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

Abstract

A polycyclic aromatic compound which is a monomer or a dimer of a structural unit represented by formula (1), and which is a homodimer or a heterodimer when the polycyclic aromatic compound is a dimer; in 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 independently represents a hydrogen atom, an alkyl group or the like, and two adjacent Rs may be bonded to each other to form a ring; em represents a divalent group in which m Es are bonded in series, one bond is bonded to the ring-constituting element of the B ring, and the other bond is bonded to the ring-constituting element of the C ring; each E independently represents an alkylene group or the like; m is an integer greater than or equal to 1 and less than or equal to 5; at least one hydrogen in the structural unit represented by the formula (1) may be substituted by a cyano group, a halogen atom, or a deuterium atom; and when the polymer is a dimer, any ring in one structural unit is bonded with any ring in the other structural unit through a single bond.

Description

Technical Field

[0001] This invention relates to a polycyclic aromatic compound having a high refractive index. Furthermore, this invention relates to an optical element, optical material, and optical device using the aforementioned polycyclic aromatic compound. Background Technology

[0002] In recent years, the demand for materials with high refractive index has been increasing in the development of optical lenses, holographic optics, image acquisition optics, spatial light modulators, projection optics, diffraction 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 optical devices to achieve lightweighting, space-saving, and wide viewing angles. Additionally, in multispectral filters, they are used to minimize chromatic aberration, reduce lens weight, and control diffraction efficiency and direction. Furthermore, materials with high refractive indices offer a wide variety of effects across various fields.

[0004] 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 polycyclic aromatic compounds with specific structures.

[0005] Existing technical documents

[0006] Patent documents

[0007] Patent Document 1: International Publication No. 2023 / 074471 Summary of the Invention

[0008] The problem that the invention aims to solve

[0009] As mentioned above, various materials have been developed for many optical components, but to increase the selection of optical materials, it is desirable to develop materials containing compounds different from those previously used. In particular, a material with a higher refractive index is desired.

[0010] The objective of this invention is to provide a novel compound with a high refractive index.

[0011] Technical means to solve the problem

[0012] Through diligent research, the inventors discovered that the aforementioned problem can be solved using polycyclic aromatic compounds with specific structures, thus completing this invention.

[0013] That is, the main idea of ​​this invention is as follows.

[0014] Item 1. A polycyclic aromatic compound, which is a monomer or dimer of the structural unit represented by the following formula (1), and in the case of a dimer, is a homodimer or a heterodimer.

[0015] [Chemistry 1]

[0016]

[0017] In the above formula (1),

[0018] Rings A, B, C, and D are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring;

[0019] R can be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and two adjacent R can be bonded to each other to form a ring.

[0020] E m It represents a divalent base formed by m E tandem bonds, which forms an elemental bond with the B ring through one of the bonds and with the C ring through the other bond.

[0021] E can be independently substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;

[0022] m is an integer that is 5 ≥ m ≥ 1;

[0023] At least one hydrogen atom in the structural unit represented by formula (1) may be substituted by a cyano group, a halogen atom, or a deuterium atom;

[0024] In the case where the polycyclic aromatic compound is a dimer of the structural unit, the A, B, C, or D rings of one structural unit are bonded to the A, B, C, or D rings of the other structural unit through single bonds.

[0025] Item 2. The polycyclic aromatic compound according to Item 1, wherein in the formula (1),

[0026] Rings A, B, C, and D are independently benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, naphthylene rings, quinoline rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, furan rings, thiophene rings, pyrrole rings, thiazole rings, benzofuran rings, benzothiophene rings, or indole rings, respectively.

[0027] E can be phenylene, naphthylene, phenanthrene, pyrene, dibenzofuranyl, or dibenzothiopheneyl, respectively.

[0028] Item 3. The polycyclic aromatic compound according to Item 1, represented by formula (1-1);

[0029] [Chemistry 2]

[0030]

[0031] In the above formula (1-1),

[0032] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by F, either Z in each structure is a carbon atom, and the carbon atom has a bond with F;

[0033] R can be a hydrogen atom, aryl, heteroaryl, or alkyl atom, respectively. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0034] F stands for phenylene.

[0035] Item 4. The polycyclic aromatic compound according to Item 3, wherein F is 1,3-phenylene.

[0036] Item 5. The polycyclic aromatic compound according to Item 3 is represented by any of the following formulas;

[0037] [Chemistry 3]

[0038]

[0039]

[0040] [Chemistry 4]

[0041] .

[0042] Item 6. The polycyclic aromatic compound according to Item 1, represented by formula (1-2);

[0043] [Chemistry 5]

[0044]

[0045] In equation (1-2),

[0046] Z is independently =N- or =C(-R) Z)-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by F, either Z in each structure is a carbon atom, and the carbon atom has a bond with F;

[0047] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0048] F is phenylene, dibenzofuranyl, or dibenzothiophene.

[0049] Item 7. The polycyclic aromatic compound according to Item 6 is represented by any of the following formulas;

[0050] [Chemistry 6]

[0051]

[0052] .

[0053] Item 8. The polycyclic aromatic compounds according to Item 1, represented by formula (1-3);

[0054] [Chemistry 7]

[0055]

[0056] In equation (1-3),

[0057] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by F, either Z in each structure is a carbon atom, and the carbon atom has a bond with F;

[0058] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0059] F is phenylene, naphthylene, dibenzofuranylene, or dibenzothiopheneylene.

[0060] Item 9. The polycyclic aromatic compound according to Item 8 is represented by any of the following formulas;

[0061] [Chemistry 8]

[0062] .

[0063] Item 10. The polycyclic aromatic compounds according to Item 1, represented by formulas (1-4);

[0064] [Chemistry 9]

[0065]

[0066] In equation (1-4),

[0067] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by -FG-Hn-, either Z in each structure is a carbon atom, the carbon atom in one structure has a bond with F, and the carbon atom in the other structure has a bond with Hn.

[0068] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0069] F, G, and H are independently phenylene, naphthylene, dibenzofuranylene, or dibenzothiopheneylene; F and G have mutually different aryl rings;

[0070] Hn represents a divalent group formed by n H tandem bonds;

[0071] n is an integer that is 2 ≥ n ≥ 0.

[0072] Item 11. The polycyclic aromatic compound according to Item 10 is represented by any of the following formulas;

[0073] [Chemistry 10]

[0074]

[0075]

[0076] [Chemistry 11]

[0077]

[0078] .

[0079] Item 12. The polycyclic aromatic compounds according to Item 1 are represented by formulas (1-5);

[0080] [Chemistry 12]

[0081]

[0082] In equation (1-5),

[0083] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by -FG-Hn-, either Z in each structure is a carbon atom, the carbon atom in one structure has a bond with F, and the carbon atom in the other structure has a bond with Hn.

[0084] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0085] F, G, and H are independently phenylene, naphthylene, dibenzofuranylene, or dibenzothiopheneylene; F and G have mutually different aryl rings;

[0086] n is an integer that is 2 ≥ n ≥ 0.

[0087] Item 13. The polycyclic aromatic compound according to Item 12 is represented by any of the following formulas;

[0088] [Chemistry 13]

[0089] .

[0090] Item 14. The compound according to Item 1 is represented by formula (1-6);

[0091] [Chemistry 14]

[0092]

[0093] In equation (1-6),

[0094] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by -FG-Hn-, either Z in each structure is a carbon atom, the carbon atom in one structure has a bond with F, and the carbon atom in the other structure has a bond with Hn.

[0095] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0096] F, G, and H are independently phenylene, naphthylene, dibenzofuranylene, or dibenzothiopheneylene; F and G have mutually different aryl rings;

[0097] n is an integer that is 2 ≥ n ≥ 0.

[0098] Item 15. The polycyclic aromatic compound according to Item 14 is represented by any of the following formulas;

[0099] [Chemistry 15]

[0100] .

[0101] Item 16. An optical material comprising a polycyclic aromatic compound according to any one of items 1 to 15.

[0102] Item 17. An optical element comprising the optical material according to Item 16.

[0103] Item 18. An optical device having an optical element according to Item 17.

[0104] The effects of the invention

[0105] According to the present invention, a novel compound having a high refractive index can be provided. Detailed Implementation

[0106] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. Furthermore, in this specification, the numerical range indicated by “~” refers to the range including the values ​​described before and after “~” as both the lower and upper limits. Additionally, in this specification, “hydrogen” in the description of the structural formula refers to “hydrogen atom (H)”. Similarly, “carbon atom (C)” is sometimes referred to as “carbon”.

[0107] In this specification, when referred to as "adjacent bases", it means two bases that are bonded to one atom, or two bases that are bonded to two adjacent atoms in the structural formula (two atoms that are directly bonded by covalent bonds).

[0108] In addition, in this specification, the expression "A or B" may be changed to "at least one of the groups consisting of A and B".

[0109] Furthermore, while multiple embodiments are described in this specification, various conditions in each embodiment can be applied interchangeably within the scope of applicability.

[0110] In this specification, "Me" represents methyl, "Ph" represents phenyl, "Np" represents naphthyl, "DBF" represents dibenzofuranyl, "DBT" represents dibenzothiophenyl, "Tf" represents trifluoromethanesulfonyl, and "D" represents deuterium.

[0111] <Explanation of rings and substituents>

[0112] First, the details of the rings and substituents used in this specification will be explained below.

[0113] As used in this specification, "aryl ring" can be exemplified by aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms.

[0114] Specific examples of "aryl rings" include: benzene rings as monocyclic systems; biphenyl rings as bicyclic systems; naphthalene rings or indene rings as condensed bicyclic systems; terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl) as tricyclic systems; acenaphthene rings, fluorene rings, fenene rings, phenanthrene rings, or anthracene rings as condensed tricyclic systems; triphenylene rings, pyrene rings, naphthacene rings, or cyclopentane rings as condensed tetracyclic systems; or perylene rings or pentacene rings as condensed pentacyclic systems. Furthermore, fluorene rings, benzo[a]fluorene rings, or indene rings may also contain structures formed by the spiral bonding of fluorene rings, benzo[a]fluorene rings, or cyclopentane rings. Furthermore, in fluorene rings, benzo[a]fluorene rings, and indene rings, there are also rings in which two of the two hydrogens of the methylene group in the structure are respectively replaced by alkyl groups such as methyl as the first substituent described later, thus becoming dimethylfluorene rings, dimethylbenzo[a]fluorene rings, or dimethylindene rings, etc.

[0115] As used in this specification, "heteroaryl ring" can be exemplified by 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, even more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Furthermore, as "heteroaryl ring," examples include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, boron, selenium, phosphorus, and tellurium as ring-forming atoms.

