Polycyclic aromatic compounds

Abstract

The present application provides a polycyclic aromatic compound which is effective as a material for organic devices such as organic electroluminescent elements, and a polycyclic aromatic compound according to an embodiment of the present application, which has a structure composed of one or two or more structural units represented by formula (1): A ring, B ring, and C ring are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring, Y 1 is B, X 1 and X 2 are each independently >O, >N-R NX , >C(-R CX )2, >Si(-R SiX )2, >S, R NX , R CX , and R SiX are each independently hydrogen, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group, wherein at least one ring selected from the group consisting of A ring, B ring, and C ring in the structure contains a group represented by formula (G-1), or at least one of the groups represented by R NX , R CX , and R SiX contains a group represented by formula (G-1).

Description

Technical Field

[0001] This invention relates to a polycyclic aromatic compound. More particularly, it relates to a polycyclic aromatic compound comprising nitrogen and boron. Furthermore, it relates to an organic device material comprising the said polycyclic aromatic compound, an organic electroluminescent element, and a display device and lighting device. 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 researched due to their ease of lightweighting or scaling. In particular, the development of organic materials exhibiting luminescent properties such as blue (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 studied to date, encompassing both high-molecular-weight and low-molecular-weight compounds.

[0003] Organic electroluminescent devices have a structure comprising: a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing an organic compound. The layers containing the organic compound may include a light-emitting layer, or a charge transport / injection layer for transporting or injecting charges such as holes or electrons, and various organic materials suitable for these layers have been developed.

[0004] Patent documents 1 to 4 disclose materials that effectively utilize boron-containing polycyclic aromatic compounds as organic electroluminescent elements.

[0005] Existing technical documents

[0006] Patent documents

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

[0008] Patent Document 2: Korean Patent No. 10-2453929

[0009] Patent Document 3: International Publication No. 2021 / 107744

[0010] Patent Document 4: U.S. Patent Application Publication No. 2023 / 0075017 Summary of the Invention

[0011] The technical problem to be solved

[0012] As mentioned above, various materials have been developed for use in organic electroluminescence (EL) devices, but in order to increase the selection of materials for organic EL devices, it is desirable to develop a material containing novel compounds.

[0013] 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.

[0014] Technical solutions for solving the problem

[0015] To solve the aforementioned problems, the inventors conducted diligent research and successfully manufactured novel polycyclic aromatic compounds with superior luminescent properties from polycyclic aromatic compounds having structures similar to those described in Patent Documents 1 to 3. Furthermore, they discovered that by configuring a layer containing the aforementioned polycyclic aromatic compound between a pair of electrodes to construct an organic EL element, excellent organic EL elements can be obtained, thus completing the present invention. In other words, the present invention provides polycyclic aromatic compounds as described below, and further provides materials for organic devices containing such polycyclic aromatic compounds.

[0016] Specifically, the present invention has the following structure.

[0017] <1> A polycyclic aromatic compound having a structure consisting of one or more structural units represented by the following formula (1):

[0018]

[0019] In equation (1),

[0020] Rings A, B, and C are each independently a substituted aryl ring or a substituted heteroaryl ring.

[0021] Y 1 For B, P, P=O, P=S, Al, Ga, As, Si-R s or Ge-R Ge The Si-R S R S and Ge-R Ge R Ge Each can be independently substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

[0022] X 1 and X 2 Independently defined as >O and >NR respectively. NX >C(-R CX )2、>Si(-R SiX)2, >S, >CO, >SO, >SO2 or >Se, wherein >NR NX R NX The >C(-R) CX )2 of R CX and the >Si(-R SiX )2 of R SiX Each of the following can be independently 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.

[0023] In the X 1 For >N–R NX >C(–R CX )2 or >Si(–R SiX In case )2, >N–R NX R NX >C(–R CX )2 of R CX and >Si(–R SiX )2 of R SiX They can independently form rings by using single bonds or linkers as mediators and bonding with A-rings or B-rings.

[0024] In the X 2 For >N–R NX >C(–R CX )2 or >Si(–R SiX In the case of )2, >N–R NX R NX >C(–R CX )2 of R CX and >Si(–R SiX )2 of R SiX They can independently form rings by using single bonds or linkers as mediators and bonding with A-rings or C-rings.

[0025] The >C(-R) CX )2 two R CX and the aforementioned >Si(-R SiX )2 two R SiX They can bond together to form a ring.

[0026] Wherein, at least one ring selected from the group consisting of rings A, B, and C in the structure contains a basis represented by the following formula (G-1), or is composed of R. S R Ge R NX R CX and R SiX At least one of the bases represented includes the base represented by the following equation (G-1).

[0027]

[0028] In equation (G-1),

[0029] P1 ring is a substituted cycloalkyl ring. For the bonding positions with structures other than those in equation (G-1), D represents deuterium.

[0030] In the structure, at least one of the aryl ring and the heteroaryl ring may be condensed via at least one cycloalkane, and at least one hydrogen atom of the cycloalkane may be substituted.

[0031] In the structure, each substituent substituted in ring A, ring B, or ring C can form a ring with the substituent-substituted ring A, ring B, or ring C via a single bond or a linker.

[0032] In the structure, at least one hydrogen atom may be substituted with a cyano group or a halogen group.

[0033] In the structure, at least one -CH2- can be substituted by -O-.

[0034] In the structure, at least one hydrogen atom may be substituted with deuterium, and at least one nitrogen atom 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.

[0035] <2> according to <1> The polycyclic aromatic compounds described herein, wherein formula (1) is represented by any one of the following formulas (1-a) to (1-m):

[0036]

[0037] In equations (1-a) to (1-m),

[0038] X 1 To X 6 Independently with X in equation (1) 1 and X 2 The definitions are the same, Y 1 To Y 2 Independently with Y in equation (1) 1 The definitions are the same.

[0039] The X1 To X 6 >NR NX R NX >C(-R CX )2 of R CX and >Si(-R SiX )2 of R SiX It can be linked to one or two Z bonds via a linker base or a single bond.

[0040] Z is independently equal to C(-R) CCX )- or =N-, the =C(-R CCX )- of R CCX Each of the following is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted diarylamino group, or a substituted or unsubstituted cycloalkyl group, wherein the =C(-R) CCX The two R's of )- CCX They can bond together to form a ring.

[0041] Wherein, the R CCX R S R Ge R NX R CX and R SiX At least one of the bases represented includes the base represented by equation (G-1).

[0042] <3> according to <1> The polycyclic aromatic compounds described herein, wherein the group represented by formula (G-1) is selected from the groups represented by formulas (g-1) to (g-10):

[0043]

[0044] In equations (g-1) to (g-10), D represents the bonding position with structures other than those in equations (g-1) to (g-10), where D is deuterium.

[0045] <4> according to <1> The polycyclic aromatic compounds described in the document, wherein Y 1 The answer is B.

[0046] <5> according to <1> The polycyclic aromatic compounds described herein contain at least one ring selected from the group consisting of the A ring, B ring and C ring, which contains at least one group represented by formula (G-1).

[0047] <6> according to <1> The polycyclic aromatic compounds described in the document, wherein X 1 and X 2 Each is independently >O or >NRNX The R NX It contains at least one basis represented by equation (G-1).

[0048] <7> according to <1> The polycyclic aromatic compounds described herein contain at least one group represented by the following formula (G-2):

[0049]

[0050] In equation (G-2),

[0051] P1 ring is a substituted cycloalkyl ring, and P2 ring is a substituted aryl ring or a substituted heteroaryl ring. D represents the bonding position with structures other than those in equation (G-2).

[0052] <8> according to <1> The polycyclic aromatic compounds described herein are represented by any of the following formulas:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] In the formula, D represents deuterium.

[0066] <9> A material for organic devices, comprising according to <1> ~ <8> Any of the polycyclic aromatic compounds recorded in the literature.

[0067] <10> An organic electroluminescent device includes: a pair of electrodes, comprising an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer containing, according to... <1> ~ <8> Any of the polycyclic aromatic compounds recorded in the literature.

[0068] <11> according to <10> The organic electroluminescent element described herein, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

[0069] <12> according to <11> The organic electroluminescent element described herein is composed of anthracene compounds, fluorene compounds, dibenzo[a]pyrene compounds, or pyrene compounds.

[0070] <13> A display device having according to <10> The organic electroluminescent element described in the document.

[0071] <14> A lighting device having according to <10> The organic electroluminescent element described in the document.

[0072] Technical effect

[0073] 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

[0074] Figure 1 This is a schematic cross-sectional view showing an example of an organic electroluminescent element.

[0075] Explanation of reference numerals in the attached figures

[0076] 100: Organic electroluminescent element

[0077] 101: Substrate

[0078] 102: Anode

[0079] 103: Hole Injection Layer

[0080] 104: Hole Transport Layer

[0081] 105: Emissive layer

[0082] 106: Electron Transport Layer

[0083] 107: Electron Injection Layer

[0084] 108: Cathode Detailed Implementation

[0085] 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".

[0086] 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.

[0087] In 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.

[0088] In this specification, organic electroluminescent elements are sometimes referred to as "organic EL elements".

[0089] 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.

[0090] This specification describes the structural formulas of several aromatic compounds. Aromatic compounds are described by combining double and single bonds; however, due to the resonance of π electrons, multiple equivalent resonance structures exist for a single substance, with alternating double and single bonds. This specification describes only one resonance structural formula for each substance, but unless otherwise specified, other equivalent resonance structural formulas in organic chemistry are also included.

[0091] In addition, the term "may" is sometimes used in this specification, but it has the same meaning as "not yet" or "or has been".

[0092] <Explanation of rings and substituents>

[0093] First, the details of the rings and substituents used in this specification are explained below.

[0094] 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.

[0095] 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 tricyclic terphenyl rings, pyrene rings, tetraphenylbenzene rings, benzo[a]anthracene rings, fluoranthracene rings, and condensed pentacyclic terphenyl rings, such as perylene rings, pentaphenyl rings, and benzo[a]fluoranthracene rings. Furthermore, fluorene rings, benzo[a]fluorene rings, and indene rings also contain structures with fluorene rings, benzo[a]fluorene rings, and cyclopentane rings linked by spiral bonds, respectively. 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.

