Polycyclic aromatic compound, organic electroluminescent element, display device, lighting device, wavelength conversion material, organic photodiode, and solar cell material

Abstract

This invention provides a polycyclic aromatic compound, an organic electroluminescent element, a display device, a lighting device, a wavelength conversion material, an organic photodiode, and a solar cell material that can be effectively used as a material for organic EL elements and other organic devices. The polycyclic aromatic compound represented by formula (I) enables the manufacture of high-efficiency and long-life organic EL elements; rings A, B, D, E, and F are aryl or heteroaryl rings, at least one of which has a cyano group as a substituent, and Z... 0 Let C(-H) = , Y be B, X 1 ~X 4 For >N-R NX >O or >S, R NX For unsubstituted aryl, where X 1 and X 2 It is R NX The N-R of the basis represented by equation (Ar) NX , or X 1 and X 3 or X 2 and X 4 They are R NX N-R of mesitylene NX G represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group, etc.

Description

Technical Field

[0001] This invention relates to a polycyclic aromatic compound. Furthermore, this invention relates to organic devices such as organic electroluminescent elements, organic field-effective transistors, and organic thin-film solar cells, wavelength conversion materials, organic photodiodes and solar cell materials, as well as display devices and lighting devices using the aforementioned polycyclic aromatic compound. Background Technology

[0002] Previously, display devices using electroluminescent elements were extensively researched due to their ability to achieve power savings or thinner designs. Furthermore, organic electroluminescent elements incorporating organic materials have been actively studied due to their ease of lightweighting or scaling. In particular, the development of organic materials exhibiting light-emitting properties such as blue or green (one of the three primary colors of light), and the development of organic materials with charge transport capabilities including holes and electrons (possibly leading to their potential as semiconductors or superconductors), have been actively researched to date, encompassing both high-molecular-weight and low-molecular-weight compounds.

[0003] Organic electroluminescence (EL) devices have a structure comprising: a pair of electrodes including an anode and a cathode, and one or more layers of organic compounds disposed between the pair of electrodes. Among the layers containing organic compounds are light-emitting layers, or charge transport / injection layers for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] Patent Documents 1 and 2 disclose materials in which boron-containing polycyclic aromatic compounds are effectively used as organic electroluminescent elements. Reports indicate that organic electroluminescent elements containing these polycyclic aromatic compounds exhibit good external quantum efficiency.

[0005] [Existing Technical Documents]

[0006] [Patent Literature]

[0007] [Patent Document 1] International Publication No. 2015 / 102118

[0008] [Patent Document 2] Japanese Patent Application Publication No. 2023-152686 Summary of the Invention

[0009] [The problem the invention aims to solve]

[0010] As mentioned above, various materials have been developed for use in organic EL devices, but in order to increase the selection of materials for organic EL devices, it is desirable to develop a material containing compounds that are different from those used before.

[0011] The subject of this invention is to provide a novel compound that can be effectively used as a material for organic devices such as organic EL elements.

[0012] [Technical means to solve the problem]

[0013] The inventors conducted diligent research to solve the aforementioned problem, and as a compound having a boron-containing structure similar to the compounds described in Patent Documents 1 and 2, they discovered a compound capable of manufacturing highly efficient and long-life organic EL devices, thus completing the present invention. Specifically, the present invention provides a polycyclic aromatic compound as described below, and further provides materials for organic devices containing such polycyclic aromatic compounds.

[0014] <1> A polycyclic aromatic compound, represented by formula (I);

[0015] [Chemistry 1]

[0016]

[0017] In formula (I),

[0018] Rings A, B, D, and E are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, wherein at least one ring selected from the group consisting of rings A, B, C, D, and E is an aryl ring having at least a cyano group as a substituent or a heteroaryl ring having at least a cyano group as a substituent.

[0019] Z 0 -C(-R) Z0 = or -N=,

[0020] R Z0 Each can be a hydrogen or a substituent, independently.

[0021] Y can be independently defined as B, P, P=O, or P=S.

[0022] X 1 X 2 X 3 and X 4 Each independently is >NR NX ,>O,>S or>Se,R NX It can be hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

[0023] R NX It can be bonded to at least one of ring A or ring B, at least one of ring A or ring c, at least one of ring B or ring D, or at least one of ring c or ring E via a single bond or a linker.

[0024] Among them, X 1 X 2 X 3 and X 4 Satisfying at least one of the following (a) and (b):

[0025] (a)X 1 and X 2 R is independent of each other. NX NR of the basis represented by equation (Ar) NX ;

[0026] (b)X 1 and X 3 They are R NX NR is trimethylbenzyl NX , or X 2 and X 4 They are R NX NR is trimethylbenzyl NX ,

[0027] In formula (Ar),

[0028] Indicates the bond position on nitrogen.

[0029] The F ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and it contains at least a 6-membered ring with atoms bonded by G as ring constituent atoms.

[0030] G is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group.

[0031] At least one of the groups consisting of aryl rings and heteroaryl rings selected from formula (I) may be condensed from at least one cycloalkane, wherein the cycloalkane may be substituted by at least one substituent, and at least one -CH2- of the cycloalkane may be substituted by -O-.

[0032] In formula (I), at least one hydrogen may be substituted with deuterium, and at least one nitrogen may be substituted with nitrogen-15 ( 15 N) substitution, at least one sulfur can be replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) substitution, at least one oxygen can be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O) substitution, at least one carbon can be replaced by carbon-13 ( O) 13C) substitution, at least one boron can be replaced by boron-11 ( 11 B) Replacement.

[0033] <2> The polycyclic aromatic compounds according to <1> are represented by formula (II);

[0034] [Chemistry 2]

[0035]

[0036] In formula (II),

[0037] Z 0 With Z in equation (I) 0 They have the same meaning.

[0038] X 3 and X 4 With X in equation (I) 3 and X 4 They have the same meaning.

[0039] Ar is the basis represented by the formula (Ar).

[0040] Z and Q are independently -C(-R) Z = or -N=, R Z It is hydrogen or a substituent.

[0041] At least one Q is -C(-CN)=.

[0042] <3> The polycyclic aromatic compounds according to <2> are represented by formula (II-1-i) to (II-1-v), (II-2-i), (II-2-ii), (II-3-i), (II-3-ii), (II-4-i) or (II-5-i);

[0043] [Chemistry 3]

[0044]

[0045] In the formula,

[0046] Z 0 and Ar and Z in equation (II) 0 Ar and Ar have the same meaning.

[0047] Z is independently -C(-R) Z = or -N=, R Z It can be hydrogen or a substituent.

[0048] <4> According to the polycyclic aromatic compound described in <1>, wherein X 1 X 2 X3 and X 4 Satisfy (b),

[0049] X 1 X 2 X 3 and X 4 All are >NR NX .

[0050] <5> A polycyclic aromatic compound according to any one of <1> to <4>, wherein the F ring is a substituted or unsubstituted benzene ring, a dibenzofuran ring or a dibenzothiophene ring.

[0051] <6> The polycyclic aromatic compounds according to <1> are represented by any of the following formulas.

[0052] [Chemistry 4]

[0053]

[0054] [Chemistry 5]

[0055]

[0056] [Chemistry 6]

[0057]

[0058] [Chemistry 7]

[0059]

[0060] [Chemistry 8]

[0061]

[0062] <7> An organic electroluminescent element comprising: a pair of electrodes, including an anode and a cathode; and an organic layer disposed between the pair of electrodes, the organic layer containing a polycyclic aromatic compound according to any one of <1> to <6>.

[0063] <8> The organic electroluminescent element according to <7>, wherein the organic layer is a light-emitting layer.

[0064] <9> The organic electroluminescent element according to <8>, wherein the light-emitting layer comprises at least one selected from the group consisting of auxiliary dopants and phosphorescent materials.

[0065] <10> A display device or lighting device comprising an organic electroluminescent element according to any one of <7> to <9>.

[0066] <11> A wavelength conversion material comprising a polycyclic aromatic compound according to any one of <1> to <6>.

[0067] <12> An organic photodiode includes a pair of electrodes and an active layer disposed between the pair of electrodes, wherein the active layer comprises a polycyclic aromatic compound according to any one of <1> to <6>.

[0068] <13> The organic photodiode according to <12>, wherein the active layer comprises the polycyclic aromatic compound.

[0069] <14> A solar cell material containing a polycyclic aromatic compound according to any one of <1> to <6>.

[0070] [The effects of the invention]

[0071] According to the present invention, a novel polycyclic aromatic compound is provided that is effectively used as a material for organic devices such as organic electroluminescent elements. The polycyclic aromatic compound of the present invention can be used to manufacture organic devices such as organic electroluminescent elements. Attached Figure Description

[0072] Figure 1 This is a schematic cross-sectional view showing an example of an organic electroluminescent element.

[0073] Explanation of icon numbers

[0074] 100: Organic electroluminescent element

[0075] 101: Substrate

[0076] 102: Anode

[0077] 103: Hole Injection Layer

[0078] 104: Hole Transport Layer

[0079] 105: Emissive layer

[0080] 106: Electron Transport Layer

[0081] 107: Electron Injection Layer

[0082] 108: Cathode Detailed Implementation

[0083] 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”.

[0084] In this specification, when referring to "adjacent base", it means two bases that are bonded to two adjacent atoms (two atoms directly bonded by covalent bonds) in the structural formula.

[0085] In the chemical and structural formulas of this specification, “Me” represents methyl, “Et” represents ethyl, “nBu” represents normal butyl, “tBu” represents tertiary butyl, “iBu” represents isobutyl, “secBu” represents secondary butyl, “nPr” represents normal propyl, “iPr” represents isopropyl, “tAm” represents tertiary pentyl, “2EH” represents 2-ethylhexyl, “tOct” represents tertiary octyl, “Ph” represents phenyl, “Mes” represents 2,4,6-trimethylphenyl, “Ad” represents 1-adamantyl, “Tf” represents trifluoromethanesulfonyl, “TMS” represents trimethylsilyl, and “D” represents deuterium.

[0086] In this specification, organic electroluminescent elements are sometimes referred to as organic EL elements.

[0087] In this specification, the number of carbon atoms is sometimes used to represent chemical structures or substituents. However, when a substituent is substituted in a chemical structure or when a substituent is further substituted on a substituent, the number of carbon atoms refers to the individual carbon atom of the chemical structure or substituent, and not the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituents. For example, "substituent B with carbon atom number X substituted by substituent A with carbon atom number X" means that "substituent A with carbon atom number X" is substituted on "substituent B with carbon atom number Y". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B. Similarly, "substituent B with carbon atom number Y substituted by substituent A" means that "substituent A (without a specified number of carbon atoms) is substituted on "substituent B with carbon atom number Y". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B.

[0088] <Explanation of rings and substituents>

[0089] First, the details of the rings and substituents used in this specification are explained below.

[0090] 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.

[0091] Specific examples of "aryl rings" include: monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthalene rings and indene rings, tricyclic terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl), condensed tricyclic acenaphthene rings, fluorene rings, phenanthene rings, anthracene rings, condensed tetracyclic triphenylene rings, pyrene rings, benzo[a]tetraphenyl rings, and benzo[b]benzene rings, and pentane rings, etc. Furthermore, fluorene rings, benzo[a]fluorene rings, and indene rings also contain structures with fluorene rings, benzo[a]fluorene rings, cyclopentane rings, etc., linked by spiral bonds. Furthermore, the fluorene ring, benzo[a]fluorene ring, and indene ring also include rings in which two of the two hydrogens of the methylene group in their structure are replaced by alkyl groups such as methyl groups described later as first substituents, thus becoming rings such as dimethylfluorene ring, dimethylbenzo[a]fluorene ring, and dimethyl indene ring.

[0092] 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 one to five heteroatoms selected from oxygen, sulfur, nitrogen, boron, silicon, selenium, phosphorus, and tellurium as ring-forming atoms, in addition to carbon atoms.

[0093] 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, benzothiophene ring, dibenzothiophene ring, thiathracene ring, indole-carbazole ring, benzoindole-carbazole ring, dibenzoindole-carbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthonium ring, thioxanthonium ring, dibenzodioxin ring, dioxaborane-naphthoanthracene ring (5,9-dioxa-13b-borane-13bH-naphtho[3,2,1-de]anthracene) (e.g., rings), benzo[selenphene] rings, dibenzo[selenphene] rings, azacarbazole rings, azadibenzothiophene rings, azadibenzofuran rings, azadibenzoselenphene rings, azatriphenylene rings, imidazo[imidazo]imidazo] rings, indole[indole] rings, benzofuran[carbazole] rings, benzothiophene[carbazole] rings, indene[carbazole] rings, and selenophene[carbazole] rings, spiro[fluorene-9,9'-xanthon] rings, spirodi[siliconfluorene] rings, etc. Furthermore, in dihydroacridine rings, xanthon rings, and thioxanthon rings, it is also preferable that two of the two hydrogens of the methylene group in its structure are respectively replaced by alkyl groups such as methyl groups described later as first substituents to form dimethyldihydroacridine rings, dimethylxanthon rings, dimethylthioxanthon rings, etc. In addition, bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, which are bicyclic systems, and terpyridine rings, bispyridylphenyl rings, and pyridylbiphenyl rings, which are tricyclic systems, can also be listed as "heteroaryl rings". Furthermore, "heteroaryl rings" also include pyran rings.

[0094] 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."

[0095] In this specification, the substituent group Zα includes the substituents of the substituent group Z and the substituents represented by formula (A30) described later.

[0096] In this specification, the substituent group Z includes:

[0097] The aryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0098] Heteroaryl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0099] The diarylamino group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the two aryl groups in the diarylamino group may be bonded to each other via a linker group.

[0100] The diheteroarylamino group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the two heteroaryl groups in the diheteroarylamino group may be bonded to each other via a linker group.

[0101] The arylheteroarylamino group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the aryl and heteroaryl groups in the arylheteroarylamino group may be bonded to each other via a linker group.

[0102] The diarylboryl group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the two aryl groups in the diarylboryl group may be bonded by a single bond or a linker group.

[0103] Alkyl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen.

[0104] Cycloalkyl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0105] The alkoxy group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen.

[0106] The aryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0107] The arylthio group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0108] The alkenyl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0109] It can replace silyl, cyano, and halogen.

[0110] The aryl group in substituent group Z, which serves as a second substituent, may be further substituted with aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen. Similarly, the heteroaryl group, which serves as a second substituent, may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen.

[0111] In this specification, the term "substituent" does not specifically limit the type of substituent, and unless otherwise specified, it can be any group selected from the substituent group Z. For example, when "substituted or unsubstituted" is used, the group can be substituted by at least one group selected from the substituent group Z.

[0112] 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.

[0113] Specific "aryl" groups can be listed as monovalent groups formed by removing one hydrogen atom from the aforementioned "aryl ring". Examples include: monocyclic phenyl groups, bicyclic biphenyl groups (2-biphenyl, 3-biphenyl, or 4-biphenyl), condensed bicyclic naphthyl groups (1-naphthyl or 2-naphthyl), tricyclic terphenyl groups (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 condensed tricyclic acenaphthene-(1-, 3-, ...) groups. 4- or 5-)yl, fluorene-(1-, 2-, 3-, 4- or 9-)yl, phenaten-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4- or 9-)yl or anthracene-(1-, 2- or 9-)yl, are tetracyclic tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl or m-tetraphenyl), are condensed tetracyclic triphenyl-(1- or 2-)yl, pyrene-(1-, 2- or 4-)yl or benzotetraphenyl-(1-, 2- or 5-)yl, or are condensed pentacyclic perylene-(1-, 2- or 3-)yl or benzopentaphenyl-(1-, 2-, 5- or 6-)yl, etc. In addition, examples include monovalent bases of spirofluorene.

[0114] 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 groups described above), alkyl groups such as methyl (specifically, the groups described below), and cycloalkyl groups such as cyclohexyl or adamantyl (specifically, the groups described below).

[0115] As an example, one could list groups at the 9-position of the fluorene group, which is a second substituent, that are substituted with aryl groups such as phenyl, alkyl groups such as methyl, or cycloalkyl groups such as cyclohexyl or adamantyl.

[0116] "Aromaticyl" is, for example, an arylene with 6 to 30 carbon atoms, preferably an arylene with 6 to 20 carbon atoms, an arylene with 6 to 16 carbon atoms, an arylene with 6 to 12 carbon atoms, or an arylene with 6 to 10 carbon atoms.

[0117] Specific examples of "aryl" include divalent groups formed by removing one hydrogen atom from the "aryl" (monovalent) group.

[0118] "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 addition to carbon, the "heteroaryl" contains one or more, preferably one to five, heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms.

[0119] As specific examples of "heteroaryl groups," a monovalent group formed by removing one hydrogen atom from the aforementioned "heteroaryl ring" can be listed. Examples include: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isoindole, 1H-indazole, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phenanthrololinyl, phthalazinyl, naphthidyl, purine, pteridinyl, carbazole, acridineyl, phenoxthiayl, phenoxazinyl. Phenothiazinyl, 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, furazinyl, thiathanyl, indolocarbazoyl, benzoindolocarbazoyl, dibenzoindolocarbazoyl, imidazolinyl or oxazolinyl, etc. In addition, examples include: spiro[fluorene-9,9'-xanthon] monovalent group, spirodi[siliconfluorene] monovalent group, and benzo[selenyl] monovalent group.

[0120] 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 groups described above), alkyl groups such as methyl (specifically, the groups described later), and cycloalkyl groups such as cyclohexyl or adamantyl (specifically, the groups described later).

[0121] As an example, groups at the 9-position of the carbazolyl group, which is a second substituent, may be substituted with aryl groups such as phenyl, alkyl groups such as methyl, or cyclohexyl or adamantyl. Furthermore, groups in which nitrogen-containing heteroaryl groups such as pyridyl, pyrimidinyl, triazine, and carbazolyl are further substituted with phenyl or biphenyl groups are also included in heteroaryl groups that are second substituents.

[0122] "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, in addition to carbon atoms, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms in a heterocycle.

[0123] Specific examples of "hybrid aryl" include divalent groups formed by removing one hydrogen atom from the aforementioned "heteroaryl" (monovalent group).

[0124] "Diarylamino" is an amino group in which two aryl groups have been substituted. For details about the aryl groups, please refer to the description of "aryl".

[0125] "Diheteroarylamino" is an amino group in which two heteroaryl groups have been substituted. For details about the heteroaryl groups, please refer to the description of "heteroaryl".

[0126] "Arylheteroarylamino" refers to an amino group in which aryl and heteroaryl groups have been substituted. For details regarding the aryl and heteroaryl groups, please refer to the description of "aryl" and "heteroaryl".

[0127] In a diarylamino group where the first substituent is present, the two aryl groups can be bonded to each other via a linking group; in a diheteroarylamino group where the first substituent is present, the two heteroaryl groups can be bonded to each other via a linking group; and in an arylheteroarylamino group where the first substituent is present, the aryl and heteroaryl groups can be bonded to each other via a linking group. Here, the phrase "bonded via a linking group" is used as follows, for example, to indicate that the two phenyl groups of a diphenylamino group form a bond through a linking group. Furthermore, this description also applies to diheteroarylamino groups and arylheteroarylamino groups formed from aryl or heteroaryl groups.

[0128] [Chemistry 9]

[0129]

[0130] ( (Indicates the location of the bond)

[0131] As linking bases, specifically, examples include: >O, >NR. X >C(-R) X )2、-C(-R X )=C(-RX )-、>Si(-R X )2,>S,>CO,>CS,>SO,>SO2,>SeO,>SeO2,>PO,>B(-R X ) and >Se. R X Each can be independently alkyl, cycloalkyl, aryl, or heteroaryl, and these can be substituted with alkyl, cycloalkyl, aryl, or heteroaryl groups. Additionally, >C(-R X )2、-C(-R X )=C(-R X )- and >Si(-R X )2 Each of the two R X It can be achieved via a single bond or a linker X. Y They bond together to form a loop. As X Y Examples include >O and >NR. Y >C(-R) Y )2、>Si(-R Y )2, >S, >CO, >CS, >SO, >SO2 and >Se, R Y Each of these can be independently alkyl, cycloalkyl, aryl, or heteroaryl, and these can be substituted with alkyl, cycloalkyl, aryl, or heteroaryl groups. Specifically, in X... Y >C(-R) Y )2 and >Si(-R Y In the case of )2, two R Y It will not bond and further form a ring. Furthermore, as a linking group, alkenyl groups can also be cited. Any hydrogen atom of the alkenyl group can be independently bonded via R... 2X Replace, R 2X They are independently alkyl, cycloalkyl, substituted silyl, aryl, and heteroaryl groups, which can be substituted by alkyl, cycloalkyl, substituted silyl, or aryl groups. -C(-R X )=C(-R X The two R's in )- X They can bond with each other and together with these bonded C=C rings to form aryl rings (such as benzene rings) or heteroaryl rings. That is, -C(-R X )=C(-R X - It can be an arylene (1,2-phenylene, etc.) or a heteroarylene.

[0132] Furthermore, in this specification, if the terms are only "diarylamino", "diheteroarylamino", or "arylheteroarylamino", unless otherwise specified, it is assumed that the following statements are added respectively: "the two aryl groups of the diarylamino can be bonded to each other via a linking group", "the two heteroaryl groups of the diheteroarylamino can be bonded to each other via a linking group", and "the aryl and heteroaryl groups of the arylheteroarylamino can be bonded to each other via a linking group".

[0133] "Diarylboryl" is a boron group in which two aryl groups have been substituted. For details about the aryl groups, please refer to the description of "aryl". In addition, the two aryl groups can be bonded via single bonds or linking groups (e.g., -CH=CH-, -CR=CR-, -C≡C-, >NR, >O, >S, >CO, >C=S, >S=O, >S(=O)2, >Se(=O), >Se(=O)2, >P(=O), >B(-R), >C(-R)2, >Si(-R)2, or >Se). Here, the R in -CR=CR-, >NR, >B(-R), >C(-R)2, and >Si(-R)2 are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy groups, wherein at least one hydrogen atom of these groups may be further substituted by aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Additionally, two adjacent R groups may bond to each other to form a ring, thereby forming a cycloalkylene, arylene, or heteroarylene. For details regarding the substituents listed herein, refer to the descriptions of "aryl," "arylene," "heteroaryl," "heteroaryl," and "diarylamino," as well as the descriptions of "alkyl," "alkenyl," "alkynyl," "cycloalkyl," "cycloalkylene," "alkoxy," and "aryloxy" as described later. Furthermore, in this specification, when it is only described as "diarylboryl", unless otherwise specified, it is assumed that "the two aryl groups of the diarylboryl group can be bonded to each other via single bonds or linking groups".

[0134] "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.

[0135] 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.

[0136] "alkylene" is a divalent group obtained by removing any hydrogen from "alkyl", such as methylene, ethylene, and propylene.

[0137] 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).

[0138] "Alkenyl" is a divalent group obtained by removing any hydrogen from "alkenyl", such as vinylene.

[0139] 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).

[0140] "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.

[0141] 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.

[0142] "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.

[0143] Specific examples of "cycloalkylene" include structures derived from the "cycloalkyl" (monovalent group) by removing one hydrogen atom to make it divalent.

[0144] "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.

[0145] "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 group."

[0146] "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".

[0147] "Substituted silyl" is, for example, a silyl substituted with at least one of aryl, alkyl, and cycloalkyl groups, preferably a triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0148] "Triarylsilyl" refers to a silyl group substituted with three aryl groups. For details regarding the aryl groups, please refer to the description of "aryl".

[0149] Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmonaphthylsilyl, monophenyldinaphthylsilyl, or triaphthylsilyl.

[0150] "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".

[0151] 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.

[0152] "Tricycloalkylsilyl" refers to a silyl group substituted with three cycloalkyl groups. For details regarding the cycloalkyl group, please refer to the description of "cycloalkyl".

[0153] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl or tricyclohexylsilyl.

[0154] "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".

[0155] "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".

[0156] The "halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and even more preferably fluorine.

[0157] When cyano or halogen is 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.

[0158] The substituent represented by formula (A30) has the following structure.

[0159] [Chemistry 10]

[0160]

[0161] In formula (A30),

[0162] Ak is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted cycloalkenyl group, wherein at least one of the alkyl, cycloalkyl, and cycloalkenyl groups may be substituted with -O- or -S-.

[0163] R Ak R is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. Ak It can be bonded to Ak via a linker base or a single bond. This indicates the location of the bond.

[0164] In formula (A30), by using Ak as the substituent without conjugating it with the non-covalent electron pairs on N, the non-covalent electron pairs can be conjugated with the π electrons of the bonding target, resulting in a greater wavelength variation compared to the case where aryl groups or the like are present at the same position. Furthermore, the same applies to the effect on the multiple resonance effect, leading to a greater improvement in thermally activated delayed fluorescence (TADF).

[0165] R Ak Preferably, it is 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 or cycloalkyl group, more preferably an aryl group that can be substituted with an alkyl group, a heteroaryl group that can be substituted with an alkyl group, an alkyl or cycloalkyl group, and even more preferably an aryl group that can be substituted with an alkyl group, and particularly preferably a phenyl group that can be substituted with a methyl group.

[0166] In formula (A30), Ak is preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and is more preferably an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.

[0167] R Ak It can be the same as or different from Ak, but it is preferred to be different.

[0168] R Ak It can be bonded to Ak via a linker group or a single bond. Examples of linker groups in this case include: >O, >S, or >Si(-R)2, etc. In >Si(-R)2, R is hydrogen, an aryl group with 6 to 12 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms. As R... AkExamples of structures that are bonded to Ak by linking bases or single bonds include the following structures.