[0116] Specific examples of "heteroaryl rings" include: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring (furazan ring, etc.), thiadiazole ring, triazole ring, tetraazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cyclophosphine ring, quinazolinite ring, quinoxaline ring, phthalazine ring, naphthidine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxthiazoline ring, phenoxazine ring, phenthiazoline ring, phenazine ring, phenazasiline ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzene ring, etc. Thiophene ring, dibenzothiophene ring, thiophene ring, indolocarbazole ring, benzoindolocarbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthonium ring, thioxanthonium ring, dibenzodioxin ring, dioxaboranenaphthalene ring (5,9-dioxa-13b-borane-13bH-naphthalo[3,2,1-de] Anthracite rings, benzo[selenyl]phene rings, dibenzo[selenyl]phene rings, azacarbazole rings, azadibenzothiophene rings, azadibenzofuran rings, azadibenzo[selenyl]phene rings, azatriphenylene rings, imidazo[imidazo]imidazo] rings, indole[indole] rings, benzofuran[carbazole] rings, benzothiophene[carbazole] rings, indole[carbazole] rings, seleno[carbazole] rings, spiro[fluorene-9,9'-xanthon] rings, or spirodi[siliconfluorene] rings, etc. Furthermore, in dihydroacridine rings, xanthon rings, or thioxanthon rings, it is also preferable that two of the two hydrogen atoms of the methylene group in its structure are respectively substituted with alkyl groups such as methyl as the first substituent described later to form a dimethyldihydroacridine ring, a dimethylxanthon ring, or a dimethylthioxanthon ring, etc. In addition, bipyridine rings, phenylpyridine rings, or pyridylphenyl rings, which are bicyclic systems, or tripyridine rings, bispyridylphenyl rings, or pyridylbiphenyl rings, which are tricyclic systems, can also be listed as "heteroaryl rings". Furthermore, "heteroaryl rings" also include pyran rings.

[0117] In this specification, "substituted or unsubstituted" means that it may or may not have substituents. When referred to as "substituent," the type of substituent is not particularly limited, especially unless otherwise stated, as long as it is any group selected from the substituent group Z described below. For example, when "substituted or unsubstituted" is substituted, the group only needs to be substituted by at least one group selected from the substituent group Z.

[0118] In this specification, substituents are sometimes substituted by further substituents. For example, a particular substituent is sometimes described as "substituted or unsubstituted." This means that the particular substituent is substituted by at least one further substituent, or is unsubstituted. In the same sense, it is sometimes also referred to as "substitutable." In this specification, the particular substituent in this case is sometimes referred to as the "first substituent," and the further substituent is referred to as the "second substituent."

[0119] In this specification, the substituent group Z includes:

[0120] The aryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl, substituted silyl, cyano, and halogen atoms;

[0121] The heteroaryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl, substituted silyl, cyano, and halogen atoms;

[0122] Alkyl groups may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, hydroxyl, substituted silyl, cyano, and halogen atoms;

[0123] The cycloalkyl group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl, substituted silyl, cyano, and halogen atoms;

[0124] The alkoxy group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, hydroxyl, substituted silyl, cyano, and halogen atoms;

[0125] The aryloxy group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, hydroxyl, substituted silyl, cyano, and halogen atoms; or

[0126] It replaces silyl, cyano, and halogen atoms.

[0127] The aryl group in substituent group Z, which is a second substituent, may be further substituted with aryl, heteroaryl, alkyl, cycloalkyl, substituted silyl, cyano, or halogen atom. Similarly, the heteroaryl group, which is a second substituent, may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, substituted silyl, cyano, or halogen atom.

[0128] In this specification, "aryl" is, for example, an aryl group with 6 to 30 carbon atoms, preferably an aryl group with 6 to 20 carbon atoms, an aryl group with 6 to 16 carbon atoms, an aryl group with 6 to 12 carbon atoms, or an aryl group with 6 to 10 carbon atoms.

[0129] Specific examples of "aryl" include monovalent groups formed by removing a hydrogen atom from the "aryl ring". Examples include: phenyl as a monocyclic compound; biphenyl as a bicyclic compound (2-biphenyl, 3-biphenyl, or 4-biphenyl); naphthyl as a condensed bicyclic compound (1-naphthyl or 2-naphthyl); terphenyl as a tricyclic compound (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); and acenaphthene as a condensed tricyclic compound (1-, 3-, 4-). Or 5-)yl, fluorene-(1-, 2-, 3-, 4-, or 9-)yl, fen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, or 9-)yl; as tetracyclic systems, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-tetraphenyl); as condensed tetracyclic systems, triphenyl-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or condensed tetraphenyl-(1-, 2-, or 5-)yl; or as condensed pentacyclic systems, perylene-(1-, 2-, or 3-)yl, or condensed pentaphenyl-(1-, 2-, 5-, or 6-)yl, etc. In addition, examples include the monovalent group of spirofluorene.

[0130] Furthermore, the aryl group serving as the second substituent also includes a structure in which the aryl group is substituted with at least one group selected from the group consisting of aryl groups such as phenyl (specifically, the group described above), alkyl groups such as methyl (specifically, the group described below), and cycloalkyl groups such as cyclohexyl or adamantyl (specifically, the group described below).

[0131] As an example, one could list groups in which the hydrogen atom at the 9-position of the fluorene group, which is a second substituent, is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl.

[0132] "Alemines" are, for example, arymines with 6 to 30 carbon atoms, preferably arymines with 6 to 20 carbon atoms, arymines with 6 to 16 carbon atoms, arymines with 6 to 12 carbon atoms, or arymines with 6 to 10 carbon atoms.

[0133] Specific examples of "aryl" include divalent groups formed by removing one hydrogen atom from the "aryl" (monovalent group).

[0134] "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. In the "heteroaryl", in addition to carbon atoms, there is one or more, preferably one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms.

[0135] As specific examples of "heteroaryl groups," a monovalent group formed by removing a hydrogen atom from the aforementioned "heteroaryl ring" can be listed. Examples include: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolel, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyridazinyl, triazinyl, indole, isoindoleyl, etc. 1 H-indazole, benzimidazole, benzoxazole, benzothiazolyl, 1 H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phenanthrolineyl, phthalazinyl, naphridinyl, purineyl, pteridinyl, carbazoleyl, acridineyl, phenoxthiayl, phenoxazinyl, phenthiazinyl, phenazinyl, phenazasilinyl, indazinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, monovalent group of benzophosphane pentadiene oxide ring, monovalent group of dibenzophosphane pentadiene oxide ring, furazolyl, thiophenyl, indolocarbazoyl, benzoindolocarbazoyl, dibenzoindolocarbazoyl, imidazolinyl, or oxazolinyl, etc. In addition, examples include: the monovalent group of spiro[fluorene-9,9'-xanthan], the monovalent group of spirodi[siliconfluorene], and the monovalent group of benzo[selenene].

[0136] Furthermore, the heteroaryl group that serves as the second substituent also includes a structure in which the heteroaryl group is substituted with at least one group selected from the group consisting of aryl groups such as phenyl (specifically, the group described above), alkyl groups such as methyl (specifically, the group described below), and cycloalkyl groups such as cyclohexyl or adamantyl (specifically, the group described below).

[0137] As an example, groups in which the hydrogen atom at the 9-position of the carbazoyl group, which is a second substituent, is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl. Furthermore, groups in which nitrogen-containing heteroaryl groups such as pyridyl, pyrimidinyl, triazine, and carbazoyl are further substituted with phenyl or biphenyl groups are also included in heteroaryl groups that are second substituents.

[0138] "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. Additionally, "heteroaryl" is, for example, a divalent group containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon atoms, in a heterocycle.

[0139] Specific examples of "hybrid aryl" include divalent groups formed by removing one hydrogen atom from the "heteroaryl" (monovalent group).

[0140] "Alkyl" can be either straight-chain or branched-chain, for example, a straight-chain alkyl with 1 to 24 carbons or a branched-chain alkyl with 3 to 24 carbons, preferably an alkyl with 1 to 18 carbons (branched-chain alkyl with 3 to 18 carbons), an alkyl with 1 to 12 carbons (branched-chain alkyl with 3 to 12 carbons), an alkyl with 1 to 6 carbons (branched-chain alkyl with 3 to 6 carbons), an alkyl with 1 to 5 carbons (branched-chain alkyl with 3 to 5 carbons), an alkyl with 1 to 4 carbons (branched-chain alkyl with 3 to 4 carbons), etc.

[0141] 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, sec-butyl, tert-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, tert-pentyl (t-amyl) (tert-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-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl, etc.

[0142] Specific examples of "hydroxyl-substituted alkyl groups" include -CH2-OH, -C2H4-OH, -C3H6-OH, or -C4H8-OH.

[0143] "alkylene" is a divalent group obtained by removing any hydrogen from an "alkyl" group, such as methylene, ethylene, and propylene.

[0144] Regarding "alkenyl", please refer to the description of "alkyl". It is a group in which the C=C single bond in the structure of "alkyl" is replaced with a C=C double bond. It also includes groups in which not only one but more single bonds are replaced with double bonds (also called diene-yl or triene-yl).

[0145] "Alkenyl" is a divalent group obtained by removing any hydrogen atom from "alkenyl", such as vinylidene.

[0146] Regarding "alkynyl", please refer to the description of "alkyl". It is a group in which the C C single bond in the structure of "alkyl" is replaced with a C≡C triple bond. It also includes groups in which not only one but more single bonds are replaced with triple bonds (also called diynyl or triynyl).

[0147] "Cycloalkyl" is, for example, a cycloalkyl group having 3 to 24 carbon atoms, preferably a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, or a cycloalkyl group having 5 carbon atoms, etc.

[0148] Specific examples of "cycloalkyl" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbons or 1 to 4 carbons, 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, diadamantyl, decahydronaphthyl, or decahydroazyl, etc.

[0149] "Cycloalkylene" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, a cycloalkylene having 3 to 14 carbon atoms, a cycloalkylene having 3 to 12 carbon atoms, a cycloalkylene having 5 to 10 carbon atoms, a cycloalkylene having 5 to 8 carbon atoms, a cycloalkylene having 5 to 6 carbon atoms, or a cycloalkylene having 5 carbon atoms, etc.

[0150] Specific examples of "cycloalkylene" include structures that are divalent by removing one hydrogen atom from the "cycloalkyl" (monovalent group).

[0151] "Cycloalkenyl" can be listed as a group having at least one set of single bonds between two carbons in the "cycloalkyl" group that form a double bond (e.g., a group where -CH2-CH2- is substituted to -CH=CH-), and is not equivalent to an aryl group. Specifically, 1-cyclohexenyl, 1-cyclopentenyl, etc., can be listed.