[0096] 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, and 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, selenium, phosphorus, and tellurium as ring-forming atoms, in addition to carbon atoms.

[0097] 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. They also include rings represented by the following formula (BO).

[0098]

[0099] 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."

[0100] In this specification, the substituent group Zα includes the substituents of the substituent group Z and the substituents represented by formula (A30) described later.

[0101] In this specification, the substituent group Z includes:

[0102] The aryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

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

[0104] 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.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] Alkyl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen.

[0109] Cycloalkyl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0110] The alkoxy group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen.

[0111] The aryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0112] The arylthio group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0113] The alkenyl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0114] It can replace silyl, deuterium, cyano and halogen.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] Specific examples of "aryl" 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), and 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-3-yl, m-terphenyl-2'-yl, m-terphenyl-2'-yl, m-terphenyl-3 ... Benzene-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), which are condensed tricyclic compounds of acenaphthene-(1-, 3-, 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-) group, which is a tetracyclic tetraphenyl group (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-tetraphenyl), which is a condensed tetracyclic triphenyl-(1- or 2-) group, pyrene-(1-, 2-, or 4-) group, or tetraphenyl-(1-, 2-, or 5-) group, cyclopentadienyl ring, benzanthracene-(1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-), 9-, 10-, 11-, or 12-)yl, fluoranthene-(1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-)yl, or perylene-(1-, 2-, or 3-)yl of a condensed pentacyclic system, or pentaphenyl-(1-, 2-, 5-, or 6-)yl, benzo[k]fluoranthene-(1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, or 12-)yl, etc. In addition, monovalent groups of spirofluorene can be listed.

[0119] Furthermore, the aryl group that serves 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 later), and cycloalkyl groups such as cyclohexyl or adamantyl (specifically, the groups described later).

[0120] 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.

[0121] "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.

[0122] Specific examples of "aryl" include divalent groups formed by removing one hydrogen atom from the aforementioned "aryl" (monovalent group).

[0123] "Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. In the "heteroaryl", in addition to carbon atoms, there are one or more, preferably one to five, heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms.

[0124] As specific examples of "heteroaryl groups," monovalent groups 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, naphridinyl, purinyl, pteridinyl, carbazole, acridineyl, phenoxthiayl, phenoxazinyl, phenanthrene ... Thiazinyl, 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[silazfluorene] monovalent group, benzo[selenophene] monovalent group, and monovalent groups obtained by removing one hydrogen atom from compounds represented by formula (BO), etc.

[0125] The following groups can be listed as monovalent groups obtained by removing a hydrogen atom from the compound represented by formula (BO). In the formula, Indicates the location of the bond.

[0126]

[0127] 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).

[0128] 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.

[0129] "Heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms. Additionally, "heteroarylene" is, for example, a divalent group containing, in addition to carbon, one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms in a heterocycle.

[0130] Specific examples of "heteroaryl" include divalent groups formed by removing one hydrogen atom from the aforementioned "heteroaryl" (monovalent group).

[0131] "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".

[0132] "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".

[0133] "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".

[0134] 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.

[0135]

[0136] ( (Indicates the location of the bond.)

[0137] As linking bases, specifically, examples include: >O, >NR X >C(-R X )2、-C(-R X )=C(-R X )-、>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 )-、>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 the C=C bonds they form 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.

[0138] 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".

[0139] "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, -C(=O)-, >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) are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in the R may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Additionally, two adjacent Rs may bond to each other to form a ring, thus forming a cycloalkylene, arylene, or heteroarylene. For details regarding the substituents listed herein, refer to the descriptions of "aryl," "arylene," "heteroaryl," "heteroarylene," and "diarylamino" above, and the descriptions of "alkyl," "alkenyl," "alkynyl," "cycloalkyl," "cycloalkylene," "alkoxy," and "aryloxy" below. 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".

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

[0141] Specific examples of "alkyl" include: methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl) (tert-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-Ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl, etc.

[0142] "alkylene" is a divalent group obtained by removing any hydrogen atom from an "alkyl" group, such as methylene, ethylene, and propylene.

[0143] 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).

[0144] Specifically, the term "alkenyl" can be exemplified by alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, and even more preferably alkenyl groups having 2 to 6 carbon atoms, particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups include 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.

[0145] "Alkenyl" is a divalent group obtained by removing any one of the hydrogen atoms from an "alkenyl" group, such as vinylidene.

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

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

[0148] Specific examples of "cycloalkyl" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbons or 1 to 4 carbons, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, or decahydroazyl, etc.

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

[0150] Specific examples of "cycloalkylene" can be listed, for instance, from the structure of "cycloalkyl" (monovalent group) with one hydrogen removed to make it divalent.

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

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

[0153] "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".

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

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

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

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

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

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

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

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

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

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

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

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

[0166] The substituent represented by formula (A30) has the following structure.

[0167]

[0168] 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-.

[0169] 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 or a single bond. This indicates the location of the bond.

[0170] 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).

[0171] 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.

[0172] 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, 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.

[0173] R Ak It can be the same as or different from Ak, but it is preferred to be different.

[0174] 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... Ak Examples of structures that are bonded to Ak via linker bases or single bonds include the following structures.

[0175]

[0176] In the aforementioned formulas, This indicates the location of the bond.

[0177] [The case where two groups bonded to the same atom are bonded together]

[0178] In this specification, when referring to two bases 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 base (which are also collectively referred to as linking bases). Examples of linking bases include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -Se(=O)-, -Se(=O)2-, -P(=O)-, -B(-R-), 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 group, an arylene group, or a heteroarylene group.

[0179]

[0180] 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-, -C(=O)-, and -Se-, more preferably a single bond, or as a linking base -CR=CR-, -N(-R)-, -O-, -S-, -C(=O)-, and -C(-R)2-, further preferably a single bond, or as a linking base -CR=CR-, -N(-R)-, -O-, and -S-, and most preferably a single bond.

[0181] 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).

[0182] <Stereoisomers, etc.>

[0183] 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.

[0184] <1. Polycyclic aromatic compounds>

[0185] <Overall Structure>

[0186] 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, which suppresses 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 changed 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.

[0187] 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.

[0188] 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.

[0189] In this invention, it was discovered that, in particular, polycyclic aromatic compounds formed by linking aromatic rings such as benzene rings and benzofuran rings, benzothiophene rings, indole rings, etc., using heteroelements such as boron and nitrogen, and having a structure composed of one or more structural units represented by formula (1) containing a specific group, have a narrow half-width of emission spectrum compared to polycyclic aromatic compounds with similar structures, and can be used to manufacture organic electroluminescent elements with longer lifespan and higher luminous efficiency.

[0190] The polycyclic aromatic compounds of the present invention are polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) (hereinafter sometimes referred to as "polycyclic aromatic compounds containing structural units represented by formula (1)").

[0191]

[0192] The following is a detailed description of polycyclic aromatic compounds containing the structural unit represented by formula (1).

[0193] <Explanation of ring structures in compounds>

[0194] In equation (1), "A", "B", and "C" inside the circles are symbols representing the ring structures represented by each circle. The structure represented by equation (1) is formed by linking at least three aromatic rings, which are rings A, B, and C, using boron and nitrogen to form a ring structure. The formed ring structure is a condensed ring structure consisting of at least 5 rings.

[0195] Rings A, B, and C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0196] Ring A forms a trivalent group consisting of three consecutive atoms (preferably carbon) bonded to each other on the aryl or heteroaryl ring in its structure. Ring A is connected to Y through these three bonds. 1 X 1 and X 2 Bonding. The ring in ring A, where the atoms having the bonded bonds are designated as ring constituent atoms, is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring. This ring can further condense with other rings. Examples of 6-membered rings include: benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, etc. Examples of 6-membered rings further 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 further condensing with other rings include: benzofuran rings, benzothiophene rings, indole rings, etc. Furthermore, the indene ring can also be listed as a condensation ring.

[0197] The aryl ring or heteroaryl ring in ring A is preferably a benzene ring.

[0198] Both rings B and C form divalent groups on two adjacent atoms (preferably carbon atoms) of the aryl or heteroaryl ring in their structure, with bonds between them. Ring B is connected to Y through these two bonds. 1 and X 1 The C-ring is connected to the Y-ring through the two bonded links. 1 and X 2 Bonding. In both rings B and C, the atom having the two bonded bonds is designated as the ring constituent atom. The ring is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring. The ring can further condense with other rings. Examples of 6-membered rings include: benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, etc. Examples of 6-membered rings further condensing with other rings include: naphthyl rings, quinoline rings, benzofuran rings, benzothiophene rings, indole rings, benzoselenene rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, 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 further condensing with other rings include: benzofuran rings, benzothiophene rings, indole rings, benzoselenene rings, etc. Furthermore, indene rings can also be listed as condensation rings.

[0199] The aryl or heteroaryl rings in rings B and C are preferably, independently, benzene rings, naphthyl rings, benzofuran rings, benzothiophene rings, indene rings, carbazole rings, benzocarbazole rings, indole-carbazole rings, indole-acridine rings, hexahydrocarbazole rings, benzothiophene-indole rings, acridine rings, phenoxazine rings, phenothiazine rings, indole rings, or benzoselenene rings; more preferably, benzene rings, carbazole rings, acridine rings, benzofuran rings, indene rings, or benzothiophene rings; and even more preferably, benzene rings, carbazole rings, acridine rings, benzofuran rings, or benzothiophene rings.

[0200] In the substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings of rings A, B, and C, 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 also be a substituted or unsubstituted diarylphosphine group, such as diphenylphosphine. When multiple substituents are present, they may be the same or different from each other. As substituents, preferred substituents are substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, substituted or unsubstituted triarylmethyl groups, or substituted or unsubstituted triarylsilyl groups; more preferably, methyl, tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, substituted or unsubstituted triphenylmethyl, or substituted or unsubstituted triphenylsilyl groups. Other preferred substituents can be found in the section on <Preferred Substituents> described below.