[0169] [Chemistry 11]

[0170]

[0171] In the aforementioned formulas, This indicates the location of the bond.

[0172] <The case where two bases bonded to the same atom are bonded to each other>

[0173] In this specification, when referring to two groups bonded to the same atom, 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 (which are also collectively referred to as linking groups). Examples of linking groups include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -Se(=O)-, -Se(=O)2-, -P(=O)-, -B(-R)-, -Si(-R)2-, or -Se-. For example, the following structures can be listed. Furthermore, the R in -CHR-CHR-, -CR2-CR2-, -CR=CR-, -N(-R)-, -C(-R)2-, -B(-R)-, and -Si(-R)2- are each independently hydrogen, an aryl group substituted with an alkyl or cycloalkyl group, a heteroaryl group substituted with an alkyl or cycloalkyl group, an alkyl group substituted with a cycloalkyl group, an alkenyl group substituted with an alkyl or cycloalkyl group, an alkynyl group substituted with an alkyl or cycloalkyl group, or a cycloalkyl group substituted with an alkyl or cycloalkyl group. Additionally, two adjacent R groups can bond to each other to form a ring, and can form a cycloalkylene, arylene, or heteroarylene.

[0174] [Chemistry 12]

[0175]

[0176] As a bonding base, it is preferred to use a single bond, or as a linking base -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-. More preferably, it is preferred to use a single bond, or as a linking base -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2-. Even more preferably, it is preferred to use a single bond, or as a linking base -CR=CR-, -N(-R)-, -O-, and -S-. Most preferably, it is preferred to use a single bond.

[0177] Regarding the position where the two Rs are bonded by the bonding group, there is no particular limitation if the position is a bondable position. 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 the adjacent (2 position) positions based on the bonding position (1 position) of the "C" or "Si" in the phenyl group (refer to the above structural formula).

[0178] <Stereoisomers, etc.>

[0179] The polycyclic aromatic compounds of the present invention may exist as enantiomers or diastereomers depending on the type of substituents, but regardless of the described structural formula, any stereoisomer in any pure form, any mixture of stereoisomers, racemic mixtures, etc. are included within the scope of the present invention.

[0180] 1. Polycyclic aromatic compounds

[0181] <Explanation of the overall structure of the compound>

[0182] Polycyclic aromatic compounds formed by linking aromatic rings with heteroelements such as boron, nitrogen, oxygen, and sulfur have been found to possess large highest occupied molecular orbital (HOMO) - lowest unoccupied molecular orbital (LUMO) gaps (band gap Eg in thin films). This is because the six-membered rings containing heteroelements have low aromaticity, suppressing the reduction of the HOMO-LUMO gap associated with the expansion of the conjugated system. Furthermore, it has been discovered that the HOMO-LUMO gap can be arbitrarily altered depending on the type of heteroelement and the linking method. This is believed to be because the energies of the HOMO and LUMO can be arbitrarily varied based on the spatial expansion and energy of the empty orbitals or lone pairs of the heteroelements.

[0183] These polycyclic aromatic compounds, due to the electronic perturbation of heteroelements, have excited-state single-occupied molecular orbitals (SOMO)1 and SOMO2 locally present on each atom. This results in a narrow half-width at half-maximum (WWHM) of the fluorescence emission peak, allowing for high-purity luminescence when used as a dopant in organic EL elements. For the same reason, ΔE... S1T1 The smaller size exhibits thermally active delayed fluorescence, which can achieve high efficiency when used as an emission dopant in organic EL elements.

[0184] Furthermore, by introducing substituents, the energies of HOMO and LUMO can be arbitrarily varied, thus allowing for optimization of ionization potential or electron affinity based on the surrounding materials.

[0185] The polycyclic aromatic compound of the present invention is equivalent to the polycyclic aromatic compound described above, which is formed by linking aromatic rings with heteroelements such as boron, nitrogen, oxygen, and sulfur, and is represented by formula (I). The inventors have discovered that using the polycyclic aromatic compound represented by formula (I), high-efficiency and long-life organic EL devices can be manufactured.

[0186] [Chemistry 13]

[0187]

[0188] In formula (I), at least one of the group consisting of rings A, B, C, D, and E is selected as an aryl ring having at least a cyano group as a substituent or a heteroaryl ring having at least a cyano group as a substituent, and X is a specified group. 1 X 2 X 3 and X 4 Satisfy at least one of (a) or (b) below.

[0189] (a)X 1 and X 2 R is independent of each other. NX NR of the basis represented by equation (Ar) NX ;

[0190] (b)X 1 and X 3 They are R NX NR is trimethylbenzyl NX , or X 2 and X 4 They are R NX NR is trimethylbenzyl NX .

[0191] The details of the notation in equation (I) will be described later.

[0192] <Explanation of ring structures in compounds>

[0193] In formula (I), rings A, B, D and E are independently substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings.

[0194] In equation (I), "A", "B", "D", and "E" within the circles are symbols representing the ring structures represented by each circle. The structure represented by equation (I) is formed by linking at least five aromatic rings (A, B, C, D, and E rings) using heteroelements such as boron, oxygen, nitrogen, and sulfur to form a ring structure. The resulting ring structure is a condensed ring structure consisting of at least nine rings.

[0195] Rings A and D each have bonds bonded to three consecutive atoms (preferably carbon) on the aryl or heteroaryl ring in their structure, thus forming a trivalent group. Through these three bonds, ring A and X... 1 X 2 and Y-bonds, D-rings and X-rings 3 X 4 and Y-bonds. When rings A and D further bond with R... NX When bonded, it can also be a tetravalent or pentavalent group. The rings in rings A and D, where the atoms having the three bonds are designated as ring constituent atoms, are preferably 5-membered or 6-membered rings, more preferably 6-membered rings. These rings can then condense with other rings. Examples of 6-membered rings include: benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, etc. Examples of 6-membered rings condensing with other rings include: naphthyl rings, quinoline rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, etc. Examples of 5-membered rings include: furan rings, thiophene rings, pyrrole rings, thiazole rings, etc. Examples of 5-membered rings condensing with other rings include: indene rings, etc.

[0196] The aryl or heteroaryl rings in the A and D rings are preferably benzene rings.

[0197] In formula (I), both rings B and E form divalent groups on two adjacent atoms (preferably carbon atoms) of the aryl or heteroaryl ring in its structure, bound together by bonds. Ring B is connected to X through these two bonds. 1 And the Y-bond, the E-ring is connected to the X-ring through the two bonding bonds. 3 and Y-bonds. When the B-ring and E-ring further bond with R... NX When bonded, it can also become a trivalent group. In each ring of the B and E rings, the ring having the two bonds is preferably a 5-membered or 6-membered ring, more preferably a 6-membered ring. The ring can then condense with other rings. Examples of 6-membered rings include: benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, etc. Examples of 6-membered rings condensing with other rings include: naphthyl rings, quinoline rings, benzofuran rings, benzothiophene rings, indole rings, benzoselenene rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, dibenzoselenene rings, etc. Examples of 5-membered rings include: furan rings, thiophene rings, pyrrole rings, thiazole rings, selenophene rings, etc. Examples of 5-membered rings condensing with other rings include: benzofuran rings, benzothiophene rings, indole rings, indene rings, benzoselenene rings, etc.

[0198] The aryl rings or heteroaryl rings in the B ring and E ring are preferably benzene rings, benzofuran rings, benzothiophene rings or benzoselenene rings, more preferably benzene rings, benzofuran rings or benzothiophene rings, and even more preferably benzene rings.

[0199] In the substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings of the A, B, D, and E rings of the compound represented by formula (I), at least one substituent selected from the substituent group Zα can be listed as a substituent when referring to "substituted or unsubstituted". Alternatively, the substituent may be a substituted or unsubstituted diarylphosphinyl group such as diphenylphosphinyl, or a substituted or unsubstituted diaryloxyphosphinyl group such as diphenyloxyphosphinyl. When multiple substituents are present, the multiple substituents may be the same or different from each other. Preferably, the substituents are substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, or halogens; more preferably, tert-butyl, diphenylamino, substituted or unsubstituted carbazole, or halogens. Other preferred substituents include those represented by formula (Ar). See also the description in <Preferred Substituents> below.

[0200] Z in the c-ring of equation (I) 0 =C(-R) Z0 )- or =N-, R Z0 It can be hydrogen or a substituent. R Z0 It can also be cyano. As a substituent, it is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, or a halogen, more preferably a tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted 2-biphenyl group, a substituted or unsubstituted 2'-m-terphenyl group, a diphenylamino group, a substituted or unsubstituted carbazolyl group, or a halogen, and even more preferably a substituted or unsubstituted 2-biphenyl group or a substituted or unsubstituted 2'-m-terphenyl group.

[0201] Z 0 The preferred value is =C(-H)-.

[0202] The compound represented by formula (I) contains at least one cyano group as a substituent or R group in the substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings in rings A, B, D, and E, when referring to "substituted or unsubstituted". Z0 The compound represented by formula (I) can significantly perturb the energy of HOMO or LUMO by having electron-withdrawing cyano groups as substituents on the polycyclic aromatic skeleton. When used as a dopant in organic EL elements, it can provide high-purity luminescence.

[0203] The compound represented by formula (I) preferably contains one to four cyano groups, more preferably one to two cyano groups. Regarding the number of cyano groups, an appropriate number can be selected from the viewpoint of energy or emission spectrum and synthesis; the more cyano groups, the deeper the HOMO of the compound represented by formula (I). Regarding the preferred position of the cyano groups, further reference can be made to the positions of the cyano groups shown in formulas (II-1-i) to (II-1-v), (II-2-i), (II-2-ii), (II-3-i), (II-3-ii), (II-4-i), or (II-5-i).

[0204] <X 1 X 2 X 3 and X 4 Explanation >

[0205] X 1 X 2 X 3 and X 4 Each independently is >NR NX ,>O,>S or>Se. R NX It is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. X 1 X 2 X 3 and X 4 R in NX It can be connected to X, which contains itself, through either a single bond or a linker base. 1 X 2 X 3 or X 4 Any one or two loop bonds that are bonded.

[0206] The compound represented by formula (I) satisfies at least one of the following (a) and (b).

[0207] (a)X 1 and X 2 R is independent of each other. NX NR of the basis represented by equation (Ar) NX ;

[0208] (b)X 1 and X 3 They are R NX NR is trimethylbenzyl NX , or X 2 and X 4 They are R NX NR is trimethylbenzyl NX .

[0209] X 1 X 2 X 3 and X 4 It may satisfy only (a), or only (b), or both (a) and (b).

[0210] Tris(methyl)methyl is equivalent to the group represented by formula (Ar). That is, X satisfies at least one of (a) and (b). 1 X 2 X 3 and X 4 At least two of them are R NX For the basis represented by equation (Ar) > NR NX .

[0211] R other than the basis represented by equation (Ar) NX Preferably, it is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group (wherein the group represented by formula (Ar) is excluded), more preferably a substituted or unsubstituted phenyl group (wherein the group represented by formula (Ar) is excluded), and even more preferably an unsubstituted phenyl group.

[0212] <By X 1 X 2 X 3 and X 4 Explanation of the changes in ring structure caused by the bonding with the ring >

[0213] X 1 X 2 X 3 and X 4 R in NX It can be connected to X, which contains itself, through a single bond or a linker base. 1 X 2 X 3 or X 4 Any one or two loop bonds that are bonded.

[0214] As R NXLinking groups that form ring bonds can be listed as: -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -Se(=O)-, -Se(=O)2-, -P(=O)-, -B(-R)-, -Si(-R)2- or -Se-, etc. Among these, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S- and -C(-R)2- are preferred, -CH=CH-, -CR=CR-, -N(-R)-, -O- and -S- are more preferred, and -CR=CR-, -N(-R)-, -O- and -S- are even more preferred. The R in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-N(-R)-", "-C(-R)2-", "-B(-R)-", and "-Si(-R)2-" are, independently, hydrogen, an aryl group substituted with alkyl or cycloalkyl, a heteroaryl group substituted with alkyl or cycloalkyl, an alkyl group substituted with alkyl or cycloalkyl, an alkenyl group substituted with alkyl or cycloalkyl, an alkynyl group substituted with alkyl or cycloalkyl, or a cycloalkyl group substituted with alkyl or cycloalkyl. Furthermore, two Rs bonded to the same atom can bond together to form a ring. Moreover, two adjacent Rs can bond together to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring. These rings can also be substituted with alkyl or cycloalkyl.

[0215] As >NR NX R in NX A condensation ring is formed by bonding with a benzene ring that is an aryl ring in rings A, B, C, D, or E. Examples include: a carbazole ring (where the R group of the phenyl group is the aryl ring). NX (via single bond bonding), phenoxazine ring (R of phenyl) NX (via -O- bonds), phenothiazine ring (where R is a phenyl group) NX (via -S-bonding) or acridinone ring (where R is a phenyl group) NX Through -C(=O)- bonds).

[0216] Alternatively, it can be done via R NX The following partial structure (A10) is formed by connecting with rings in ring A, ring B, ring c, ring D, or ring E.

[0217] [Chemistry 14]

[0218]

[0219] In formula (A10), R A1 ~R A4R is independently hydrogen, a substituted alkyl group, or a substituted cycloalkyl group. A1 ~R A4 Any two to four can be bonded to each other through linking bases or single bonds, in two The position of >NR NX (X) 1 X 2 X 3 and X 4 One of the two loops bonded by either of them, in The position is linked to another loop bond. That is, N in equation (A10) is greater than NR. NX N. In two The atoms on the ring bonded at the position need only be adjacent atoms (preferably carbon atoms). The partial structure represented by formula (A10) contains NC bonds with weak bond dissociation energy (BDE), but due to the presence of another bond forming the ring, the NC bond breaking also promotes a reverse reaction (rebonding reaction), thus becoming a more stable structure. Therefore, in organic EL elements manufactured using polycyclic aromatic compounds with this structure, a longer device lifetime can be expected. When the polycyclic aromatic compound contains the structure represented by formula (A10), its quantity only needs to be one or two (preferably one).

[0220] In formula (A10), R A1 ~R A4 Any two to four can be linked together through linking bases or single bonds.

[0221] R A1 ~R A4 Preferably any two (R) A1 and R A4 R A1 and R A4 and R A2 and R A3 R A1 and R A2 R A3 and R A4 R A1 and R A2 and R A3 and R A4 They are bonded to each other through linking bases or single bonds, more preferably R. A1 and R A4They are bonded together by linking groups or single bonds. Alkyl groups can be listed as divalent groups formed by mutual bonding. At least one hydrogen atom in the alkyl group may be substituted with an alkyl or cycloalkyl group, and at least one (preferably one) -CH2- in the alkyl group may be substituted with -O- and -S-. The divalent groups formed by mutual bonding are preferably straight-chain alkyl groups having 2 to 5 carbon atoms, more preferably straight-chain alkyl groups having 3 or 4 carbon atoms, and even more preferably straight-chain alkyl groups having 4 carbon atoms (-(CH2)4-). Straight-chain alkyl groups having 4 carbon atoms (-(CH2)4-) are particularly preferred to be unsubstituted.

[0222] The remaining R that did not participate in the connections made using the link base A1 ~R A4 Preferably, each is independently hydrogen or a substituted alkyl group, more preferably a substituted alkyl group having 1 to 6 carbon atoms, and even more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, and most preferably all of them are methyl.

[0223] That is, as part of the structure represented by formula (A10), the structure represented by formula (A11) is preferred.

[0224] [Chemistry 15]

[0225]

[0226] In formula (A11), Me is a methyl group, and in two... The position of >NR NX One of the two loops that are bonded, in It is located at another loop bond.

[0227] <The basis represented by formula (Ar)>

[0228] The polycyclic aromatic compound represented by formula (I) contains at least one of the following groups represented by formula (Ar) as X. 1 X 2 X 3 or X 4 That is, >NR NX R NX .

[0229] [Chemistry 16]

[0230]

[0231] In formula (Ar),

[0232] Indicates the bond position on nitrogen.

[0233] The F ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0234] G is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group.

[0235] The inventors discovered that by having a cyano group as a substituent for an aryl or heteroaryl ring in ring A, ring B, ring C, ring D, or ring E, and having a group represented by formula (Ar) as R NX The polycyclic aromatic compounds of the present invention can be used to manufacture organic EL elements that provide high-efficiency and long-life emission with high color purity, particularly TADF-assisted fluorescence (TAF) elements or phosphor-sensitized fluorescence (PSF) elements.

[0236] In formula (Ar), the "F" inside the circle is a symbol representing the ring structure represented by the circle. The F ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and at least contains a 6-membered ring with an atom bonded by G as a ring-forming atom. The F ring forms a divalent group with a bonded bond between two adjacent atoms (preferably carbon) on the aryl or heteroaryl ring in its structure, and is bonded to G and the remaining part of the structure represented by formula (I) through two bonds. That is, the ring-forming atom located at the bonding position of the group represented by formula (Ar) (the ring-forming atom bonded to nitrogen) is adjacent to the ring-forming atom bonded by G.

[0237] In the F ring, the ring containing the atoms bonded by G is a 6-membered ring, which facilitates the manufacture of compounds and also ensures the stability of the device during operation. The F ring is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted indole ring. More preferably, it is a substituted or unsubstituted benzene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, or a substituted or unsubstituted carbazole ring. It is even more preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted dibenzothiophene ring, or a substituted or unsubstituted dibenzofuran ring. It is especially preferred to be a substituted or unsubstituted benzene ring.

[0238] In the substituted or unsubstituted aryl ring or the substituted or unsubstituted heteroaryl ring in the F ring, the substituent, when referring to "substituted or unsubstituted", is preferably at least one substituent selected from the substituent group Zα.

[0239] In formula (Ar), G is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. To increase the steric hindrance caused by the group represented by formula (Ar), G is preferably a group with a size of alkyl or more having three carbon atoms; specifically, it is preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted aryl group, and even more preferably an alkyl-substituted phenyl group. From the viewpoint of ease of synthesis, G is preferably an unsubstituted phenyl group. When G is an unsubstituted alkyl group having one to two carbon atoms, the F ring is preferably a substituted aryl ring or a substituted heteroaryl ring.

[0240] As a preferred example of the basis represented by formula (Ar), the basis represented by formula (Ar-a) can be listed.

[0241] [Chemistry 17]

[0242]

[0243] In equation (Ar-a), G has the same meaning as G in equation (Ar). 1 -C(-R) Z1 = or -N=, Z 2 -C(-R) Z2 = or -N=, Z 3 -C(-R) Z3 = or -N=, Z 4 -C(-R) Z4 = or -N=. Z 1 Preferably -C(-R) Z1 =, Z 2 Preferably -C(-R) Z2 =, Z 3 Preferably -C(-R) Z3 =, Z 4 Preferably -C(-R) Z4 = . R Z1 R Z2 R Z3 R Z4 Each of the following is independently hydrogen and any substituent selected from the substituent group Zα.

[0244] In formula (Ar-a), R Z1 Preferably, it is hydrogen, unsubstituted alkyl, unsubstituted cycloalkyl, or substituted or unsubstituted aryl, more preferably hydrogen, unsubstituted alkyl, or alkyl-substituted phenyl. R Z2 and R Z4 Preferably, all are hydrogen. R Z3 Preferably, it is hydrogen, unsubstituted alkyl, unsubstituted cycloalkyl, or substituted or unsubstituted aryl, more preferably hydrogen or unsubstituted alkyl.

[0245] When G is an unsubstituted alkyl group with 1 to 2 carbon atoms, Z 1 -C(-R) Z1 =, Z 2 -C(-R) Z2 =, Z 3 -C(-R) Z3 =, Z 4 -C(-R) Z4 =, and R Z1 and R Z3 Each is independently an unsubstituted alkyl group having 1 to 2 carbon atoms, R Z2 and R Z4 Preferably, all of them are hydrogen. As a preferred example of a group represented by formula (Ar) where G is an unsubstituted alkyl group having 1 to 2 carbon atoms, mesitylene is an example.

[0246] The following shows an example of a basis represented by equation (Ar).

[0247] [Chemistry 18]

[0248]

[0249] [Chemistry 19]

[0250]

[0251] In this context, the basis is preferably represented by any one of formulas (Ar-1) to (Ar-16), more preferably by any one of formulas (Ar-1) to (Ar-12), further preferably by any one of formulas (Ar-1) to (Ar-8), (Ar-10) to (Ar-12), and particularly preferably by any one of formulas (Ar-1), (Ar-2), and (Ar-10). Furthermore, when X 1 X 2 X 3 and X 4 When condition (b) is satisfied, at least two (X) in the basis represented by equation (Ar) 1 and X 3 or X 2 and X4 ) is the base (trimethylbenzene) represented by formula (Ar-16).

[0252] The number of groups represented by formula (Ar) in the polycyclic aromatic compounds of the present invention is not particularly limited, but is preferably 2 to 4. More preferably, it is represented by X. 1 X 2 X 3 and X 4 And includes >NR NX All R NX The group represented by formula (Ar) is used in polycyclic aromatic compounds. When multiple groups represented by formula (Ar) exist, they may be the same or different from each other, but from the viewpoint of ease of synthesis, they are preferred to be the same.

[0253] <Structures that satisfy (a)>

[0254] As a preferred example of the structure that satisfies (a) in the structure represented by equation (I), the structure represented by any one of equations (1) to (7) can be listed below.

[0255] [Chemistry 20]

[0256]

[0257] In equations (1) to (7), R NX Preferably, it is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, more preferably a group represented by formula (Ar).

[0258] Of the compounds represented by any of formulas (1) to (7), from the viewpoint of high TADF properties, the compounds represented by any of formulas (1), (3), (4) and (5) are preferred; from the viewpoint of short emission wavelength, the compounds represented by any of formulas (2), (3), (4) and (6) are preferred; from the viewpoint of narrow half-width, the compounds represented by any of formulas (1), (6) and (7) are preferred; from the viewpoint of balance of the properties, the compounds represented by any of formulas (1) to (5) are preferred, more preferably the compounds represented by any of formulas (1), (2), (3) and (4), and even more preferably the compounds represented by any of formulas (1), (3) and (4).

[0259] From another perspective, as a preferred example of a structure that satisfies (a), polycyclic aromatic compounds represented by formula (II) can be listed.

[0260] [Chemistry 21]

[0261]

[0262] In equation (II), Z 0 X 3 and X 4 With Z in equation (I) 0 X 3 and X 4 They have the same meaning and the same preferred range. Ar is the basis represented by equation (Ar), and Z and Q are independently -C(-R). Z = or -N=, R Z It is hydrogen or a substituent, and at least one Q is -C(-CN)=.

[0263] The inventors have discovered that by using a polycyclic aromatic compound of formula (II) with Ar as the base represented by (Ar) and at least one Q as -C(-CN)= as a dopant for an organic EL element, particularly by using it as an emission dopant for a TAF element or a PSF element, a long-life organic EL element that provides high efficiency and blue light emission can be manufactured.

[0264] In formula (II), when either Z or Q is -N, its quantity in a ring (6-element single ring) is preferably 1 to 2, preferably 1. In formula (II), the quantity of -N is preferably 1 to 2, preferably 1. Z and Q are preferably both -C(-R). Z = ). As Z, -C(-R) Z R in )= Z The substituent is preferably other than hydrogen or CN (cyano), preferably hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted diarylamino, more preferably methyl, tert-butyl, or a phenyl that can be substituted with methyl or tert-butyl, more preferably hydrogen. The substituent may also be a group represented by formula (Ar). Q is preferably -C(-H)=, which is not -C(-CN)=.

[0265] In equation (II), as shown in any of the following equations (II-1) to (II-5), X 3 and X 4 Preferably >NR NX >O or >S.

[0266] [Chemistry 22]

[0267]

[0268] Regarding the preferred positions of the cyano groups in each of formulas (II-1) to (II-5), they are represented by formulas (II-1-i) to (II-1-i) in formula (II-1), by formulas (II-2-i) and (II-2-ii) in formula (II-2), by formulas (II-3-i) and (II-3-ii) in formula (II-3), by formula (II-4-i) in formula (II-4), and by formula (II-5-i) in formula (II-5).

[0269] [Chemistry 23]

[0270]

[0271] In the aforementioned formulas, Z is -C(-R) Z = or -N=, preferably -C(-R) Z = ). In the above formulas, R Z The substituent is hydrogen or a substituent, preferably a substituent other than hydrogen or CN (cyano), more preferably hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted diarylamino, and even more preferably hydrogen, methyl, tert-butyl, phenyl that can be substituted with methyl or tert-butyl, 2-biphenyl that can be substituted with methyl or tert-butyl, 2'-m-terphenyl that can be substituted with methyl or tert-butyl, diphenylamino that can be substituted with methyl, tert-butyl, or phenyl, or carbazole that can be substituted with methyl, tert-butyl, or phenyl, especially preferably hydrogen, tert-butyl, phenyl, 2-biphenyl, 2'-m-terphenyl, diphenylamino, or carbazole, and particularly preferably hydrogen.

[0272] <Structures that satisfy (b)>

[0273] The inventors have discovered that by using a polycyclic aromatic compound represented by formula (I) satisfying (b) as a dopant for an organic EL element, particularly by using it as an emission dopant for a TAF element or a PSF element, an organic EL element that provides high-efficiency blue light emission can be manufactured.

[0274] As a preferred example of the structure that satisfies (b) in the structure represented by equation (I), the structures represented by any one of equations (b1-1) to (b1-5) and equations (b2-1) to (b2-5) can be listed below.