[0152] "Alkoxy" is the group represented by "Alk-O- (Alk is alkyl)", and for details about the alkyl group, please refer to the description of the "alkyl".

[0153] Specific examples of "hydroxyl-substituted alkoxy groups" include -O-CH2-OH, -O-C2H4-OH, -O-C3H6-OH, or -O-C4H8-OH.

[0154] "Aryloxy group" is the group represented by "Ar-O- (Ar is aryl)". For details about the aryl group, please refer to the description of "aryl".

[0155] "Substituted silyl" refers to, for example, a silyl group substituted with at least one of aryl, alkyl, and cycloalkyl groups, preferably a triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0156] "Triarylsilyl" refers to a silyl group substituted with three aryl groups. For details regarding the aryl groups, please refer to the description of "aryl".

[0157] Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmonaphthylsilyl, monophenyldinaphthylsilyl, or triaphthylsilyl, etc.

[0158] "Trialkylsilyl" refers to a silyl group substituted with three alkyl groups. For details regarding the alkyl group, please refer to the description of the "alkyl group".

[0159] Specific examples of "trialkylsilyl" include: trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, ethyl dimethylsilyl, n-propyl dimethylsilyl, isopropyl dimethylsilyl, n-butyl dimethylsilyl, isobutyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, methyl diethylsilyl, n-propyl Diethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyl di-n-propylsilyl, ethyl di-n-propylsilyl, n-butyl di-n-propylsilyl, sec-butyl di-n-propylsilyl, tert-butyl di-n-propylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, n-butyl diisopropylsilyl, sec-butyl diisopropylsilyl, or tert-butyl diisopropylsilyl, etc.

[0160] "Tricycloalkylsilyl" refers to a silyl group substituted with three cycloalkyl groups. For details regarding the cycloalkyl group, please refer to the description of "cycloalkyl".

[0161] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl or tricyclohexylsilyl.

[0162] "Dialkylcycloalkylsilyl" refers to a silyl group substituted with two alkyl groups and one cycloalkyl group. For details regarding the alkyl and cycloalkyl groups, please refer to the description of "alkyl" and "cycloalkyl".

[0163] "alkyl-dicycloalkyl-silyl" refers to a silyl group substituted with one alkyl group and two cycloalkyl groups. For details regarding the alkyl and cycloalkyl groups, please refer to the description of "alkyl" and "cycloalkyl".

[0164] The "halogen atom" is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, preferably a fluorine atom, a chlorine atom, or a bromine atom, more preferably a fluorine atom or a chlorine atom, and even more preferably a fluorine atom.

[0165] When cyano or halogen atoms are substituted, it is preferred that all or part of the hydrogens in the aryl or heteroaryl groups in the structure are substituted by cyano or halogen atoms.

[0166] [The case where two groups bonded to the same atom are bonded to each other]

[0167] In this specification, when referring to two groups bonded to the same atom (also called "adjacent groups"), if it is mentioned that they can bond to each other to form a ring, they can be bonded by a single bond or a linking group (also collectively referred to as linking groups). Examples of linking groups include -CH2-CH2- and -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 structures can be listed. Furthermore, the -CHR 1 -CHR 1 -of R 1 -CR 1 2-CR 1 2-of-R 1 -CR 1 =CR 1 -of R 1 -N(-R) 1 )- of R 1 -C(-R) 1 )2-ofR 1 and -Si(-R 1 )2-ofR 1 Each is independently a hydrogen atom; an aryl group that can be substituted with an alkyl or cycloalkyl group; a heteroaryl group that can be substituted with an alkyl or cycloalkyl group; an alkyl group that can be substituted with a cycloalkyl group; an alkenyl group that can be substituted with an alkyl or cycloalkyl group; or a cycloalkyl group that can be substituted with an alkyl or cycloalkyl group. Additionally, the two adjacent R groups... 1 They can bond together to form rings, and can form cycloalkylene, arylene, or heteroarylene compounds.

[0168] [Chemistry 16]

[0169]

[0170] As a bonding base, a single bond is preferred, or -CR is preferred as a linking base. 1 =CR 1 -、-N(-R 1 -, -O-, -S-, -C(-R) 1 )2-、-Si(-R 1 )2- or -Se-, more preferably a single bond, or -CR as a linker 1 =CR 1 -、-N(-R 1 -, -O-, -S-, or -C(-R) 1 )2-, and more preferably a single bond, or -CR as a linker. 1 =CR 1 -、-N(-R 1-, -O-, or -S-, with a single bond being the most preferred.

[0171] Regarding the two Rs 1 The position of the bond formed by the bonding group is not particularly limited if it is a position that can be bonded. It is preferred to bond at the most adjacent position. For example, in the case where the two groups are phenyl, it is preferred to bond at adjacent (2-position) positions based on the bonding position (1-position) of the "C" or "Si" in the phenyl group (refer to the structural formula).

[0172] [Stereoheterogeneities, etc.]

[0173] The polycyclic aromatic compounds described later may exist as mirror-image isomers or non-mirror-image isomers depending on the type of substituents, but regardless of the described structural formula, any pure form of any stereoisomer, any mixture of stereoisomers, racemic mixtures, etc., are included within the scope of this invention.

[0174] <Polycyclic aromatic compounds>

[0175] Through diligent research, the inventors have discovered that polycyclic aromatic compounds having a structure in which two fluorene skeletons are bonded via a linker group containing arylene groups or the like have high refractive indices.

[0176] The polycyclic aromatic compound (hereinafter also simply referred to as "polycyclic aromatic compound") of one embodiment of the present invention is a monomer or dimer of the structural unit represented by the following formula (1) which links the aromatic ring (aryl ring or heteroaryl ring) and has a fluorene skeleton. In the case of a dimer, it is a homodimer or a heterodimer.

[0177] [Chemistry 17]

[0178]

[0179] In the case where the polycyclic aromatic compound is a dimer of the aforementioned structural units, rings A, B, C, or D in one structural unit are bonded to rings A, B, C, or D in the other structural unit via single bonds. Furthermore, the dimer in the polycyclic aromatic compound is either a dimer linked by chemical bonds such as covalent bonds, or a dimer linked by physical bonds such as hydrogen bonds or intermolecular forces, where two monomers exist.

[0180] The structural unit represented by Equation (1) has the following structure: one of the m independent E units bonded in series has a hydrogen atom bonded to the ring of the B ring of the structure represented by Equation (1), which is elementally bonded to the ring of the C ring of the structure represented by Equation (1), and the other unit has a hydrogen atom bonded to the ring of the C ring of the structure represented by Equation (1).

[0181] [Explanation of the ring structure]

[0182] The following equation (1A) shows the ratio E in equation (1). m The structures further to the left and further to the right are obtained separately. In formula (1A), “A”, “B”, “C” and “D” are symbols representing the ring structures represented by each circle. Ring A, ring B, ring C and ring D are independently substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings.

[0183] [Chemistry 18]

[0184]

[0185] In formula (1A), rings A, B, C, and D all have bonds between two adjacent elements (preferably carbon) on the aryl or heteroaryl rings in their structure. A monovalent group is formed using the structure on the left side of formula (1A), and a monovalent group is also formed using the structure on the right side of formula (1A). The bonds from ring B in the structure on the left side of formula (1A), the bonds from ring C in the structure on the right side, and the divalent E... m Formation of bonds. Among rings A, B, C, and D, the element having the two bonds described above is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring. The ring may further condense with other rings. Examples of 6-membered rings include: benzene rings, pyridine rings, pyrazine rings, or pyrimidine rings. Examples of 6-membered rings further condensing with other rings include: naphthyl rings, quinoline rings, benzofuran rings, benzothiophene rings, indole rings, benzoselenene rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, or dibenzoselenene rings. Examples of 5-membered rings include: furan rings, thiophene rings, pyrrole rings, thiazole rings, or selenene rings. Examples of 5-membered rings further condensing with other rings include: benzofuran rings, benzothiophene rings, indole rings, or benzoselenene rings.

[0186] The aryl or heteroaryl rings in rings A, B, C, and D are preferably, independently, benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, naphthyl rings, quinoline rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, furan rings, thiophene rings, pyrrole rings, thiazole rings, benzofuran rings, benzothiophene rings, or indole rings. More preferably, they are benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, naphthyl rings, quinoline rings, benzofuran rings, benzothiophene rings, or benzoselenene rings. Further preferably, they are benzene rings, pyridine rings, naphthyl rings, or quinoline rings. More preferably, they are benzene rings or naphthyl rings.

[0187] In the substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings in rings A, B, C, and D of the structure represented by formula (1A), the substituents used when referring to "substituted or unsubstituted" are not particularly limited, and examples 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, etc., preferably halogen atom or cyano. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0188] Ring A, ring B, ring C, and ring D are each preferably benzene rings or naphthalene rings that can be substituted with halogen atoms or cyano groups, and more preferably unsubstituted benzene rings or naphthalene rings.

[0189] R is independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, preferably a hydrogen atom; an alkyl group; a cycloalkyl group; an aryl group that can be substituted by an alkyl or cycloalkyl group; or a heteroaryl group that can be substituted by an alkyl or cycloalkyl group, wherein two adjacent R groups can be bonded to each other to form a ring. R is more preferably a phenyl group, a group in which two adjacent R groups are bonded to each other by a phenyl group, or a methyl group.

[0190] Furthermore, in this specification, alkyl groups are not considered as substituents for alkyl groups.

[0191] As specific examples of the partial structures represented by equation (1A) (the structures on the left and right sides of equation (1A)), they are independently represented by the following equations (1A-1) and (1A-2). In equation (1A-1), the left ring of the quintuple bonded by R can be either ring A or ring B of equation (1A). If the left ring is ring A, the right ring is ring B; if the left ring is ring B, the right ring is ring A. Similarly, in equation (1A-2), the left ring of the quintuple bonded by R can be either ring C or ring D of equation (1A). If the left ring is ring C, the right ring is ring D; if the left ring is ring D, the right ring is ring C.

[0192] Furthermore, as two structures of equation (1A), both can apply the structure of equation (1A-1), both can apply the structure of equation (1A-2), and both can apply either equation (1A-1) or equation (1A-2).

[0193] [Chemistry 19]

[0194]

[0195] In equations (1A-1) and (1A-2), Z is independently -N = or -C(-R) Z =, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups. In each fluorene skeleton, any one of Z has a relationship with E. m The carbon atom (C) that forms the bond.

[0196] R can be applied independently and in the same way as the conditions of R, preferably unsubstituted aryl, unsubstituted heteroaryl, or unsubstituted alkyl, more preferably phenyl, pyridyl, in the form where the two adjacent R are bonded to each other through phenyl, methyl or ethyl, and even more preferably phenyl, in the form where the two adjacent R are bonded to each other through phenyl, or methyl.