[0201] Each substituent substituted in ring A, ring B, or ring C can form a ring with the substituted ring A, ring B, or ring C via a single bond or a linking group. The description of the linking group can be replaced by the description of the linking group described in the <Description of Rings and Substituents> section. For example, as described later in <Specific Examples of Polycyclic Aromatic Compounds> (1-127), (1-135), (1-148), (1-208), etc., when ring B is a benzene ring and cyclohexyl is substituted, the cyclohexyl can form a ring with the benzene ring via a linking group. Furthermore, when ring B is a carbazole ring and phenyl is substituted, the phenyl can form a ring with the carbazole ring via a single bond, but this is not a limitation.

[0202] <Y 1 >

[0203] In equation (1), Y 1 For B, P, P=O, P=S, Al, Ga, As, Si-R s or Ge-R Ge The Si-R S R S and Ge-R Ge R GeEach can be independently a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. As for the "substituted or unsubstituted" case, at least one substituent selected from the substituent group Zα can be listed. Other preferred substituents can be found in the description of <Preferred Substituents> below. The Y... 1 Option B is preferred.

[0204] <X 1 and X 2 >

[0205] In equation (1), X 1 and X 2 Independently defined as >O and >NR respectively. NX >C(-R CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2 or >Se, wherein >NR NX R NX The >C(-R) CX )2 of R CX and the >Si(-R SiX )2 of R SiX Each of the following can be independently 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.

[0206] In the X 1 For >N–R NX >C(–R CX )2 or >Si(–R SiX In the case of )2, >N–R NX R NX >C(–R CX )2 of R CX and >Si(–R SiX )2 of R SiX They can independently form rings by using single bonds or linkers as mediators and bonding with A-rings or B-rings.

[0207] In the X 2 For >N–R NX >C(–R CX )2 or >Si(–R SiX In the case of )2, >N–R NX R NX >C(–R CX )2 of R CX and >Si(–R SiX )2 of R SiXThey can independently form rings by using single bonds or linkers as mediators and bonding with A-rings or C-rings.

[0208] The >C(-R) CX )2 two R CX and the aforementioned >Si(-R SiX )2 two R SiX They can bond together to form a ring.

[0209] The X 1 and X 2 Preferably, they are >O and >NR, respectively. NX >C(-R CX 2. As for the substituent in the case of "substituted or unsubstituted", at least one substituent selected from the substituent group Zα can be listed. As for other preferred substituents, refer to the description in <Preferred Substituents> below.

[0210] The >NR NX R NX The >C(-R) CX )2 of R CX Preferably, each is independently methyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted dibenzofuranyl.

[0211] Regarding the >NR NX R NX The >C(-R) CX )2 of R CX and the >Si(-R SiX )2 of R SiX The explanation can be replaced by the explanation of the linking group described in the <Explanation of Rings and Substituents>. For example, as described in (1-106), (1-151), (1-209), (1-210), etc. of <Specific Examples of Polycyclic Aromatic Compounds> described later, in X 1 or X 2 For >NR NX In the case of R NX It can form a ring with ring A, ring B or ring C via a single bond, but is not limited to these.

[0212] <g-1>

[0213] At least one ring in the structure selected from the group consisting of rings A, B, and C contains a basis represented by the following formula (G-1), or is composed of R. S R Ge R NX R CX and R SiX At least one of the represented groups comprises a group represented by the following formula (G-1). The bulky substituent represented by formula (G-1) can distort the condensed ring planar structure of a polycyclic aromatic compound containing a structural unit represented by formula (1). In particular, by bonding the group represented by formula (G-1) at the ortho position of the aryl substituent within the structural unit, a more distorted structure will encapsulate the molecule to suppress concentration quenching, thereby potentially improving the luminous efficiency of an organic electroluminescent element utilizing a polycyclic aromatic compound comprising a structural unit containing formula (1).

[0214] Furthermore, by deuterating the hydrogen at the α-position of the cycloalkyl group, the chemical stability of polycyclic aromatic compounds containing the structural unit represented by formula (1) is improved, and it is expected to contribute to the long lifetime of organic electroluminescent devices using them.

[0215]

[0216] In equation (G-1),

[0217] P1 ring is a substituted cycloalkyl ring. D represents deuterium, indicating the bonding position with structures other than those in equation (G-1). For example, in the case where the base represented by equation (G-1) is directly bonded to ring A, ring B, or ring C, For the bonding positions with ring A, ring B, or ring C, in the case of bonding with substituents of ring A, ring B, or ring C, This refers to the bonding position with the substituent. In these cases, This can be the bonding position with the aryl ring in equation (1). The group represented by equation (G-1) and Si-R s Si or Ge-R Ge In the case of Ge bonding, For the bonding positions with Si or Ge, in relation to R s Or R Ge In the case of bonding, To be with R s Or R Ge The bonding positions. In the base and NR represented by equation (G-1) NX N, C(-R) CX C or Si(-R)2 SiX In the case of Si bonding of )2, For the bonding positions with N, C, or Si, in relation to R NX R CX Or R SiX In the case of bonding, To be with R NX R CX Or R SiX The bond position.

[0218] The bonding pattern of the base represented by formula (G-1) is preferably a pattern of direct bonding with ring A, ring B or ring C, a pattern of bonding with substituents of ring A, ring B or ring C, or a pattern of bonding with NR. NX R NX The bonding pattern is more preferably a bonding pattern with substituents of ring A, ring B, or ring C, or a bonding pattern with NR. NX R NX The bonding pattern is particularly preferred to be with NR. NX R NX The bonding configuration. When bonded to substituents of ring A, ring B, or ring C, the substituents of ring A, ring B, or ring C are preferably diarylamino or aryl, more preferably aryl, and particularly preferably phenyl. When bonded to NR... NX R NX In the case of bonding, R NX Preferably aryl, particularly phenyl. The aryl or phenyl group may contain substituents other than those of formula (G-1).

[0219] <(1-a) to (1-m)>

[0220] Preferred examples of polycyclic aromatic compounds having the structure represented by formula (1) include polycyclic aromatic compounds represented by formulas (1-a) to (1-m).

[0221]

[0222] In equations (1-a) to (1-m),

[0223] X 1 To X 6 Independently with X in equation (1) 1 and X 2 The definitions are the same, Y 1 and Y 2 Independently with Y in equation (1) 1 The definition is the same, the X 1 To X 6 >NR NX R NX >C(-R CX )2 of R CX and >Si(-R SiX )2 of R SiX It can be linked to one or two Z bonds via a linker base or a single bond.

[0224] The Z is independently defined as =C(-R) CCX )- or =N-, the =C(-R CCX )- of R CCX The elements are, independently, hydrogen, deuterium, cyano, halogen, substituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted diarylamino, or substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, or substituted or unsubstituted diarylboryl, wherein the two heteroaryl groups of the diheteroarylamino, the aryl and heteroaryl groups of the arylheteroarylamino, and the two aryl groups of the diarylboryl can be bonded to each other via linker groups, and the =C(-R CCX The two R's of )- CCX They can be bonded together to form a ring, wherein the R CCX R S R Ge R NX R CX and R SiX At least one of the bases represented includes the base represented by equation (G-1). The =C(-R) CCX )- of R CCX Preferably, each is independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuranyl group, a tert-butyl group, a vinyl group, a substituted or unsubstituted diphenylamino group, or a substituted or unsubstituted cyclohexyl group. In the =C(-R CCX The two R's of )- CCX When all components are vinyl groups, they can bond together to form rings, and preferably form naphthalene rings.

[0225] <(g-1) to (g-10)>

[0226] Preferred examples of the basis represented by equation (G-1) can be the bases represented by equations (g-1) to (g-10).

[0227]

[0228] In equations (g-1) to (g-10), For the bonding positions with structures other than those in equations (g-1) to (g-10), D is deuterium. Regarding... For more details, please refer to the above. <g-1>Explanation.

[0229] <g-2>

[0230] A polycyclic aromatic compound containing a structural unit represented by formula (1) contains at least one group represented by the following formula (G-2).

[0231]

[0232] In equation (G-2),

[0233] P1 ring is a substituted cycloalkyl ring, and P2 ring is a substituted aryl ring or a substituted heteroaryl ring. For the bonding positions with structures other than those in equation (G-2), D represents deuterium. Regarding... For more details, please refer to the above. <g-1>The explanation. Having via The elements of the linked P2 ring are adjacent to the elements of the linked P1 ring. That is, the P1 ring is bonded to the adjacent position of the P2 ring.

[0234] The cycloalkyl ring is preferably a cycloalkyl ring contained in the base represented by formulas (g-1) to (g-10).

[0235] The aryl ring or heteroaryl ring is preferably a benzene ring, naphthyl ring, benzofuran ring, benzothiophene ring, indene ring, carbazole ring, acridine ring, phenoxazine ring, phenothiazine ring, indole ring, or benzoselenene ring. As a substituent in the "substitutable" case, at least one substituent selected from the substituent group Zα can be listed. When multiple substituents are present, the multiple substituents may be the same or different. Preferred substituents are substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, or substituted or unsubstituted diarylamino groups. Other preferred substituents can be found in the <Preferred Substituents> section described later.

[0236] In the structure, at least one hydrogen atom may be substituted with a cyano group or a halogen, and at least one -CH2- group may be substituted with an -O- group. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine.

[0237] <Preferred Substituents>

[0238] 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 substitute for 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 given of the substitution of some or all of the hydrogens of the aryl ring or benzene ring in these groups by the group of formula (tR).

[0239]

[0240] In equation (tR), R a R b and R c Each is an alkyl group having 1 to 24 carbon atoms. Furthermore, R a R b and R c Each group can be one or more non-adjacent alkyl groups having carbon numbers from 1 to 24, and not a -O-substituted group of the terminal CH3 group. The group represented by formula (tR) will... Set as the bond location.

[0241] 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. Examples include: straight-chain alkyl groups having 1 to 24 carbon atoms or branched alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched alkyl groups having 3 to 4 carbon atoms).