[0275] [Chemistry 24]

[0276]

[0277] [Chemistry 25]

[0278]

[0279] In this context, the structure represented by formula (b1-1) or formula (b2-1) is more preferred. That is, from the viewpoint of ease of synthesis, X 1 X 2 X 3 and X 4 Preferably, all are >NR NX In any of the structures represented by equations (b1-1) to (b1-3) and (b2-1) to (b2-3), R NX Preferably, it is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, more preferably an alkyl-substituted aryl group, and even more preferably an alkyl-substituted phenyl group, particularly preferably phenyl or mesitylene.

[0280] In any of the structures represented by formulas (b1-1) to (b1-5) and (b2-1) to (b2-5), the preferred substitution positions of the cyano group when rings A, B, D, and E are substituted or unsubstituted benzene rings are the same as those described in the structure represented by formula (II).

[0281] <Preferred Substituents>

[0282] In polycyclic aromatic compounds used as emission dopants (and in compounds used as dopants), tertiary alkyl groups represented by the following formula (tR) are particularly preferred as substituents containing "alkyl". This is because the intermolecular distance increases with such a large substituent, thus increasing the photoluminescence quantum yield (PLQY). Furthermore, it is also preferred to use a tertiary alkyl group represented by formula (tR) as a second substituent to replace other substituents. Specifically, examples include diarylamino groups substituted with a tertiary alkyl group represented by formula (tR), carbazolyl groups substituted with a tertiary alkyl group represented by formula (tR) (preferably N-carbazolyl), or benzo[a]carbazolyl groups substituted with a tertiary alkyl group represented by formula (tR) (preferably N-benzo[a]carbazolyl). As for the substitution forms of the group of formula (tR) for diarylamino, carbazolyl and benzocarbazolyl, examples can be listed of the substitution of some or all of the hydrogens of the aryl ring or benzene ring in these groups with the group of formula (tR).

[0283] [Chemistry 26]

[0284]

[0285] In equation (tR), R a R b and R cEach is an alkyl group having 1 to 24 carbon atoms, wherein any -CH2- group in the alkyl group may be substituted with -O-, and the group represented by formula (tR) will... Set as the bond location.

[0286] As R a R b and R c The term "alkyl group having 1 to 24 carbon atoms" can be either straight-chain or branched-chain. Examples include: straight-chain alkyl groups having 1 to 24 carbon atoms or branched-chain alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched-chain alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched-chain alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched-chain alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched-chain alkyl groups having 3 to 4 carbon atoms).

[0287] R in equation (tR) a R b and R c The total number of carbons is preferably 3 to 20, and more preferably 3 to 10.

[0288] As R a R b and R c Specific alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0289] Examples of groups represented by formula (tR) include: tert-butyl, tert-pentyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-Ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, tert-butyl and tert-pentyl are preferred.

[0290] As a substituent, the substituent represented by formula (A30) is preferred.

[0291] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the substituents in the compound used as a dopant (auxiliary dopant or emission dopant). Preferably, the radicals are those represented by the following structural formulas, more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, 3,6-di-tert-butylcarbazole, and phenoxy, and even more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, 3,6-di-tert-butylcarbazole, and tribenzozazolyl. From the viewpoint of ease of synthesis, sterically hindered groups are preferred for selective synthesis. Specifically, tert-butyl, tert-pentyl, tert-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole are preferred.

[0292] In the following structural formula, Indicates the location of the bond.

[0293] [Chemistry 27]

[0294]

[0295] [Chemistry 28]

[0296]

[0297] [Chemistry 29]

[0298]

[0299] [Chemistry 30]

[0300]

[0301] [Chemistry 31]

[0302]

[0303] [Chemistry 32]

[0304]

[0305] [Chemistry 33]

[0306]

[0307] [Chemistry 34]

[0308]

[0309] [Chemistry 35]

[0310]

[0311] [Chemistry 36]

[0312]

[0313] [Chemistry 37]

[0314]

[0315] [Chemistry 38]

[0316]

[0317] [Chemistry 39]

[0318]

[0319] [Chemistry 40]

[0320]

[0321] In a particularly preferred embodiment, the polycyclic aromatic compound represented by formula (I) preferably comprises a structure containing at least one tertiary alkyl group (tert-butyl or tert-pentyl, etc.), neopentyl, or adamantyl group represented by formula (tR), and more preferably a tertiary alkyl group (tert-butyl or tert-pentyl, etc.) represented by formula (tR). This is because the intermolecular distance increases with such a large substituent, thus improving the luminescent quantum yield (PLQY). Furthermore, diarylamino groups are also preferred as substituents. Moreover, diarylamino groups substituted with the group of formula (tR), carbazolyl groups substituted with the group of formula (tR) (preferably N-carbazolyl), or benzo[a]carbazolyl groups substituted with the group of formula (tR) (preferably N-benzo[a]carbazolyl) are also preferred. Examples of substitution forms for the group of formula (tR) of diarylamino, carbazolyl, and benzo[a]carbazolyl groups include substitution of some or all of the hydrogen atoms of the aryl ring or benzene ring in these groups with the group of formula (tR).

[0322] In the polycyclic aromatic compounds represented by formula (I), the inclusion of a substituted or unsubstituted N-carbazole group in the substituents of the B and D rings, when referring to "substituted or unsubstituted," is also considered a preferred configuration. When compounds with an N-carbazole group as a substituent are used as dopants in the luminescent layer, organic EL devices with longer lifetimes and lower driving voltages are found. It is believed that by having an N-carbazole group as a substituent, the HOMO of the compound becomes deeper, hole trapping activity decreases, and the driving voltage is reduced. Furthermore, it is believed that carrier recombination is less likely to occur on the dopant, and the dopant is less likely to enter the T1 state, thereby extending the lifetime. Here, the substituent when the N-carbazole group is substituent is preferably selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, and substituted or unsubstituted cycloalkyl. As a substituted or unsubstituted N-carbazolyl group, it is preferred to be an unsubstituted N-carbazolyl group or an N-carbazolyl group having substituents at the 1, 3, 6, or 8 positions, particularly preferably an unsubstituted N-carbazolyl group or a 3,6-di(tert-butyl)N-carbazolyl group or a deuterated N-carbazolyl group. Substituents having the following structures formed by condensing an indole ring, benzofuran ring, benzothiophene ring, benzoselenene ring, indene ring, or benzosiloxane ring on at least one benzene ring in the N-carbazolyl group are also preferred, more preferably benzofurano[3,2-a]carbazolyl, benzo[4,5]thieno[3,2-a]carbazolyl, benzofurano[3,2-c]carbazolyl, or benzo[4,5]thieno[3,2-c]carbazolyl.

[0323] [Chemistry 41]

[0324]

[0325] In the structure represented by formula (I), the substituents of the aryl ring or heteroaryl ring can be the substituents represented by the following formula (A20).

[0326] [Chemistry 42]

[0327]

[0328] The substituents represented by formula (A20) are in two Each R is bonded to two adjacent atoms on the aryl or heteroaryl ring. In formula (A20), L is >NR, >O, >Si(-R)2, or >S. The R in >NR is a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. The R in >Si(-R)2 is hydrogen, a substituted aryl, a substituted alkyl, or a substituted cycloalkyl. Furthermore, the two Rs in >Si(-R)2 can bond to each other to form a ring. Additionally, at least one of the Rs in >NR and >Si(-R)2 can be bonded to the aryl or heteroaryl ring via a linker group or a single bond.

[0329] r is an integer from 1 to 4.

[0330] R A Each is independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and any R A It can be linked to any R through a base or a single bond. A Interconnected.

[0331] Examples of the substituents can be listed as any of the following.

[0332] [Chemistry 43]

[0333]

[0334] Of all the varieties, as long as in It can be formed by two or three consecutive (adjacent) atomic bonds to any aryl ring or heteroaryl ring.

[0335] <Cycloalkane condensation>

[0336] At least one of the groups consisting of aryl and heteroaryl rings in the polycyclic aromatic compound represented by formula (I) can be condensed from at least one cycloalkane. The same applies to the structures represented by formulas (II), (II-1-i) to (II-1-v), (II-2-i), (II-2-ii), (II-3-i), (II-3-ii), (II-4-i), or (II-5-i), and the following description also applies to the polycyclic aromatic compounds represented by any of these formulas.

[0337] As a cycloalkane, it is acceptable to have a cycloalkane with 3 to 24 carbon atoms. At least one hydrogen atom in the cycloalkane may be substituted by an aryl group with 6 to 30 carbon atoms, a heteroaryl group with 2 to 30 carbon atoms, an alkyl group with 1 to 24 carbon atoms, or a cycloalkyl group with 3 to 24 carbon atoms, and at least one -CH2- atom in the cycloalkane may be substituted by -O- atom.

[0338] The cycloalkanes are preferably cycloalkanes with 3 to 20 carbon atoms, and at least one hydrogen atom in the cycloalkanes may be substituted by an aryl group with 6 to 16 carbon atoms, a heteroaryl group with 2 to 22 carbon atoms, an alkyl group with 1 to 12 carbon atoms, or a cycloalkyl group with 3 to 16 carbon atoms.

[0339] Examples of "cycloalkanes" include: cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0340] Specific examples of cycloalkanes include: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.2]octane, adamantane, diadamantane, decahydronaphthalene and decahydroazine, and their alkyl (especially methyl) substituted derivatives, halogen (especially fluorine) substituted derivatives, and deuterium substituted derivatives, etc., having carbon numbers of 1 to 5.

[0341] In the examples described, a preferred structure is one where, for example, the carbon atom at the α-position of the cycloalkane (the carbon atom adjacent to the carbon at the condensation site in a cycloalkane condensed in an aryl or heteroaryl ring) has at least one substituent, more preferably a structure where the carbon atom at the α-position has two substituents, and even more preferably a structure where both α-position carbons have two substituents (having a total of four substituents). Examples of such substituents include alkyl groups (especially methyl groups) having 1 to 5 carbon atoms, halogens (especially fluorine groups), and deuterium. A particularly preferred structure is one where the carbon atom adjacent to the aryl or heteroaryl ring has a partial structure represented by the following formula (B11) or formula (B12), and a more preferred structure is one where the carbon atom adjacent to the aryl or heteroaryl ring has a partial structure represented by the following formula (B11).

[0342] [Chemistry 44]

[0343]

[0344] In equations (B11) and (B12), Indicates the location of the bond.

[0345] The number of cycloalkanes condensed on an aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are condensed on a benzene ring (phenyl). This indicates the bond position, which can be any carbon atom that forms the benzene ring and does not form a cycloalkane. Cycloalkanes that undergo condensation as in formulas (Cy-1-4) and (Cy-2-4) can also condense with each other. This applies regardless of whether the condensed ring (group) is an aryl ring or heteroaryl ring other than a benzene ring, or whether the condensing cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0346] [Chemistry 45]

[0347]

[0348] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows examples of one or more -CH2- substituents of a cycloalkane condensed on a benzene ring (phenyl) with -O- substitution. This applies whether the condensed ring (group) is an aryl ring or a heteroaryl ring other than a benzene ring (phenyl), or whether the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0349] [Chemistry 46]

[0350]

[0351] Cycloalkanes may be substituted with at least one substituent, which may be any substituent selected from substituent group Z. Among these substituents, alkyl groups (e.g., alkyl groups having 1 to 6 carbon atoms) and cycloalkyl groups (e.g., cycloalkyl groups having 3 to 14 carbon atoms) are preferred. Additionally, substitution of any hydrogen atom with a halogen (e.g., fluorine) or deuterium is also preferred. Furthermore, in the case of cycloalkyl substitution, a spirocyclic structure may be formed; for example, examples of spirocyclic structures formed in cycloalkanes condensed on a benzene ring (phenyl) are shown below. Regarding the various structural formulas... In the case of a benzene ring, it refers to the benzene ring contained in the skeletal structure of the compound; in the case of a phenyl ring, it refers to the substituted bonds in the skeletal structure of the compound.

[0352] [Chemistry 47]

[0353]

[0354] As forms of cycloalkane condensation, firstly, examples of polycyclic aromatic compounds represented by formula (I) show forms where the aryl and heteroaryl rings in rings A, B, D, and E are condensed from cycloalkane. Secondly, examples of compounds represented by formula (Ar) show forms where the aryl and heteroaryl rings in ring E or G are condensed from cycloalkane.

[0355] Other forms of cycloalkane condensation can be listed as other R-type compounds among the polycyclic aromatic compounds represented by formula (I). NX >NR is an aryl group formed by the condensation of cycloalkanes. NX Examples include diarylamino groups condensed from cycloalkanes (condensed to their aryl moiety), carbazolyl groups condensed from cycloalkanes (condensed to their benzene ring moiety), or benzocarbazolyl groups condensed from cycloalkanes (condensed to their benzene ring moiety).

[0356] Furthermore, by introducing a cycloalkane structure into the polycyclic aromatic compound represented by formula (I), a further reduction in melting point or sublimation temperature can be expected. This means that in sublimation purification, which is almost indispensable for the purification of materials for organic devices such as organic EL elements requiring high purity, purification can be carried out at a lower temperature, thus avoiding thermal decomposition of the material. Similarly, this also applies to vacuum evaporation processes, which are powerful means for manufacturing organic devices such as organic EL elements; the process can be carried out at a lower temperature, thus avoiding thermal decomposition of the material and resulting in high-performance organic devices. Furthermore, since the solubility in organic solvents is improved by introducing a cycloalkane structure, it can also be applied to the fabrication of elements using coating processes. However, the present invention is not particularly limited to these principles.

[0357] <Replacement with heavy stable isotopes>

[0358] Unless otherwise specified, the elements in the polycyclic aromatic compounds represented by formula (I) include multiple naturally occurring isotopes in a naturally occurring ratio. Furthermore, all or some of the elements in each structural formula may also include elements in a ratio exceeding the naturally occurring ratio (e.g., in boron-11...). 11 B) refers to a heavy stable isotope (90 atoms or more). In this specification, it is simply referred to as "replaced with" or "heavy stable isotope". More specifically, at least one hydrogen atom may be substituted with deuterium, and at least one nitrogen atom may be substituted with nitrogen-15 (…). 15 N), at least one sulfur can be substituted with sulfur-33 (N), 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be substituted with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be substituted with carbon-13 ( 13 C), at least one boron may be substituted with boron-11 ( 11 B). The same applies to the structures represented by formulas (II), (II-1-i) to (II-1-v), (II-2-i), (II-2-ii), (II-3-i), (II-3-ii), (II-4-i), or (II-5-i), and the following description also applies to polycyclic aromatic compounds represented by any of these formulas. This is achieved by substituting at least a portion of the elements with heavy stable isotopes, particularly by using boron-11 ( 11 B) Substituting at least one boron can achieve a longer lifetime for organic electroluminescent elements using polycyclic aromatic compounds represented by formula (I) as dopants.

[0359] For example, in the polycyclic aromatic compounds represented by formula (I), the hydrogens in the A, B, C, D, and E rings and their substituents may be deuterated. Examples of deuterated substitution include all or some of the hydrogens in the aryl or heteroaryl groups. Furthermore, from the viewpoint of durability, it is also preferable that all or some of the hydrogens in the polycyclic aromatic compounds represented by formula (I) are deuterated.

[0360] <Specific examples of polycyclic aromatic compounds>

[0361] Examples of polycyclic aromatic compounds represented by formula (I) include compounds represented by any of the following structural formulas.

[0362] [Chemistry 48]

[0363]

[0364] [Chemistry 49]

[0365]

[0366] [Transformation 50]

[0367]

[0368] [Chemistry 51]

[0369]

[0370] [Chemistry 52]

[0371]

[0372] [Chemistry 53]

[0373]

[0374] [Chemistry 54]

[0375]

[0376] [Chemistry 55]

[0377]

[0378] [Chemistry 56]

[0379]

[0380] [Chemistry 57]

[0381]

[0382] [Chem.58]

[0383]

[0384] [Chemistry 59]

[0385]

[0386] [Transformation 60]

[0387]

[0388] [Chemistry 61]

[0389]

[0390] [Chemistry 62]

[0391]

[0392] [Chemistry 63]

[0393]

[0394] [Chemistry 64]

[0395]

[0396] [Chemistry 65]

[0397]

[0398] [Chemistry 66]

[0399]

[0400] [Chemistry 67]

[0401]

[0402] [Chemistry 68]

[0403]

[0404] [Chemistry 69]

[0405]

[0406] [Chemistry 70]

[0407]

[0408] [Chemistry 71]

[0409]

[0410] [Chemistry 72]

[0411]

[0412] [Chemistry 73]

[0413]

[0414] [Chemistry 74]

[0415]

[0416] [Chemistry 75]

[0417]

[0418] [Chemistry 76]

[0419]

[0420] [Chemistry 77]

[0421]

[0422] [Chemistry 78]

[0423]

[0424] [Chemistry 79]

[0425]

[0426] [Chemistry 80]

[0427]

[0428] [Chemistry 81]

[0429]

[0430] <Methods for manufacturing polycyclic aromatic compounds>

[0431] In the polycyclic aromatic compounds represented by formula (I), compounds in which Y is boron can be synthesized, for example, by the methods described in Japanese Patent Application Publication No. 2021-063074 and Japanese Patent Application Publication No. 2023-152686. Furthermore, the polycyclic aromatic compounds of the present invention can be manufactured according to the methods described in numerous known documents, such as International Publication No. 2015 / 102118 and International Publication No. 2018 / 212169.

[0432] Basically, the process begins by bonding the ring structures together to create an intermediate (first reaction). Then, using Y (e.g., boron atoms) to bond the ring structures together, the final product is produced (second reaction). In the first reaction, general etherification reactions such as nucleophilic substitution and the Ullmann reaction, or general amination reactions such as the Buchwald-Hartwig reaction, nucleophilic substitution, and Goldberg amination can be used. In the second reaction, a tandem Hetero-Friedel-Crafts reaction (a continuous aromatic electrophilic substitution reaction, as described below) can be used.

[0433] As shown in the following process (1), the second reaction is the introduction of the Y (e.g., boron atom) that bonds the ring structures. First, the two X (X) on the ring are bonded using n-butyllithium, sec-butyllithium, or tert-butyllithium, etc. 1 X 2 X 3 and X 4The hydrogen atoms between the two atoms undergo ortho-metallization. Subsequently, a chloride or bromide of Y (e.g., boron trichloride or boron tribromide) is added to perform a lithium-Y (e.g., boron) metal exchange. Then, a Brenstein base such as N,N-diisopropylethylamine is added, thereby initiating a tandem borone-friedel-Crafts reaction to obtain the target compound. In the second reaction, a Lewis acid such as aluminum trichloride may also be added to promote the reaction.

[0434] [Chemistry 82]

[0435]

[0436] In process (1), lithium is introduced to the desired position through ortho-metallization. However, as in process (2) below, a halogen atom (Hal) is introduced beforehand at the desired lithium position, and lithium can also be introduced to the desired position through halogen-metal exchange. This method is useful even when ortho-metallization is not possible due to the influence of substituents. The halogen atom (Hal) in the formula can be any of F, Cl, Br, or I, and can be appropriately selected considering the reactivity of the matrix.

[0437] [Chemistry 83]

[0438]

[0439] The following is an example of a boron introduction reaction. The one-shot boronization in a tandem borofried-Krawtz reaction is described below. After reacting the intermediate with boron reagents such as boron tribromide or boron triiodide, a Brinzyl base such as 2,6-di-tert-butylpyridine is added as needed, thereby obtaining the compound represented by the target formula (1) (Y is a boron compound).

[0440] [Chemistry 84]

[0441]

[0442] Furthermore, the sites for tandem borofried-Krawst reactions can vary depending on factors such as the rotation of amino groups in intermediates, potentially leading to the formation of byproducts. In such cases, the target polycyclic aromatic compound can be separated from these mixtures by chromatography or recrystallization.

[0443] In addition, the two Y atoms in the polycyclic aromatic compounds of the present invention can be introduced simultaneously in the same reaction step, or sequentially, or sequentially in different reaction steps.

[0444] In the polycyclic aromatic compounds of the present invention, at least a portion of the hydrogen atoms are substituted with cyano groups. However, such compounds can be synthesized in the same manner using a starting material whose desired site is cyano-substituted. Alternatively, after obtaining a halogenated polycyclic aromatic compound by using a precursor containing a halogen at a suitable position, the cyano group can be introduced using conventional methods, or a cyano-containing substituent can be introduced using cross-coupling, thereby achieving the same synthesis.

[0445] In addition, cyano-substituted polycyclic aromatic compounds can also be synthesized by synthesizing precursors with detachable groups such as halogens or trifluoromethanesulfonyl groups, followed by replacing the detachable groups with cyanides using cyanide. Besides cyanide salts such as sodium cyanide or potassium cyanide, potassium hexacyanoferrate(II) can also be used as cyanide. The reaction can be promoted by using catalysts such as palladium. When synthesizing precursors with detachable groups such as halogens or trifluoromethanesulfonyl groups, the substituents can be introduced into the matrix beforehand to create steric hindrance, or selectively introduced to the desired position considering the reactivity of the reagents used, the reaction temperature, or the reaction mechanism.

[0446] By appropriately selecting the raw materials used, polycyclic aromatic compounds with substituents at the desired positions can be synthesized.

[0447] To promote the reaction, Lewis acids such as aluminum trichloride can also be added. Furthermore, in the formula of the intermediate in process (1), the halogen atom that is Cl can also be F, Br or I, and the halogen atom can be appropriately selected considering the reactivity of the matrix.

[0448] Specific examples of solvents used in the aforementioned reaction include: chlorobenzene, o-dichlorobenzene, tert-butylbenzene, xylene, toluene, benzene, mesitylene, dichloromethane, chloroform, dichloroethylene, benzotrifluoride, decahydronaphthalene, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, diphenyl ether, anisole, cyclopentylmethyl ether, tetrahydrofuran (THF), dioxane, methyl-tert-butyl ether, tert-butanol, N,N-dimethylacetamide, N,N-dimethylformamide (DMF), etc.

[0449] In addition, as organometallic reagents used in the process (1), examples include: alkyl lithiums such as methyl lithium, n-butyl lithium, sec-butyl lithium, and tert-butyl lithium, and organoalkali metal compounds such as diisopropylamide lithium, tetramethylpiperidinium lithium, hexamethyldisilamide lithium, and hexamethyldisilamide potassium.

[0450] In addition, examples of boron reagents used in process (1) include boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide, boron alkoxyides, and boron aryloxyides.

[0451] Furthermore, examples of Brønsted base used in process (1) include: N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-dimethylpyridine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, Ar4Si (where Ar is phenyl or other aryl groups), etc.

[0452] Examples of Lewis acids used in process (1) include: AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, BI3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, CoBr3, etc.

[0453] In process (1), Brønsted bases or Lewis acids can be used to promote the tandem heterofried-Krawtz reaction. When using boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds; therefore, using Brønsted bases to capture these acids is effective. On the other hand, when using boron amino halides or boron alkoxy compounds, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds; therefore, in most cases, Brønsted bases are not necessary. However, because the desorption capacity of amino or alkoxy groups is low, using Lewis acids that promote their desorption is effective.

[0454] In addition, the polycyclic aromatic compounds of the present invention also include compounds in which at least some hydrogen atoms are substituted with deuterium or substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials that are deuterated, fluorinated or chlorinated at the desired positions.

[0455] 2. Organic devices

[0456] The polycyclic aromatic compounds of the present invention can be used as materials for organic devices. Examples of organic devices include organic electroluminescent elements, organic field-effective transistors, organic thin-film solar cells, and organic photodiodes. The polycyclic aromatic compounds of the present invention are preferably used as materials for forming any one or more organic layers in organic electroluminescent elements.

[0457] 2-1. Organic electroluminescent element

[0458] 2-1-1. Structure of Organic Electroluminescent Element

[0459] Figure 1 This is a schematic cross-sectional view showing an example of an organic EL element.

[0460] Figure 1 The organic EL element 100 shown includes: a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

[0461] Furthermore, the organic EL element 100 can also be fabricated in reverse order to form a structure such as the following, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

[0462] Not all of the layers are indispensable. The smallest structural unit is set to include an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are arbitrarily arranged layers. In addition, each layer may consist of a single layer or multiple layers.

[0463] In addition to the aforementioned structure of "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", the morphology of the layers constituting an organic EL device can also be "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode". The structural forms of “electron transport layer / cathode”, “substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode”, “substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode”, “substrate / anode / light-emitting layer / electron transport layer / cathode”.

[0464] Organic EL devices may further include either or both of an electron blocking layer and a hole blocking layer. The electron blocking layer has a low-level non-emitting magnetic field (LUMO) shallower than the emissive layer and a high-level non-emitting magnetic field (HOMO) close to the emissive or hole transport layer, and is disposed between the emissive layer and the hole transport layer. Because electrons are retained within the emissive layer and do not leak into the hole transport layer, it prevents shortened lifetimes caused by degradation of the hole transport layer and efficiency reductions caused by decreased recombination efficiency. The hole blocking layer has a high-level non-emitting magnetic field (HOMO) deeper than the emissive layer and a low-level non-emitting magnetic field (LUMO) close to the emissive or hole transport layer, and is disposed between the emissive layer and the electron transport layer. Because holes are retained within the emissive layer and do not leak into the electron transport layer, it prevents shortened lifetimes caused by degradation of the electron transport layer and efficiency reductions caused by decreased recombination efficiency. The hole injection / transport layer may also function as an electron blocking layer.