[0197] [E m ]

[0198] E m It represents a divalent base formed by m E series bonds, which forms an elemental bond with the B ring through one of the bonds and with the C ring through the other bond.

[0199] m is an integer greater than or equal to 1 and less than or equal to 5 (5 ≥ m ≥ 1). When m is an integer greater than or equal to 2 and less than or equal to 5 (5 ≥ m ≥ 2), multiple E's can be the same or different.

[0200] E can be independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. Preferably, both the arylene and heteroarylene groups in E have two bonds located on the same monocyclic ring or the same condensed ring, more preferably on the same monocyclic ring. The substituents used when referring to "substituted or unsubstituted" are not particularly limited, but can include: aryl (substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), heteroaryl (substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), alkyl (substituted with aryl, heteroaryl, alkyl, halogen atom, or cyano), halogen atom, or cyano, etc. When multiple substituents are present, the substituents can be the same or different. Preferably, the arylene and heteroarylene groups in E are unsubstituted.

[0201] Examples of E are preferably phenylene, naphthylene, phenanthrene, pyrene, dibenzofuranyl, or dibenzothiophene, and examples include phenylene, naphthylene, dibenzofuranyl, or dibenzothiophene. More preferably, E is 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,5-naphthylene, 2,6-naphthylene, 2,8-dibenzofuranyl, or 2,8-dibenzothiophene.

[0202] As E m Preferred examples can be listed as structures represented by any of the following formulas.

[0203] [Chemistry 20]

[0204]

[0205] [Chemistry 21]

[0206]

[0207] [Chemistry 22]

[0208]

[0209] Substitution using cyano, halogen, or deuterium atoms

[0210] At least one hydrogen atom in the structural unit represented by formula (1) may be substituted by a cyano group, a halogen atom, or a deuterium atom.

[0211] For example, in the structural unit represented by equation (1), rings A, B, C, D, and E... m The aryl or heteroaryl rings in the formula, and the hydrogen atoms in the substituents of these rings, may be replaced by cyano, halogen, or deuterium atoms. Examples of substituted hydrogen atoms in all or part of the aryl and / or heteroaryl groups are provided. From the point of view of durability, it is also preferred that all or part of the hydrogen atoms in the structural unit represented by formula (1) are deuterated.

[0212] [Specific examples of polycyclic aromatic compounds]

[0213] 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 applied similarly to the conditions for the corresponding structure in formula (1) to the extent applicable.

[0214] [Chemistry 23]

[0215]

[0216] In equation (1-1),

[0217] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by F, either Z in each structure is a carbon atom, and the carbon atom has a bond with F;

[0218] R can be a hydrogen atom, aryl, heteroaryl, or alkyl atom, respectively. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0219] F stands for phenylene.

[0220] In formula (1-1), F is preferably 1,3-phenylene.

[0221] As examples of polycyclic aromatic compounds represented by formula (1-1), compounds represented by any of the following structural formulas can be listed.

[0222] [Chemistry 24]

[0223]

[0224] [Chemistry 25]

[0225]

[0226] Examples of polycyclic aromatic compounds include compounds represented by the following formulas (1-2). The conditions for the structure of formula (1-2) can be applied similarly to the conditions for the corresponding structure in formula (1) to the extent applicable.

[0227] [Chemistry 26]

[0228]

[0229] In equation (1-2),

[0230] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by F, either Z in each structure is a carbon atom, and the carbon atom has a bond with F;

[0231] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0232] F is phenylene, dibenzofuranyl, or dibenzothiophene.

[0233] As examples of polycyclic aromatic compounds represented by formulas (1-2), compounds represented by any of the following structural formulas can be listed.

[0234] [Chemistry 27]

[0235]

[0236] Examples of polycyclic aromatic compounds include compounds represented by the following formulas (1-3). The conditions for the structures of formulas (1-3) can be applied similarly to the conditions for the corresponding structures in formula (1) to the extent applicable.

[0237] [Chemistry 28]

[0238]

[0239] In equation (1-3),

[0240] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by F, either Z in each structure is a carbon atom, and the carbon atom has a bond with F;

[0241] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0242] F is phenylene, naphthylene, dibenzofuranylene, or dibenzothiopheneylene.

[0243] Examples of polycyclic aromatic compounds represented by formulas (1-3) can be listed as compounds represented by any of the following structural formulas.

[0244] [Chemistry 29]

[0245]

[0246]

[0247] Examples of polycyclic aromatic compounds include compounds represented by the following formulas (1-4). The conditions for the structures of formulas (1-4) can be applied similarly to the conditions for the corresponding structures in formula (1) to the extent applicable.

[0248] [Chemistry 30]

[0249]

[0250] In equation (1-4),

[0251] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by -FG-Hn-, either Z in each structure is a carbon atom, the carbon atom in one structure has a bond with F, and the carbon atom in the other structure has a bond with Hn.

[0252] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0253] Hn represents a divalent group formed by n H tandem bonds;

[0254] F, G, and H are independently phenylene, naphthylene, dibenzofuranylene, and dibenzothiopheneylene; F and G have mutually different aryl rings;

[0255] n is an integer that is 2 ≥ n ≥ 0.

[0256] Examples of polycyclic aromatic compounds represented by formulas (1-4) can be listed as compounds represented by any of the following structural formulas.

[0257] [Chemistry 31]

[0258]

[0259] [Chemistry 32]

[0260]

[0261] Examples of polycyclic aromatic compounds include compounds represented by the following formulas (1-5). The conditions for the structures of formulas (1-5) can be applied similarly to the conditions for the corresponding structures in formula (1) to the extent applicable.

[0262] [Chemistry 33]

[0263]

[0264] In equation (1-5),

[0265] Z is independently =N- or =C(-R)Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by -FG-Hn-, either Z in each structure is a carbon atom, the carbon atom in one structure has a bond with F, and the carbon atom in the other structure has a bond with Hn.

[0266] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0267] F, G, and H are independently phenylene, naphthylene, dibenzofuranylene, or dibenzothiopheneylene; F and G have mutually different aryl rings;

[0268] n is an integer that is 2 ≥ n ≥ 0.

[0269] Examples of polycyclic aromatic compounds represented by formulas (1-5) can be listed as compounds represented by any of the following structural formulas.

[0270] [Chemistry 34]

[0271]

[0272]

[0273] Examples of polycyclic aromatic compounds include compounds represented by the following formulas (1-6). The conditions for the structures of formulas (1-6) can be applied similarly to the conditions for the corresponding structures in formula (1) to the extent applicable.

[0274] [Chemistry 35]

[0275]

[0276] In equation (1-6),

[0277] Z is independently =N- or =C(-R) Z )-, R Z Each is an independent hydrogen atom or substituent, and the two adjacent R atoms are... Z They can bond with each other to form substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings; in the two structures separated by -FG-Hn-, either Z in each structure is a carbon atom, the carbon atom in one structure has a bond with F, and the carbon atom in the other structure has a bond with Hn.

[0278] R can be a hydrogen atom, aryl, heteroaryl, or alkyl independently. When both R are aryl or heteroaryl, adjacent carbon atoms can bond to each other.

[0279] F, G, and H are independently phenylene, naphthylene, dibenzofuranylene, or dibenzothiopheneylene; F and G have mutually different aryl rings;

[0280] n is an integer that is 2 ≥ n ≥ 0.

[0281] Examples of polycyclic aromatic compounds represented by formulas (1-6) can be listed as compounds represented by any of the following structural formulas.

[0282] [Chemistry 36]

[0283]

[0284] In the case where the polycyclic aromatic compound is a dimer, as an example, the polycyclic aromatic compound can also be represented by the following formulas (2-1) to (2-6).

[0285] [Chemistry 37]

[0286]

[0287]

[0288] In equations (2-1) to (2-6), rings A', B', C', and D' can be subject to the same conditions as those for rings A, B, C, and D in this specification. These conditions can be identical (homodimer) or different (heterodimer). Heterodimer in this specification refers to a structure where any structural unit satisfies equation (1) but includes rings A, B, C, D, R, and E. m The dimer of two structural units with at least one of the following structures being structurally different is preferably a morphology in which the backbone of each ring structure is the same in rings A, B, C, and D as in rings A', B', C', and D', but each ring structure may have at least one of the following substituents, R, and R'. Furthermore, for example, in formulas (2-1) and (2-2), the bonds connecting the two structural units are single bonds connecting ring D and ring A' and single bonds connecting ring D and ring D', respectively, but could also be single bonds connecting ring A and ring C' or single bonds connecting ring C and ring C', etc. Additionally, R' can be applied independently under the same conditions as R in this specification. Furthermore, E m 'Applicable to E in this specification' m Under the same conditions, therefore, the following operations proceed through loops A, B, C, D, R, and E. mThe descriptions provided are for A', B', C', D', R', and E' rings, but these descriptions can also be applied to rings A', B', C', D', R', and E'. m 'middle.

[0289] There are no particular restrictions on the form of the dimer. From the viewpoint of ease of synthesis, formula (2-1) or formula (2-2) is preferred. Furthermore, from the viewpoint of easier suppression of crystallization, formula (2-3) or formula (2-4) is preferred. From the viewpoint of further easier suppression of crystallization, formula (2-5) or formula (2-6) is preferred.

[0290] In particular, the compound represented by any of the following is preferred as the compound of general formula (1-1).

[0291] [Chemistry 38]

[0292]

[0293]

[0294] [Chemistry 39]

[0295]

[0296]

[0297] [Chemistry 40]

[0298]

[0299]

[0300] [Chemistry 41]

[0301]

[0302] In particular, the compounds represented by any of the following are preferred as compounds of general formula (1-2).

[0303] [Chemistry 42]

[0304]

[0305] [Chemistry 43]

[0306]

[0307] [Chemistry 44]

[0308]

[0309]

[0310] [Chemistry 45]

[0311]

[0312]

[0313] In particular, the compounds represented by any of the following formulas are preferred as compounds of general formulas (1-3).

[0314] The preferred form of general formula (1-3) is a compound represented by formula (1-3-a) or formula (1-3-b).

[0315] [Chemistry 46]

[0316]

[0317] In equations (1-3-a) and (1-3-b),

[0318] Aa is a divalent base selected from the bases represented below.

[0319] The bonding sites Xa and Xb of fluorene are each selected from the sites indicated below.

[0320] [Chemistry 47]

[0321]

[0322] [Chemistry 48]

[0323]

[0324] The specific combinations of Aa, Xa, and Xb in the various formulas are shown in Tables 1-1 to 1-5 below.