[0242] 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.

[0243] 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.

[0244] 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.

[0245] As a substituent, the substituent represented by formula (A30) is preferred.

[0246] 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.

[0247] In the following structural formula, Indicates the location of the bond.

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258] Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) are preferably those comprising at least one tertiary alkyl group (tert-butyl or tert-pentyl, etc.), neopentyl or adamantyl group represented by formula (tR), and more preferably comprising 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 increasing the luminescent quantum yield (PLQY). In addition, diarylamino groups are preferred as substituents. Furthermore, 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 those in which part or all of the hydrogen atoms of the aryl ring or benzene ring are substituted with the group of formula (tR).

[0259] In a structure composed of one or more structural units represented by formula (1), the substituents of the aryl ring or heteroaryl ring may be the substituents represented by the following formula (A20).

[0260]

[0261] 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. The two Rs can bond to each other to form a ring. Furthermore, 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.

[0262] r is an integer from 1 to 4.

[0263] 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 with any R through a linker or a single bond. A Interconnected.

[0264] Examples of the substituents can be listed as substituents represented by any of the following.

[0265]

[0266] 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.

[0267] <Cycloalkane condensation>

[0268] At least one of the polycyclic aromatic compounds having a structure consisting of one or two structural units represented by formula (1), selected from the group consisting of aryl rings and heteroaryl rings, can be condensed by at least one cycloalkane.

[0269] 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.

[0270] 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.

[0271] Examples of "cycloalkanes" include: cycloalkanes with 3-24 carbon atoms, cycloalkanes with 3-20 carbon atoms, cycloalkanes with 3-16 carbon atoms, cycloalkanes with 3-14 carbon atoms, cycloalkanes with 5-10 carbon atoms, cycloalkanes with 5-8 carbon atoms, cycloalkanes with 5-6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0272] 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 from 1 to 5.

[0273] In the examples described, a preferred structure is one where at least one substituent is present on the carbon atom at the α-position of the cycloalkane (in a cycloalkane condensed in an aryl or heteroaryl ring, the carbon atom adjacent to the carbon at the condensation site), as shown in the following structural formula. A more preferred structure is one where two substituents are present on the carbon atom at the α-position, and a more preferred structure is one where both α-position carbons have two substituents (a total of four substituents). Examples of such substituents include alkyl groups (especially methyl), halogens (especially fluorine), and deuterium, which have 1 to 5 carbon atoms. A particularly preferred structure is one where a portion of the structure represented by formula (B11) or formula (B12) is bonded to the adjacent carbon atom in the aryl or heteroaryl ring. A more preferred structure is one where a portion of the structure represented by formula (B11) is bonded to the adjacent carbon atom in the aryl or heteroaryl ring.

[0274]

[0275] In equations (B11) and (B12), Indicates the location of the bond.

[0276] 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.

[0277]

[0278] 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.

[0279]

[0280] 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 substituted form forming 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 skeleton structure of the compound; in the case of a phenyl group, it refers to the substituted bond in the skeleton structure of the compound.

[0281]

[0282] As a form of cycloalkane condensation, the following can be listed first: aryl or heteroaryl rings in the A, B, or C rings of polycyclic aromatic compounds having a structure composed of one or more structural units represented by formula (1) formed by cycloalkane condensation; Ar 1 and Ar 2 The aryl ring or heteroaryl ring in the form of a cycloalkane condensation; and the aryl ring or heteroaryl ring in the form of a cycloalkane condensation when any of the other substituents is a group containing an aryl ring or heteroaryl ring.

[0283] Furthermore, by introducing a cycloalkane structure into a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1), 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, the purification can be carried out at a lower temperature, thus avoiding thermal decomposition of the material. Furthermore, 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, resulting in high-performance organic devices. Additionally, 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.

[0284] <Replaced with heavy stable isotopes>

[0285] In polycyclic aromatic compounds containing structural units represented by formula (1), each element is an element that contains multiple naturally occurring isotopes in a naturally occurring ratio, unless otherwise specified. All or some elements in each structural formula may also contain heavy stable isotopes in a ratio exceeding the naturally occurring ratio. In this specification, this is simply referred to as "replaced with" or "heavy stable isotopes". More specifically, at least one hydrogen may be replaced with deuterium, and at least one nitrogen may be replaced 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). By substituting at least a portion of the elements with restable isotopes, particularly by substituting at least one boron element with boron-11 ( 11 B), which enables the long lifetime of organic electroluminescent devices using polycyclic aromatic compounds containing the structural units represented by formula (1) as dopants. As for the presence ratio of each isotope, for example in boron-10 ( 10 In B), each atom% is preferably 70 or more, more preferably 80 or more, and even more preferably 90 or more. In Boron-11 ( 11 In B), each atom% is preferably 85% or more, more preferably 90% or more, and even more preferably 95% or more.

[0286] <Using the substitution of deuterium>

[0287] In polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), all or part of the hydrogen may be deuterium. From the viewpoint of component lifetime and high efficiency, it is more preferable that the hydrogen in the polycyclic aromatic compound is replaced with deuterium. The deuteration rate of each hydrogen atom in the polycyclic aromatic compound is preferably 50% or more, more preferably 60% or more, more preferably 70% or more, even more preferably 80% or more, even more preferably 90%, and particularly more preferably 95% or more. Furthermore, in cases where it is difficult to specify the deuteration rate of individual hydrogen atoms in substituents such as the CD3 group, the overall deuteration rate of the group can be calculated, and the preferred range of such deuteration rate can be referred to the foregoing description.

[0288] For example, polycyclic aromatic compounds having a structure composed of one or more structural units represented by formula (1) including rings A, B, C, and R. S R Ge R NX R CX and R SiX The hydrogen in any of them may be deuterated, and examples of deuterated forms of all or part of the hydrogen in the aryl or heteroaryl groups can be listed. In addition, from the point of view of durability, it is also preferred that all or part of the hydrogen in the polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) is deuterated.

[0289] The descriptions of "substitution with heavy stable isotopes" and "substitution using deuterium" may not be part of the descriptions of deuterium in formulas (G-1) and (G-2).

[0290] <Specific examples of polycyclic aromatic compounds>

[0291] As a specific example of a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1), any of the following compounds can be listed.

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304] In the formula, D represents deuterium.

[0305] <Preparation methods of polycyclic aromatic compounds>

[0306] Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) are generally prepared by first bonding a bonding group with a condensation ring containing rings A, B, and C to prepare an intermediate (first reaction). Subsequently, the final product is prepared by bonding a bonding group (containing a boron group) with the condensation ring containing rings A, B, and C. In the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or a Ullmann reaction can be used. If it is an amination reaction, a general reaction such as a Buchwald-Hartwig reaction, a nucleophilic substitution reaction, or a Goldberg amination can be used. In addition, in the second reaction, a tandem Hetero-Friedel-Crafts reaction (a continuous aromatic electrophilic substitution reaction, the same below) can be used. The target compound can be prepared by using a starting material with the desired condensed ring at some point in the reaction process or by adding a step to condense the ring.

[0307] [Preparation method via intermediates]

[0308] The polycyclic aromatic compounds of the present invention can be prepared by a method comprising the following steps. For details of the following steps, please refer to International Publication No. 2015 / 102118.

[0309] The following describes a reaction comprising the following steps: synthesizing the intermediate from a halogenation precursor; metallizing the halogen atom (Hal) in intermediate 1 using an organic base compound; and reacting the metal with Y using a reagent selected from the group consisting of boron halides, boron amino halides (e.g., BCl3, BBr3, or BI3), boron alkoxyides, and boron aryloxyides. 1 (B, etc.) are exchanged; and boron is used to bond the B ring to the C ring via a series of aromatic electrophilic substitution reactions using Brønsted bases. The halogen atom (Hal) in the formula can be any of F, Cl, Br, I, or they can be the same, or they can be different independently, and can be appropriately selected considering the reactivity of the matrix.

[0310]

[0311] Examples of metallizing reagents used in the halogen-metal exchange reaction described so far include alkyl lithiums such as methyl lithium, n-butyl lithium, sec-butyl lithium, and tert-butyl lithium, as well as isopropyl magnesium chloride, isopropyl magnesium bromide, phenyl magnesium chloride, phenyl magnesium bromide, and lithium chloride complexes of isopropyl magnesium chloride known as Turbo Grignard reagents.

[0312] In addition to the reagents described above, other examples of metallizing agents used in the ortho-metal exchange reaction in the process described so far include: lithium diisopropylamide, lithium tetramethylpiperidinide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium chloride tetramethylpiperidinylmagnesium-lithium chloride complex, lithium tri-n-butylmagnesium oxide, and other organic base compounds.

[0313] Furthermore, examples of additives that promote the reaction when using alkyllithium as a metallizing agent include: N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethylpropylene urea.

[0314] In addition, Lewis acids used in the process described above can be listed as follows: AlCl3, AlBr3, AlF3, BF4. 3· The Lewis acids include 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, and CoBr3. Alternatively, substances formed by supporting these Lewis acids on a solid can also be used in the same way.

[0315] In addition, examples of Brinzyl acids used in the processes described above include: p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboxylic acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, and hydrogen fluoride. Examples of solid Brinzyl acids include: Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and Taycacure (trade name: Tayca Corporation).

[0316] In addition, examples of amines that can be added to the process described above include: diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylamine, etc.

[0317] In addition, the solvents used in the process described above can be listed as: o-dichlorobenzene, chlorobenzene, toluene, benzene, dichloromethane, chloroform, dichloroethylene, trifluorotoluene (benzotrifluoride), decahydronaphthalene, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentylmethyl ether, tetrahydrofuran, dioxane, methyl-tert-butyl ether, etc.

[0318] Here, Y is recorded. 1 Taking B as an example, Y can also be synthesized by appropriately changing the raw materials. 1 Compounds of P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R.

