g) synthesized by the synthesis method of Synthesis Example (3), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.13 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (0.59 g), potassium carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (2.54 g), toluene (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (32.0 ml), and water (32.0 ml) were added, and the mixture was heated and stirred for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound (3.81 g) represented by formula (1-4-188).

[0328] １ H-NMR (500MHz, CDCl３ ) δ = 8.270 (d, 2H), 7.834 (t, 2H), 7.794-7.761 (m, 4H), 7.632 (d, 2H), 7.600 (t, 2H), 7.502 (d, 2H), 7.433 (d, 2H), 7.371 (d, 2H), 7.303 (t, 2H), 7.267-7.135 (m, 24H), 7.065-7.018 (m, 4H).

[0329] Refractive index (nD25) = 1.78; Abbe number (νd) = 20.5

[0330] <<Examples>> Synthesis Example (7)

[0331] Compound (A-26) (3.00 g) synthesized by the synthesis method of Synthesis Example (5), compound (A-28) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.94 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.13 g), tetrabutylammonium bromide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (TBAB) (0.58 g), potassium carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (2.50 g), toluene (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (31.0 ml), and water (31.0 ml) were added and heated with stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound (1.31 g) represented by formula (1-5-244).

[0332] １ H-NMR (500MHz, CDCl ３ ) δ = 8.872 (d, 2H), 8.420 (d, 2H), 8.103 (t, 2H), 7.917 (s, 2H), 7.817 (d, 2H) , 7.669-7.479 (m, 20H), 7.401 (t, 2H), 7.368-7.327 (m, 4H), 1.577 (s, 12H).

[0333] Refractive index (nD25) = 1.79; Abbe number (νd) = 11.5

[0334] <<Examples>> Synthesis Example (8)

[0335] First Step: Compound (A-29) (manufactured by Merck Ltd.) (55.00 g), boron tribromide (BBr ３ ) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (131.48 g), dichloromethane (CH ２ Cl ２ ) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (550.0 ml) was added and stirred overnight. After completion of the reaction, the mixture was poured into pure water and extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure to obtain a compound represented by formula (A-30) (42.00 g).

[0336] Second step: Compound (A-30) (42.00 g), chloromethyl methyl ether (CH ３ OCH ２ Cl) (Tokyo Chemical Industry Co., Ltd.) (36.32 g), sodium hydride (10.83 g), dichloromethane (CH ２ Cl ２ ) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (420.0 ml) was added and stirred overnight. After completion of the reaction, the mixture was poured into pure water and extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure to obtain a compound represented by formula (A-31) (35.23 g).

[0337] Compound (A-10) (50.25 g) synthesized by the synthesis method of Synthesis Example 3, compound (A-31) (35.23 g), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.), (2.38 g), tetrabutylammonium bromide (Fujifilm Wako Pure Chemical Industries, Ltd.) (TBAB) (10.93 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (46.88 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (250.0 ml), and water (250.0 ml) were added and heated and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene / ethyl acetate = 4 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound (46.50 g) represented by formula (A-32).

[0338] Fourth Step: Compound (A-32) (46.50 g), Compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (21.51 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (Pd(dppf)Cl ２ ・CH ２ Cl ２ To the mixture were added potassium acetate (KOAc) (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.33 g), potassium acetate (KOAc) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (24.93 g), and cyclopentyl methyl ether (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (450.0 ml), followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and purified water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene / ethyl acetate = 4 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure, yielding the compound represented by formula (A-33) (20.00 g).

[0339] Step 5: Compound (A-33) (20.00 g), compound (A-13) (17.63 g) synthesized by the synthesis method of Synthesis Example (3), bis(triphenylphosphine)palladium(II) dichloride (Tokyo Chemical Industry Co., Ltd.), (0.65 g), tetrabutylammonium bromide (Fujifilm Wako Pure Chemical Industries, Ltd.) (TBAB) (3.02 g), potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd.) (12.94 g), toluene (Fujifilm Wako Pure Chemical Industries, Ltd.) (200.0 ml), and water (200.0 ml) were added and heated and stirred for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and pure water and toluene were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene / ethyl acetate = 4 / 1 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain a compound represented by formula (A-34) (10.50 g).