[0325] [Table 1-1]

[0326]

[0327] [Table 1-2]

[0328]

[0329] [Table 1-3]

[0330]

[0331] [Table 1-4]

[0332]

[0333] [Table 1-5]

[0334]

[0335] In particular, the compounds represented by any of the following formulas are preferred as compounds of general formulas (1-4).

[0336] [Chemistry 49]

[0337]

[0338]

[0339] [Transformation 50]

[0340]

[0341]

[0342] [Chemistry 51]

[0343]

[0344] [Chemistry 52]

[0345]

[0346] [Chemistry 53]

[0347]

[0348] [Chemistry 54]

[0349]

[0350]

[0351] [Chemistry 55]

[0352]

[0353]

[0354] [Chemistry 56]

[0355]

[0356]

[0357] [Chemistry 57]

[0358]

[0359]

[0360] [Chem.58]

[0361]

[0362]

[0363] [Chemistry 59]

[0364]

[0365]

[0366] [Transformation 60]

[0367]

[0368] [Chemistry 61]

[0369]

[0370] [Chemistry 62]

[0371]

[0372]

[0373] [Chemistry 63]

[0374]

[0375]

[0376] [Chemistry 64]

[0377]

[0378]

[0379] [Chemistry 65]

[0380]

[0381]

[0382] [Chemistry 66]

[0383]

[0384]

[0385] [Chemistry 67]

[0386]

[0387]

[0388] [Chemistry 68]

[0389]

[0390]

[0391] [Chemistry 69]

[0392]

[0393] [Chemistry 70]

[0394]

[0395] [Chemistry 71]

[0396]

[0397]

[0398] [Chemistry 72]

[0399]

[0400]

[0401] [Chemistry 73]

[0402]

[0403]

[0404] [Chemistry 74]

[0405]

[0406]

[0407] [Chemistry 75]

[0408]

[0409] [Chemistry 76]

[0410]

[0411] [Chemistry 77]

[0412]

[0413] [Chemistry 78]

[0414]

[0415]

[0416] [Chemistry 79]

[0417]

[0418]

[0419] [Chemistry 80]

[0420]

[0421]

[0422] [Chemistry 81]

[0423]

[0424] [Chemistry 82]

[0425]

[0426] [Chemistry 83]

[0427]

[0428]

[0429] [Chemistry 84]

[0430]

[0431]

[0432] [Chemistry 85]

[0433]

[0434]

[0435] [Chemistry 86]

[0436]

[0437] [Chemistry 87]

[0438]

[0439] [Chemistry 88]

[0440]

[0441]

[0442] In particular, the compounds represented by any of the following formulas are preferred as compounds of general formulas (1-5).

[0443] [Chemistry 89]

[0444]

[0445]

[0446] [Chemistry 90]

[0447]

[0448]

[0449] [Chemistry 91]

[0450]

[0451]

[0452] [Chemistry 92]

[0453]

[0454]

[0455] [Chemistry 93]

[0456]

[0457] [Chemistry 94]

[0458]

[0459]

[0460] [Chem. 95]

[0461]

[0462]

[0463] [Chemistry 96]

[0464]

[0465]

[0466] [Chemistry 97]

[0467]

[0468]

[0469] [Chem. 98]

[0470]

[0471] [Chemistry 99]

[0472]

[0473] [Chemistry 100]

[0474]

[0475]

[0476] [Chemistry 101]

[0477]

[0478]

[0479] [Chemistry 102]

[0480]

[0481]

[0482] [Chemistry 103]

[0483]

[0484] [Chemistry 104]

[0485]

[0486] [Chemistry 105]

[0487]

[0488] [Chemistry 106]

[0489]

[0490]

[0491] [Chemistry 107]

[0492]

[0493]

[0494] [Chemistry 108]

[0495]

[0496]

[0497] [Chemistry 109]

[0498]

[0499]

[0500] [Chemical 110]

[0501]

[0502]

[0503] [Chemistry 111]

[0504]

[0505] [Chemistry 112]

[0506]

[0507] [Chemistry 113]

[0508]

[0509] [Chemistry 114]

[0510]

[0511]

[0512] [Chemistry 115]

[0513]

[0514]

[0515] [Chemistry 116]

[0516]

[0517]

[0518] [Chemistry 117]

[0519]

[0520] [Chemistry 118]

[0521]

[0522] [Chemistry 119]

[0523]

[0524]

[0525] [Chemistry 120]

[0526]

[0527]

[0528] [Chemistry 121]

[0529]

[0530]

[0531] [Chemistry 122]

[0532]

[0533]

[0534] [Chemistry 123]

[0535]

[0536] [Chemistry 124]

[0537]

[0538] In particular, the compounds represented by any of the following formulas are preferred as compounds of general formulas (1-6).

[0539] The preferred form of general formula (1-6) is the compound represented by the following formula (1-6-a).

[0540] [Chemistry 125]

[0541]

[0542] In the aforementioned formula (1-6-a),

[0543] A1, A2, and A3 are two-valent bases selected from the bases represented below.

[0544] The bonding sites Xa and Xb of fluorene are each selected from the sites indicated below.

[0545] [Chemistry 126]

[0546]

[0547] [Chemistry 127]

[0548]

[0549]

[0550] [Chemistry 128]

[0551]

[0552] The specific combinations of A1, A2, A3, Xa, and Xb in the various formulas are shown in Tables 2-1 to 2-6 below.

[0553] [Table 2-1]

[0554]

[0555] [Table 2-2]

[0556]

[0557] [Table 2-3]

[0558]

[0559] [Table 2-4]

[0560]

[0561] [Table 2-5]

[0562]

[0563] [Table 2-6]

[0564]

[0565] Of the compounds represented by the aforementioned formulas, the more preferred compounds are those represented by any of the following formulas.

[0566] The compound represented by formula (1-1)

[0567] The preferred formulas are Equations 1-1-4, 1-1-5, 1-1-6, 1-1-11, 1-1-12, 1-1-17, 1-1-18, 1-1-19, 1-1-25, 1-1-26, 1-1-30, 1-1-34, 1-1-35, and 1-1-36.

[0568] The compound represented by formula (1-2)

[0569] The preferred formulas are Equations 1-2-4, 1-2-5, 1-2-7, 1-2-8, 1-2-12, 1-2-13, 1-2-27, and 1-2-28.

[0570] The compounds represented by formula (1-3)

[0571] The preferred formulas are Equations 1-3-7, 1-3-62, 1-3-65, and 1-3-114.

[0572] The compounds represented by formula (1-4)

[0573] The preferred formulas are: 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.

[0574] The compounds represented by formula (1-5)

[0575] The preferred formulas are Equations 1-5-6, 1-5-48, 1-5-131, 1-5-165, 1-5-244, 1-5-321, 1-5-323, and 1-5-331.

[0576] The compounds represented by formula (1-6)

[0577] The preferred formulations are Equation 1-6-69 and Equation 1-6-135.

[0578] <Methods for manufacturing polycyclic aromatic compounds>

[0579] The polycyclic aromatic compounds are not particularly limited and can be produced, for example, by known synthetic methods such as the Suzuki coupling reaction. The Suzuki coupling reaction is a method of coupling an aromatic halide or trifluoromethanesulfonate with an aromatic boric acid or aromatic borate in the presence of a base using a palladium catalyst. Specific examples of reaction pathways for obtaining polycyclic aromatic compounds using the above method are described below (processes 1 to 3). Furthermore, the following reaction pathway is for obtaining a polycyclic aromatic compound containing only one structural unit represented by formula (1).

[0580] In addition, R in each process 1 ~R 4 As described above, TfO is trifluoromethanesulfonate, and Pin is pinacol. Additionally, L in (process 3) n n and L o The sum of o is (n+o) to get m.

[0581] [Chemistry 129]

[0582]

[0583] Specific examples of palladium catalysts used in the reaction include Pd(PPh3)4, PdCl2(PPh3)2, Pd(OAc)2, tris(dibenzylacetone)dipalladium(0), tris(dibenzylacetone)dipalladium(0)chloroform complex, or bis(dibenzylacetone)palladium(0), etc. Phosphine compounds may also be added to these palladium compounds as appropriate to promote the reaction. Specific examples of the phosphine compounds are tris(tert-butyl)phosphine, tricyclohexylphosphine, 1-(N,N-dimethylaminomethyl)-2-(di-tert-butylphosphine)ferrocene, 1-(N,N-dibutylaminomethyl)-2-(di-tert-butylphosphine)ferrocene, 1-(methoxymethyl)-2-(di-tert-butylphosphine)ferrocene, 1,1'-bis(di-tert-butylphosphine)ferrocene, 2,2'-bis(di-tert-butylphosphine)-1,1'-binaphthyl, or 2-methoxy-2'-(di-tert-butylphosphine)-1,1'-binaphthyl, etc.

[0584] Specific examples of the bases used in the reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium tert-butoxide, sodium acetate, tripotassium phosphate, or potassium fluoride.

[0585] Furthermore, specific examples of solvents used in the reaction include benzene, toluene, xylene, N,N-dimethylformamide, tetrahydrofuran, diethyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, 1,4-dioxane, methanol, ethanol, isopropanol, or water. These solvents can be appropriately selected based on the structure of the aromatic halides, trifluoromethanesulfonates, aromatic borates, and aromatic boric acids involved in the reaction. Solvents can be used alone or in combination.

[0586] In addition, regarding R in polycyclic aromatic compounds 1 and R 2 or R 3 and R 4 Compounds that form rings (e.g., aliphatic or aromatic rings) by bonding can be manufactured, for example, by a method for manufacturing benzo[a]fluorene compounds with a spirostructure as described in Japanese Patent Application Publication No. 2009-184993. Paragraph 0055 of that publication describes a method for manufacturing compounds in which a fluorene ring is spiro-bonded to a five-membered ring of benzo[a]fluorene (process 1c). Referring to that manufacturing method, the polycyclic aromatic compound can be manufactured according to process 4 below. Furthermore, M in the following process is Li, MgCl, MgBr, or MgI.

[0587] [Chemistry 130]

[0588]

[0589] Polycyclic aromatic compounds also include compounds in which at least some hydrogen atoms are replaced by deuterium atoms, and such compounds can be manufactured in the same manner as described above by using raw materials with the desired deuterated sites.

[0590] <Composition>

[0591] Another embodiment of the present invention is a composition comprising the aforementioned polycyclic aromatic compound. There are no particular limitations on the composition as long as it contains a polycyclic aromatic compound, and other ingredients may be included depending on the intended use.