[0319] In the aforementioned process, Brønsted bases or Lewis acids may also be used to promote the tandem heterofried-Krawtz reaction. Specifically, when using Y... 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Triiodide, etc. 1 In the case of halides, as the aromatic electrophilic substitution reaction proceeds, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated; therefore, using a Brinzyl base that captures these acids is effective. On the other hand, when using Y... 1 Aminated halides, Y 1 In the case of alkoxylates, amines and alcohols are generated as aromatic electrophilic substitution reactions proceed. Therefore, in most cases, the use of Brentstein bases is unnecessary. However, due to the low desorption capacity of amino or alkoxy groups, the use of Lewis acids that promote their desorption is effective.

[0320] In addition, the polycyclic aromatic compounds of the present invention also include compounds in which at least a portion of the hydrogen is substituted with deuterium or substituted with various substituents. Such compounds can be synthesized in the same manner as described above using raw materials that are deuterated or derivatized at the desired positions.

[0321] <2. Organic Devices>

[0322] The polycyclic aromatic compounds of this invention can be used as materials for organic devices. Examples of organic devices include organic electroluminescent elements, organic field-effective transistors, and organic thin-film solar cells.

[0323] 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, and organic thin-film solar cells, but organic electroluminescent elements are preferred. The polycyclic aromatic compounds of the present invention are preferably materials for organic electroluminescent elements, more preferably materials for light-emitting layers (light-emitting materials), and most preferably dopant materials for light-emitting layers.

[0324] <2-1. Organic electroluminescent elements>

[0325] <2-1-1. Structure of Organic Electroluminescent Element>

[0326] Figure 1 This is a schematic cross-sectional view showing an example of an organic EL element.

[0327] 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.

[0328] 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.

[0329] 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.

[0330] 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 / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / " 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”, “substrate / anode / light-emitting layer / electron transport layer / cathode”.

[0331] <2-1-2. Emitting Layer in Organic Electroluminescent Devices>

[0332] The polycyclic aromatic compound of the present invention is preferably used as a material for forming any one or more organic layers in an organic electroluminescent element, and more preferably as a material for forming a light-emitting layer. The light-emitting layer 105 is a layer that emits light by recombination of holes injected from the anode 102 with electrons injected from the cathode 108 between electrodes to which an electric field is applied. As a material for forming the light-emitting layer 105, any compound that emits light upon excitation by the recombination of holes and electrons (a luminescent compound) is acceptable; preferably, it is a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state. The polycyclic aromatic compound of the present invention can be used as a material for a light-emitting layer, as a dopant material, or as a host material, but is preferably used as a material for a light-emitting layer, and more preferably as a dopant material.

[0333] Furthermore, there are examples of using auxiliary dopants and emission dopants together as dopants, but in this specification, when referred to only as "dopant", it means emission dopant without the use of auxiliary dopants.

[0334] Polycyclic aromatic compounds containing the structural unit represented by formula (1) can be used as emission dopants for TTF elements that utilize the phenomenon of generating singlet excitons from multiple triplet excitons (Triplet-Triplet Fusion, TTF).

[0335] Furthermore, polycyclic aromatic compounds containing the structural units represented by formula (1) can be used as emission dopants for TADF devices as "thermally active delayed phosphors". 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 therefore cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, enabling high-efficiency organic EL devices.

[0336] The light-emitting layer can be a single layer or multiple layers, either of which is acceptable, and is formed from light-emitting layer materials (host material and dopant material). The host material and dopant material can be one type or a combination of multiple types, either of which is acceptable. The dopant material can be contained entirely within the host material or partially within the host material, either of which is acceptable. As a doping method, it can be formed by co-evaporation with the host material, or it can be pre-mixed with the host material and then simultaneously evaporated. The following shows specific examples of dopants combined with the compounds of the present invention when multiple dopants are combined.

[0337]

[0338] From a durability point of view, it is also preferable that some or all of the hydrogen atoms in the dopant material are deuterated.

[0339] The amount of main material used varies depending on the type of main material, and can be determined by considering the characteristics of the main material. 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 total mass, and even more preferably 90% to 99.9% of the total mass.

[0340] The amount of dopant material used varies depending on the type of dopant material, and can be determined in accordance with the characteristics of the dopant material. The preferred amount of dopant material used 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. Such a range is preferred, for example, in terms of preventing concentration quenching.

[0341] On the other hand, in organic EL devices using thermally active delayed fluorescence dopant materials, a low concentration of dopant material is preferable in terms of preventing concentration quenching, but a high concentration of dopant material is preferable in terms of the efficiency of the thermally active delayed fluorescence mechanism. Furthermore, in organic EL devices using thermally active delayed fluorescence auxiliary dopant materials, a low concentration of auxiliary dopant material is preferable in terms of the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant material compared to the amount of dopant material used. The polycyclic aromatic compound of the present invention can be used as a dopant (also called an emission dopant) in organic EL devices using thermally active delayed fluorescence auxiliary dopant materials.

[0342] When using auxiliary dopant materials, the base amounts of the main material, auxiliary dopant materials, and dopant materials are 40% to 99.999% by mass, 59% to 1% by mass, and 20% to 0.001% by mass of the total material used in the luminescent layer, respectively. Preferably, they are 60% to 99.99% by mass, 39% to 5% by mass, and 10% to 0.01% by mass, respectively. More preferably, they are 70% to 99.95% by mass, 29% to 10% by mass, and 5% to 0.05% by mass.

[0343] <Main Material>

[0344] Examples of main materials include: condensed ring derivatives such as anthracene, pyrene, dibenzo[a]fluorene or fluorene, which have been known as luminescent bodies since ancient times; bis(styrene) derivatives such as bis(styrene)-anthracene derivatives or bis(styrene)-benzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; benzo[a]fluorene derivatives, etc.

[0345] 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 form the light-emitting layer by combining 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.

[0346] [A compound represented by any of formulas (H1), (H2), and (H3)]

[0347] As the main material, for example, a compound represented by any of the following formulas (H1), (H2) and (H3) can be used.

[0348]

[0349] 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 group having 6-24 carbon atoms, a heteroarylene group having 2-24 carbon atoms, a heteroarylene arylene group having 6-24 carbon atoms, or a arylene heteroarylene arylene group having 6-24 carbon atoms, or any two of these groups linked by -O-, -S-, -CH2-, -Si(-Arx)2- (Arx being an aryl group) or a cycloalkylene group, forming a divalent 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 listed. 1 The heteroarylene group in the ring is preferably a heteroarylene group with 2 to 24 carbon atoms, more preferably a heteroarylene group with 2 to 20 carbon atoms, and even more preferably a heteroarylene group with 2 to 15 carbon atoms, particularly preferably a heteroarylene 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, indole ring, etc. 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, 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.

[0350] 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.

[0351]

[0352] (mCP)

[0353]

[0354]

[0355]

[0356] [Anthracene compounds]

[0357] Examples of anthracene compounds that are the main components include those represented by formula (3-H) and those represented by formula (3-H2).

[0358]

[0359] In equation (3-H),

[0360] X and Ar 4 Each of the following is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkyl group, a substituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group, all of X and Ar. 4 It will not become hydrogen at the same time.

[0361] 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.

[0362] 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, where X can be a single bond, an arylene (phenylene, biphenylene, and naphthylene, etc.), or a heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., groups having a divalent bonding valence).

[0363] 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.

[0364]

[0365] 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).

[0366] 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, where X can be a single bond, an arylene (phenylene, biphenylene, and naphthylene, etc.), or a heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., groups having a divalent bonding valence).

[0367] 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.

[0368]

[0369] Ar 1 and Ar 2 Each 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).

[0370] 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).

[0371] 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 phenylene group, a pyrene group, or a group represented by formula (A) (including carbazole and phenyl-substituted carbazole groups). Furthermore, in Ar... 3 When the substituent is a base represented by formula (A), the base represented by formula (A) in the case of... Ar in equation (3-X3) 3 Bond.

[0372] Ar 4 The silane is independently substituted with hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or alkyl with 1 to 4 carbon atoms (methyl, ethyl, tert-butyl, etc.) and / or cycloalkyl with 5 to 10 carbon atoms.

[0373] 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 position is substituted with at least one hydrogen atom in the compound represented by formula (3-H).

[0374] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have.

[0375]

[0376] In equation (A), Y is -O-, -S-, >C(-R) 29-1 )2 or >NR 29 R 21 ~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.

[0377] In formula (A), Y is preferably -O-.

[0378] As Y > NR 29 R in " 29 It is hydrogen or a substituted aryl group.

[0379] As Y > C(-R) 29-1 R in )2” 29-1 Each is independently hydrogen, alkyl, or a substituted aryl group. Furthermore, both R... 29-1 They can also bond with each other to form hydrocarbon rings or aryl rings.

[0380] R 21 ~R 28 The adjacent groups in the formula can bond to 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, 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.

[0381]

[0382] As R 21 ~ 28 A ring formed by the mutual bonding of two adjacent groups; if it is a hydrocarbon ring, for example, the cyclohexane ring; if it is an aryl ring or a heteroaryl ring, the R group can be listed as an example. 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).

[0383] 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 formula (A), or the atoms in the structure of Y as ">NR 29 "R" 29 Any position in or ">NR 29 "N(R) 29 The same applies to the bases directly bonded by (for bonding bonds). The same applies to the bases represented by any of the equations (A-1) to (A-14).

[0384] As a basis represented by formula (A), for example, any of the bases represented by formulas (A-1) to (A-14) can be listed, preferably any of the bases represented by formulas (A-1) to (A-5) and (A-12) to (A-14), more preferably any of the bases represented by formulas (A-1) to (A-4), and even more preferably any of the bases represented by formulas (A-1), (A-3) and (A-4), and particularly preferably the base represented by formula (A-1).

[0385] As a basis represented by equation (A), the following bases can be listed, for example. Y and The definition is the same as above.

[0386]

[0387]

[0388] 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 form of any of the bonds in the structure.

[0389] The group represented by formula (B) is one of the substituents that the anthracene compound represented by formula (3-H) may have.

[0390]

[0391] In formula (B), Y b -O-, -S-, >C(-R) 42 )2 or >NR 41 R 31 ~R 40 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. 31 ~R 40 The adjacent groups in R can bond with each other to form hydrocarbon rings, aryl rings, or heteroaryl rings. 41 It is hydrogen or a substituted aryl group.