[0340] Sixth Step: Compound (A-34) (10.50 g), trifluoroacetic acid (TFA) (Fujifilm Wako Pure Chemical Industries, Ltd.) (23.82 g), dichloromethane (CH ２ Cl ２) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (100.0 ml) was added and stirred overnight. After completion of the reaction, the mixture was poured into pure water and extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure to obtain a compound represented by formula (A-35) (8.60 g).

[0341] Step 7: Compound (A-13) (8.60 g), compound (manufactured by Tokyo Chemical Industry Co., Ltd.) (A-36) (2.18 g), potassium carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (5.47 g), and N,N-dimethylformamide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (31.0 ml) were added and heated and stirred for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, poured into pure water, and extracted with ethyl acetate to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and ethyl acetate and passed through a silica gel short-path column (solvent: toluene / ethyl acetate = 7 / 3 (volume ratio)). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain the compound represented by formula (1-4-360) (3.20 g).

[0342] １ H-NMR (500MHz, CDCl ３ ) δ = 8.235 (s, 1H), 8.027 (d, 1H), 8.009 (s, 1H), 7.954 (d, 1H), 7.899 (d, 1H) H), 7.560 (d, 1H), 7.459 (d, 1H), 7.452 (s, 1H), 7.385-7.129 (m, H), 7.04 2-6.969 (m, 3H), 6.811 (d, 1H), 4.910 (dd, 1H), 4.542 (dd, 1H), 4.303-4. 214 (m, 2H), 4.078 (dt, 1H), 3.875 (dt, 1H), 3.792 (q, 2H), 3.238 (q, 2H).

[0343] Refractive index (nD25) = 1.81; Abbe number (νd) = 13.3

[0344] <<Comparative Example>> Comparison of Physical Properties The following compound (S-1) was selected as a comparative compound. This compound is described in JP-A Nos. 2008-520542 and 2019-34940, and has uses similar to those of the present invention.

[0345]

[0346] Refractive index (nD25) = 1.66.

[0347] <<Comparative Example>> Comparison of Physical Properties The following compound (S-2) was selected as a comparative compound. This compound is described in JP 2019-34940 A and has uses similar to those of the present invention.

[0348] Refractive index (nD25) = 1.75.

[0349] Table 3: Refractive index (nD25) of Example Compounds (1-1-25), (1-4-2), (1-4-42), (1-4-46), (1-4-188), (1-4-360), (1-5-6), (1-5-244) and Comparative Compounds (S-1) and (S-2)

[0350]

[0351] The refractive indices (nD25) of the compounds obtained in Synthesis Examples (1) to (8) and the comparative compounds are summarized in Table 3. All of the compounds obtained in Synthesis Examples (1) to (8) have higher refractive indices than the comparative compounds (S-1) and (S-2). The above results demonstrate that the present compounds (1-1-25), (1-4-2), (1-4-42), (1-4-46), (1-4-188), (1-4-360), (1-5-6), and (1-5-244) are superior to the comparative compounds (S-1) and (S-2) in material systems where a high refractive index is required.

[0352] The polycyclic aromatic compound according to an embodiment of the present invention has a high refractive index and is suitable for use in optical fields such as holographic optics, image capture optics, projection optics, diffractive optics, electromagnetic energy absorption optics, and combiner optics. For example, the compound can be used in optical lenses, spatial light modulators, transmission control mirrors, reflective displays, composite materials, color sensors, multispectral filters, image sensing, and other applications, making it extremely useful.