[0592] There are no particular limitations on the content of polycyclic aromatic compounds in the composition, and it can be appropriately set according to the application. For example, from the viewpoint of ensuring sufficient refractive index, it can be 1.0% by mass or more, or 10.0% by mass or more, or 50.0% by mass or more, or 90.0% by mass or more. Alternatively, it can be 10.0% by mass or less, or 50.0% by mass or less, or 90.0% by mass or less, or 99.0% by mass or less.

[0593] The composition may include a solvent. There are no particular limitations on the solvent, as long as it can dissolve the components constituting the composition, such as polycyclic aromatic compounds. Examples 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 with a diester skeleton, and fluorine-containing solvents. Furthermore, the solvent can be used alone or in combination.

[0594] The composition may contain antioxidants, light stabilizers, heavy metal passivators, flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, release agents, ultraviolet absorbers, plasticizers, compatibilizers, or blueing agents, etc.

[0595] The use of the composition is not limited and can be applied in the same way to the uses of polycyclic aromatic compounds described later.

[0596] <In DC form>

[0597] As another embodiment of the present invention, the molded body is a molded body containing the polycyclic aromatic compound, or a molded body as a hardened product of the composition.

[0598] The applications of the molded articles are not limited, and they can be used in the same way in the applications of polycyclic aromatic compounds described later.

[0599] Uses of polycyclic aromatic compounds

[0600] The uses of the polycyclic aromatic compounds are not particularly limited, but they can be applied particularly effectively in fields requiring high refractive indices, such as optics, electrical engineering, or semiconductors, and more specifically, in optical materials. Another embodiment of the invention is an optical material comprising the polycyclic aromatic compounds.

[0601] There are no particular restrictions on the form in which polycyclic aromatic compounds are contained in optical materials. Optical materials can consist solely of polycyclic aromatic compounds, or they can contain polycyclic aromatic compounds and other components. For example, compositions containing polycyclic aromatic compounds can be used as optical materials. Alternatively, hardened materials containing polycyclic aromatic compounds can also be used as optical materials.

[0602] In the field of high refractive index materials, especially high refractive index resins, halogen-free materials are sometimes required. Through the morphology of polycyclic aromatic compounds described in the embodiments, halogen-free and high refractive index materials can be obtained.

[0603] In addition, previously, obtaining products with high refractive index required either an increase in material quantity or a larger product size. By using the aforementioned high-refractive-index polycyclic aromatic compounds as materials, it is possible to reduce material costs through material reduction, as well as to reduce manufacturing costs through miniaturization of products and the promotion of mass production.

[0604] The application of the optical material is not particularly limited, and it can be used in various forms described later, such as optical elements like lenses (optical lenses), prisms, mirrors, or diffraction gratings. Another embodiment of the invention is an optical element comprising the aforementioned polycyclic aromatic compound, and yet another embodiment is an optical device having the aforementioned optical element. Specifically, when used as a lens, its form is not particularly limited, and it can be used as a camera lens, image acquisition lens, projection lens, electron energy absorption lens, high numerical aperture (NA) objective lens, collimate lens, or telecentric lens, etc. Its size is also not limited, and it can also be used as a microlens.

[0605] The applications of optical materials will be explained in more detail below.

[0606] Optical materials are suitable for various optical fields, including holographic optics, image acquisition optics, projection optics, diffraction optics, electromagnetic energy absorption optics, and combiner optics. Specifically, they can be used in augmented reality (AR) glasses; AR goggles; imaging devices; head-up displays (HUDs), organic electroluminescence (EL) displays, or light field displays; optical sensors such as image sensors, automotive sensors, infrared sensors, light sensors, or multispectral sensors; distance measuring devices; spatial light phase modulators; cameras such as digital cameras, smartphone cameras, automotive cameras, or personal computer cameras; beam steering devices; projectors; microscopes; endoscopes; free-space optical communication systems; reflectors for aerial displays; light-emitting diode (LED) encapsulants; photoelectric converters; and navigation devices. Devices; adhesives used in optical devices such as automotive lighting and laser processing optical equipment, road markings, anti-reflective films, and glass bonding; action recorders; game consoles; drones; autonomous driving assistance sensing; ophthalmic applications; and medical imaging for surgical robotics. Additionally, polycyclic aromatic compounds or compositions containing polycyclic aromatic compounds can also be used as materials for three-dimensional (3D) printers (e.g., filaments for 3D printers), and by using these materials for 3D printing, components in the aforementioned articles can be formed.

[0607] In AR glasses or AR goggles, polycyclic aromatic compounds may be used in components related to holographic or multispectral filtering, light diffraction, spatial modulation, or absorption of electromagnetic energy, specifically light waveguides, diffraction gratings, surface structure forming films of optical elements (especially films for forming nanopillars on the surface), sealing layers, buffer layers, or polymer films designed to absorb electromagnetic energy.

[0608] There are no particular limitations on the method of AR (Augmented Optical Waveguide), such as using a waveguide. In addition, when used as an optical waveguide, it can be used as a planar waveguide or a curved diffraction waveguide. Furthermore, by embedding these in lenses, weight reduction can be achieved.

[0609] Furthermore, diffraction gratings are typically installed in conjunction with waveguides. Since the refractive index of the waveguide is determined by the refractive index of this adjacent component, the use of the aforementioned polycyclic aromatic compounds in the diffraction grating is particularly effective. On the other hand, from the viewpoint that the waveguide has a large volume ratio relative to the product among components requiring a high refractive index, the use of the aforementioned polycyclic aromatic compounds in the waveguide is also effective.

[0610] In addition, as mentioned above, the polycyclic aromatic compounds can be used as waveguides and the like, but can also be used as coating materials for waveguides and other components, which can compensate for the refractive index characteristics of the coated components.

[0611] Furthermore, the specific use cases in AR glasses and the like can also be applied to other devices related to virtual reality (VR), mixed reality (MR), or substitutional reality (SR) and other cross-realization (XR) devices.

[0612] In imaging devices, polycyclic aromatic compounds may be used in components related to imaging, multispectral filtering, image acquisition, electromagnetic energy absorption, specifically lenses (preferably one or more of five lenses), components with core or hollow structures for filtering multispectral data, and microlenses designed to absorb electromagnetic energy.

[0613] Polycyclic aromatic compounds are used in components such as photoconductive layers in HUDs, diffraction gratings or antireflective coatings in HUDs designed to absorb electromagnetic energy, and regressive reflective materials in light field displays.

[0614] Polycyclic aromatic compounds are used in components such as 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 vehicle sensors; components related to image acquisition, specifically lenses; hard mask layers serving as photoconductive layers in image sensors; components designed to absorb electromagnetic energy, specifically infrared transmission filters in infrared sensors; and components related to projection, specifically lenses in image sensors.

[0615] Multispectral sensors are particularly effective in applications such as color inspection or quality inspection in camera systems, and their integration into smartphones is also a preferred form.

[0616] In distance measuring devices, polycyclic aromatic compounds may be used in components such as beamsplitters; lenses associated with imaging (preferably one or more of five lenses); nanostructures associated with spatial modulation; or lenses associated with projection.

[0617] In spatial optical phase modulators, polycyclic aromatic compounds can be used, for example, in components such as photoconductive layers.

[0618] In cameras, polycyclic aromatic compounds can be used, for example, in components related to multispectral filtering, such as the photoconductive layer in a smartphone camera; and in components related to image acquisition, such as lenses in a digital camera.

[0619] In beam steering devices, polycyclic aromatic compounds can be used, for example, in components such as nanostructures that are associated with spatial modulation.

[0620] In projectors, polycyclic aromatic compounds may be used, for example, in components related to imaging, specifically lenses (preferably one or more of five lenses).

[0621] In microscopes, polycyclic aromatic compounds may be used, for example, in imaging-related components, specifically lenses (preferably one or more of five lenses).

[0622] In endoscopes, polycyclic aromatic compounds can be used, for example, in components such as holographic-related lens pointing structures.

[0623] In free-space optical communication systems, polycyclic aromatic compounds can be used, for example, in components such as lenses associated with projection.

[0624] In reflectors for aerial displays, polycyclic aromatic compounds may be used, for example, in components such as regressive reflective materials.

[0625] In road marking, polycyclic aromatic compounds can be used, for example, in components such as microspheres that serve as photoconductive layers or microspheres designed to absorb electromagnetic energy. These microspheres can be used in any form; for example, they can be assembled into strips or sheets, or contained within strips or sheets. In applications where polycyclic aromatic compounds are used in road marking, they can be utilized, for example, as reflective materials.

[0626] In antireflective films, for example, polycyclic aromatic compounds can be used in components such as antireflective coatings designed to absorb electromagnetic energy.

[0627] Example

[0628] The present invention will be further described in detail below through examples, but the present invention is not limited thereto.

[0629] <Nuclear Magnetic Resonance (NMR) Spectroscopy>

[0630] Using a 500 MHz NMR measuring apparatus manufactured by Nippon Electron Ltd., for 1 H-NMR involves dissolving the sample in a deuterated solvent such as deuterated chloroform for determination.

[0631] <Liquid Chromatography Quality Analysis>

[0632] The liquid chromatography-mass analysis equipment was manufactured by Thermo Fisher Scientific ( Inc.). The column used was Mightysil RP-18 GP 100-4.6 (5 μm) manufactured by Kanto Chemical ( Inc.). The sample was dissolved in solvents such as toluene or chloroform for determination.

[0633] <Glass transition temperature (°C)>

[0634] The glass transition temperature (°C) was determined using a scanning calorimeter manufactured by PerkinElmer (S.) and a Diamond differential scanning calorimetry (DSC) system.

[0635] <Optical Refractive Index>

[0636] The sample was dissolved in o-dichlorobenzene (manufactured by Fujifilm and Hikari Pure Chemical Industries, Ltd.), and the refractive index of the solution was measured using an Abbe refractometer (NAR-2T; manufactured by Atago Ltd.) and D-rays from a sodium lamp at 25°C. The refractive index of the sample was then calculated by extrapolation.

[0637] <<Example>>

[0638] Synthesis example (1)

[0639] [Chemistry 131]

[0640]

[0641] Compound (A-1) (4.00 g), synthesized using the method described in Korean Patent 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 and Hikari Pure Chemical Industries Co., Ltd.) (0.24 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (3.27 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (20.0 ml), and purified water (20.0 ml) were added and heated and stirred for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, purified water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude compound was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (1-1-25) (2.80 g).

[0642] 1 H-NMR (500 MHz, DMSO-d6) δ=7.720 (t, 1H), 7.627 (d, 2H), 7.494 (s,1H), 7.432 (d, 1H), 7.380-7.326 (m, 4H), 7.263-7.068 (m, 26H), 6.939-6.927(m, 2H).

[0643] Glass transition point (Tg) = 148.0℃; refractive index (nD25) = 1.77; Abbe number (νd) = 11.4.