[0392] Y in equation (B) b The preferred option is -O-.

[0393] As Y b >C(-R) 42 R in )2” 42 Each is independently hydrogen, alkyl, or a substituted aryl group. Furthermore, both R... 42 They can also bond with each other to form hydrocarbon rings or aryl rings.

[0394] In equation (B), R is... 31 ~R 40 A ring formed by the bonding of two adjacent groups can be described as follows: if it is a hydrocarbon ring, for example, the cyclohexane ring; if it is an aryl ring or a heteroaryl ring, the R group can be described as follows. 31 ~R 40 The ring structure described in "aryl" or "heteroaryl" is formed by condensation with one or both benzene rings of formula (A-1).

[0395] The base represented by formula (B) is the base obtained by removing a hydrogen atom from any position in formula (B). The position is indicated. That is, the base represented by formula (B) 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 (B), or R in the structure of formula (B). 31 ~R 40 The atoms on any ring formed by the mutual bonding of adjacent bases in the formula (B), or the atoms in the structure of Y, are considered as Y. b NR 41 "R" 41 Any position in or ">NR 41 "N(R) 41 (For the bond) is the base of direct bonding.

[0396] As a basis represented by equation (B), the following bases can be listed, for example. Y in the equation b and The definition is the same as above.

[0397]

[0398] In addition, all or part of the hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) can be deuterium.

[0399] The anthracene compound that serves as the main component can be, for example, a compound represented by the following formula (3-H2).

[0400]

[0401] In equation (3-H2), Ar c R is a substituted aryl group or a substituted heteroaryl group. c Ar is hydrogen, alkyl, or cycloalkyl. 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18 The hydrogen atom in the compound represented by formula (3-H2) may be substituted by a halogen, a substituted aryl group, a substituted heteroaryl group, a substituted diarylamino group (the two aryl groups may be bonded to each other via a linking group), a substituted diheteroarylamino group (the two heteroaryl groups may be bonded to each other via a linking group), a substituted arylheteroarylamino group (the aryl and heteroaryl groups may be bonded to each other via a linking group), a substituted alkyl group, a substituted cycloalkyl group, a substituted alkenyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, or a substituted silyl group, and at least one hydrogen atom in the compound may be substituted by a halogen, a cyano group, or a deuterium.

[0402] 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).

[0403]

[0404] 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).

[0405] In equations (3-H2-X4) to (3-H2-X8), Ar 24 Ar 25 Ar 26 Ar 27 Ar 28 Ar 29 and Ar 30 Each group may be independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorenyl, alkyl, 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).

[0406] 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).

[0407] 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.

[0408] 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.

[0409] In equation (3-H2), R c It is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or tert-butyl, and more preferably hydrogen.

[0410] 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.

[0411] 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.

[0412] Among the anthracene compounds represented by formula (3-H2), Ar is more preferred. 11 ~Ar 18 Any two of them are substituted aryl or substituted heteroaryl groups, and the other six are hydrogen, methyl, or tert-butyl.

[0413] Therefore, in equation (3-H2), R is preferred. c It is hydrogen, and Ar 11 ~Ar 18 Any six of them are hydrogen.

[0414] 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).

[0415]

[0416] In formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E), Arc', 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.

[0417] 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).

[0418] Ar c' Ar 11' Ar 12' Ar 13' Ar 14' Ar 15' Ar 17' and Ar 18' More preferably, the group is independently 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 with a group represented by phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4).

[0419] Furthermore, at least one hydrogen atom in the compounds represented by formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (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 the form in which all hydrogen atoms are deuterated.

[0420] As particularly preferred anthracene compounds represented by formula (3-H2), examples include anthracene compounds represented by the following formula (3-H2-Aa).

[0421]

[0422] 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 carbon atom of the anthracene ring may be substituted with a methyl or tert-butyl group instead of a hydrogen atom. 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.

[0423] 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 atom 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).

[0424] In compounds represented by formula (3-H2-Aa), the preferred carbon atom is at least at the 10th position 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.

[0425]

[0426] 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), and (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 deuterium substitution 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, R 30 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).

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447] In the above formula, D represents deuterium.

[0448] Among these compounds, the preferred formulas are (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 (3-134-Y). 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.

[0449] 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 Compounds with reactive groups in some structures, such as those of formula (A), are used as starting materials and prepared by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in the aforementioned reactive compounds include halogens or boric acids. For specific preparation methods, please refer, for example, to the synthetic methods described in paragraphs

[0089] to

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

[0450] [fluorene compounds]

[0451] The compound represented by formula (4-H) essentially functions as the main component.

[0452]

[0453] In equation (4-H),

[0454] R 1 To R 10 Each of these can be independently hydrogen, aryl, heteroaryl (the heteroaryl group may be bonded to the fluorene skeleton of formula (4-H) via a single bond or a linker), diarylamino (the two aryl groups may be bonded to each other via a linker), diheteroarylamino (the two heteroaryl groups may be bonded to each other via a linker), arylheteroarylamino (the aryl and heteroaryl groups may be bonded to each other via a linker), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen atom may be substituted by 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 aryl, heteroaryl (the heteroaryl can be bonded to the formed ring via a single bond or a linker), diarylamino (two aryl groups can be bonded to each other via a linker), diheteroarylamino (two heteroaryl groups can be bonded to each other via a linker), arylheteroarylamino (aryl and heteroaryl can be bonded to each other via a linker), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these can be substituted by aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in the compound represented by formula (4-H) can be substituted by halogen, cyano or deuterium.

[0455] 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).

[0456]

[0457] 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.

[0458] These heteroaryl groups can be bonded to the fluorene skeleton in formula (4-H) via single bonds or linkers. 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 linkers. Examples of linkers include: phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, etc.

[0459] 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.

[0460] 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.

[0461]

[0462] 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-H) 1 To R 10 same.

[0463] 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.

[0464]

[0465] 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.

[0466] In addition, all or part of the hydrogens in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0467] More specific examples of fluorene compounds that are the subject of this invention can be listed as compounds represented by the following structural formulas.

[0468]

[0469] [Dibenzo[a]ene compounds]

[0470] The main dibenzo[a]oxane compound is, for example, a compound represented by the following formula (5-H).

[0471]

[0472] In equation (5-H), R 1 To R 16 Each of these is independently hydrogen, aryl, heteroaryl (the heteroaryl group may be bonded to the dibenzoxane skeleton of formula (5-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 by an aryl, heteroaryl, alkyl, or cycloalkyl group. Additionally, R 1 To R 16 The adjacent groups in the compound can bond to each other to form a condensation ring, 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, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy group, and at least one hydrogen in these groups can be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group, and at least one hydrogen in the compound represented by formula (5-H) can be substituted by a halogen, cyano or deuterium group.

[0473] As an alkenyl group in the definition of formula (5-H), examples include alkenyl groups with 2 to 30 carbon atoms, preferably alkenyl groups with 2 to 20 carbon atoms, more preferably alkenyl groups with 2 to 10 carbon atoms, and even more preferably alkenyl groups with 2 to 6 carbon atoms, particularly preferably alkenyl groups 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.

[0474] 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 (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5).

[0475]

[0476] In equations (5-Ar1) to (5-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 (5-Ar1) to (5-Ar5) can be substituted with phenyl, biphenyl, naphthyl, anthracene, phenanthryl, methyl, ethyl, propyl or butyl.

[0477] These heteroaryl groups can be bonded to the dibenzo[a]benzyl skeleton in formula (5-H) via single bonds or linkers. That is, the dibenzo[a]benzyl skeleton in formula (5-H) can be directly bonded to the heteroaryl groups, or they can be bonded to each other via linkers. Examples of linkers include: phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, etc.

[0478] The compound represented by formula (5-H) is preferably R. 1 R 4 R 5 R 8 R 9 R 12 R 13 and R 16 It is hydrogen. In this case, R in formula (5-H) 2 R 3 R 6 R 7 R 10 R 11 R 14 and R 15 Preferably, the group is a monovalent group that is independently hydrogen, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, has a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the monovalent group having the structure can be bonded to the dibenzoxane skeleton of formula (5-H) via phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-), methyl, ethyl, propyl, or butyl.

[0479] The compound represented by formula (5-H) is more preferably R. 1 R 2 R 4 R 5 R 7 R 8 R 9 R 10 R 12 R 13 R 15 and R 16 It is hydrogen. In this case, R in formula (5-H) 3 R 6 R 11 and R 14 At least one of them (preferably one or two, more preferably one) is a monovalent group having a structure of formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) having a mesostatic single bond, phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O- or -OCH2CH2O-, and the other than at least one (i.e., the position not replaced by the monovalent group having the structure) is hydrogen, phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl or butyl, and at least one of these hydrogens may be substituted by phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl or butyl.

[0480] Additionally, R in equation (5-H) 2 R 3 R 6 R 7 R 10 R 11 R 14 and R 15 When selecting a monovalent group having a structure represented by formulas (5-Ar1) to (5-Ar5), at least one hydrogen in the structure can react with R in formula (5-H). 1 To R 16 A single bond is formed by bonding between any two of them.

[0481] More specific examples of dibenzo[a]pyroxene compounds, which are the subject of this invention, can be listed as compounds represented by the following structural formulas.

[0482]

[0483]

[0484] The light-emitting layer material (both the host material and the dopant material) may also be used in the light-emitting layer material as a polymeric compound or a polymeric crosslink thereof, or as a suspended polymeric compound or a suspended polymeric crosslink thereof. The polymeric compound is obtained by polymerizing a reactive compound, which is a monomer formed by replacing reactive substituents in the light-emitting layer material (both the host material and the dopant material). The suspended polymeric compound is obtained by reacting a main-chain polymer with the reactive compound. As a reactive substituent in this case, the description of the polycyclic aromatic compounds represented by formula (1) can be referenced.

[0485] [Pyrene compound]

[0486] The main pyrene compound is, for example, a compound represented by the following formula (6-H).