Claims

1. A polycyclic aromatic compound which is a monomer or dimer of a structural unit represented by the following formula (1), and in the case of a dimer, is a homodimer or heterodimer; In the formula (1), ring A, ring B, ring C, and ring D are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; each R is independently a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl, and two adjacent Rs may be bonded to each other to form a ring; ｍ represents a divalent group in which m E's are bonded in series, one bond being bonded to a ring-constituting element of ring B and the other bond being bonded to a ring-constituting element of ring C; each E is independently a substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene; m is an integer satisfying 5≧m≧1; at least one hydrogen in the structural unit represented by formula (1) may be substituted with cyano, a halogen atom, or a deuterium atom; when the polycyclic aromatic compound is a dimer of the structural units, ring A, ring B, ring C, or ring D in one structural unit is bonded to ring A, ring B, ring C, or ring D in the other structural unit by a single bond.

2. The polycyclic aromatic compound according to claim 1, wherein in the formula (1), ring A, ring B, ring C and ring D are each independently a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a naphthalene ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, a benzofuran ring, a benzothiophene ring or an indole ring, and each E is independently phenylene, naphthalenylene, phenanthrenylene, pyrenylene, dibenzofuranylene or dibenzothiophenylene.

3. The polycyclic aromatic compound according to claim 1, represented by formula (1-1). In the formula (1-1), each Z is independently =N- or =C(-R Ｚ )-, and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, one of Z in each structure is a carbon atom, and the carbon atom has a bond to F; R is each independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene.

4. The polycyclic aromatic compound according to claim 3, wherein F is 1,3-phenylene.

5. The polycyclic aromatic compound according to claim 3, which is represented by any one of the following formulas:

6. The polycyclic aromatic compound according to claim 1, represented by formula (1-2). In formula (1-2), each Z is independently =N- or =C(-R Ｚ )-, and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, one of Z in each structure is a carbon atom, and said carbon atom has a bond to F; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene, dibenzofuranylene, or dibenzothiophenylene.

7. The polycyclic aromatic compound according to claim 6, which is represented by any one of the following formulas:

8. The polycyclic aromatic compound according to claim 1, represented by formula (1-3). In formula (1-3), each Z is independently =N- or =C(-R Ｚ )-, and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in the two structures on either side of F, one of Z in each structure is a carbon atom, and said carbon atom has a bond to F; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F is phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene.

9. The polycyclic aromatic compound according to claim 8, which is represented by any one of the following formulas:

10. The polycyclic aromatic compound according to claim 1, represented by formula (1-4). In formula (1-4), each Z is independently =N- or =C(-R Ｚ )-, and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, any one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; H ｎ represents a divalent group in which n H's are bonded in series; and n is an integer satisfying 2≧n≧0.

11. The polycyclic aromatic compound according to claim 10, which is represented by any one of the following formulas:

12. The polycyclic aromatic compound according to claim 1, represented by formula (1-5). In formula (1-5), each Z is independently =N- or =C(-R Ｚ )-, and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; n is an integer of 2≧n≧0.

13. The polycyclic aromatic compound according to claim 12, which is represented by any one of the following formulas:

14. The compound according to claim 1, represented by formula (1-6). In formula (1-6), each Z is independently =N- or =C(-R Ｚ )-, and R Ｚ are each independently a hydrogen atom or a substituent, and two adjacent R Ｚ may be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on either side of -F-G-Hn-, one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bond to F, and the carbon atom in the other structure has a bond to Hn; R is independently a hydrogen atom, aryl, heteroaryl, or alkyl, and when two R are aryl or heteroaryl, adjacent carbon atoms may be bonded to each other; F, G, and H are independently phenylene, naphthalenylene, dibenzofuranylene, or dibenzothiophenylene; F and G have different aryl rings; n is an integer of 2≧n≧0.

15. The polycyclic aromatic compound according to claim 14, which is represented by any one of the following formulas:

16. An optical material comprising the polycyclic aromatic compound according to any one of claims 1 to 15.

17. An optical element comprising the optical material according to claim 16.

18. An optical instrument comprising the optical element according to claim 17.

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