[0465] Organic EL devices can further have a high T1 layer. The high T1 layer has a higher T1 than the host compound, auxiliary dopant compound, or emission dopant compound used in the emissive layer, and is disposed between the emissive layer and the hole transport layer and / or between the emissive layer and the electron blocking layer. The value of the T1 energy varies depending on the device's emission mechanism, but it has a higher T1 than the compound used in the host. By having a high T1 layer around the emissive layer, triplet energy can be trapped, converting triplet energy, which is normally irrelevant to emission in fluorescent molecules, into singlet energy, thereby achieving high efficiency. The hole injection / transport layer or the electron blocking layer can also serve as a high T1 layer.

[0466] The polycyclic aromatic compounds of the present invention are preferably used as materials for forming a light-emitting layer or an electron transport layer, and more preferably as materials for forming a light-emitting layer. The polycyclic aromatic compounds of the present invention are particularly preferably used as green light-emitting materials.

[0467] 2-1-2. Substrate in organic electroluminescent devices

[0468] The substrate 101 serves as the support for the organic EL element 100 and can typically be made of quartz, glass, metal, or plastic. Depending on the purpose, the substrate 101 can be formed in the form of a plate, film, or sheet, and can be made of materials such as glass plates, metal plates, metal foils, plastic films, or plastic sheets. Glass plates and plates made of transparent synthetic resins such as polyester, polymethyl methacrylate, polycarbonate, or polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used, and the thickness is only required to maintain sufficient mechanical strength. Furthermore, to improve gas barrier properties, a fine gas barrier film, such as a silicon oxide film, can be provided on at least one side of the substrate 101. When using a plate, film, or sheet made of synthetic resin with low gas barrier properties as the substrate 101, providing a gas barrier film is particularly preferred.

[0469] 2-1-3. Anode in organic electroluminescent devices

[0470] The anode 102 functions to inject holes into the light-emitting layer 105. Furthermore, if at least one hole injection layer 103 and a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these layers.

[0471] Materials forming the anode 102 can include both inorganic and organic compounds. Examples of inorganic compounds include: metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (oxides of indium, oxides of tin, indium tin oxide (ITO), indium zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, or Nesa glass. Examples of organic compounds include: conductive polymers such as poly(3-methylthiophene), polypyrrole, and polyaniline. Furthermore, appropriate materials can be selected from those used as anodes in organic EL elements.

[0472] 2-1-4. Hole injection layer and hole transport layer in organic electroluminescent devices

[0473] Hole injection layer 103 efficiently injects holes migrating from anode 102 into light-emitting layer 105 or hole transport layer 104. Hole transport layer 104 efficiently transports holes injected from anode 102 or holes injected from anode 102 via hole injection layer 103 to light-emitting layer 105. Hole injection layer 103 and hole transport layer 104 are formed by stacking or mixing one or more hole injection / transport materials. Alternatively, inorganic salts such as ferric chloride (III) can be added to the hole injection / transport materials to form the layers.

[0474] As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied. Ideally, it should have high hole injection efficiency and efficient transport of the injected holes. Therefore, a material with a low ionization potential, high hole mobility, and thus excellent stability, and which is less likely to generate impurities that could become traps during manufacturing and use, is preferred.

[0475] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from those compounds commonly used as hole charge transport materials in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Specific examples of these include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) and other biscarbazole derivatives, triarylamine derivatives (polymers with aromatic tertiary amino groups on the main chain or side chain), 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 N 4' -diphenyl-N 4 N 4' -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 N 4 N 4' N 4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4''-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarboxynitrile, etc.), porphyrin derivatives and other heterocyclic compounds, polysilanes, etc. In polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole and polysilanes having the aforementioned monomers on the side chains are preferred, but there is no particular limitation as long as it is a thin film required for the fabrication of the light-emitting element, and a compound that can inject holes from the anode and transport holes.

[0476] Furthermore, it is known that the conductivity of organic semiconductors is strongly affected by their doping. The matrix material for such organic semiconductors contains compounds with good electron-donating or electron-accepting properties. For doping with electron-donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known (e.g., see references “M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204(1998)” and “J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204(1998)” and “J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., Appl. Phys. Lett., 73(22), 3202-3204(1998)” and “J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., Appl. Phys. Lett., 73(22), 3202-3204(1998)”). Phys. Lett., 73(6), 729-731 (1998)”. These holes are generated through electron migration processes of electron-donating base materials (hole transport materials). The conductivity of the base material varies considerably depending on the number and mobility of holes. As matrix materials with hole transport properties, known examples include benzidine derivatives (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (TPD, etc.) or starburst amine derivatives (4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA, etc.) or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc, etc.)) (Japanese Patent Application Publication No. 2005-167175).

[0477] The hole injection layer material and the hole transport layer material can also be used in the hole layer material as the following polymer compounds or their polymer cross-linked forms, or as the following suspended polymer compounds or their suspended polymer cross-linked forms. The polymer compound is obtained by polymerizing a reactive compound that replaces a reactive substituent in the hole injection layer material and the hole transport layer material as a monomer. The suspended polymer compound is obtained by reacting a main-chain polymer with the reactive compound.

[0478] 2-1-5. The light-emitting layer in organic electroluminescent devices

[0479] The light-emitting layer 105 emits light by recombination of holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material forming the light-emitting layer 105 can be any compound that emits light upon excitation by the recombination of holes and electrons (a luminescent compound), and preferably a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state.

[0480] The luminescent layer can be a single layer or multiple layers, either of which is acceptable, and each layer is formed from the same material used for luminescent layers. In the case of multiple luminescent layers, it is preferable that any one layer contains the polycyclic aromatic compound of the present invention. The luminescent layer is preferably a single layer.

[0481] The light-emitting layer is formed from a light-emitting layer material (a host material and a dopant material). The host material and the dopant material can be one or a combination of multiple materials; either is acceptable. For example, as a dopant material, an emission dopant and an auxiliary dopant can be used. Furthermore, the light-emitting layer preferably includes at least two materials selected from the group consisting of an emission dopant, a hole-transporting host material, an electron-transporting host material, and an auxiliary dopant material. The dopant material can be contained entirely within the host material or partially within the host material; either is acceptable. As a doping method, it can be formed by co-evaporation with the host material, or by pre-mixing and simultaneously evaporating with the host material. Alternatively, the light-emitting layer can also be formed by a wet film deposition method using a light-emitting layer forming composition prepared by dissolving the material in an organic solvent.

[0482] The amount of main material used varies depending on the type of main material, and can be determined by considering its characteristics. The preferred basis for the amount of main material used is 50% to 99.999% of the total mass of the material used in the light-emitting layer, more preferably 80% to 99.95% of the mass, and even more preferably 90% to 99.9% of the mass. When the main material is a combination of hole-transporting and electron-transporting main materials, the amount of main material used is the sum of the amounts of hole-transporting and electron-transporting main materials. The mass ratio of hole-transporting to electron-transporting main materials should be 1:9 to 9:1, preferably 4:6 to 6:4, and more preferably approximately 1:1.

[0483] The amount of emission dopant used varies depending on the type of emission dopant, and can be determined according to its characteristics. The preferred amount of emission dopant is 0.001% to 50% of the total mass of the material used in the luminescent layer, more preferably 0.05% to 20% of the total mass, and even more preferably 0.1% to 10% of the total mass. If within this range, it is preferred, for example, in terms of preventing concentration quenching.

[0484] In organic light-emitting devices that use auxiliary dopants (thermally active delayed phosphors or phosphorescent materials) in addition to emitting dopants, it is preferable to use a low concentration of emitting dopant material to prevent concentration quenching. Regarding energy transfer efficiency, it is preferable to use a high concentration of auxiliary dopants. Regarding the efficiency of the thermally active delayed fluorescence mechanism, it is preferable to use a high concentration of auxiliary dopants. In organic light-emitting devices using thermally active delayed phosphors as auxiliary dopants, regarding the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopants, it is preferable that the amount of emitting dopants used is low compared to the amount of auxiliary dopants used.

[0485] When using auxiliary dopant materials, the base amounts of the main material, auxiliary dopant material, and emission dopant material relative to the total mass of the material used in the light-emitting layer are 40%–99% by mass, 59%–1% by mass, and 20%–0.001% by mass, respectively; preferably 60%–95% by mass, 39%–5% by mass, and 10%–0.01% by mass, respectively; and more preferably 70%–90% by mass, 29%–10% by mass, and 5%–0.05% by mass, respectively.

[0486] The polycyclic aromatic compound represented by formula (I) is preferably used as a material for forming the light-emitting layer, more preferably as a dopant, and particularly preferably as an emission dopant.

[0487] The polycyclic aromatic compound represented by formula (I) can be used as an emission dopant for a TTF element that utilizes the phenomenon of generating singlet excitons from multiple triplet excitons (Triplet-Triplet Fusion, TTF).

[0488] Furthermore, the polycyclic aromatic compound represented by formula (I) can be used as an emission dopant for TADF elements as a "thermally active delayed phosphor". In a "thermally active delayed phosphor", by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, the inverse intersystem transition from the lowest excited triplet state to the lowest excited singlet state, which usually has a low transition probability, is generated efficiently, thereby exhibiting emission from the singlet state (thermally active delayed fluorescence, TADF). In conventional fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal inactivation path and cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, enabling high-efficiency organic EL elements.

[0489] It is generally believed that fast delayed fluorescence exhibits excellent TADF properties. Specifically, when luminescent materials with a delayed fluorescence lifetime of 100 μsec or less are used as emitting dopants in light-emitting elements, high device efficiency and long device lifetime can be provided. The delayed fluorescence lifetime is preferably 20 μsec or less, more preferably less than 20 μsec, further preferably 10 μsec or less, and most preferably 5 μsec or less.

[0490] In addition, generally speaking, ΔE S1T1 The smaller the value, the better the TADF property. Furthermore, ΔE S1T1 It is the lowest excited singlet state energy level (E S1 ) and the lowest excited triplet energy level (E T1 The energy difference. Specifically, ΔE S1T1 The value is preferably 0.20 eV or less, more preferably 0.15 eV or less, and particularly preferably 0.10 eV or less.

[0491] In addition, the polycyclic aromatic compounds represented by formula (I) can also be applied to phosphor-assisted thermally activated delayed fluorophore-sensitized fluorescence (TPSF) elements that use a "thermally active delayed phosphor" in the host and use phosphorescent materials as auxiliary dopants.

[0492] <Main Material>

[0493] Examples of suitable host materials include: condensation ring derivatives of anthracene or pyrene, which have been known as luminescent materials since the past; bis(styrene) derivatives such as bis(styrene)-anthracene derivatives or styrene-based benzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; benzo[a]fluorene derivatives; N-phenylcarbazole derivatives; carbazole nitrile derivatives; dibenzo[a]fluorene derivatives; and compounds described later as host materials for hole transport or electron transport. Furthermore, from the viewpoint of durability, it is preferable that some or all of the hydrogen atoms in the host material are deuterated. Moreover, it is also preferable to combine a host compound with some or all of its hydrogen atoms deuterated with a dopant compound with some or all of its hydrogen atoms deuterated to form the luminescent layer.

[0494] The host material can be a single material or a combination of multiple materials. In the case of multiple combinations, a combination of a hole-transporting host material and an electron-transporting host material is preferred.

[0495] [Anthracene compounds]

[0496] Anthracene compounds that are the main component include, for example, compounds represented by formula (3-H) and compounds represented by formula (3-H2).

[0497] [Chemistry 85]

[0498]

[0499] In equation (3-H),

[0500] X and Ar 4 Each is independently hydrogen or selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, all of X and Ar 4 It will not become hydrogen at the same time.

[0501] At least one hydrogen atom in the compound represented by formula (3-H) may be substituted by halogen, cyano, deuterium or a substituted heteroaryl group.

[0502] Alternatively, the structure represented by formula (3-H) can be used as a unit structure to form a polymer (preferably a dimer). In this case, examples can be given of unit structures represented by formula (3-H) that are linked to each other via X bonds. As X, examples can include single bonds, arylene groups (phenylene, biphenylene, and naphthylene, etc.), and heteroarylene groups (pyridine rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, benzocarbazole rings, and phenyl-substituted carbazole rings, etc., groups with divalent bonding valences).

[0503] Details of each group in the compound represented by formula (3-H) can be found in the description in formula (I), and further described in the preferred form section below.

[0504] The preferred forms of the anthracene compounds are described below. The definitions of the symbols in the following structures are the same as those described above.

[0505] [Chemistry 86]

[0506]

[0507] In equation (3-H), X is independently a basis represented by equation (3-X1), equation (3-X2), or equation (3-X3), and the basis represented by equation (3-X1), equation (3-X2), or equation (3-X3) is in... The anthracene ring is bonded to the structure of formula (3-H). Preferably, neither of the two X groups is simultaneously a group represented by formula (3-X3). More preferably, neither of the two X groups is simultaneously a group represented by formula (3-X2).

[0508] Alternatively, the structure represented by formula (3-H) can be used as a unit structure to form a polymer (preferably a dimer). In this case, examples can be given of unit structures represented by formula (3-H) that are linked to each other via X bonds. As X, examples can include single bonds, arylene groups (phenylene, biphenylene, and naphthylene, etc.), and heteroarylene groups (pyridine rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, benzocarbazole rings, and phenyl-substituted carbazole rings, etc., groups with divalent bonding valences).

[0509] The naphthyl group in formulas (3-X1) and (3-X2) can be formed by the condensation of a benzene ring. The structure formed by the condensation in this manner is shown below.

[0510] [Chemistry 87]

[0511]

[0512] Ar 1 and Ar 2Each can be independently hydrogen, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or a group represented by formula (A) (including carbazole, benzo[a]carbazole, and phenyl-substituted carbazole). Furthermore, in Ar... 1 Or Ar 2 In the case of a basis represented by equation (A), the basis represented by equation (A) is in the... It is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2).

[0513] Ar 3 It is phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or any group represented by formula (A) (including carbazole, benzo[a]carbazole, and phenyl-substituted carbazole). Furthermore, in Ar... 3 In the case of a basis represented by equation (A), the basis represented by equation (A) is in the... The single bond represented by the straight line in formula (3-X3). That is, the anthracene ring in formula (3-H) is directly bonded to the base represented by formula (A).

[0514] Additionally, Ar 3 It can have substituents, Ar 3 At least one hydrogen atom in Ar can be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a cycloalkyl group, a triphenylene group, a pyrene group, or a group represented by formula (A) (including carbazole groups and phenyl-substituted carbazole groups). Furthermore, in Ar... 3 When the substituent is the base represented by formula (A), the base represented by formula (A) in the case of... Ar in equation (3-X3) 3 Bond.

[0515] Ar 4 Each is independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or a silyl group substituted with an alkyl group having 1 to 4 carbon atoms (methyl, ethyl, tert-butyl, etc.) and / or a cycloalkyl group having 5 to 10 carbon atoms.

[0516] Examples of alkyl groups with 1 to 4 carbon atoms that can be substituted in silanes include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, and cyclobutyl, etc., in which the three hydrogens in the silane are independently substituted by these alkyl groups.

[0517] Specific examples of "silyl groups substituted with alkyl groups having 1 to 4 carbon atoms" include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl diethylsilyl, butyl diethylsilyl, sec-butyl diethylsilyl, tert-butyl diethylsilyl, methyl dipropylsilyl, ethyl dipropylsilyl, butyl dipropylsilyl, sec-butyl dipropylsilyl, tert-butyl diisopropylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, butyl diisopropylsilyl, sec-butyl diisopropylsilyl, tert-butyl diisopropylsilyl, etc.

[0518] Examples of cycloalkyl groups with 5 to 10 carbon atoms that can be substituted in silanes include: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, 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, decahydronaphthyl, decahydroazyl, etc., in which the three hydrogens in the silane are independently substituted by these cycloalkyl groups.

[0519] Specific examples of "silyl groups substituted by cycloalkyl groups having 5 to 10 carbon atoms" include tricyclopentylsilane and tricyclohexylsilane.

[0520] As substituted silyl groups, there are also dialkylcycloalkylsilyl groups substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyl groups substituted with one alkyl group and two cycloalkyl groups. As specific examples of substituted alkyl and cycloalkyl groups, the groups described above can be listed.

[0521] Furthermore, the hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) can also be substituted by the group represented by formula (A). In the case of substitution by the group represented by formula (A), the group represented by formula (A) in the... The hydrogen atom is substituted with at least one hydrogen atom in the compound represented by formula (3-H).

[0522] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have.

[0523] [Chemistry 88]

[0524]

[0525] In equation (A), Y is -O-, -S-, or >NR. 29 R21 ~R 28 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 21 ~R 28 The adjacent groups in R can bond with each other to form hydrocarbon rings, aryl rings, or heteroaryl rings. 29 It is hydrogen or a substituted aryl group.

[0526] In formula (A), Y is preferably -O-.

[0527] R 21 ~R 28 The adjacent groups in the formula can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. The group that does not form a ring is represented by the group in formula (A-1) below; for example, the groups represented by formulas (A-2) to (A-14) below can be used to form a ring. Furthermore, at least one hydrogen atom in any of the groups represented by formulas (A-1) to (A-14) can be substituted with an alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (where the two aryl groups can be bonded to each other via a linker), diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano group.

[0528] [Chemistry 89]

[0529]

[0530] A ring formed by the mutual bonding of adjacent groups can be a hydrocarbon ring, such as the cyclohexane ring; or an aryl or heteroaryl ring, such as the R group. 21 ~R 28 The ring structure described in “aryl” or “heteroaryl” is formed by condensation with one or both benzene rings of formula (A-1).

[0531] The base represented by formula (A) is the base obtained by removing a hydrogen atom from any position in formula (A). The position is indicated. That is, the base represented by formula (A) can be any position as the bonding position. For example, it can be any carbon atom on the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 The atoms on any ring formed by the mutual bonding of adjacent bases in the structure of formula (A) or ">NR" as Y in the structure of formula (A) 29"R" 29 Any position in or ">NR 29 "N(R) 29 The same applies to the bases directly bonded by the bonding bonds (for example, the bases represented by equations (A-1) to (A-14).

[0532] As a basis represented by formula (A), for example, any of the formulas (A-1) to (A-14) can be listed as a basis, preferably any of the formulas (A-1) to (A-5) and (A-12) to (A-14), more preferably any of the formulas (A-1) to (A-4), and even more preferably any of the formulas (A-1), (A-3) and (A-4), and particularly preferably the basis represented by formula (A-1).

[0533] As a basis represented by equation (A), the following bases can be listed, for example. Y and The definition is the same as above.

[0534] [Chemistry 90]

[0535]

[0536] [Chemistry 91]

[0537]

[0538] In the compound represented by formula (3-H), the group represented by formula (A) is preferably related to the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and the Ar group in formula (3-X3). 3 The shape of any one of the bonds in the structure.

[0539] In addition, all or part of the hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) can be deuterium.

[0540] The anthracene compound that is the main component can be, for example, a compound represented by the following formula (3-H2).

[0541] [Chemistry 92]

[0542]

[0543] In equation (3-H2), Ar c R is a substituted aryl group or a substituted heteroaryl group. c It is hydrogen, alkyl or cycloalkyl, Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 A 16Ar 17 and Ar 18 Each of the following is independently hydrogen, a substituted aryl, a substituted heteroaryl, a substituted diarylamino, a substituted diheteroarylamino, a substituted arylheteroarylamino, a substituted alkyl, a substituted cycloalkyl, a substituted alkenyl, a substituted alkoxy, a substituted aryloxy, a substituted arylthio, or a substituted silyl, wherein at least one hydrogen atom in the compound represented by formula (3-H2) may be substituted with halogen, cyano, or deuterium.

[0544] The definitions of “substituted aryl,” “substituted heteroaryl,” “substituted diarylamino,” “substituted diheteroarylamino,” “substituted arylheteroarylamino,” “substituted alkyl,” “substituted cycloalkyl,” “substituted alkenyl,” “substituted alkoxy,” “substituted aryloxy,” “substituted arylthio,” or “substituted silyl” in formula (3-H2) are the same as those shown in formula (3-H) and can be referenced from the description in formula (3-H).

[0545] As a "substitutable aryl group", it is also preferred to be a group represented by any one of the following formulas (3-H2-X1) to (3-H2-X8).

[0546] [Chemistry 93]

[0547]

[0548] In equations (3-H2-X1) to (3-H2-X8), Indicates the bond location. In equations (3-H2-X1) to (3-H2-X3), Ar 21 Ar 22 and Ar 23 Each group can be independently hydrogen, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, anthracene, or a group represented by formula (A). Furthermore, in the description of formula (3-H2), the group represented by formula (A) is the same as the group described in the anthracene compound represented by formula (3-H).

[0549] In equations (3-H2-X4) to (3-H2-X8), Ar 24 Ar 25 Ar 26 Ar 27 Ar 28 Ar 29 and Ar 30Each group may be independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, phenyl, triphenylene, pyrene, or a group represented by formula (A). Furthermore, any one or more hydrogen atoms in each of the groups represented by formulas (3-H2-X1) to (3-H2-X8) may be substituted with an alkyl group having 1 to 6 carbon atoms (preferably methyl or tert-butyl).

[0550] Furthermore, as a preferred example of "substitutable aryl", examples include terphenyl (especially meta-terphenyl-5'-yl) that can be substituted by one or more substituents selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, hydroxyl, triphenylene, pyrene and the group represented by formula (A).

[0551] As a "substitutable heteroaryl", the group represented by formula (A) can also be listed. In addition, as specific examples of "substitutable aryl" and "substitutable heteroaryl", dibenzofuranyl, naphthobenzofuranyl, phenyl-substituted dibenzofuranyl, etc. can be listed.

[0552] At least one hydrogen atom in the compound represented by formula (3-H2) may be substituted with a halogen, a cyano group, or a deuterium group. Examples of "halogen" in this case include fluorine, chlorine, bromine, and iodine. Compounds in which all hydrogen atoms in the compound represented by formula (3-H2) are substituted with deuterium are particularly preferred.

[0553] In equation (3-H2), R c It is hydrogen, alkyl or cycloalkyl, preferably hydrogen, methyl or tert-butyl, and more preferably hydrogen.

[0554] In formula (3-H2), Ar is preferred. 11 ~Ar 18 At least two of them are substituted aryl groups or substituted heteroaryl groups. That is, the anthracene compound represented by formula (3-H2) is preferably a structure having at least three substituents bonded to the anthracene ring, selected from the group consisting of substituted aryl groups and substituted heteroaryl groups.

[0555] Among the anthracene compounds represented by formula (3-H2), Ar is more preferred. 11 ~Ar 18 Two of them are substituted aryl or substituted heteroaryl groups, and the other six are hydrogen, substituted alkyl, substituted cycloalkyl, substituted alkenyl or substituted alkoxy groups. That is, the anthracene compound represented by formula (3-H2) is more preferably a structure having three substituents bonded to the anthracene ring, selected from the group consisting of substituted aryl and substituted heteroaryl groups.

[0556] Among the anthracene compounds represented by formula (3-H2), Ar is more preferred. 11 ~Ar18 Any two of them are substituted aryl or substituted heteroaryl, and the other six are hydrogen, methyl or tert-butyl.

[0557] Furthermore, in equation (3-H2), R is preferred. c It is hydrogen, and Ar 11 ~Ar 18 Any six of them are hydrogen.

[0558] The anthracene compound represented by formula (3-H2) is preferably anthracene compound represented by the following formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E).

[0559] [Chemistry 94]

[0560]

[0561] In formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E), Ar c' Ar 11' Ar 12' Ar 13' Ar 14' Ar 15' Ar 17' and Ar 18' Each group is independently phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or a group represented by formula (A), wherein at least one hydrogen atom in these groups may be substituted by a group represented by phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or a group represented by formula (A). Here, when the hydrogen atoms of the methylene groups in the fluorenyl and benzo[a]fluorenyl groups are both substituted by phenyl groups, these phenyl groups may be bonded to each other by single bonds. Unbonded Ar c' Ar 11' Ar 12' Ar 13' Ar 14' Ar 15' Ar 17' and Ar 18' The carbon atom of the anthracene ring can be bonded with a methyl or tert-butyl group instead of a hydrogen atom.

[0562] When Ar c' Ar 11' Ar 12' Ar 13' Ar 14' Ar 15' Ar 17' and Ar 18'When the radical is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, it is preferably represented by any one of the formulas (3-H2-X1) to (3-H2-X8).

[0563] Ar c' Ar 11' Ar 12' Ar 13' Ar 14' Ar 15' Ar 17' and Ar 18' More preferably, the group is independently represented by phenyl, biphenyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenyl (especially meta-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl or any of the groups represented by formulas (A-1) to (A-4), wherein at least one hydrogen of these groups may be substituted by a group represented by phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl or any of the groups represented by formulas (A-1) to (A-4).

[0564] Furthermore, at least one hydrogen atom in the compounds represented by formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D), or formula (3-H2-E) may be substituted with a halogen, a cyano group, or a deuterium group. Additionally, the deuterated form is preferred, and more preferably, the form in which all anthracene rings are deuterated or all hydrogen atoms are deuterated.

[0565] As particularly preferred anthracene compounds represented by formula (3-H2), examples include anthracene compounds represented by the following formula (3-H2-Aa).