[0487]

[0488] In the aforementioned formula (6-H), R 1 ~R 11 Each of these is independently hydrogen, aryl, heteroaryl, 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 ~R 11 The adjacent groups in the compound can bond to each other to form a condensation ring, 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 group, and at least one hydrogen in these groups can be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group. In addition, at least one hydrogen in the compound represented by formula (6-H) can be independently substituted by a halogen, cyano or deuterium group.

[0489] More specific examples of pyrene compounds that are the subject of this invention can be listed as compounds represented by the following structural formulas.

[0490]

[0491]

[0492]

[0493]

[0494] [Fluoranthracene compounds]

[0495] The main fluoranthene compound is, for example, a compound represented by the following formula (7-H).

[0496]

[0497] In the aforementioned formula (7-H), R 1 ~R 10 Each of these is independently hydrogen, aryl, heteroaryl, 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 ~R 10 The adjacent groups in the compound can bond to each other to form a condensation ring, 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 group, and at least one hydrogen in these groups can be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group. In addition, at least one hydrogen in the compound represented by formula (7-H) can be independently substituted by a halogen, cyano or deuterium group.

[0498] The fluoranthene compound represented by formula (7-H) is also preferably the one represented by formula (7-H-1).

[0499]

[0500] In the formula (7-H-1), R 1 ~R 12 The definition of R in equation (7-H) 1 ~R 10 The definition is the same, and in addition, at least one hydrogen atom in the compound represented by formula (7-H-1) can be independently substituted by halogen, cyano or deuterium.

[0501] More specific examples of fluoranthene compounds, which are the subject of this invention, can be listed by compounds represented by the following structural formulas.

[0502]

[0503] [Benzanthracene compounds]

[0504] The main benzene anthracene compound is, for example, a compound represented by the following formula (8-H).

[0505]

[0506] In the aforementioned formula (8-H), R 1 ~R 12 Each of these is independently hydrogen, aryl, heteroaryl, 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 ~R 12 The adjacent groups in the compound can bond to each other to form a condensation ring, 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 group, and at least one hydrogen in these groups can be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group. In addition, at least one hydrogen in the compound represented by formula (8-H) can be independently substituted by a halogen, cyano or deuterium group.

[0507] More specific examples of benzanthracene compounds, which are the subject of this invention, can be listed by compounds represented by the following structural formulas.

[0508]

[0509]

[0510] Auxiliary dopants (thermally active delayed phosphors or phosphorescent materials)

[0511] The emitting layer of an organic electroluminescent element may comprise a host compound as a first component, an auxiliary dopant as a second component, and an emitting dopant as a third component. The polycyclic aromatic compound of the present invention is preferably used as the emitting dopant. Thermally active delayed phosphors or phosphorescent materials may be used as the auxiliary dopant (compound).

[0512] In the following description, organic electroluminescent devices that use thermally activated delayed fluorescence (TADF) as auxiliary dopant are sometimes referred to as "TAF devices" (Thermally Activated Delayed Fluorescence, TADF Assisting Fluorescence devices). Additionally, organic electroluminescent devices that use phosphorescent materials as auxiliary dopant are sometimes referred to as PSF devices (Phosphorescence-sensitized fluorescent devices).

[0513] In this embodiment, the light-emitting layer can be a single layer or multiple layers, either is acceptable. Furthermore, the host compound, auxiliary dopant, and the polycyclic aromatic compound of the present invention can be contained within the same layer, or at least one of each can be contained in multiple layers. The host compound, auxiliary dopant, and polycyclic aromatic compound of the present invention contained in the light-emitting layer can each be one type, or a combination of multiple types, either is acceptable. The auxiliary dopant and emission dopant can be contained in the entire host compound serving as the matrix, or in a portion of the host compound serving as the matrix. The light-emitting layer doped with the auxiliary dopant and emission dopant can be formed by methods such as: a method of forming a film of the host compound, auxiliary dopant, and emission dopant by ternary co-evaporation; a method of pre-mixing the host compound, auxiliary dopant, and emission dopant and then simultaneously evaporating; a wet film-forming method by coating a composition (coating) for forming a light-emitting layer prepared by dissolving the host compound, auxiliary dopant, and emission dopant in an organic solvent, etc.

[0514] The amount of the host compound used varies depending on the type of host compound, and can be determined based on the characteristics of the host compound. The preferred basis for the amount of the host compound used is 40% to 99% of the total mass of the material used in the luminescent layer, more preferably 50% to 98% of the total mass, and even more preferably 60% to 95% of the total mass. Such a range is preferred, for example, in terms of efficient charge transport and efficient energy movement toward the dopant.

[0515] The amount of auxiliary dopant used varies depending on the type of auxiliary dopant, and can be determined based on the characteristics of the auxiliary dopant. The preferred basis for the amount of auxiliary dopant used is 1% to 60% of the total mass of the material used in the emitting layer, more preferably 2% to 50% of the total mass, and even more preferably 5% to 30% of the total mass. If it falls within this range, it is preferred, for example, in terms of efficiently transferring energy to the emitting dopant.

[0516] The amount of emission dopant (a compound containing boron atoms) used varies depending on the type of emission dopant, and can be determined based on the characteristics of the emission dopant. The preferred amount of emission dopant used is 0.001% to 30% of the total mass of the material used in the luminescent layer, more preferably 0.01% to 20% of the total mass, and even more preferably 0.1% to 10% of the total mass. Such a range is preferred, for example, in terms of preventing concentration quenching.

[0517] In terms of preventing concentration quenching, it is preferable to use a low concentration of the emission dopant. In terms of the efficiency of the thermally active delayed fluorescence mechanism, it is preferable to use a high concentration of the auxiliary dopant. Furthermore, in terms of the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant, it is preferable that the amount of emission dopant used is low compared to the amount of auxiliary dopant used.

[0518] In this embodiment, a known compound may be used as the main compound.

[0519] From the viewpoint of promoting rather than hindering the generation of TADF within the emissive 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 emissive 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 or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. Alternatively, a TADF-active compound may be used as the host compound.

[0520] In addition, the "host compound" in TAF elements 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 that of the thermally active delayed phosphor as the second component and the emission dopant as the third component.

[0521] Examples of host compounds include compounds having at least one of a carbazole ring and a furan ring, with compounds preferably being formed by bonding at least one of a furanyl group and a carbazole group to at least one of an arylene group and a heteroarylene group. As host compounds, compounds represented by any of the formulas (H1), (H2), and (H3) can be used, and more specifically, mCP or mCBP can be used.

[0522] [Thermally active delayed phosphor (auxiliary dopant)]

[0523] 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 deactivated 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.

[0524] The polycyclic aromatic compounds of the present invention can function as emission dopants, and the "thermally active delayed phosphor" can function as an auxiliary dopant to assist the luminescence of the polycyclic aromatic compounds of the present invention.

[0525] The thermally active delayed fluorescent cells (TADF compounds) used in TAF elements are preferably donor-acceptor type thermally active delayed fluorescent cells (DA-type TADF compounds): they are designed to locally contain the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) within the molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby producing efficient reverse intersystem crossing. Here, in this specification, the term "electron-donating substituent" (donor) refers to the substituent and part of the structure locally present in the HOMO of the thermally active delayed fluorescent cell molecule, and the term "electron-accepting substituent" (acceptor) refers to the substituent and part of the structure locally present in the LUMO of the thermally active delayed fluorescent cell molecule.

[0526] Generally, thermally active delayed phosphors using donors or acceptors exhibit high spin-orbit coupling (SOC) and low exchange interaction between HOMO and LUMO due to their structure, resulting in a small ΔE(ST) and thus achieving very fast reverse intersystem crossing velocities. By using the polycyclic aromatic compounds of this invention as emission dopant and thermally active delayed phosphors (TADF materials) as auxiliary dopant, devices that meet any or all of the requirements for high efficiency, high color purity, and long lifetime can be provided.

[0527] A thermally active delayed phosphor is simply a 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 may both be contained in the same layer, or they may be contained in adjacent layers or other close layers.

[0528] 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-type structure) and electron-accepting group (acceptor-type 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-cyclopenta[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.

[0529] As the second component of the emitting layer in a TAF element, a thermally active delayed phosphor is preferably used, whose emission spectrum at least partially overlaps with the absorption peak of the emission dopant. Hereinafter, compounds that can be used as the second component (thermally active delayed phosphor) of the emitting layer in a TAF element are illustrated. However, the compounds that can be used as thermally active delayed phosphors in a TAF element are not limited to the illustrated compounds below.

[0530]

[0531]

[0532]

[0533]

[0534]

[0535] Furthermore, as a thermally active delayed phosphor, any compound represented by any of the following formulas (AD1), (AD2), and (AD3) may also be used.

[0536]

[0537] In formulas (AD1), (AD2), and (AD3), M is independently a single bond, -O-, >N-Ar, or >CAr2, and is preferably a single bond, -O-, or >N-Ar from the viewpoint of the depth of the HOMO of the formed partial structure and the height of the lowest excited singlet and triplet energy levels. 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 is preferably an arylene group with 6 to 12 carbon atoms from the viewpoint of the magnitude of conjugation from the donor and acceptor partial structures. More specifically, examples include: phenylene, methylphenylene, and dimethylphenylene. Q is independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of the shallowness of the LUMO of the formed partial structure and the height of the lowest excited singlet and triplet energy levels. Ar is independently hydrogen, aryl (6-24 carbons), heteroaryl (2-24 carbons), alkyl (1-12 carbons), or cycloalkyl (3-18 carbons). From the viewpoint of the depth of the HOMO of the formed partial structure and the height of the lowest excited singlet and triplet energy levels, it is preferably hydrogen, aryl (6-12 carbons), heteroaryl (2-14 carbons), alkyl (1-4 carbons), or cycloalkyl (6-10 carbons), more preferably hydrogen, phenyl, tolyl, xylyl, mesitylelel, biphenyl, pyridyl, bipyridyl, triazine, carbazole, dimethylcarbazole, di-tert-butylcarbazole, benzimidazole, or phenylbenzimidazole, and even more preferably hydrogen, phenyl, or carbazole. m is 1 or 2. n is an integer of (6-m) or less, and from the viewpoint of steric hindrance, it is preferably an integer of 4 to (6-m). Furthermore, at least one hydrogen atom in the compounds represented by the formulas may be substituted with halogen or deuterium.