[0644] <<Example>>

[0645] Synthesis example (2)

[0646] [Chemistry 132]

[0647]

[0648] Compound (A-3) (3.70 g) synthesized using the method described in Chinese Patent No. 112661714, compound (A-4) (4.37 g) synthesized using the method described in International Publication No. 2011 / 018951, bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.20 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (0.90 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (3.87 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (40.0 ml), and purified water (40.0 ml) were added, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, purified water and toluene were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude compound was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 4 / 1 (volume ratio)). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (1-4-2) (2.10 g).

[0649] 1 H-NMR (500 MHz, CDCl3) 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).

[0650] Glass transition point (Tg) = 106.15℃; refractive index (nD25) = 1.79; Abbe number (νd) = 10.2

[0651] <<Example>>

[0652] Synthesis example (3)

[0653] [Chemistry 133]

[0654]

[0655] First process

[0656] 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 and Wako Pure Chemical Industries Co., Ltd.) (1.22 g), potassium carbonate (manufactured by Fujifilm and Wako Pure Chemical Industries Co., Ltd.) (5.22 g), Solmix A-11 (manufactured by Nippon Alcohol Sales Co., Ltd.) (25.0 ml), and water (25.0 ml) were added, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was removed by vacuum distillation to obtain the compound represented by formula (A-8) (4.72 g).

[0657] Second process

[0658] Added compound (A-7) (54.72 g), compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.79 g), and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl2). CH2Cl2 (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.33 g), potassium acetate (KOAc) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (3.23 g), and cyclopentyl methyl ether (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (45.0 ml) were heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-9) (3.25 g).

[0659] Third process

[0660] Add 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), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl2). CH2Cl2 (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.31 g), potassium acetate (KOAc) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (3.71 g), and cyclopentyl methyl ether (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (50.0 ml) were heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-9) (5.02 g).

[0661] Fourth process

[0662] Compound (A-9) (5.02 g), compound (A-11) (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.51 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.23 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (1.09 g), potassium carbonate (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (4.67 g), Solmix A-11 (manufactured by Nippon Alcohol Sales Co., Ltd.) (50.0 ml), and water (50.0 ml) were added, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-12) (4.15 g).

[0663] Fifth process

[0664] Compound (A-12) (4.15 g), trifluoromethanesulfonic anhydride (Tf₂O) (manufactured by Tokyo Chemical Industry Co., Ltd.) (3.05 g), pyridine (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (1.42 g), and dichloromethane (CH₂Cl₂) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (40.0 ml) were added and stirred overnight. After the reaction was complete, pure water and dichloromethane were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-13) (3.70 g).

[0665] Sixth process

[0666] Compound (A-9) (1.5 g), compound (A-13) (1.71 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.06 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (0.28 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (1.20 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (15.0 ml), and water (15.0 ml) were added, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (1-4-42) (1.20 g).

[0667] 1 H-NMR (500 MHz, CDCl3) 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).

[0668] Glass transition point (Tg) = 158.11℃; refractive index (nD25) = 1.89; Abbe number (νd) = 18.4

[0669] <<Example>>

[0670] Synthesis example (4)

[0671] [Chemistry 134]

[0672]

[0673] First process

[0674] 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 and Wako Pure Chemical Industries Co., Ltd.) (8.67 g), potassium carbonate (manufactured by Fujifilm and Wako Pure Chemical Industries Co., Ltd.) (37.18 g), Solmix A-11 (manufactured by Nippon Alcohol Sales Co., Ltd.) (200.0 ml), and water (200.0 ml) were added, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was removed by vacuum distillation to obtain the compound represented by formula (A-14) (11.43 g).

[0675] Second process

[0676] Compound (A-14) (11.43 g), trifluoromethanesulfonic anhydride (Tf₂O) (manufactured by Tokyo Chemical Industry Co., Ltd.) (19.00 g), pyridine (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (4.26 g), and dichloromethane (CH₂Cl₂) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (250.0 ml) were added and stirred overnight. After the reaction was complete, pure water and dichloromethane were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-15) (3.70 g).

[0677] Third process

[0678] Add compound (A-15) (3.00 g), compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.17 g), and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl2). CH2Cl2 (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.20 g), potassium acetate (KOAc) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (2.28 g), and cyclopentyl methyl ether (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (30.0 ml) were heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-16) (2.80 g).

[0679] Fourth process

[0680] Compound (A-16) (2.80 g), compound (A-17) (manufactured by Tokyo Chemical Industry Co., Ltd.) (3.03 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.16 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (0.74 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (3.18 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (30.0 ml), and water (30.0 ml) were added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent containing the target compound was removed by vacuum distillation to obtain the compound represented by formula (A-18) (2.10 g).

[0681] Fifth process

[0682] Add compound (A-18) (2.10 g), compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.16 g), and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl2). CH2Cl2 (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.21 g), potassium acetate (KOAc) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (1.12 g), and cyclopentyl methyl ether (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (20.0 ml) were heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-19) (2.20 g).

[0683] Sixth process

[0684] Compound (A-19) (1.00 g), compound (A-17) (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.61 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.03 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (0.15 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (0.64 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (10.0 ml), and water (10.0 ml) were added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude product was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (1-4-62) (0.80 g).

[0685] 1 H-NMR (500 MHz, CDCl3) 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).

[0686] Glass transition point (Tg) = 191.23℃; refractive index (nD25) = 1.86; Abbe number (νd) = 21.6

[0687] <<Example>>

[0688] Synthesis example (5)

[0689] [Chemistry 135]

[0690]

[0691]

[0692] First process

[0693] The following compounds were added: compound (A-20) (19.00 g) synthesized using the method described in Korean Patent Publication No. 10-2015-0103241; compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (14.93 g); and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl2). CH2Cl2 (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.29 g), potassium acetate (KOAc) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (17.3 g), and cyclopentyl methyl ether (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (190.0 ml) were heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-21) (16.45 g).

[0694] Second process

[0695] Compound (A-21) (4.00 g), compound (A-22) (manufactured by Tokyo Chemical Industry Co., Ltd.) (3.06 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.22 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (1.05 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (4.48 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (30.0 ml), and water (30.0 ml) were added, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-23) (2.50 g).

[0696] Third process

[0697] Compound (A-21) (7.67 g), compound (A-24) (manufactured by Tokyo Chemical Industry Co., Ltd.) (5.00 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.43 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (2.00 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (8.58 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (50.0 ml), and water (50.0 ml) were added, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-25) (6.47 g).

[0698] Fourth process

[0699] Added compound (A-25) (6.47 g), compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (4.87 g), and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl2). CH2Cl2 (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.22 g), potassium acetate (KOAc) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (4.70 g), and cyclopentyl methyl ether (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (65.0 ml) were heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-26) (7.40 g).

[0700] Fifth process

[0701] Compound (A-23) (2.00 g), compound (A-26) (2.49 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.11 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (0.48 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (2.08 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (25.0 ml), and water (25.0 ml) were added, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 4 / 1 (volume ratio)). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (1-5-6) (1.15 g).

[0702] Glass transition point (Tg) = 159.76℃; refractive index (nD25) = 1.79; Abbe number (νd) = 16.2

[0703] <<Example>>

[0704] Synthesis example (6)

[0705] [Chemistry 136]

[0706]

[0707] Compound (A-27) (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.00 g), compound (A-9) (6.39 g) synthesized using the synthetic method of Synthetic Example (3), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.13 g), tetrabutylammonium bromide (TBAB) (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (0.59 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (2.54 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (32.0 ml), and water (32.0 ml) were added and heated and stirred for 6 hours. After the reaction was completed, 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 obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent containing the target compound was removed by vacuum distillation to obtain the compound represented by formula (1-4-188) (3.81 g).

[0708] 1H-NMR (500 MHz, 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).

[0709] Refractive index (nD25) = 1.78; Abbe number (νd) = 20.5

[0710] <<Example>>

[0711] Synthesis example (7)

[0712] [Chemistry 137]

[0713]

[0714] Compound (A-26) (3.00 g) synthesized using the synthetic method of Synthetic 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.), tetrabutylammonium bromide (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (TBAB) (0.58 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (2.50 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (31.0 ml), and water (31.0 ml) were added and heated and stirred for 8 hours. After the reaction was completed, 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 obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: heptane / toluene = 3 / 1 (volume ratio)). The solvent containing the target compound was removed by vacuum distillation to obtain the compound represented by formula (1-5-244) (1.31 g).

[0715] 1 H-NMR (500 MHz, CDCl3) 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).

[0716] Refractive index (nD25) = 1.79; Abbe number (νd) = 11.5

[0717] <<Example>>

[0718] Synthesis example (8)

[0719] [Chemistry 138]

[0720]

[0721] First process

[0722] Compound (A-29) (manufactured by Merck, Inc.) (55.00 g), boron tribromide (BBr3) (manufactured by Fujifilm and Hikari Pure Chemical Industries, Inc.) (131.48 g), and dichloromethane (CH2Cl2) (manufactured by Fujifilm and Hikari Pure Chemical Industries, Inc.) (550.0 ml) were added and stirred overnight. After the reaction was complete, the mixture was poured into pure water and extracted with ethyl acetate. The organic layer was separated. The organic layer was concentrated under reduced pressure to obtain the compound represented by formula (A-30) (42.00 g).

[0723] Second process

[0724] Compound (A-30) (42.00 g), chloromethyl methyl ether (CH3OCH2Cl) (manufactured by Tokyo Chemical Industry Co., Ltd.) (36.32 g), sodium hydride (10.83 g), and dichloromethane (CH2Cl2) (manufactured by Fujifilm and Wako Pure Chemical Industries Co., Ltd.) (420.0 ml) were added and stirred overnight. After the reaction was complete, the mixture was poured into pure water and extracted with ethyl acetate to separate the organic layer. The organic layer was concentrated under reduced pressure to obtain the compound represented by formula (A-31) (35.23 g).

[0725] Third process

[0726] Compound (A-10) (50.25 g), compound (A-31) (35.23 g), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.), tetrabutylammonium bromide (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (TBAB) (10.93 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (46.88 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (250.0 ml), and water (250.0 ml) were added and heated and stirred for 5 hours. After the reaction was completed, 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 obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene / ethyl acetate = 4 / 1 (volume ratio)). The solvent containing the target compound was removed by vacuum distillation to obtain the compound represented by formula (A-32) (46.50 g).