[0566] [Chem. 95]

[0567]

[0568] In formula (3-H2-Aa), Ar c' Ar 14' and Ar 15' Each group is independently represented by a phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or any group represented by formulas (A-1) to (A-11), wherein at least one hydrogen atom in these groups may be substituted by a phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or any group represented by formulas (A-1) to (A-11). Here, when the hydrogen atoms of the methylene groups in the fluorenyl and benzo[a]fluorenyl groups are both substituted by phenyl groups, these phenyl groups may be bonded to each other by single bonds. Additionally, unbonded Ar... c' Ar 14' and Ar 15'The anthracene ring may be substituted with a methyl or tert-butyl group instead of a hydrogen atom. Preferably, at least one hydrogen atom in the compound represented by formula (3-H2-Aa) may be substituted with a halogen or cyano group, and at least one hydrogen atom in the compound represented by formula (3-H2-Aa) may be substituted with a deuterium group.

[0569] In formula (3-H2-Aa), Ar c' Ar 14' and Ar 15' Preferably, the group is independently represented by phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl or any of the groups (A-1) to (A-4), wherein at least one hydrogen of these groups may be substituted by a group represented by phenyl, naphthyl, phenanthryl, fluorenyl or any of the groups (A-1) to (A-4).

[0570] In compounds represented by formula (3-H2-Aa), the preferred element is at least the carbon at position 10 of the anthracene ring (with Ar... c' The hydrogen at the 9-position (where the carbon atom is set to 9) is replaced with deuterium. That is, the compound represented by formula (3-H2-Aa) is preferably the compound represented by formula (3-H2-Ab). Furthermore, in formula (3-H2-Ab), D is deuterium, and Ar... c' Ar 14' and Ar 15' Same as the definition in formula (3-H2-Aa). In formula (3-H2-Ab), D indicates that at least the position is deuterium, and any one or more other hydrogens in formula (3-H2-Ab) can be deuterium at the same time, and preferably all hydrogens in formula (3-H2-Ab) are deuterium.

[0571] [Chemistry 96]

[0572]

[0573] Specific examples of anthracene compounds include compounds represented by formulas (3-131-Y) to (3-182-Y), (3-183-N), (3-184-Y) to (3-284-Y), (3-500) to (3-557), (3-600) to (3-605), and (3-606-Y) to (3-626-Y). The hydrogen atoms in these formulas may be partially or completely substituted with deuterium, but particularly preferred forms of deuteration are listed individually. Y in the formulas may be -O-, -S-, or >NR. 29 (R) 29 (The definition is the same as above) or >C(-R 30 )2(R 30 R is any of the linked aryl or alkyl groups. 29 For example, phenyl, R30 For example, methyl. Regarding formula numbering, for example, when Y is O, formula (3-131-Y) is set as formula (3-131-O), and when Y is -S- or >NR... 29 In the case of , they are respectively set as equation (3-131-S) or equation (3-131-N).

[0574] [Chemistry 97]

[0575]

[0576] [Chem. 98]

[0577]

[0578] [Chemistry 99]

[0579]

[0580] [Chemistry 100]

[0581]

[0582] [Chemistry 101]

[0583]

[0584] [Chemistry 102]

[0585]

[0586] [Chemistry 103]

[0587]

[0588] [Chemistry 104]

[0589]

[0590] [Chemistry 105]

[0591]

[0592] [Chemistry 106]

[0593]

[0594] [Chemistry 107]

[0595]

[0596] [Chemistry 108]

[0597]

[0598] [Chemistry 109]

[0599]

[0600] [Chemical 110]

[0601]

[0602] [Chemistry 111]

[0603]

[0604] [Chemistry 112]

[0605]

[0606] [Chemistry 113]

[0607]

[0608] [Chemistry 114]

[0609]

[0610] [Chemistry 115]

[0611]

[0612] [Chemistry 116]

[0613]

[0614] In the above formula, D represents deuterium.

[0615] Among these compounds, those of formulas (3-131-Y) to (3-134-Y), (3-138-Y), (3-140-Y) to (3-143-Y), (3-150-Y), (3-153-Y) to (3-156-Y), (3-166-Y), (3-168-Y), (3-173-Y), (3-177-Y), (3-180-Y) to (3-183-N), (3-185-Y), (3-190-Y), (3-223-Y), and (…) are preferred. Compounds represented by formulas (3-241-Y), (3-250-Y), (3-252-Y) to (3-254-Y), (3-270-Y) to (3-284-Y), (3-501), (3-507), (3-508), (3-509), (3-513), (3-514), (3-519), (3-521), (3-538) to (3-547), or (3-600) to (3-605) and (3-606-Y) to (3-626-Y). Furthermore, Y is preferably -O- or >NR. 29 More preferably, it is -O-. In addition, it is also preferred to be a deuterium-substituted form.

[0616] The anthracene compound may be a compound having a reactive group at a desired position on the anthracene skeleton, or, if it is an anthracene compound represented by formula (3-H), at X, Ar 4 The compound having a reactive group in part of its structure, such as that of formula (A), is used as a starting material and manufactured by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in the said reactive compound include halogens or boric acids. For a specific manufacturing method, see, for example, the synthesis method described in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725.

[0617] [fluorene compounds]

[0618] The compound represented by formula (4-H) essentially functions as the main component.

[0619] [Chemistry 117]

[0620]

[0621] In equation (4-H),

[0622] R 1 To R 10Each of these is independently hydrogen, aryl, heteroaryl (the heteroaryl group may be bonded to the fluorene skeleton in formula (4-H) via a single bond or a linker), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen atom may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, and R 1 With R 2 R 2 With R 3 R 3 With R 4 R 5 With R 6 R 6 With R 7 R 7 With R 8 Or R 9 With R 10 They can be independently bonded to form condensed rings or spiro rings, and at least one hydrogen in the formed ring can be substituted by an aryl, heteroaryl (the heteroaryl can be bonded to the formed ring via a single bond or a linker), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these can be substituted by an aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in the compound represented by formula (4-H) can be substituted by a halogen, cyano or deuterium.

[0623] For details of the bases in the definition of equation (4-H), please refer to the description in equation (I).

[0624] As R 1 To R 10 The alkenyl group in the text can be, for example, an alkenyl group with 2 to 30 carbon atoms, preferably an alkenyl group with 2 to 20 carbon atoms, more preferably an alkenyl group with 2 to 10 carbon atoms, and even more preferably an alkenyl group with 2 to 6 carbon atoms, particularly preferably an alkenyl group with 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0625] Furthermore, as specific examples of heteroaryl groups, monovalent groups can also be represented by removing any one hydrogen atom from compounds of the following formulas (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5).

[0626] [Chemistry 118]

[0627]

[0628] In equations (4-Ar1) to (4-Ar5), Y 1 Each of the following can be independently O, S or NR, where R is phenyl, biphenyl, naphthyl, anthracene or hydrogen, and at least one hydrogen in the structure of formula (4-Ar1) to (4-Ar5) can be substituted with phenyl, biphenyl, naphthyl, anthracene, phenanthryl, methyl, ethyl, propyl or butyl.

[0629] These heteroaryl groups can be bonded to the fluorene skeleton in formula (4-H) via single bonds or linking groups. That is, the fluorene skeleton in formula (4-H) can be directly bonded to the heteroaryl groups, or they can be bonded to each other via single bonds or linking groups. Examples of linking groups include: phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0630] Additionally, R in equation (4-H) 1 With R 2 R 2 With R 3 R 3 With R 4 R 5 With R 6 R 6 With R 7 Or R 7 With R 8 They can be independently bonded and form condensation loops, R 9 With R 10 They can bond and form helical rings. (From R) 1 To R 8 The resulting condensation ring is a ring formed by condensation on the benzene ring in formula (4-H), and is either an aliphatic ring or an aromatic ring. An aromatic ring is preferred; examples of structures containing the benzene ring in formula (4-H) include naphthalene rings or phenanthrene rings. (From R...) 9 With R 10 The formed helical ring is a ring with a helical bond on the 5-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, such as a fluorene ring.

[0631] The compound represented by formula (4-H) is preferably a compound represented by formula (4-H-1), formula (4-H-2) or formula (4-H-3), wherein R in formula (4-H) is a specific compound. 1 With R 2 Compounds formed by the condensation of benzene rings through bonding, and R in formula (4-H) 3 With R 4 Compounds formed by the condensation of benzene rings through bonding, where R in formula (4-H) 1 To R 8 Compounds in which neither of the elements is bonded.

[0632] [Chemistry 119]

[0633]

[0634] R in equations (4-H-1), (4-H-2), and (4-H-3) 1 To R 10 The definition of R in equation (4-H) 1 To R 10 Similarly, R in equations (4-H-1) and (4-H-2) 11 To R 14 The definition is also the same as R in equation (4). 1 To R 10 same.

[0635] The compound represented by formula (4-H) is further preferably a compound represented by formula (4-H-1A), formula (4-H-2A), or formula (4-H-3A), wherein R is a molecule in formula (4-H-1), formula (4-H-2), or formula (4-H-3), respectively. 9 With R 10 Compounds that form spirofluorene rings through bonding.

[0636] [Chemistry 120]

[0637]

[0638] R in equations (4-H-1A), (4-H-2A), and (4-H-3A) 2 To R 7 The definition of R corresponding to equations (4-H-1), (4-H-2), and (4-H-3) 2 To R 7 The same, and R in equations (4-H-1A) and (4-H-2A) 11 To R 14 The definition is also the same as R in equations (4-H-1) and (4-H-2). 11 To R 14 same.

[0639] In addition, all or part of the hydrogens in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0640] More specific examples of fluorene compounds as the main component can be listed in the compounds represented by the following structural formulas.

[0641] [Chemistry 121]

[0642]

[0643] [A compound represented by any of formulas (H1), (H2), and (H3)]

[0644] As the main material, compounds represented by any of the following formulas (H1), (H2) and (H3) may also be used.

[0645] [Chemistry 122]

[0646]

[0647] In equations (H1), (H2), and (H3), L 1 It is a single bond, or at least a divalent group containing an arylene or heteroarylene. Specifically, L 1 It can be a single bond, or any arylene with 6 to 24 carbon atoms, a heteroarylene with 2 to 24 carbon atoms, a heteroarylene with 6 to 24 carbon atoms, or a heteroarylene with 6 to 24 carbon atoms, or a divalent group formed by linking any two of these with -O-, -S-, -CH2-, -Si(-Arx)2- (Arx is an aryl group) or a cycloalkyl group. As L 1 The arylene group in the L group is preferably an arylene group with 6 to 16 carbon atoms, more preferably an arylene group with 6 to 12 carbon atoms, and particularly preferably an arylene group with 6 to 10 carbon atoms. Specifically, divalent groups such as benzene rings, biphenyl rings, terphenyl rings, and fluorene rings can be included. 1 The heteroaryl group in the ring is preferably a heteroaryl group with 2 to 24 carbon atoms, more preferably a heteroaryl group with 2 to 20 carbon atoms, and even more preferably a heteroaryl group with 2 to 15 carbon atoms, particularly preferably a heteroaryl group with 2 to 10 carbon atoms. Specifically, examples 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, and indole ring. The compounds may contain divalent groups such as isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, borazolin ring, quinoxaline ring, phthalazine ring, naphthidine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxthia ring, phenoxazine ring, phenthiazine ring, phenazine ring, inazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, and thiathracene ring. At least one hydrogen atom in the compounds represented by the formulas may be substituted with at least one group selected from substituent group Z or with deuterium, for example, with an alkyl group, cyano group, halogen, or deuterium having 1 to 6 carbon atoms.

[0648] As preferred examples, compounds represented by any of the structural formulas listed below can be cited. Furthermore, in the structural formulas listed below, at least one hydrogen atom may be substituted with a halogen, a cyano group, an alkyl group having 1 to 4 carbon atoms (e.g., methyl or tert-butyl), a phenyl group, or a naphthyl group.

[0649] [Chemistry 123]

[0650]

[0651] [Chemistry 124]

[0652]

[0653] [Chemistry 125]

[0654]

[0655] [Chemistry 126]

[0656]

[0657] Hole transport host materials (HH) and electron transport host materials (EH)

[0658] Hole transport host materials (HH) and electron transport host materials (EH) satisfy the following relationship with respect to the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).

[0659] The HOMO of the hole transport host material (HH) is shallower than that of the electron transport host material (EH), and the LUMO of the electron transport host material (EH) is deeper than that of the hole transport host material (HH).

[0660] In addition, it is preferable that the HOMO of the emission dopant is shallower than that of the hole transport host material (HH), or that the LUMO of the emission dopant is deeper than that of the electron transport host material (EH).

[0661] Furthermore, from the viewpoint of promoting rather than hindering the generation of TADF within the emissive layer, the lowest excited triplet energy level (E) of the hole transport host material (HH) and the electron transport host material (EH) is preferred. T1 (Higher than the highest E within the luminescent layer) T1 E emission dopants or auxiliary dopants T1 Specifically, the main material E T1 Preferably, the E of the emission dopant or auxiliary dopant is greater than that of the emission dopant or auxiliary dopant.T1 The voltage is 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. Additionally, the E of the main material... T1 Preferably, it is 2.47 eV or higher, more preferably 2.49 eV or higher, and even more preferably 2.56 eV or higher.

[0662] Furthermore, it is preferable to use a hole-transporting host material in the hole transport layer adjacent to the light-emitting layer, and an electron-transporting host material in the electron transport layer adjacent to the light-emitting layer. This is because it reduces the likelihood of carrier leakage and energy leakage from the light-emitting layer to the adjacent layers, resulting in a high-efficiency organic EL device. The host material (hole-transporting host material) in the light-emitting layer can be the same as or different from the material of the hole transport layer. Similarly, the host material (electron-transporting host material) in the light-emitting layer can be the same as or different from the material of the electron transport layer.

[0663] Examples of preferred hole-transporting host materials (HH) include compounds represented by formula (HH-1), or compounds having a partial structure represented by formula (HH-1) and having a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. These compounds preferably do not contain an imine structure (-N=C-; a ​​partial structure containing a heteroaryl ring), boron (>B-), or cyano (CN). Furthermore, these compounds can also be used alone as host materials.

[0664] [Chemistry 127]

[0665]

[0666] In formula (HH-1),

[0667] Q is greater than O, greater than S, or greater than NA. H ,

[0668] In formula (HH-1), the carbon atom adjacent to the carbon atom bonded to Q in each of the two phenyl groups can bond to each other through L.

[0669] L represents a single bond, >O, >S, or >C(-A) H )2,

[0670] A H It is hydrogen, aryl, or heteroaryl, and >C(-A) H The two A's in )2 H They can be bonded together.

[0671] When the hole-transporting host material includes the structure represented by formula (HH-1) as a partial structure, it may include one of the partial structures, but preferably two or more. In the case of two or more partial structures, the two or more partial structures may be identical or different from each other. The two or more partial structures may be bonded to each other by single bonds, or by sharing any ring contained in the partial structure, or by condensation of any ring contained in the partial structure with each other. The partial structure may further have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy groups.

[0672] The compound represented by formula (HH-1), or a compound having a partial structure represented by formula (HH-1), has a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings contained is preferably 6 or more, more preferably 8 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of single rings; with respect to condensed rings, it is defined as the number obtained by counting the single rings constituting the condensed ring.

[0673] The hole-transporting host material is preferably a compound comprising one or more partial structures selected from the group consisting of a triarylamine structure, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a condensed polycyclic ring containing a phenoxazine or phenothiazine. The hole-transporting host material may comprise one such partial structure, but is preferably comprising two or more. In the case of comprising two or more partial structures, the two or more partial structures may be identical or different from each other.

[0674] Specific examples of hole transport host materials include the following compounds.

[0675] [Chemistry 128]

[0676]

[0677] [Chemistry 129]

[0678]

[0679] [Chemistry 130]

[0680]

[0681] [Chemistry 131]

[0682]

[0683] [Chemistry 132]

[0684]

[0685] [Chemistry 133]

[0686]

[0687] [Chemistry 134]

[0688]

[0689] [Chemistry 135]

[0690]

[0691] [Chemistry 136]

[0692]

[0693] [Chemistry 137]

[0694]

[0695] [Chemistry 138]

[0696]

[0697] [Chemistry 139]

[0698]

[0699] [Chemistry 140]

[0700]

[0701] Among the above, HH-1-1, HH-1-2, HH-1-4~HH-1-12, HH-1-17, HH-1-18, HH-1-20~HH-1-24, HH-1 are preferred -82, HH-1-84~HH-1-89, HH-1-91, HH-1-92, HH-1-106~HH-1-108 and HH-1-109~HH-1-115.

[0702] Examples of electron transport host materials (EH) include compounds represented by formulas (EH-1A) to (EH-1D), or compounds having a partial structure represented by formulas (EH-1A) to (EH-1D) and having a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. Furthermore, these compounds may also be used alone as host materials.

[0703] [Chemistry 141]

[0704]

[0705] In formulas (EH-1A) to (EH-1D),

[0706] Ar is a heteroaryl ring containing N=C as part of the ring structure.

[0707] Z represents a single bond, -O-, -S-, or -N (-A). E )-,

[0708] The carbon atom adjacent to the carbon atom in the Z-junction and the A atom in the Z-junction E They can be bonded to each other through L.

[0709] L represents a single bond, >O, >S, or >C(-A) E )2,

[0710] A E It is an aryl, heteroaryl, or triarylsilyl group, in formula (EH-1C), any one of the A groups is... E It can be a diarylamino group.

[0711] Two A atoms with the same atomic bond E They can bond with each other using L.

[0712] X is C, P, or S.

[0713] When X is C, n=2, m=1.

[0714] When X is P, n=3, m=1.

[0715] When X is S, n=2, m=1~2.

[0716] The compounds represented by formulas (EH-1A) to (EH-1D), or compounds having a partial structure represented by formulas (EH-1A) to (EH-1D), have a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings included is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of single rings; with respect to condensed rings, it is defined as the number obtained by counting the single rings constituting the condensed ring.

[0717] When the electron transport host material comprises the structures represented by formulas (EH-1A) to (EH-1D) as partial structures, it may include one of the partial structures, but preferably two or more. In the case of two or more partial structures, the two or more partial structures may be identical or different from each other. The two or more partial structures may be bonded to each other by single bonds, or by sharing any ring contained in the partial structure, or by condensation of any ring contained in the partial structure with each other. The partial structures may further have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy groups.

[0718] The following compounds can be cited as specific examples of electron transport host materials.

[0719] [Chemistry 142]

[0720]

[0721] [Chemistry 143]

[0722]

[0723] [Chemistry 144]

[0724]

[0725] [Chemistry 145]

[0726]

[0727] [Chemistry 146]

[0728]

[0729] [Chemistry 147]

[0730]

[0731] [Chemistry 148]

[0732]

[0733] [Chemistry 149]

[0734]

[0735] [Chemistry 150]

[0736]

[0737] As the host material for electron transport, it is also preferred to be a polycyclic aromatic compound represented by the following formula (EH-1b), or a polymer of a plurality of polycyclic aromatic compounds having the structure represented by the following formula (EH-1b).

[0738] [Chemistry 151]

[0739]

[0740] In formula (EH-1b),

[0741] R 1 R 2 R 3 R 4 and R 5 (Hereinafter also referred to as "R")1 Each of the substituents ("etc.") can be either hydrogen or a substituent. The substituents need only be selected from the substituent group Z.

[0742] In equation (EH-1b), X 1 and X 2 X can be independently classified as >NR (amine nitrogen), >O, >C(-R)2, >S, or >Se. 1 and X 2 Not simultaneously >C(-R)2,

[0743] The R in >NR and >C(-R)2 is independently hydrogen or a substituent selected from substituent group Z, and may be further substituted by aryl, heteroaryl, alkyl or cycloalkyl (the above are second substituents). The R in >NR and >C(-R)2 may be independently bonded to at least one of the a ring, b ring and c ring through a linking group or a single bond.

[0744] Y 1 Y 2 Y 3 Y 4 Y 5 and Y 6 (Hereinafter also referred to as "Y") 1 "etc." are independently =C(-R)- or =N- (pyridine nitrogen), with at least one being =N- (pyridine nitrogen).

[0745] In the =C(-R)-, R is independently hydrogen or a substituent selected from the substituent group Z.

[0746] The R 1 R 2 R 3 R 4 and R 5 and as the Y 1 ~Y 6 The adjacent groups in the =C(-R)- of the R can be bonded to each other and together with at least one of the rings a, b and c to form an aryl ring or a heteroaryl ring. At least one hydrogen in the formed ring can be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups can be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy (the above are the first substituents), and at least one of these hydrogens can be further substituted by an aryl, heteroaryl, alkyl or cycloalkyl (the above are the second substituents).

[0747] At least one hydrogen atom in the compound and structure represented by formula (EH-1b) may be substituted by a cyano group, a halogen, or a deuterium.

[0748] In formula (EH-1b), R is preferred. 1 R 2 R 3 R 4 and R 5 All are hydrogen, or R 3 and R 4 All are hydrogen, and are chosen freely from R 1 R 2 and R 5 In this group, one or more substituents other than hydrogen are present, while the others are hydrogen. Preferred substituents are alkyl groups, aryl groups substituted with alkyl or heteroaryl groups, heteroaryl groups substituted with alkyl or aryl groups, or diarylamino groups substituted with alkyl or aryl groups. Specifically, alkyl groups are preferably alkyl groups having 1 to 6 carbon atoms (methyl, tert-butyl, etc.), aryl groups are preferably phenyl or biphenyl, and heteroaryl groups are preferably triazine, carbazole (2-carbazole, 3-carbazole, 9-carbazole, etc.), pyrimidinyl, pyridinyl, dibenzofuranyl, or dibenzothiophene. Specific examples include: phenyl, biphenyl, diphenyltriazine, carbazoletriazine, monophenylpyrimidinyl, diphenylpyrimidinyl, carbazoletriazine, pyridinyl, dibenzofuranyl, and dibenzothiophene.

[0749] Y 1 Each of them is independently =C(-R)- or =N-, with at least one being =N-. Y 1 ~Y 6 Either of them can be =N-. Preferably, it is Y. 1 and Y 6 =N- (a ring is a pyrimidine ring), Y 1 Or Y 6 =N- (a ring is a pyridine ring), Y 2 and Y 5 =N- (b- and c-rings are pyridine rings), Y 3 and Y 4 =N- (b- and c-rings are pyridine rings), Y 2 ~Y 5 =N- (both ring b and ring c are pyrimidine rings), Y 1 Y 3 Y 4 and Y 6 =N- (a ring is a pyrimidine ring, b and c rings are pyridine rings), Y 1 Y 2 Y 5 and Y 6 =N- (a ring is a pyrimidine ring, b and c rings are pyridine rings), Y 1 ~Y 6 =N- (a, b, and c rings are pyrimidine rings), Y 2 Or Y5 =N- (the b ring or c ring is a pyridine ring).

[0750] In addition to the above =N- configuration relationship, X is preferred. 1 and X 2 The value is >0, preferably a polycyclic aromatic compound containing a partial structure represented by any of the following formulas.

[0751] [Chemistry 152]

[0752]

[0753] In particular, polycyclic aromatic compounds with partial structures represented by the inclusion formula (EH-1b-N1) have higher E values ​​compared to structures without N. S1 High E T1 Small ΔE S1T1 .

[0754] The following shows specific examples of polycyclic aromatic compounds represented by formula (EH-1b).

[0755] [Chemistry 153]

[0756]

[0757] [Chemistry 154]

[0758]

[0759] [Chemistry 155]

[0760]

[0761] [Chemistry 156]

[0762]

[0763] [Chemistry 157]

[0764]

[0765] [Chemistry 158]

[0766]

[0767] Among the above, preferred ones are EH-1-1 to EH-1-4, EH-1-10, EH-1-21 to EH-1-25, EH-1-32, EH-1-33, EH-1-51 to EH-1-59, EH-1-61, EH-1-66, EH-1-68, EH-1-71, and EH-1-7. 2. EH-1-90, EH-1-94~EH-1-99, EH-1-100, EH-1-101, EH-1-104, EH-1- 115. EH-1-117, EH-1-120, EH-1-122, EH-1-123, EH-1-127~EH-1-130.

[0768] [A combination of hole-transporting host materials and electron-transporting host materials]

[0769] The combination of hole transport host materials and electron transport host materials is based on the HOMO, LUMO, and lowest excited triplet energy level (E) of the hole transport host material, electron transport host material, and dopant material. T1 Use ) to choose.

[0770] Regarding HOMO and LUMO, a combination is selected in which the HOMO (HH) of the hole transport host material is shallower than the HOMO (EH) of the electron transport host material, and the LUMO (EH) of the electron transport host material is deeper than the LUMO (HH) of the hole transport host material. More specifically, a combination in which HOMO (HH) is shallower than HOMO (EH) by 0.10 eV or more, and LUMO (HH) is deeper than HOMO (EH) by 0.10 eV or more, more preferably a combination in which HOMO (HH) is shallower than HOMO (EH) by 0.20 eV or more, and LUMO (HH) is deeper than HOMO (EH) by 0.20 eV or more, and even more preferably a combination in which HOMO (HH) is shallower than HOMO (EH) by 0.25 eV or more, and LUMO (HH) is deeper than HOMO (EH) by 0.25 eV or more.

[0771] Hole-transporting host materials and electron-transporting host materials can be combinations that form an associative complex called an exciplex. It is generally known that exciplexes readily form between materials with a relatively deep LUMO level and materials with a shallow HOMO level. The interaction between the hole-transporting host materials and the electron-transporting host materials, specifically whether an exciplex forms, can be determined as follows: A monolayer film containing only the hole-transporting host material and the electron-transporting host material is formed under the same conditions as the luminescent layer. The emission spectra (fluorescence and phosphorescence spectra) are measured, and the obtained emission spectra are compared with the individual emission spectra of the hole-transporting host material and the electron-transporting host material. It can also be determined as follows: the spectrum of the mixed film containing the hole-transporting host material and the electron-transporting host material shows emission wavelengths that are different from the spectra of both the hole-transporting host material film and the electron-transporting host material film. Specifically, a difference of more than 10 nm in the peak wavelength of the spectrum is sufficient as an indicator.