[0727] Fourth process

[0728] Add compound (A-32) (46.50 g), compound (A-8) (manufactured by Tokyo Chemical Industry Co., Ltd.) (21.51 g), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl2). CH2Cl2 (manufactured by Tokyo Chemical Industry Co., Ltd.) (2.33 g), potassium acetate (KOAc) (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (24.93 g), and cyclopentyl methyl ether (manufactured by Fujifilm and Koimitsu Chemical Co., Ltd.) (450.0 ml) were heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and pure water and toluene were added. The organic layer was separated. The organic layer was concentrated under reduced pressure, and the obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene / ethyl acetate = 4 / 1 (volume ratio)). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-33) (20.00 g).

[0729] Fifth process

[0730] Compound (A-33) (20.00 g), compound (A-13) (17.63 g) synthesized using the synthetic method of Synthetic Example (3), bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.), (0.65 g) tetrabutylammonium bromide (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.), (TBAB) (3.02 g), potassium carbonate (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (12.94 g), toluene (manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.) (200.0 ml), and water (200.0 ml) were added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, 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 obtained crude substance was dissolved in toluene and passed through a silica gel short-path column (solvent: toluene / ethyl acetate = 4 / 1 (volume ratio)). The solvent containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (A-34) (10.50 g).

[0731] Sixth process

[0732] Compound (A-34) (10.50 g), trifluoroacetic acid (TFA) (manufactured by Fujifilm and Hikari Pure Chemical Industries, Ltd.) (23.82 g), and dichloromethane (CH2Cl2) (manufactured by Fujifilm and Hikari Pure Chemical Industries, Ltd.) (100.0 ml) were added and stirred overnight. After the reaction was complete, the mixture was poured into pure water and extracted with ethyl acetate to separate the organic layer. The organic layer was concentrated under reduced pressure to obtain the compound represented by formula (A-35) (8.60 g).

[0733] Seventh process

[0734] Compound (A-13) (8.60 g), compound (A-36) (2.18 g) (manufactured by Tokyo Chemical Industry Co., Ltd.), potassium carbonate (manufactured by Fujifilm and Kohden Chemical Industry Co., Ltd.) (5.47 g), and N,N-dimethylformamide (manufactured by Fujifilm and Kohden Chemical Industry Co., Ltd.) (31.0 ml) were added and heated and stirred for 6 hours. After the reaction was completed, 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 obtained crude substance 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 containing the target compound was distilled off under reduced pressure to obtain the compound represented by formula (1-4-360) (3.20 g).

[0735] 1H-NMR (500 MHz, CDCl3) δ=8.235 (s, 1H), 8.027 (d, 1H), 8.009 (s, 1H), 7.954 (d, 1H), 7.899 (d, 1H), 7.560 (d, 1H), 7.459 (d, 1H), 7.452 (s, 1H),7.385-7.129 (m, H), 7.042-6.969 (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).

[0736] Refractive index (nD25) = 1.81; Abbe number (νd) = 13.3

[0737] <<Comparative Examples>>

[0738] Comparison of physical properties

[0739] As a comparative compound, the following compound (S-1) was selected. This compound is described in Japanese Patent Application Publication No. 2008-520542 and Japanese Patent Application Publication No. 2019-34940, and is a compound with a similar use to the present invention.

[0740] [Chemistry 139]

[0741]

[0742] Refractive index (nD25) = 1.66.

[0743] <<Comparative Examples>>

[0744] Comparison of physical properties

[0745] As a comparative compound, the following compound (S-2) was selected. This compound is described in Japanese Patent Application Publication No. 2019-34940 and is a compound with a similar use to the present invention.

[0746] [Chemistry 140]

[0747]

[0748] Refractive index (nD25) = 1.75.

[0749] Table 3: Refractive indices (nD25) of 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) of the examples.

[0750] [Table 3]

[0751] Table 3

[0752]

[0753] The refractive indices (nD25) of the compounds obtained in Synthetic Examples (1) to (8) and the comparative compounds are summarized in Table 3. The refractive indices of the compounds obtained in Synthetic Examples (1) to (8) are all greater than those of the comparative compounds (S-1) and (S-2). Based on the above results, it is shown that 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) of this application are superior to the comparative compounds (S-1) and (S-2) in material systems requiring high refractive indices.

[0754] Industrial availability

[0755] The polycyclic aromatic compounds in the embodiments of the present invention have high refractive index and are suitable for optical fields such as holographic optics, image acquisition optics, projection optics, diffraction optics, electromagnetic energy absorption optics, or combiner optics. For example, they can be used in applications such as optical lenses, spatial light modulators, transmission control mirrors, reflective displays, composite materials, color sensors, multispectral filters, and image sensing, and are extremely useful.

Claims

1. A polycyclic aromatic compound, which is a monomer or a dimer of a structural unit represented by the following formula (1), and is a homodimer or a heterodimer in the case of being a dimer; [Chemical Formula 1] ###0001### In the formula (1), the A ring, the B ring, the C ring, and the D ring are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and adjacent two R's can be bonded to each other to form a ring; E m represents a divalent group formed by m E serially bonded, bonded to a ring-forming element of the B ring through one bonding linkage and to a ring-forming element of the C ring through another bonding linkage; E is each independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group; m is an integer of 5 ≧ m ≧ 1; at least one hydrogen in the structural unit represented by the formula (1) can be substituted with a cyano group, a halogen atom, or a deuterium atom; in the case where the polycyclic aromatic compound is a dimer of the structural unit, the A ring, the B ring, the C ring, or the D ring in one of the structural units is bonded to the A ring, the B ring, the C ring, or the D ring in the other structural unit via a single bond.

2. The polycyclic aromatic compound according to claim 1, wherein in the formula (1), the A ring, the B ring, the C ring, and the D ring 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, E is each independently a phenylene group, a naphthylene group, a phenanthrylene group, a pyrenylene group, a dibenzofuranylene group, or a dibenzothiophenylene group.

3. The polycyclic aromatic compound according to claim 1, which is represented by the following formula (1-1); [Chemical Formula 2] ###0002### In the formula (1-1), Z are each independently =N- or =C(-R Z )-, R Z are each independently a hydrogen atom or a substituent, and two R Z adjacent to each other can be bonded to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on both sides of F, any one of Z in each structure is a carbon atom having a bonding bond with F; R is each independently a hydrogen atom, an aryl group, a heteroaryl group, or an alkyl group, and adjacent carbon atoms can be bonded to each other when both of the R's are an aryl group or a heteroaryl group; F is a phenylene group.

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

5. The polycyclic aromatic compound according to claim 3, which is represented by any one of the following formulas; [Chemical Formula 3] ###0003### [Chemical Formula 4] 6. The polycyclic aromatic compound according to claim 1, which is represented by the following formula (1-2); 。 [Chemical Formula 5] ###0004### In the formula (1-2), R is each independently a hydrogen atom, an aryl group, a heteroaryl group, or an alkyl group, and adjacent carbon atoms can be bonded to each other when both of the R's are an aryl group or a heteroaryl group; Z are each independently =N- or =C(-R Z )-, R Z are each independently a hydrogen atom or a substituent, and two R Z adjacent to each other can bond to each other to form a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; in two structures on both sides of F, any one of Z in each structure is a carbon atom having a bonding bond with F; F is a phenylene group, a dibenzofuranylene group, or a dibenzothiophenylene group.

7. The polycyclic aromatic compound according to claim 6, which is represented by any one of the following formulas; [Chemical Formula 6] ###0005### 8. The polycyclic aromatic compound according to claim 1, which is represented by the following formula (1-3); 。 [Chemical Formula 7] ###0006### In the formula (1-3), R is each independently a hydrogen atom, an aryl group, a heteroaryl group, or an alkyl group, and adjacent carbon atoms can be bonded to each other when both of the R's are an aryl group or a heteroaryl group; Z are each independently =N- or =C(-R Z )-, R Z are each independently a hydrogen atom or a substituent, and two 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 both sides of F, any one of Z in each structure is a carbon atom having a bonding bond with F; F is a phenylene group, a naphthylene group, a dibenzofuranylene group, or a dibenzothiophenylene group. ​ 9. The polycyclic aromatic compound according to claim 8, represented by any one of the following formulae; [Chemical formula 8] 。 10. The polycyclic aromatic compound according to claim 1, represented by formula (1-4); [Chemical formula 9] In formula (1-4), Z are each independently =N- or =C(-R Z )-, R Z are each independently a hydrogen atom or a substituent, and two R Z adjacent to each other can bond 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 bonding bond with F, and the carbon atom in the other structure has a bonding bond with Hn; R is independently a hydrogen atom, an aryl group, a heteroaryl group, or an alkyl group, and when two R's are an aryl group or a heteroaryl group, the adjacent carbon atoms can be bonded to each other; F, G, and H are independently a phenylene group, a naphthylene group, a dibenzofuranyl group, or a dibenzothiophenyl group; F and G have mutually different aryl rings; H n represents a divalent group formed by n H atoms linked in series; n is an integer of 2 ≧ n ≧ 0.

11. The polycyclic aromatic compound according to claim 10, represented by any one of the following formulae; [Chemical formula 10] [Chemical formula 11] 。 12. The polycyclic aromatic compound according to claim 1, represented by formula (1-5); [Chemical formula 12] In formula (1-5), Z are each independently =N- or =C(-R Z )-, R Z are each independently a hydrogen atom or a substituent, and two 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 across both sides of -F-G-Hn-, any one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bonding bond with F, and the carbon atom in the other structure has a bonding bond with Hn; R is independently a hydrogen atom, an aryl group, a heteroaryl group, or an alkyl group, and when two R's are an aryl group or a heteroaryl group, the adjacent carbon atoms can be bonded to each other; F, G, and H are independently a phenylene group, a naphthylene group, a dibenzofuranyl group, or a dibenzothiophenyl group; F and G have mutually different aryl rings; n is an integer of 2 ≧ n ≧ 0.

13. The polycyclic aromatic compound according to claim 12, represented by any one of the following formulae; [Chemical formula 13] 。 14. The compound according to claim 1, represented by formula (1-6); [Chemical formula 14] In formula (1-6), Z are each independently =N- or =C(-R Z )-, R Z are each independently a hydrogen atom or a substituent, and two 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 across both sides of -F-G-Hn-, any one of Z in each structure is a carbon atom, and the carbon atom in one structure has a bonding bond with F, and the carbon atom in the other structure has a bonding bond with Hn; R is independently a hydrogen atom, an aryl group, a heteroaryl group, or an alkyl group, and when two R's are an aryl group or a heteroaryl group, the adjacent carbon atoms can be bonded to each other; F, G, and H are independently a phenylene group, a naphthylene group, a dibenzofuranyl group, or a dibenzothiophenyl group; F and G have mutually different aryl rings; n is an integer of 2 ≧ n ≧ 0.

15. The polycyclic aromatic compound according to claim 14, represented by any one of the following formulae; [Chemical formula 15] 。 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 device having the optical element according to claim 17.

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