[0772] Specific examples of combinations of hole-transporting host materials and electron-transporting host materials that do not form excimer complexes include the following combinations. To satisfy the aforementioned HOMO, LUMO, and E... T1 Regarding the physical properties, in hole transport host materials, compounds having carbazole, dibenzofuran, dibenzothiophene, triarylamine, indolocarbazole, and benzoxazinophenazozine as partial structures are preferred; compounds having carbazole, dibenzofuran, and dibenzothiophene as partial structures are more preferred; and compounds having carbazole as a partial structure are even more preferred. Similarly, in electron transport host materials, compounds having pyridine, triazine, phosphine oxide, benzofuran-pyridine, and dibenzoxazinophenaline as partial structures are preferred; compounds having triazine, phosphine oxide, benzofuran-pyridine, and dibenzoxazinophenaline as partial structures are even more preferred; and compounds having triazine are even more preferred.

[0773] More specifically, the hole transport host material is preferably selected from the group consisting of HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1-20 to HH-1-24, HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92 and HH-1-106 to HH-1-108, and the electron transport host material is preferably selected from EH-1-1 to EH-1-4. EH-1-10, EH-1-21~EH-1-25, EH-1-32, EH-1-33, EH-1-51~EH-1-59, EH-1-61, EH-1-71, EH-1-72, EH-1-90, In the group consisting of EH-1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123 and EH-1-127~EH-1-130. As preferred examples of combinations, compounds HH-1-1 and EH-1-22, HH-1-1 and EH-1-23, HH-1-1 and EH-1-24, HH-1-2 and EH-1-22, HH-1-2 and EH-1-23, HH-1-2 and EH-1-24, or HH-1-1 and EH-1-128 can be listed.

[0774] Specific examples of combinations of hole-transporting host materials and electron-transporting host materials for forming excimer complexes include the following combinations. To satisfy the aforementioned HOMO, LUMO, and E... T1 Regarding the physical properties, in hole transport host materials, compounds having carbazole, triarylamine, indolocarbazole, and benzoxazinophenazine as partial structures are preferred, more preferably compounds having triarylamine, indolocarbazole, and benzoxazinophenazine as partial structures are even more preferred, and compounds having triarylamine as a partial structure are even more preferred. Similarly, in electron transport host materials, compounds having pyridine, triazine, phosphine oxide, and benzofuran-pyridine as partial structures are preferred, more preferably compounds having triazine, phosphine oxide, benzofuran-pyridine, and dibenzoxadiazine as partial structures are even more preferred, and compounds having phosphine oxide and triazine are even more preferred.

[0775] More specifically, the hole transport host material is preferably selected from the group consisting of HH-1-1, HH-1-2, HH-1-11, HH-1-12, HH-1-17, HH-1-18, HH-1-23, HH-1-24 and HH-1-115, and the electron transport host material is preferably selected from EH-1-1 to EH-1-4, EH-1-21 to EH-1-25, and EH-1 The group consisting of -51 to EH-1-57, EH-1-59, EH-1-66, EH-1-68, EH-1-90, EH-1-94, EH-1-99, EH-1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123 and EH-1-127 to EH-1-130. Preferred examples of combinations include compounds HH-1-1 and EH-1-21, HH-1-2 and EH-1-21, HH-1-12 and EH-1-94, HH-1-12 and EH-1-117, HH-1-1 and EH-1-130, HH-1-33 and EH-1-117, HH-1-48 and EH-1-117, HH-1-49 and EH-1-117, or HH-1-115 and EH-1-99.

[0776] Furthermore, for specific combinations of hole-transporting host materials and electron-transporting host materials, please refer to: *Organic Electronics* (66 (2019) 227-24), *Advanced Functional Materials* (25 (2015) 361-366), *Advanced Materials* (26 (2014) 4730-4734), *ACS Applied Materials and Interfaces* (8 (2016) 32984-32991), *ACS Applied Materials and Interfaces* (2016, 8, 9806-9810), *ACS Applied Materials and Interfaces* (2016, 8, 32984-32991), and *Journal of Materials Chemistry*. The records can be found in publications such as Chemistry (C, 2018, 6, 8784-8792), Angewante Chemie International Edition (2018, 57, 12380-12384), Advanced Functional Materials (24, 2014, 3970), Advanced Materials (26, 2014, 5684), Synthetic Metals (201, 2015, 49), and Nature Photonics (16, 212-218 (2022)).

[0777] <Auxiliary dopants (thermally active delayed phosphors or phosphorescent materials)>

[0778] The emitting layer preferably includes an emitting dopant, a host material, and an auxiliary dopant. The auxiliary dopant is preferably a thermally active delayed phosphor or a phosphorescent material.

[0779] The polycyclic aromatic compounds represented by formula (I) have emission spectra with narrow half-widths and small ΔE values. S1T1 High TADF properties, deep HOMO, and large steric hindrance make it a preferred candidate for use as an emitter dopant in TAF or PSF elements. Specifically, the polycyclic aromatic compound represented by formula (I) adopts two Y and X...2 and X 4 The structure, with the c-ring bonded to each other at the m-site, results in a narrow half-width emission spectrum and a small ΔE. S1T1 With high TADF properties, it has a deep HOMO due to the presence of a cyano group in the molecule. The interaction with adjacent molecules is suppressed due to the steric hindrance caused by the group represented by formula (Ar). In TAF elements, it can suppress Dexter energy shift from auxiliary dopants, and in PSF elements, it can suppress Dexter energy shift from phosphorescent materials. Therefore, it can be preferably used as an emission dopant for TAF elements or PSF elements.

[0780] In this embodiment, known compounds can be used as the host compound, such as compounds having at least one of a carbazole ring and a furan ring. Preferably, compounds formed by bonding at least one of a furanyl group and a carbazole group with at least one of an aryl group and a heteroaryl group are used. Specific examples include compounds represented by any of formulas (H1), (H2), and (H3), particularly mCP or mCBP, and compounds HH-1-115 and EH-1-99. Additionally, TADF-active compounds can also be used as the host compound. In this embodiment, a combination of a hole-transporting host material and an electron-transporting host material is also preferred as the host.

[0781] From the viewpoint of promoting rather than hindering the generation of TADF within the emitting layer, the lowest excited triplet energy level E(1, T, Sh) of the host compound, determined from the shoulder peak on the short wavelength side of the phosphorescence spectrum peak, is preferably higher than the lowest excited triplet energy levels E(2, T, Sh) and E(3, T, Sh) of the emitting dopant or auxiliary dopant that have the highest lowest excited triplet energy level within the emitting layer. Specifically, compared to E(2, T, Sh) and E(3, T, Sh), the lowest excited triplet energy level E(1, T, Sh) of the host compound is preferably 0.01 eV higher, more preferably 0.03 eV higher, and even more preferably 0.1 eV higher.

[0782] [Thermoactive Delayed Fluorescent Electron]

[0783] A "thermally active delayed fluorescence" refers to a compound that absorbs thermal energy, undergoes a reverse intersystem transition from the lowest excited triplet state to the lowest excited singlet state, and is radioactively inactivated from the lowest excited singlet state, thereby emitting delayed fluorescence. "Thermally active delayed fluorescence" also includes cases where the excitation process from the lowest excited triplet state to the lowest excited singlet state involves a higher-order triplet state. For example, examples include the paper by Monkman et al. from Durham University (Nature Communications (7:13680, Digital Object Identifier, DOI: 10.1038 / ncomms13680)), the paper by Hosokai et al. from the National Institute of Advanced Industrial Science and Technology (SIST) (Science Advances (2017); 3:e1603282)), and the paper by Sato et al. from Kyoto University (Scientific Reports). Reports (7:4820, DOI: 10.1038 / s41598-017-05007-7), a conference presentation by Sato et al. from Kyoto University (98th Spring Meeting of the Chemical Society of Japan, Presentation No.: 2I4-15, "Mechanism of High-Efficiency Luminescence in Organic Electroluminescence Using Diazaboranaphthoanthracene (DABNA) as a Luminescent Molecule," Graduate School of Engineering, Kyoto University), a commentary by Bui et al. (DOI: 10.3762 / bjoc.14.18), a commentary by Duan et al. (DOI: 10.1063 / 1.5143501), a commentary by Ding et al. (DOI: 10.1088 / 1674-4926 / 42 / 5 / 050201), and a commentary by Xie et al. (DOI: (e.g., 10.1002 / adom.202002204). In this invention, a sample containing the target compound is determined to be a "thermally active delayed phosphor" based on the observation of a slow fluorescence component when the fluorescence lifetime is measured at 300 K. Here, a slow fluorescence component refers to a component with a fluorescence lifetime of 0.1 μsec or more. The fluorescence lifetime can be measured, for example, using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics, C11367-01).

[0784] In the luminescent layer that further includes a "thermally active delayed phosphor" as an auxiliary dopant, the polycyclic aromatic compound of the present invention can function as an emission dopant. That is, the "thermally active delayed phosphor" can function as an auxiliary dopant to assist the luminescence of the polycyclic aromatic compound of the present invention.

[0785] In this specification, organic electroluminescent elements that use thermally active delayed phosphors as auxiliary dopants are sometimes referred to as "TAF elements" (TADF Assisting Fluorescence elements).

[0786] The so-called "host compound" in a TAF element refers to a compound whose lowest excited singlet state energy level, determined by the shoulder peak on the short wavelength side of the fluorescence spectrum peak, is higher than the lowest excited singlet state energy level of thermally active delayed phosphors and emission dopants used as auxiliary dopants.

[0787] The thermally active delayed fluorescent (TADF) compounds used in TAF elements are preferably donor-acceptor type thermally active delayed fluorescent (DA-type TADF) compounds: they are designed to use electron-donating substituents called donors and electron-accepting substituents called acceptors to locally exist the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) in the molecule to produce efficient reverse intersystem crossing.

[0788] In this specification, the term "electron-donating substituent" (donor) refers to the substituent and part of the structure that is locally present in the HOMO of a thermally active delayed fluorophore molecule, and the term "electron-accepting substituent" (acceptor) refers to the substituent and part of the structure that is locally present in the LUMO of a thermally active delayed fluorophore molecule.

[0789] Generally, thermally active delayed fluorescent phosphors using donors or acceptors have high spin-orbit coupling (SOC) and low exchange interaction between HOMO and LUMO due to their structure, resulting in low ΔE. S1T1The small size allows for a very fast reverse intersystem crossing speed. By using the polycyclic aromatic compound of the present invention as the emission dopant and a thermally active delayed phosphor (TADF material) as the auxiliary dopant, devices that meet any or all of the requirements for high efficiency, high color purity, and long lifetime can be provided. The thermally active delayed phosphor is any compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound of the present invention. The polycyclic aromatic compound and the thermally active delayed phosphor of the present invention can both be contained in the same layer, or in adjacent layers or other nearby layers.

[0790] As a thermally active delayed phosphor in a TAF element, a compound in which the donor and acceptor are directly or via a spacer can be used, for example. The electron-donating group (donor-like structure) and electron-accepting group (acceptor-like structure) used in the thermally active delayed phosphor of the present invention can, for example, use the structures described in *Chemistry of Materials* (2017, 29, 1946-1963). Examples of donor structures include: carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothiophenecarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazole, tetraphenylcarbazole diamine, phenoxazine, dihydrophenazine, phenthiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylphenyl-1,4-diamine, dimethyltetraphenyldihydroacridine diamine, tetramethyl-dihydro-indoacridine, and diphenyl-dihydrodibenzodiazeline, etc. Examples of receptor-like structures include: sulfonyl diphenyl, benzophenone, phenylene bis(phenyl ketone), benzonitrile, isoniconitrile, o-phthalonitrile, isophthalonitrile, terephthalonitrile, benzotricarbonyl, triazole, oxazole, thiadiazole, benzothiazolium, benzobis(thiazolium), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazafinaene, thioxanone dioxide, dimethylanthrone, anthrone, 5H-cyclohepta[1,2-b:5,4-b']bipyridine, fluorenedicarbonyl, triphenyltriazine, pyrazinedicarbonyl, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonyl, dibenzoquinoxalinedicarbonyl, bis(phenylsulfonyl)benzene, dimethylthioxanone dioxide, thiathronetetraoxide, and tri(dimethylphenyl)borane. In particular, the compound with thermally active delayed fluorescence in the TAF element is preferably a compound having at least one of the following as a partial structure: carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanol, benzonitrile, o-phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, oxadiazole, thiadiazole and benzophenone.

[0791] The compounds used as auxiliary dopants in the emitting layer of a TAF element are thermally active delayed phosphors, and preferably compounds whose emission spectra at least partially overlap with the absorption peak of the emitting dopant. Hereinafter, examples of thermally active delayed phosphor compounds that can be used as the emitting layer in a TAF element are given. However, the compounds that can be used as thermally active delayed phosphors in a TAF element are not limited to the examples given below.

[0792] [Chemistry 159]

[0793]

[0794] [Chemistry 160]

[0795]

[0796] [Chemistry 161]

[0797]

[0798] [Chemistry 162]

[0799]

[0800] [Chemistry 163]

[0801]

[0802] [Chemistry 164]

[0803]

[0804] [Chemistry 165]

[0805]

[0806] [Chemistry 166]

[0807]

[0808] [Chemistry 167]

[0809]

[0810] [Chemistry 168]

[0811]

[0812] [Chemistry 169]

[0813]

[0814] [Chemistry 170]

[0815]

[0816] [Chemistry 171]

[0817]

[0818] [Chemistry 172]

[0819]

[0820] [Chemistry 173]

[0821]

[0822] [Chemistry 174]

[0823]

[0824] [Chemistry 175]

[0825]

[0826] [Chemistry 176]

[0827]

[0828] [Chemistry 177]

[0829]

[0830] [Chemistry 178]

[0831]

[0832] Furthermore, as a thermally active delayed phosphor, any compound represented by any of the following formulas (AD1), (AD2), and (AD3) may also be used.

[0833] [Chemistry 179]

[0834]

[0835] In the aforementioned formulas (AD1), (AD2), and (AD3),

[0836] M is independently a single bond, -O-, >N-Ar, or >CAr2, and from the viewpoint of the depth of the HOMO of the formed partial structure and the height of the excited singlet and triplet energy levels, it is preferably a single bond, -O-, or >N-Ar. J is a spacer structure separating the donor and acceptor partial structures, and is independently an arylene group with 6 to 18 carbon atoms, and from the viewpoint of the magnitude of conjugation from the donor and acceptor partial structures, it is preferably an arylene group with 6 to 12 carbon atoms. More specifically, examples include: phenylene, methylphenylene, and dimethylphenylene. Q is independently =C(-H)- or =N-, and from the viewpoint of the shallowness of the LUMO of the formed partial structure and the height of the excited singlet and triplet energy levels, it is preferably =N-. Ar is independently hydrogen, an aryl group with 6 to 24 carbons, a heteroaryl group with 2 to 24 carbons, an alkyl group with 1 to 12 carbons, or a cycloalkyl group with 3 to 18 carbons. From the viewpoint of the depth of the HOMO of the formed partial structure and the height of the excited singlet and triplet energy levels, it is preferably hydrogen, an aryl group with 6 to 12 carbons, a heteroaryl group with 2 to 14 carbons, an alkyl group with 1 to 4 carbons, or a cycloalkyl group with 6 to 10 carbons. More preferably, it is hydrogen, phenyl, tolyl, xylyl, mesitylelel, biphenyl, pyridyl, bipyridyl, triazine, carbazole, dimethylcarbazole, di-tert-butylcarbazole, benzimidazole, or phenylbenzimidazole. More preferably, it is hydrogen, phenyl, or carbazole. m is 1 or 2. n is an integer from 1 to (6-m), and from the viewpoint of steric hindrance, it is preferably an integer from 4 to (6-m). Furthermore, at least one hydrogen atom in the compounds represented by the formulas may be substituted with halogen or deuterium.

[0837] More specifically, the compounds used as the second component of this form are 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz.

[0838] The compound used as the second component of this form can be an donor-acceptor type TADF compound represented by DA, in which an donor D is directly bonded to an acceptor A or is bonded via a linker group. However, compounds with a structure represented by the following formula (DAD1) having multiple donor Ds directly bonded to or bonded via a linker group to an acceptor A are preferred as they improve the properties of organic electroluminescent elements.

[0839] (D1 -L 1 )nA 1 (DAD1)

[0840] Formula (DAD1) contains the compound represented by the following formula (DAD2).

[0841] D 2 -L 2 -A 2 -L 3 -D 3 (DAD2)

[0842] In equations (DAD1) and (DAD2), D 1 D 2 and D 3 Each donor base can be represented independently. The structure of the donor base described above can be adopted. A 1 and A 2 Each receptor group can be represented independently. The structure described above can be used as the receptor group. L 1 L 2 and L 3 Each can be represented independently as a single bond or a conjugated linker. The conjugated linker is a spacer structure separating the donor and acceptor groups, preferably an arylene group with 6 to 18 carbon atoms, more preferably an arylene group with 6 to 12 carbon atoms. 1 L 2 and L 3 Furthermore, it is preferred that each of the following is independently phenylene, methylphenylene, or dimethylphenylene. In formula (DAD1), n ​​is 2 or more, and represents A. 1 The integer less than the maximum number of substitutions. n can be chosen, for example, in the range of 2 to 10, or in the range of 2 to 6. When n is 2, it represents the compound represented by formula (DAD2). n D 1 They can be the same or different, n L 1 They may be the same or different. Preferred examples of compounds represented by formulas (DAD1) and (DAD2) include 2PXZ-TAZ or compounds described below, but the second component that may be used in this invention is not limited to these compounds.

[0843] [Chemistry 180]

[0844]

[0845] [Phosphorescent materials (auxiliary dopants)]

[0846] In the luminescent layer, phosphorescent materials can be used as auxiliary dopants. In this specification, organic electroluminescent elements using phosphorescent materials as auxiliary dopants are sometimes referred to as phosphorescent auxiliary elements: phosphor-sensitized fluorescent elements, PSF elements. Phosphorescent materials utilize intramolecular spin-orbit interactions (heavy atom effect) caused by metal atoms to obtain luminescence from the excited triplet state. For example, luminescent metal complexes can be used as such phosphorescent materials. Examples of luminescent metal complexes include compounds represented by the following formulas (B-1) and (B-2).

[0847] [Chemistry 181]

[0848]

[0849] In formula (B-1), M is selected from at least one of the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu, n is an integer from 1 to 3, and "XY" are independently bidentate ligands.

[0850] In formula (B-2), M is selected from at least one of the group consisting of Pt, Re and Cu, and "WXYZ" is a tetradentate ligand.

[0851] In equation (B-1), from the viewpoint of efficiency and lifespan, M is preferably Ir, and n is preferably 3.

[0852] In equation (B-2), from the viewpoint of efficiency and lifespan, M is preferably Pt.

[0853] The ligand (XY) in formula (B-1) has at least one ligand selected from the group consisting of the following. The ligand (WXYZ) in formula (B-2) has at least one ligand selected from the group consisting of the following as part thereof.

[0854] [Chemistry 182]

[0855]

[0856] In the formula,

[0857] It bonds to the central metal M at ---.

[0858] Y is independently BR e NR e PR e ,O,S,Se,C=O,S=O,SO2,CR e R f SiR e R f Or GeRe R f ,

[0859] The aromatic carbons CH in the ring can be independently substituted to N.

[0860] R e and R f They can be arbitrarily condensed or bonded to form rings.

[0861] R a R b R c and R d Each is independently represented as either unsubstituted or substituted up to 1, representing the largest number that can be substituted.

[0862] R a R b R c R d R e and R f Each of these can be independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, mercapto, or a combination thereof.

[0863] Among them, R a R b R c and R d Any two adjacent substituents can condense or bond to form a ring, or they can form a polydentate ligand.

[0864] Examples of compounds represented by formula (B-1) include: Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium (III) (fac-tris(2-(3-p-xylyl)phenyl)pyridinium(III)), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(aca c), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(2-phq)3, Ir(BT)2 (acac), Ir(DMP)3, Ir(Mphq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Pi q)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, etc.

[0865] Other compounds that can be listed, for example, are those represented by formula (B-1).

[0866] [Chemistry 183]

[0867]

[0868] [Chemistry 184]

[0869]

[0870] [Chemistry 185]

[0871]

[0872] [Chemistry 186]

[0873]

[0874] Alternatively, iridium complexes described in Japanese Patent Application Publication No. 2006-089398, Japanese Patent Application Publication No. 2006-080419, Japanese Patent Application Publication No. 2005-298483, Japanese Patent Application Publication No. 2005-097263, and Japanese Patent Application Publication No. 2004-111379, U.S. Patent Application Publication No. 2019 / 0051845, Energy Chemistry (EnergyChem) (6, 2, 100120 (2024)), or Advanced Materials (26: 7116-7121), NPG Asia Materials (13, 53 (2021)), and Applied Physics Letters may also be used. Letters (117, 253301 (2020)), Light-Emitting Diode - An Outlook On the Empirical Features and Its Recent Technological Advancements (Chapter 5), Journal of Material Chemistry C (2022, 10, 210-218), Advanced Materials (35, 2303066 (2023)), Communications Chemistry (8, 140 (2025)), Advanced Optical Materials (11, 220269 (2023)), Nature Communications (15, 2977 (2024)), Chemical Engineering The platinum complex described in *Journal of Chemical Research* (505, 159169 (2025)) and *ACS Applied Materials & Interfaces* (14, 30, 34901-34908 (2022)) may also be used. Alternatively, the complex described in *Chemistry Society Review* (54, 266-340 (2025)) may also be used.

[0875] <Other Doped Materials>

[0876] The polycyclic aromatic compound represented by formula (I) can be used in combination with other dopant materials. In a single luminescent layer, the other dopant materials are preferably less than 100% by mass, more preferably less than 50% by mass, even more preferably less than 30% by mass, and particularly preferably less than 10% by mass, relative to the total mass of the polycyclic aromatic compound represented by formula (I). Known compounds can be used as other dopant materials, and a variety of materials can be selected according to the desired luminescence color. Specifically, examples include: phenanthrene, anthracene, pyrene, tetraphenylene, pentaphenylene, perylene, naphthylpyrene, dibenzopyrene, rubrene, and condensation ring derivatives such as benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bis(styrene)anthracene derivatives, or... Distyrene-based derivatives such as stilbene (Japanese Patent Application Publication No. 1-245087), stilbene-based arylene derivatives (Japanese Patent Application Publication No. 2-247278), diazabenzodiindene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimethyltrimethylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobenzofuran and other isobenzofuran derivatives, dibenzofuran Coumarin derivatives, including 7-dialkylaminocoumarin derivatives, 7-piperidinylcoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, etc.; dicyanomethylenepyran derivatives; dicyanomethylenethiaran derivatives; polymethine derivatives; anthocyanin derivatives; oxobenzanthracene derivatives; and xanthones derivatives. Rhodamine derivatives, fluorescein derivatives, pyranone derivatives, quinolone derivatives, acridine derivatives, oxazine derivatives, phenyl ether derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furanopyridine derivatives, 1,2,5-thiadiazolpyrene derivatives, pyrrole methylene derivatives, violetone derivatives, pyrrolopyrrole derivatives, squaric acid lactone salt derivatives, violet anthrone derivatives, phenazine derivatives, acridineone derivatives, denitroflavin derivatives, fluorene derivatives, and benzo[a]fluorene derivatives, etc.

[0877] Other dopant materials are preferably boron-containing polycyclic aromatic compounds as described in International Publication No. 2015 / 102118, International Publication No. 2020 / 162600, and Japanese Patent Application Publication No. 2021-077890, paragraphs 0097 to 0269.

[0878] 2-1-6. Electron injection layer and electron transport layer in organic electroluminescent devices

[0879] The electron injection layer 107 efficiently injects electrons migrating from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 efficiently transports electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or more electron transport / injection materials, or by forming a mixture of electron transport / injection materials and a polymer binder.

[0880] The electron injection / transport layer is a layer responsible for the injection and transport of electrons from the cathode. Ideally, it should have high electron injection efficiency and efficient transport of the injected electrons. Therefore, materials with high electron affinity and high electron mobility, resulting in excellent stability and minimizing the formation of impurities that could become traps during manufacturing and use, are preferred. However, considering the balance between hole and electron transport, materials that effectively prevent unrecombined holes from the anode from flowing to the cathode can achieve the same effect of improving luminous efficiency as materials with high electron transport capabilities, even if their electron transport capability is not very high. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that effectively prevents hole migration.

[0881] The material (electron transport material) used to form the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds commonly used as electron transport compounds in photoconductive materials, and known compounds used in electron injection layers and electron transport layers of organic EL elements.

[0882] The materials used in the electron transport layer or electron injection layer are preferably compounds containing at least one of the following: compounds containing an aromatic ring or heteroaromatic ring comprising one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their condensed ring derivatives; and metal complexes with electron-accepting nitrogen. Specifically, examples include: condensed ring aromatic ring derivatives such as naphthalene and anthracene; styryl aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl; violet ketone derivatives; coumarin derivatives; naphthalenedicarboximide derivatives; quinone derivatives such as anthraquinone or biphenylquinone; phosphine oxide derivatives; aryl nitrile derivatives; and indole derivatives. Examples of metal complexes with electron-accepting nitrogen include: hydroxyazole complexes such as hydroxyphenyloxazole complexes; azomethyl base complexes; cycloheptatrienolone metal complexes; flavonol metal complexes; and benzoquinone metal complexes. These materials can be used alone or in combination with different materials.

[0883] In addition, specific examples of other electron-transfer compounds include: pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthrene-rhein derivatives, violet ketone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole compounds, gallium complexes, pyrazole derivatives, and perfluorinated phenylene derivatives. Biological derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirodifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2':6',2''-terpyridine-4'-yl)benzene, naphthidine derivatives (bis(1-naphthyl)-4-(1,8-naphthidin-2-yl)phenylphosphine oxide, etc.), aldehyde azo derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyrene derivatives, etc.

[0884] Alternatively, metal complexes with electron-accepting nitrogen can be used, such as hydroxyquinoline metal complexes or hydroxyphenyloxazole complexes, azomethyl base complexes, cycloheptatrienolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0885] The material can be used alone or in combination with different materials.

[0886] The preferred materials are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and hydroxyquinoline-based metal complexes.

[0887] The electron transport layer or electron injection layer may also contain a substance that can reduce the material forming the electron transport layer or electron injection layer. The reducing substance can be any substance with a certain reducing property, and for example, preferably at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

[0888] Preferred reducing agents include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV), or alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 eV–2.5 eV), or Ba (work function 2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Among these, alkali metals such as K, Rb, or Cs are more preferred, Rb or Cs are more preferred, and Cs is most preferred. These alkali metals have particularly high reducing power, and by adding a relatively small amount of these alkali metals to the material forming the electron transport layer or electron injection layer, the luminous brightness or lifetime of organic EL devices can be improved. Furthermore, combinations of two or more alkali metals are preferred as reducing agents with a work function of 2.9 eV or less, and combinations containing Cs are particularly preferred, such as Cs with Na, Cs with K, Cs with Rb, or combinations of Cs with Na and K. By including Cs, the reducing ability can be effectively utilized, and by adding it to the material forming the electron transport layer or electron injection layer, the luminous brightness or lifetime of organic EL devices can be improved.

[0889] 2-1-7. Cathode in Organic Electroluminescent Devices

[0890] The cathode 108 functions to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0891] The material forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, and the same material as the material forming the anode 102 can be used. Preferred materials include metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloys, magnesium-indium alloys, lithium fluoride / aluminum and other aluminum-lithium alloys, etc.). To improve the electron injection efficiency and thus enhance the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, generally, these low work function metals are unstable in the atmosphere in most cases. To improve this, methods such as doping the organic layer with trace amounts of lithium, cesium, or magnesium and using a highly stable electrode are known. Inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used as other dopants. However, these are not limited to these.

[0892] Furthermore, the following are preferred examples: To protect the electrodes, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys of these metals, as well as inorganic materials such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymers are layered. There are no particular restrictions on the methods used to fabricate these electrodes, as long as they are methods that achieve conductivity, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0893] 2-1-8. Fabrication method of organic electroluminescent elements

[0894] The layers constituting an organic electroluminescent (EL) element can be formed by depositing thin films of the materials to be formed into each layer using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating, casting, and coating. The film thickness of each layer formed in these methods is not particularly limited and can be appropriately set according to the properties of the material, but is typically in the range of 2 nm to 5000 nm. The film thickness can usually be measured using a quartz oscillating film thickness measuring device. When using vapor deposition for thin film formation, the vapor deposition conditions vary depending on the type of material, the crystal structure of the target film, and the associative structure. Generally, the preferred vapor deposition conditions are a boat heating temperature of +50°C to +400°C and a vacuum degree of 10... -6 Pa~10 -3 The Pa, evaporation rate (0.01 nm / sec to 50 nm / sec), substrate temperature (-150℃ to +300℃), and film thickness (2 nm to 5 μm) are appropriately set within the range.

[0895] When a DC voltage is applied to the organic EL element obtained in the manner described, it is sufficient to apply the voltage with the anode as the positive polarity and the cathode as the negative polarity. If a voltage of approximately 2 V to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode and both). Furthermore, the organic EL element also emits light when a pulsed current or alternating current is applied. Moreover, the waveform of the applied alternating current can be arbitrary.

[0896] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device including an anode / hole injection layer / hole transport layer / light-emitting layer containing a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described.

[0897] <Evaporation Method>

[0898] On a suitable substrate, an anode is fabricated by forming a thin film of anode material using a vapor deposition method, followed by the formation of a hole injection layer and a hole transport layer on the anode. A light-emitting layer is then formed by co-depositing a host material and a dopant material onto the light-emitting layer. An electron transport layer and an electron injection layer are formed on the light-emitting layer, and finally, a thin film containing a cathode material is formed using a vapor deposition method to serve as the cathode, thereby obtaining the target organic EL device. Alternatively, the fabrication sequence of the organic EL device can be reversed, with the order being cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0899] <Wet film formation method>

[0900] A low-molecular-weight compound capable of forming organic layers of an organic EL element is prepared as a liquid composition for forming organic layers, and used to perform a wet film-forming method. In the absence of a suitable organic solvent for dissolving the low-molecular-weight compound, a composition for forming organic layers may also be prepared from polymeric compounds, wherein the polymeric compound is polymerized together with other monomers or main-chain polymers that are reactive compounds formed by substituting reactive substituents into the low-molecular-weight compound and thus possess solubility functionality.

[0901] Wet film-forming methods generally form a coating film through the following steps: a coating step of applying an organic layer-forming composition to a substrate, and a drying step of removing the solvent from the coated organic layer-forming composition. In cases where the polymer compound has crosslinking substituents (also referred to as a crosslinked polymer compound), further crosslinking is achieved through the drying step to form a polymer crosslinked body. Depending on the coating step, methods using a spin coater are called spin coating, methods using a slot coater are called slot coating, methods using a printing plate are called gravure, offset, reverse offset, or flexographic printing, methods using an inkjet printer are called inkjet printing, and methods using a mist are called spraying. Drying steps include air drying, heating, and vacuum drying. The drying step can be performed only once or multiple times using different methods or conditions. Alternatively, different methods can be used, such as calcination under reduced pressure.

[0902] Wet film deposition refers to film deposition methods that use solutions, such as partial printing (inkjet printing), spin coating, casting, and coating. Unlike vacuum evaporation, wet film deposition does not require expensive vacuum evaporation equipment and can be performed under atmospheric pressure. Furthermore, wet film deposition allows for large-area or continuous production, resulting in lower manufacturing costs.

[0903] On the other hand, compared with vacuum evaporation, wet film deposition methods are sometimes difficult to laminate. When using wet film deposition methods to fabricate laminated films, it is necessary to prevent the dissolution of the lower layer caused by the composition of the upper layer, and to use compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (mutually insoluble solvents). However, even with these techniques, it is difficult to apply wet film deposition methods to all types of film coating.

[0904] Therefore, the following method is generally used: a wet film deposition method is used to form only a few layers, and a vacuum evaporation method is used to form the remaining layers, thereby fabricating organic EL devices.

[0905] For example, the following describes a procedure for fabricating organic EL elements using a wet film deposition method.

[0906] (Procedure 1) Film formation of the anode using vacuum evaporation method

[0907] (Procedure 2) Film formation using a wet film formation method of a composition for forming a hole injection layer containing a material for the hole injection layer.

[0908] (Procedure 3) Film formation of a composition for forming a hole transport layer containing a material for the hole transport layer using a wet film formation method.

[0909] (Procedure 4) Film formation using a wet film formation method for a composition comprising a host material and a dopant material for forming a light-emitting layer.

[0910] (Procedure 5) Electron transport layer film formation using vacuum evaporation

[0911] (Procedure 6) Electron injection layer film formation using vacuum evaporation method

[0912] (Program 7) Film formation of the cathode using vacuum evaporation method

[0913] By going through the aforementioned process, an organic EL element comprising an anode / hole injection layer / hole transport layer / light-emitting layer containing host material and dopant material / electron transport layer / electron injection layer / cathode can be obtained.

[0914] Of course, for the electron transport layer and the electron injection layer, a layer-forming composition containing materials for the electron transport layer and the electron injection layer, respectively, can be used to form the film by a wet film-forming method. In this case, it is preferable to use a method that prevents the dissolution of the underlying light-emitting layer, or a method that forms the film from the cathode side in the opposite direction to the above procedure.

[0915] <Other film-forming methods>

[0916] Laser-induced thermal imaging (LITI) can be used in the film formation of compositions for forming organic layers. LITI refers to a method of heating and vaporizing a compound attached to a substrate using a laser, and the compositions for forming organic layers can be used in materials coated on a substrate.

[0917] <Any process>

[0918] Appropriate processing steps, cleaning steps, and drying steps can be added before and after each film-forming process. Examples of processing steps include: exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using appropriate solvents, and heat treatment. Furthermore, a series of steps for creating the bank can also be listed.

[0919] Photolithography can be used in the fabrication of the embankment. Positive and negative resist materials can be used as embankment materials suitable for photolithography. Alternatively, printing methods capable of creating patterns, such as inkjet printing, gravure printing, reverse lithography, and screen printing, can also be used. In these cases, permanent resist materials can also be used.

[0920] <Organic layer-forming compositions used in wet film-forming methods>

[0921] Organic layer forming compositions are obtained by dissolving low-molecular-weight compounds capable of forming organic EL elements, or high-molecular-weight compounds obtained by polymerizing said low-molecular-weight compounds, in an organic solvent. For example, a light-emitting layer forming composition contains at least one dopant material, namely a polycyclic aromatic compound (or its polymeric form), as a first component; at least one host material, as a second component; and at least one organic solvent, as a third component. The first component functions as the dopant component of the light-emitting layer obtained from the composition, and the second component functions as the host component of the light-emitting layer. The third component functions as a solvent for dissolving the first and second components in the composition, and provides a smooth and uniform surface shape during coating by utilizing the controlled evaporation rate of the third component itself.

[0922] <Organic solvent>

[0923] The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, film-forming properties, the presence or absence of coating defects, surface roughness, and smoothness can be controlled and improved. Furthermore, when using inkjet printing for film formation, the meniscus stability at the inkjet head's pinhole can be controlled, and ejection performance can be controlled / improved. Moreover, by controlling the film drying rate and the orientation of derivative molecules, the electrical properties, luminescent properties, efficiency, and lifetime of organic EL devices having an organic layer obtained from the aforementioned composition for forming an organic layer can be improved.

[0924] After film formation, the organic solvent is removed from the coating film through drying processes such as vacuum, reduced pressure, and heating. When heating is performed, from the viewpoint of improving film formation properties, it is preferable to heat at a temperature below +30°C of the glass transition temperature (Tg) of at least one solute. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at a temperature above -30°C of the glass transition temperature (Tg) of at least one solute. Even if the heating temperature is below the boiling point of the organic solvent, the organic solvent is sufficiently removed due to the thin film. Additionally, multiple drying processes can be performed at different temperatures, and various drying methods can be used in combination.

[0925] (2) Specific examples of organic solvents

[0926] Examples of organic solvents used in compositions for forming organic layers include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents with a diester skeleton, and fluorine-containing solvents, but these are not limited to these. Furthermore, solvents can be used alone or in mixtures.

[0927] <Any ingredient>

[0928] The composition for forming organic layers may also contain any components without impairing its properties. Examples of such components include adhesives and surfactants.

[0929] <Composition and Properties of the Composition for Organic Layer Formation>

[0930] The content of each component in the organic layer forming composition is determined from the perspectives of good solubility, storage stability and film-forming properties of each component in the composition, high quality of the coating obtained from the composition, good ejection properties when using inkjet printing, and good electrical properties, luminescence properties, efficiency and lifespan of the organic EL element with the organic layer made using the composition.

[0931] The composition for forming an organic layer can be manufactured by appropriately selecting the components through stirring, mixing, heating, cooling, dissolving, dispersing, etc., using known methods. Alternatively, after preparation, it can be appropriately subjected to filtration, degassing (also known as degassing), ion exchange treatment, and inert gas replacement / sealing treatment, etc.

[0932] 2-1-9. Examples of applications of organic electroluminescent elements

[0933] This invention can also be applied to display devices that include organic EL elements or lighting devices that include organic EL elements.

[0934] Display devices or lighting devices including organic EL elements can be manufactured by known methods such as connecting the organic EL element of this embodiment to a known driving device, and can be driven by known driving methods such as DC driving, pulse driving, AC driving, etc.

[0935] Examples of display devices include panel displays such as color flat panel displays and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Application Publication No. 10-335066, Japanese Patent Application Publication No. 2003-321546, and Japanese Patent Application Publication No. 2004-281086). Furthermore, examples of display methods include matrix displays and segmented displays. Moreover, matrix displays and segmented displays can coexist on the same panel.

[0936] In a matrix, pixels for display are arranged two-dimensionally in a grid or mosaic pattern, so that text or images are displayed by the collection of pixels. The shape or size of the pixels is determined by the application. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with one side less than 300 μm are usually used. In the case of large displays such as screens, pixels with one side in the millimeter range are used. In the case of monochrome display, pixels of the same color are simply arranged. In the case of color display, red, green, and blue pixels are displayed side by side. In these cases, triangular and striped patterns are typical. Moreover, the driving method of the matrix can be either a line-sequential driving method or an active matrix. Line-sequential driving has the advantage of simple structure, but when considering operating characteristics, sometimes an active matrix is ​​superior. Therefore, the driving method also needs to be selected according to the application.

[0937] In the segmented method (type), a pattern is formed to display pre-determined information, and the determined area is illuminated. Examples include: time or temperature displays in digital clocks or thermometers, operating status displays in audio equipment or induction cookers, and panel displays in automobiles.

[0938] Examples of lighting devices include indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Application Publication Nos. 2003-257621, 2003-277741, and 2004-119211). Backlights are primarily used to improve the visibility of display devices that do not emit light themselves, and are used in liquid crystal displays, clocks, audio devices, automotive panels, display boards, and signs. In particular, for backlights used in personal computers where thinning is becoming a challenge in liquid crystal displays, considering that existing methods are difficult to make thinner due to the inclusion of fluorescent lamps or light guide plates, the backlight using the light-emitting element of this embodiment is characterized by its thinness and light weight.

[0939] 2-2. Other organic devices

[0940] In addition to being used in the aforementioned organic electroluminescent elements, the polycyclic aromatic compounds of the present invention can also be used in the fabrication of organic field-effective transistors, organic thin-film solar cells, or organic photodiodes (organic photodetectors).

[0941] An organic field-effect transistor (FET) is a transistor that controls current by using an electric field generated by a voltage input. In addition to active and drain electrodes, it also has a gate electrode. An organic field-effect transistor works as follows: when a voltage is applied to the gate electrode, an electric field is generated, which can arbitrarily block the flow of electrons (or holes) between the source and drain electrodes to control the current. Compared to a single transistor (bipolar transistor), FETs are easier to miniaturize and are commonly used as components in integrated circuits.

[0942] Regarding the structure of an organic field-effective transistor, generally, the source electrode and drain electrode are simply provided in contact with the organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and the gate electrode is provided in contact with an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following.

[0943] (1) Substrate / Gate electrode / Insulator layer / Source electrode, Drain electrode / Organic semiconductor active layer

[0944] (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode, drain electrode

[0945] (3) Substrate / Organic semiconductor active layer / Source electrode, drain electrode / Insulator layer / Gate electrode

[0946] (4) Substrate / source electrode, drain electrode / organic semiconductor active layer / insulator layer / gate electrode

[0947] Organic field-active transistors constructed in this way can be used as pixel driving switching elements in liquid crystal displays or organic electroluminescent displays with active matrix driving.

[0948] Organic thin-film solar cells have a structure in which an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, such as ITO, are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compounds of the present invention, depending on their physical properties, can be used as materials for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer. In organic thin-film solar cells, the polycyclic aromatic compounds of the present invention can function as hole transport materials or electron transport materials. In addition to the aforementioned layers, organic thin-film solar cells may also appropriately include hole blocking layers, electron blocking layers, electron injection layers, hole injection layers, smoothing layers, etc. In organic thin-film solar cells, known materials for organic thin-film solar cells can be appropriately selected and combined.

[0949] Organic photodiodes are mechanisms that use organic materials to convert light into electrical signals; for example, they can be used as organic light-receiving elements or organic light detectors. An organic photodiode comprises an organic layer containing a light absorber and has a sandwich structure in which the organic layer is held as an active layer by electrodes.

[0950] The polycyclic aromatic compounds of the present invention can be used to form the active layer of organic photodiodes.

[0951] Generally, the active layer contains donor compounds (electron-donating compounds) and acceptor compounds (electron-accepting compounds). After light is absorbed by the active layer, it moves to the donor-acceptor interface through an excited state, inducing charge separation. Subsequently, the generated holes and electrons are captured by the electrodes to generate an electric current.

[0952] On the other hand, the polycyclic aromatic compounds of the present invention, which exhibit multiple resonance effects, can be used as light absorbers to form an active layer as a single component (Advanced Materials, Adv. Mater. (2024, 2414465)). That is, the active layer can be formed using only the polycyclic aromatic compounds of the present invention.

[0953] Furthermore, the polycyclic aromatic compounds of the present invention can also be used as donor or acceptor compounds in the active layer, depending on the selection of substituents. In this case, the combined acceptor or donor compound can be a polymer, an ionic compound, a metal complex, or an inorganic material; in the case of a polymer, a crosslinking agent may also be added.

[0954] Examples of donor compounds that combine with the polycyclic aromatic compounds of the present invention include tetrathiotetraphenyl. Examples of polymeric materials include poly(9,9-di-n-octylfluorenyl-2,7-diyl)-co-1,4-benzo-(2,1,3)-thiadiazole (F8BT) and poly(9,9-din-octylfluorene) (PFO). Furthermore, as inorganic materials, alkali metals, alkaline earth metals, rare earth metals, or metals belonging to Group 13 of the periodic table, as well as their oxides or carbonates, can be used, such as lithium, cesium, magnesium, calcium, indium, ytterbium, lithium oxide, and cesium carbonate.

[0955] Examples of acceptor compounds that can be combined with the polycyclic aromatic compounds of the present invention include 7,7,8,8,-tetracyano-2,3,5,6-tetrafluoroquinodimethane (F4-TCNQ) and tetrachloro-1,4-benzoquinone (chloroquinone). Additionally, molybdenum oxide, tin oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide can be used as inorganic materials.

[0956] When the active layer contains both donor and acceptor compounds, methods such as dissolving and mixing them together (bulk heterojunction) or bonding them separately into a planar shape (parallel heterojunction) can be used, and the choice can be made by considering the characteristics of the compounds used. Alternatively, materials with quantum dot properties can be mixed to form a nanocomposite active layer (Advanced Materials (2016, 28, 2043-2048)).

[0957] In addition to a pair of electrodes and an active layer disposed between the electrodes, organic photodiodes may also have hole-blocking layers and electron-blocking layers. Typically, hole-blocking layers and electron-blocking layers are disposed above and below the active layer, grounded, thereby enabling the placement of anode and cathode electrodes. Examples of such structures include the following. Depending on the characteristics of the active layer, the hole-blocking or electron-blocking layer may sometimes be omitted; alternatively, layers functioning as electron or hole transport layers may be added.

[0958] (1) Substrate / Anode electrode / Electron blocking layer / Active layer / Hole blocking layer / Cathode electrode

[0959] (2) Substrate / Cathode electrode / Hole blocking layer / Active layer / Electron blocking layer / Anode electrode

[0960] Inorganic or polymeric materials can be used in the electron blocking layer and hole blocking layer. For example, poly(3,4-ethylenedioxythiophene / poly(4-styrene sulfonate), PEDOT / PSS, can be used as a polymeric material.

[0961] Regarding organic photodiodes, in addition to the above, see also: *Advanced Materials* (2016, 28, 4766), *Advanced Optical Materials* (2024, 12, 2303216), *Advanced Materials* (2016, 28, 2043), *Nature Communications* (2020, 11, 2871), *Nano Letters* (2017, 17, 1995), *Advanced Materials* (2017, 29, 1702184), and *Chemistry Materials* (2021, 33, 5147), etc.

[0962] 3. Wavelength conversion materials

[0963] The polycyclic aromatic compounds of this invention can be used as wavelength conversion materials.

[0964] Currently, research is actively underway to apply multicolor technology based on color conversion to liquid crystal displays (LCDs), organic EL displays, and lighting. Color conversion refers to converting light emitted from a light source into light with longer wavelengths, such as converting ultraviolet or blue light into green or red light. By film-coating a wavelength conversion material with this color conversion function, for example, and combining it with a blue light source, the three primary colors—blue, green, and red—can be extracted from the blue light source, resulting in white light. Using this white light source, formed by combining a blue light source with a wavelength conversion film with color conversion function, as a light source unit, and combining it with a liquid crystal driving section and color filters, a full-color display can be fabricated. Alternatively, without a liquid crystal driving section, it can be used directly as a white light source, for example, as a white light source for light-emitting diode (LED) lighting. Furthermore, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green and red light, a full-color organic EL display without a metal mask can be fabricated. Furthermore, by using blue microLEDs as a light source and combining them with wavelength conversion films that convert blue light into green and red light, it is possible to produce low-cost full-color microLED displays.

[0965] The polycyclic aromatic compounds of the present invention can be used as the wavelength conversion material. A wavelength conversion material containing the polycyclic aromatic compounds of the present invention can be used to convert ultraviolet light or light from a light source or light-emitting element that generates blue light into green light with a color purity suitable for use in a display device (a display device utilizing organic EL elements or a liquid crystal display device). The converted color can be adjusted by appropriately selecting the substituents of the polycyclic aromatic compounds of the present invention, the adhesive resin used in the wavelength conversion composition described later, etc. The wavelength conversion material is prepared as a wavelength conversion composition containing the polycyclic aromatic compounds of the present invention. Alternatively, the wavelength conversion composition can also be used to form a wavelength conversion film.

[0966] In addition to the polycyclic aromatic compounds of the present invention, the wavelength conversion composition may also contain a binder resin, other additives, and a solvent. As a binder resin, for example, the resin described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283 may be used. As other additives, compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283 may be used. As a solvent, refer to the description of the solvent contained in the composition for forming the light-emitting layer.

[0967] The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. As a method for producing the wavelength conversion layer from the wavelength conversion composition, known film formation methods can be referenced. The wavelength conversion film may contain only a wavelength conversion layer formed from a composition comprising the polycyclic aromatic compounds of the present invention, or it may contain other wavelength conversion layers (e.g., a wavelength conversion layer that converts blue light to green or red light, or a wavelength conversion layer that converts blue or green light to red light). Furthermore, the wavelength conversion film may also include a substrate layer or a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[0968] [Example]

[0969] The present invention will be described in more detail below through examples, but the present invention is not limited thereto.

[0970] <<Synthesis example>>

[0971] Synthesis Example (1): Synthesis of compounds (1-3)

[0972] [Chemistry 187]

[0973]

[0974] <First Process>

[0975] Under nitrogen atmosphere and at -10°C, N-bromosuccinimide (1.07 g, 6 mmol) was added to a solution of compound (S-3) (2.54 g, 3 mmol) in o-dichlorobenzene (10 mL). After stirring the mixture at -10°C for 2 hours, it was injected into water (30 mL) and extracted with dichloromethane (3 × 20 mL). The combined organic layers were washed with saturated brine and dried with anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (eluent: toluene, dichloromethane) to obtain the target compound (S-4) (1.48 g, 1.47 mmol).

[0976] [Chem.188]

[0977]

[0978] Furthermore, compound (S-3) was synthesized according to the synthesis example described in International Publication No. 2018 / 212169.

[0979] <Second Process>

[0980] Under nitrogen atmosphere, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (85 mg, 0.12 mmol), compound (S-4) (1.205 g, 1.2 mmol), potassium hexacyanoferrate(II) (2.14 g, 4.8 mmol), and sodium carbonate (0.20 g, 1.92 mmol) were dissolved in N,N-dimethylacetamide (5.0 mL). After stirring at 140 °C for 24 hours, the reaction mixture was diluted with toluene (30 mL), and the reaction was stopped by adding water (30 mL) at 0 °C. The aqueous layer was separated and extracted with dichloromethane (30 mL, 3 times). The combined organic layers were washed with saturated brine and dried with anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (eluent: toluene, dichloromethane). The product was washed with octane to obtain compounds (1-3) (401 mg, 0.36 mmol).

[0981] [Chemistry 189]

[0982]

[0983] Synthesis Example (2): Synthesis of Compounds (1-9)

[0984] [Chemistry 190]

[0985]

[0986] <First Process>

[0987] Boron triiodide (4.05 g, 4.0 mmol) and compound (S-5) (6.26 g, 16.0 mmol) were dissolved in 1,2-dichlorobenzene (5.0 mL) under nitrogen atmosphere. After stirring at 70 °C for 24 hours, the reaction mixture was diluted with dichloromethane (20 mL), and the reaction was stopped at 0 °C with phosphate buffer (pH 7, 20 mL). The aqueous layer was separated and extracted with dichloromethane (20 mL, 3 times). After removing the solvent under vacuum, the crude product was separated into highly polar and low polar components by silica gel column chromatography (eluent: hexane / dichloromethane = 1 / 1, ethyl acetate). Acetic acid (1.0 mL, 35.0 mmol) was added to the highly polar component in toluene (10.0 mL) at room temperature. After stirring at 60 °C for 1 hour, saturated sodium carbonate aqueous solution (10 mL) was added to the reaction mixture, and the aqueous layer was extracted with toluene (30 mL, 3 times). The combined organic layers were concentrated under vacuum. The crude product was purified by silica gel column chromatography (elution: hexane / dichloromethane = 3 / 1, 2 / 1). The product was washed with octane and acetonitrile to obtain compound (S-6) (620 mg, 0.6 mmol).

[0988] [Chemistry 191]

[0989]

[0990] <Second Process>

[0991] Using dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (39 mg, 0.055 mmol), compound (S-6) (0.55 g, 0.557 mmol), potassium hexacyanoferrate(II) (0.98 g, 2.2 mmol), sodium carbonate (0.88 g, 0.093 mmol) and N,N-dimethylacetamide (5.0 mL), the same operation as the second step of synthesis example (2) was performed to obtain the target compounds (1-9).

[0992] [Chemistry 192]

[0993]

[0994] Synthesis Example (3): Synthesis of Compounds (1-13)

[0995] [Chemistry 193]

[0996]

[0997] <First Process>

[0998] Under nitrogen atmosphere and at -60°C, a 20 mL solution of compound (S-7) (175 mg, 0.2 mmol) in THF was cooled for 30 minutes, followed by the addition of a 3 mL solution of dibromoisocyanuric acid (DBI, 75 mg, 0.26 mmol) in THF. The mixture was then stirred at -60°C for 10 minutes, followed by stirring at -20°C for 1 hour. After purification of the reaction mixture using a short column (packing material: alumina, eluent: THF), the solvent was removed under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: hexane / toluene = 5 / 1) to obtain the target compound (S-8) (167 mg, 0.162 mmol).

[0999] [Chemistry 194]

[1000]

[1001] Furthermore, compound (S-7) was synthesized according to the synthesis example described in International Publication No. 2018 / 212169.

[1002] 1 ¹H nuclear magnetic resonance (NMR) (CD₂Cl₂, 495 MHz); 10.30 (s, 1H), 8.84 (s, 2H), 7.51 (d, J=8.8 Hz, 3H), 7.41–7.36 (m, 6H), 7.34 (dd, J=8.8, 2.0 Hz, 2H), 7.21–7.19 (m, 4H), 7.17 (s, 4H), 6.69 (d, J=8.8 Hz, 2H), 6.14 (d, J=9.1 Hz, 2H), 2.44 (s, 6H), 2.43 (s, 6H), 1.84 (s, 12H).

[1003] <Second Process>

[1004] Compound (S-8) (125 mg, 0.12 mmol) obtained in the first step and copper cyanide (I) (90 mg, 1.0 mmol) were placed in a 25 mL Schlenk tube. After nitrogen purging, N,N-dimethylformamide (6.0 mL) was added under a nitrogen stream. After stirring at 150 °C for 24 hours, water, ferric chloride (III), and concentrated hydrochloric acid were added to the reaction mixture, which had been cooled to room temperature. The reaction was stopped by stirring for 5 minutes. The aqueous layer was separated and extracted with dichloromethane (30 mL, 3 times). The combined organic layers were washed with saturated brine and dried with anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude product was purified by flash chromatography (eluent: hexane / ethyl acetate = 4 / 1) to obtain compound (1-13) (48 mg, 0.052 mmol).

[1005] 1 HNMR (CDCl3, 495 MHz); 10.67 (s, 1H), 9.01 (s, 2H), 7.61 (t, J=7.7 Hz, 2H), 7.54 (d, J=9.1 Hz, 2H), 7.45 (t, J=7.9 Hz, 4H), 7.38 (dd, J=8.8, 1.7 Hz,2H), 7.27 (dd, J=8.4, 1.0 Hz, 4H), 7.18 (s, 4H), 6.76 (d, J=8.8 Hz, 2H), 6.21(d, J=8.8 Hz, 2H), 6.18 (s, 1H), 2.54 (s, 6H), 2.47 (s, 6H), 1.87 (s, 12H).

[1006] [Chemistry 195]

[1007]

[1008] Synthesis Example (4): Synthesis of Compounds (1-14)

[1009] [Chemistry 196]

[1010]

[1011] <First Process>

[1012] Boron triiodide (2.11 g, 5.4 mmol) and compound (S-9) (1.30 g, 1.35 mmol) were dissolved in 1,2-dichlorobenzene (8.0 mL) under nitrogen atmosphere. After stirring at 100 °C for 10 hours, the reaction was stopped by adding phosphate buffer to the reaction mixture, which had been cooled to room temperature. The aqueous layer was separated and extracted with toluene. After removing the solvent by vacuum distillation, the crude product was purified by silica gel column chromatography (eluent: hexane / dichloromethane = 5 / 1) to obtain compound (S-10) (420 mg, 0.43 mmol).

[1013] [Chemistry 197]

[1014]

[1015] <Second Process>

[1016] [1,2-bis(diphenylphosphino)ethane]nitrogen(II) dichloro(II) (45 mg, 0.082 mmol), compound (S-10) (0.40 g, 0.41 mmol), and sodium borohydride (95 mg, 2.5 mmol) were placed in a flask, purged with nitrogen, and N,N-dimethylacetamide (15 mL) was added. After stirring at 110 °C for 17 hours, an aqueous solution of ammonium chloride was added to the reaction mixture, which had been cooled to room temperature, to stop the reaction. The aqueous layer was separated and extracted with toluene. After removing the solvent by vacuum distillation, the crude product was purified by silica gel column chromatography (eluent: hexane / dichloromethane = 5 / 1) to obtain compound (S-11) (300 mg, 0.328 mmol).

[1017] [Chemistry 198]

[1018]

[1019] <Third Process>

[1020] Under nitrogen atmosphere, a THF (15 mL) solution of compound (S-11) (226 mg, 0.25 mmol) was cooled to -60 °C, and a THF (3 mL) solution of N-bromosuccinimide (90 mg, 0.5 mmol) was added dropwise. The mixture was then stirred at -60 °C for 10 minutes, followed by stirring at -20 °C for 11 hours. The reaction mixture was purified using a short column (packing material: alumina, eluent: THF), the solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography (eluent: hexane / toluene = 5 / 1) to obtain compound (S-12) (180 mg, 0.17 mmol).

[1021] 1 HNMR (495 MHz, CD2Cl2) δ 10.47 (s, 1H), 8.73 (s, 2H), 7.54 (d, J=8.8Hz, 2H), 7.46 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.2 Hz, 6H), 7.28 (d, J=9.4 Hz, 4H), 6.92 (s, 4H), 6.11 (d, J=8.8 Hz, 2H), 5.80 (s, 1H), 2.44-2.41 (m, 18H), 1.74 (s, 12H).

[1022] [Chemistry 199]

[1023]

[1024] <Fourth Process>

[1025] Using the compound (S-12) (138 mg, 0.13 mmol) obtained in the third step, copper cyanide (I) (70 mg, 0.78 mmol) and N,N-dimethylformamide (5.0 mL), the same operation as the second step of the synthesis example (3) was performed to obtain compound (1-14) (85 mg, 0.088 mmol).

[1026] [Chemistry 200]

[1027]

[1028] 1 HNMR (CDCl3, 495 MHz); δ 10.72 (s, 1H), 8.97 (s, 2H), 7.59 (d, J=8.8Hz, 2H), 7.50 (d, J=7.9 Hz, 4H), 7.41 (d, J=8.2 Hz, 4H), 7.36 (dd, J=8.9, 1.8Hz, 2H), 6.94 (s, 4H), 6.87 (d, J=8.8 Hz, 2H), 6.17 (d, J=9.1 Hz, 2H), 5.94(s, 1H), 2.60 (s, 6H), 2.51 (s, 6H), 2.44 (s, 6H), 1.73 (s, 12H).

[1029] Synthesis Example (5): Synthesis of Compounds (1-15)

[1030] [Chemical Engineering 201]

[1031]

[1032] <First Process>

[1033] Boron triiodide (1.56 g, 4.0 mmol), compound (S-13) (985 mg, 1.0 mmol) and 1,2-dichlorobenzene (10.0 mL) were used to perform the same operation as the first step of synthesis example (5) to obtain compound (S-14) (300 mg, 0.3 mmol).

[1034] [Chemical Engineering 202]

[1035]

[1036] <Second Process>

[1037] Using [1,2-bis(diphenylphosphino)ethane] nickel(II) dichloro(II) (32 mg, 0.082 mmol), compound (S-14) (0.30 g, 0.3 mmol), sodium borohydride (70 mg, 1.8 mmol) and N,N-dimethylacetamide (10 mL), the same operation as the second step of synthesis example (5) was performed to obtain compound (S-15) (225 mg, 0.24 mmol).

[1038] [Chemical Engineering 203]

[1039]

[1040] <Third Process>

[1041] Under nitrogen atmosphere, compound (S-16) (152 mg, 0.14 mmol) was obtained by performing the same operation as the third step of synthesis example (4) using a 10 mL THF solution of compound (S-15) (185 mg, 0.2 mmol) and a 2 mL THF solution of N-bromosuccinimide (72 mg, 0.4 mmol).

[1042] [Chemical 204]

[1043]

[1044] <Fourth Process>

[1045] Using the compound (S-16) (152 mg, 0.14 mmol) obtained in the third step, copper cyanide (I) (75 mg, 0.84 mmol) and N,N-dimethylformamide (5.0 mL), the same operation as the second step of the synthesis example (3) was performed to obtain compound (1-15) (82 mg, 0.084 mmol).

[1046] [Chemical Engineering 205]

[1047]

[1048] Synthesis Example (6): Synthesis of Compounds (1-16)

[1049] [Chemical Engineering 206]

[1050]

[1051] <First Process>

[1052] Under nitrogen atmosphere, compound (S-18) (140 mg, 0.11 mmol) was obtained by performing the same operation as the third step of synthesis example (4) using a 15 mL THF solution of compound (S-17) (336 mg, 0.3 mmol) and a 3 mL THF solution of N-bromosuccinimide (107 mg, 0.6 mmol).

[1053] [Chemical 207]

[1054]

[1055] <Second Process>

[1056] Using the compound (S-18) (128 mg, 0.1 mmol) obtained in the first step, copper cyanide (I) (54 mg, 0.6 mmol) and N,N-dimethylformamide (4.0 mL), the same operation as the second step of synthesis example (3) was performed to obtain compound (1-16) (67 mg, 0.057 mmol).

[1057] [Chemical Engineering 208]

[1058]

[1059] Synthesis Example (7): Synthesis of Compounds (1-17)

[1060] [Chemical Engineering 209]

[1061]

[1062] <First Process>

[1063] Under nitrogen atmosphere, compound (S-19) (345 mg, 0.3 mmol) in THF (15 mL) solution and N-bromosuccinimide (107 mg, 0.6 mmol) in THF (3 mL) solution were used in the same operation as the third step of synthesis example (4) to obtain compound (S-20) (124 mg, 0.095 mmol).

[1064] [Chemical 210]

[1065]

[1066] <Second Process>

[1067] Using the compound (S-20) (105 mg, 0.08 mmol) obtained in the first step, copper cyanide (I) (37 mg, 0.48 mmol) and N,N-dimethylformamide (3.0 mL), the same operation as the second step of synthesis example (3) was performed to obtain compound (1-17) (60 mg, 0.05 mmol).

[1068] [Chemistry 211]

[1069]

[1070] Synthesis Example (8): Synthesis of Compounds (1-18)

[1071] [Chemistry 212]

[1072]

[1073] <First Process>

[1074] Under nitrogen atmosphere, compound (S-22) (81 mg, 0.072 mmol) was obtained by performing the same operation as the third step of synthesis example (4) using a 15 mL THF solution of compound (S-21) (336 mg, 0.3 mmol) and a 3 mL THF solution of N-bromosuccinimide (107 mg, 0.6 mmol).

[1075] [Chemistry 213]

[1076]

[1077] <Second Process>

[1078] Using the compound (S-22) (73 mg, 0.065 mmol) obtained in the first step, copper cyanide (I) (35 mg, 0.39 mmol) and N,N-dimethylformamide (3.0 mL), the same operation as the second step of synthesis example (3) was performed to obtain compound (1-18) (42 mg, 0.041 mmol).

[1079] [Chemistry 214]

[1080]

[1081] Synthesis Example (9): Synthesis of Compounds (1-19)

[1082] [Chemical 215]

[1083]

[1084] <First Process>

[1085] Under nitrogen atmosphere, compound (S-24) (78 mg, 0.068 mmol) was obtained by performing the same operation as the third step of synthesis example (4) using a 15 mL THF solution of compound (S-23) (345 mg, 0.3 mmol) and a 3 mL THF solution of N-bromosuccinimide (107 mg, 0.6 mmol).

[1086] [Chemistry 216]

[1087]

[1088] <Second Process>

[1089] Using the compound (S-24) (69 mg, 0.06 mmol) obtained in the first step, copper cyanide (I) (32 mg, 0.36 mmol) and N,N-dimethylformamide (3.0 mL), the same operation as the second step of synthesis example (3) was performed to obtain compound (1-19) (35 mg, 0.033 mmol).

[1090] [Chemistry 217]

[1091]

[1092] Compounds (1-1), (1-2), (1-4) to (1-8), (1-10) to (1-12), (2-1) to (2-5), (3-1) to (3-5), (4-1) to (4-5), and (5-1) to (5-5) were synthesized using the methods of Synthesis Examples (1) to (9).

[1093] [Chemistry 218]

[1094]

[1095] [Chemistry 219]

[1096]

[1097] [Chem.220]

[1098]

[1099] [Chemistry 221]

[1100]

[1101] [Chemistry 222]

[1102]

[1103] Compounds (C1-1) to (C1-5), (C2-1) to (C2-5), (C3-1), (C4-1) to (C4-4), (C5-1) and (C5-2) are compounds disclosed in Japanese Patent Application Publication No. 2023-152686, and are synthesized using the method described in the publication.

[1104] [Chemistry 223]

[1105]

[1106] [Chemistry 224]

[1107]

[1108] [Chemistry 225]

[1109]

[1110] [Chemistry 226]

[1111]

[1112] [Chemistry 227]

[1113]

[1114] The formation of the target analyte was confirmed by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF-MS).

[1115] [Table 1]

[1116]

[1117] <<Evaluation Methods for Basic Physical Properties>>

[1118] Sample preparation

[1119] The basic physical properties of the synthesized compounds (1-13) and (1-14) were evaluated.

[1120] In this embodiment, polymethyl methacrylate (PMMA) and the compound to be evaluated are dissolved in toluene, and then a thin film is formed on a transparent support substrate made of quartz or glass by spin coating to prepare a sample. The concentration of the compound to be evaluated in the coating film is set to 1% by mass.

[1121] Evaluation of luminescent properties

[1122] A coating formed on a transparent glass support substrate was used as the sample for measurement. The fluorescence spectrum of the sample was measured using a spectrophotometer (Hitachi High Technology Co., Ltd., F-7000).

[1123] Fluorescence spectroscopy was performed by exciting the sample at room temperature. The excitation wavelength for the spectral measurements was set to 340 nm. The half-width at half-maximum (WHM) was determined as the width between wavelengths above and below the wavelength at which the maximum emission wavelength is centered and its intensity is 50%.

[1124] [Table 2]

[1125]

[1126] <<Manufacturing and Evaluation of Vapor Deposited Organic Electron Devices>>

[1127] Organic EL elements such as TAF and PSF are manufactured using the synthesized compounds of the present invention and comparative compounds.

[1128] <TAF Structure: Examples T1-1 to T1-19, Examples T2-1 to T2-5, Examples T3-1 to T3-5, Examples T4-1 to T4-5, Examples T5-1 to T5-5, Comparative Examples CT1-1 to CT1-5, Comparative Examples CT2-1 to CT2-5, Comparative Examples CT3-1, Comparative Examples CT4-1 to CT4-4, Comparative Examples CT5-1 and CT5-2>

[1129] ITO (50 nm) / HAT-CN (10 nm) / HT-1 (60 nm) / SiCzCz (5 nm) / SiCzCz:SiTrzCz2:TADF-1: Compounds listed in Table 3 (60:26:13:1) (35 nm) / mSiTrz (5 nm) / mSiTrz:Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm)

[1130] A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science, Inc.) with an ITO film thickness of 200 nm ground to 50 nm was used as a transparent support substrate. The transparent support substrate was fixed on the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum, Inc.), and a molybdenum vapor deposition boat containing HAT-CN, HT-1, SiCzCz, SiTrzCz2, the compounds listed in Table 3, mSiTrz, and Liq, and a tungsten vapor deposition boat containing LiF and aluminum were installed.

[1131] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 5 × 10⁻⁶. -4First, HAT-CN was heated and vapor-deposited to a thickness of 10 nm to form a hole injection layer. Next, HT-1 was heated and vapor-deposited to a thickness of 60 nm to form a hole transport layer 1. Then, SiCzCz was heated and vapor-deposited to a thickness of 5 nm to form a hole transport layer 2. Next, SiCzCz, SiTrzCz2, (TADF-1), and each compound listed in Table 3 were simultaneously heated and vapor-deposited to a thickness of 35 nm to form a light-emitting layer. The vapor deposition rate was adjusted so that the mass ratio of SiCzCz, SiTrzCz2, (TADF-1), and each compound listed in Table 3 was approximately 60:26:13:1. Next, mSiTrz is heated and vapor-deposited to a thickness of 5 nm to form electron transport layer 1. Then, mSiTrz and Liq are heated and vapor-deposited to a thickness of 30 nm to form electron transport layer 2. The vapor deposition rate is adjusted to maintain an approximately 1:1 mass ratio of mSiTrz to Liq. The vapor deposition rate for each layer is 0.01 nm / s to 1 nm / s. Following this, LiF is heated and vapor-deposited to a thickness of 1 nm at a rate of 0.01 nm / s to 0.1 nm / s. Then, aluminum is heated and vapor-deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. Here, the vapor deposition rate for aluminum is adjusted to 1 nm / s to 10 nm / s. Furthermore, the SiCzCz of the light-emitting layer acts as the host material for hole transport, and SiTrzCz2 acts as the host material for electron transport.

[1132] <PSF Structure: Examples P1-1 to P1-19, Examples P2-1 to P2-5, Examples P3-1 to P3-5, Examples P4-1 to P4-5, Examples P5-1 to P5-5, Comparative Examples CP1-1 to CP1-5, Comparative Examples CP2-1 to CP2-5, Comparative Examples CP3-1, Comparative Examples CP4-1 to CP4-4, Comparative Examples CP5-1 and CP5-2>

[1133] ITO (50 nm) / HAT-CN (10 nm) / HT-1 (60 nm) / SiCzCz (5 nm) / SiCzCz: SiTrzCz2: PtON-TBBI: Each compound listed in Table 4 (60:26:13:1) (35 nm) / mSiTrz (5 nm) / mSiTrz: Liq (1:1) (30 nm) / LiF (1 nm) / Al(100 nm)

[1134] The (TADF-1) structure of the TAF is replaced with PtON-TBBI, and the element is fabricated in the same way.

[1135] The chemical structures of the compounds used in the manufacture of the aforementioned components are shown below.

[1136] [Chemistry 228]

[1137]

[1138] [evaluate]

[1139] Evaluation parameters include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength of emission spectrum (nm), and half-width (nm). These evaluation parameters can be, for example, 1000 cd / m². 2 The value when it emits light.

[1140] The quantum efficiency of a light-emitting element has internal quantum efficiency and external quantum efficiency. Internal quantum efficiency represents the proportion of external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element that is purely converted into photons. On the other hand, external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element. Some of the photons generated in the light-emitting layer are absorbed internally by the light-emitting element or continuously reflected without being released to the outside of the light-emitting element. Therefore, external quantum efficiency is lower than internal quantum efficiency.

[1141] The methods for measuring spectroradiance (emission spectrum) and external quantum efficiency are as follows. Using an Advantest voltage / current generator R6144, an application was made to achieve a brightness of 1000 cd / m². 2 The element emits light due to the voltage applied. Using a Topcon SR-3AR spectroradiometer, the spectroradiance in the visible light region was measured from a direction perpendicular to the emitting surface. Assuming the emitting surface is a perfectly diffused surface, the number of photons at each wavelength was obtained by dividing the measured spectroradiance value of each wavelength component by the wavelength energy and multiplying by π. The number of photons was then accumulated across the entire observed wavelength range and set as the total number of photons emitted from the element. The number of carriers injected into the element was obtained by dividing the applied current value by the elementary charge, and the external quantum efficiency was obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element. Furthermore, the half-width of the emission spectrum was calculated as the width between wavelengths above and below the maximum emission wavelength where its intensity is 50%.

[1142] A DC voltage was applied using an ITO electrode as the anode and a LiF / aluminum electrode as the cathode, and the voltage was measured at 1000 cd / m². 2 Characteristics of light emission (emission wavelength, external quantum efficiency). Additionally, the time it takes to maintain more than 50% of the initial brightness (lifetime) is measured.

[1143] The results are shown in Tables 3 and 4.

[1144] [Table 3]

[1145]

[1146]

[1147] [Table 4]

[1148]

[1149]

[1150] Based on the results obtained, it can be seen that the elements of the embodiments have a longer lifespan and are more efficient and have a longer lifespan than the elements of the comparative examples that utilize compounds having a skeleton corresponding to the compounds of the embodiments.

Claims

1. A polycyclic aromatic compound, represented by formula (I); [Chemistry 1] In formula (I), Rings A, B, D, and E are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, wherein at least one ring selected from the group consisting of rings A, B, C, D, and E is an aryl ring having at least a cyano group as a substituent or a heteroaryl ring having at least a cyano group as a substituent. Z 0 -C(-R) Z0 = or -N=, R Z0 Each can be a hydrogen or a substituent, independently. Y can be independently defined as B, P, P=O, or P=S. X 1 X 2 X 3 and X 4 Each independently is >NR NX ,>O,>S or>Se,R NX It can be hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. R NX It can be bonded to at least one of ring A or ring B, at least one of ring A or ring c, at least one of ring B or ring D, or at least one of ring c or ring E via a single bond or a linker. in, X 1 X 2 X 3 and X 4 Satisfying at least one of the following (a) and (b): (a)X 1 and X 2 R is independent of each other. NX NR of the basis represented by equation (Ar) NX ; (b)X 1 and X 3 They are R NX NR is trimethylbenzyl NX , or X 2 and X 4 They are R NX NR is trimethylbenzyl NX , In formula (Ar), Indicates the bond position on nitrogen. The F ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and it contains at least a 6-membered ring with atoms bonded by G as ring constituent atoms. G is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. At least one of the groups consisting of aryl rings and heteroaryl rings selected from formula (I) may be condensed from at least one cycloalkane, wherein the cycloalkane may be substituted by at least one substituent, and at least one -CH2- of the cycloalkane may be substituted by -O-. In formula (I), at least one hydrogen may be substituted with deuterium, and at least one nitrogen may be substituted with nitrogen-15 ( 15 N) substitution, at least one sulfur can be replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) substitution, at least one oxygen can be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O) substitution, at least one carbon can be replaced by carbon-13 ( O) 13 C) substitution, at least one boron can be replaced by boron-11 ( 11 B) Replacement.

2. The polycyclic aromatic compound according to claim 1, which is represented by formula (II); [Chemistry 2] In formula (II), Z 0 With Z in equation (I) 0 They have the same meaning. X 3 and X 4 With X in equation (I) 3 and X 4 They have the same meaning. Ar is the basis represented by the formula (Ar). Z and Q are independently -C(-R) Z = or -N=, R Z It is hydrogen or a substituent. At least one Q is -C(-CN)=.

3. The polycyclic aromatic compound according to claim 2, which is represented by formula (II-1-i) to (II-1-v), (II-2-i), (II-2-ii), (II-3-i), (II-3-ii), (II-4-i) or (II-5-i); [Chemistry 3] In the formula, Z 0 and Ar and Z in equation (II) 0 Ar and Ar have the same meaning. Z is independently -C(-R) Z = or -N=, R Z It can be hydrogen or a substituent.

4. The polycyclic aromatic compound according to claim 1, wherein, The F ring can be a substituted or unsubstituted benzene ring, a dibenzofuran ring, or a dibenzothiophene ring.

5. The polycyclic aromatic compound according to claim 1, wherein, X 1 X 2 X 3 and X 4 Satisfy (b), X 1 X 2 X 3 and X 4 All are >NR NX .

6. The polycyclic aromatic compound according to claim 1, wherein it is represented by any of the following formulas; [Chemistry 4] [Chemistry 5] [Chemistry 6] [Chemistry 7] [Chemistry 8] 。 7. An organic electroluminescent element comprising: a pair of electrodes, including an anode and a cathode; and an organic layer disposed between the pair of electrodes, the organic layer containing a polycyclic aromatic compound as claimed in any one of claims 1 to 6.

8. The organic electroluminescent element according to claim 7, wherein, The organic layer is a light-emitting layer.

9. The organic electroluminescent element according to claim 8, wherein, The light-emitting layer comprises at least one selected from the group consisting of auxiliary dopants and phosphorescent materials.

10. A display device or lighting device, comprising the organic electroluminescent element as described in claim 7.

11. A wavelength conversion material comprising a polycyclic aromatic compound as described in any one of claims 1 to 6.

12. An organic photodiode, comprising a pair of electrodes and an active layer disposed between the pair of electrodes, wherein the active layer comprises a polycyclic aromatic compound as described in any one of claims 1 to 6.

13. The organic photodiode according to claim 12, wherein, The active layer contains the polycyclic aromatic compound.

14. A solar cell material comprising a polycyclic aromatic compound as described in any one of claims 1 to 6.

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