[0538] More specifically, the compounds used as the second component of the light-emitting layer in the TAF element are preferably 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.

[0539] The compound used as the second component of the light-emitting layer in the TAF element can be a 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. Compounds with a structure represented by the following formula (DAD1) having multiple donors D directly bonded to an acceptor A or bonded via a linker group are preferred compounds with superior properties for organic electroluminescent elements.

[0540] (D 1 -L 1 )nA 1 (DAD1)

[0541] Formula (DAD1) contains the compound represented by the following formula (DAD2).

[0542] D 2 -L 2 -A 2 -L 3 -D 3 (DAD2)

[0543] 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 independently represented by 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.

[0544]

[0545] [Phosphorescent materials (auxiliary dopants)]

[0546] In the luminescent layer, phosphorescent materials can be used as auxiliary dopants. Phosphorescent materials utilize intramolecular spin-orbit interactions (heavy atom effect) caused by metal atoms to obtain luminescence from the excited triplet state. As such phosphorescent materials, luminescent metal complexes can be used, for example. Examples of luminescent metal complexes include compounds represented by the following formulas (B-1) and (B-2).

[0547]

[0548] 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.

[0549] 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.

[0550] In equation (B-1), from the viewpoint of efficiency and lifespan, M is preferably Ir, and n is preferably 3.

[0551] In equation (B-2), from the viewpoint of efficiency and lifespan, M is preferably Pt.

[0552] 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.

[0553]

[0554] In the formula,

[0555] It bonds to the central metal M at ---.

[0556] Y is independently represented by BR. e NR e PR e ,O,S,Se,C=O,S=O,SO2,CR e R f SiR e R f or GeR e R f ,

[0557] The aromatic carbons CH in the ring can be independently substituted to N.

[0558] R e and R f They can be arbitrarily condensed or bonded to form rings.

[0559] R a R b R c and R d Each number can be independently represented as either unsubstituted or substituted up to 1, representing the largest number that can be substituted.

[0560] 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.

[0561] 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.

[0562] 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), and 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(acac), 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)( Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, etc.

[0563] In addition to the compounds represented by formula (B-1), the following compounds may be listed as examples.

[0564]

[0565]

[0566]

[0567] Alternatively, iridium complexes described in Japanese Patent Application Publication Nos. 2006-089398, 2006-080419, 2005-298483, 2005-097263, and 2004-111379, as well as U.S. Patent Application Publication No. 2019 / 0051845, may also be used, or those described in *Advanced Materials* (26:7116-7121), *Nature Asia Materials* (13, 53(2021)), and *Applied Physics Letters* (117, 253301(2020)). The platinum complex described in 117, 253301(2020) and Chapter 5 of "Light-Emitting Diode - An Outlook On the Empirical Features and Its Recent Technological Advancements".

[0568] <2-1-3. Anode in Organic Electroluminescent Devices>

[0569] The anode 102 functions to inject holes into the light-emitting layer 105. Furthermore, if either a hole injection layer 103 or a hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these layers.

[0570] 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.

[0571] <2-1-4. Hole injection layer and hole transport layer in organic electroluminescent devices>

[0572] 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 layering or mixing one or more hole injection / transport materials, or by a mixture of hole injection / transport materials and polymer binders. Alternatively, inorganic salts such as ferric chloride (III) can be added to the hole injection / transport materials to form the layers.

[0573] As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes under an applied electric field. Ideally, it should have high hole injection efficiency and efficient transport of the injected holes. Therefore, materials with low ionization potential, high hole mobility, excellent stability, and low likelihood of generating impurities that could become traps during preparation and use are preferred.

[0574] 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 (4,4',4''-tris(N-carbazole)triphenylamine, 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.

[0575] 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 the purpose of doping with electron-donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetetracyano-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(6), 729-731 (1998)"). These generate so-called holes through electron migration processes from electron-donating base materials (hole-transporting materials). The conductivity of the base material varies considerably depending on the number and mobility of holes. Known matrix materials with hole transport properties include, for example, 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). The polycyclic aromatic compounds of the present invention can also be used as materials for forming hole injection layers or hole transport layers.

[0576] <2-1-5. Electron blocking layer in organic electroluminescent devices>

[0577] An electron blocking layer can also be provided between the hole injection / transport layer and the light-emitting layer to prevent the diffusion of electrons from the light-emitting layer. The electron blocking layer can be formed using compounds represented by any of formulas (H1), (H2), and (H3). The polycyclic aromatic compounds of the present invention can be used as materials for forming the electron blocking layer.

[0578] <2-1-6. Electron injection layer and electron transport layer in organic electroluminescent devices>

[0579] 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.

[0580] 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 low likelihood of generating impurities that could become traps during preparation 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.

[0581] 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.

[0582] 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.

[0583] In addition, specific examples of other electron-transfer compounds include: pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO series derivatives, anthracene derivatives, phenanthrene-rhein derivatives, violaceanone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole series compounds, gallium complexes, pyrazole derivatives, and perfluorinated phenylene 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, thiazole 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 azide derivatives, pyrimidine derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyrene derivatives, thiophene derivatives, and azoline derivatives, etc.

[0584] 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.

[0585] The material can be used alone or in combination with different materials.

[0586] 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, hydroxyquinoline-based metal complexes, thiazole derivatives, benzo[a]thiazole derivatives, thiophene derivatives, and azoline derivatives.

[0587] The polycyclic aromatic compounds of the present invention can also be used as materials for forming electron injection layers or electron transport layers.

[0588] 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.

[0589] 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, K, Rb, or Cs are more preferred as alkali metals, 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, as a reducing agent with a work function of 2.9 eV or less, a combination of two or more of these alkali metals is preferred, and combinations containing Cs are particularly preferred, such as Cs with Na, Cs with K, Cs with Rb, or a combination 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 the organic EL device can be improved.

[0590] <2-1-7. Cathode in Organic Electroluminescent Devices>

[0591] 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.

[0592] 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.

[0593] 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.

[0594] <2-1-8. Fabrication Method of Organic Electroluminescent Element>

[0595] 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, inkjet printing, spin coating, casting, and coating. The film thickness of each layer formed by 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 value, evaporation rate (0.01 nm / s to 50 nm / s), substrate temperature (-150℃ to +300℃), and film thickness (2 nm to 5 μm) are appropriately set within the range.

[0596] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device including an anode, a hole injection layer, a hole transport layer, a light-emitting layer containing a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described. On a suitable substrate, an anode is fabricated by forming a thin film of an anode material using a vapor deposition method or the like. Then, thin films of a hole injection layer and a hole transport layer are formed on the anode. A thin film containing a host material and a dopant material is co-deposited on the thin film to form a light-emitting layer. An electron transport layer and an electron injection layer are formed on the light-emitting layer. Finally, a thin film containing a cathode material is formed using a vapor deposition method or the like to form a cathode, thereby obtaining the target organic EL device. Furthermore, in the fabrication of the organic EL device, the fabrication order can also be reversed, fabricating the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order.

[0597] 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 2V to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or 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.

[0598] <2-1-9. Examples of Applications of Organic Electroluminescent Elements>

[0599] Organic EL elements can also be used in display devices or lighting devices.

[0600] Display devices or lighting devices including organic EL elements can be manufactured by known methods such as connecting organic EL elements to known driving devices, and can be driven by known driving methods such as DC driving, pulse driving, AC driving, etc.

[0601] 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 either matrix display or segmented display. Moreover, matrix display and segmented display can coexist on the same panel.

[0602] 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 300μm 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.

[0603] 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.

[0604] 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 displays 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, backlights using organic EL elements offer advantages such as thinness and light weight, considering that existing methods are difficult to make thinner due to the inclusion of fluorescent lamps or light guide plates.

[0605] <2-2. Other Organic Devices>

[0606] In addition to being used in the organic electroluminescent elements, the polycyclic aromatic compounds of the present invention can also be used in the fabrication of organic electro-effective transistors or organic thin-film solar cells.

[0607] 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.

[0608] 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.

[0609] (1) Substrate / Gate electrode / Insulator layer / Source electrode, Drain electrode / Organic semiconductor active layer

[0610] (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode, drain electrode

[0611] (3) Substrate / Organic semiconductor active layer / Source electrode, drain electrode / Insulator layer / Gate electrode

[0612] (4) Substrate / source electrode, drain electrode / organic semiconductor active layer / insulator layer / gate electrode

[0613] 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.

[0614] 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.

[0615] <3. Wavelength Conversion Materials>

[0616] The polycyclic aromatic compounds of this invention can be used as wavelength conversion materials.

[0617] 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.

[0618] [Example]

[0619] The present invention will be described in more detail below through embodiments, but the present invention is not limited to these embodiments.

[0620] <<Synthesis example>>

[0621] Synthesis Example (1): Synthesis of Compound (1-1)

[0622]

[0623] Synthesis of compound (1-1)

[0624] Under a nitrogen atmosphere and at -30°C, compound (T-1-1) (17.5 g) and tert-butylbenzene (T-1-1) were placed in an atmosphere containing nitrogen. t A 1.6 M solution of tert-butyllithium pentane (tBuLi, 10 ml) was added to a flask containing tert-butylbenzene (200 ml). After the addition was complete, the temperature was raised to 60 °C and stirred for 2 hours. Low-boiling components were then removed from the tert-butylbenzene by vacuum distillation. The mixture was cooled to -30 °C and boron tribromide (8.0 g) was added. The temperature was raised to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0 °C and N,N-diisopropylethylamine (EtN(iPr)2, 7.2 ml) was added. The mixture was stirred at room temperature until heating stopped, then heated to 120 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath was added. Heptane was then added for separation. The mixture was then purified using a silica gel short-path column (developing solvent: toluene). The solid obtained by vacuum distillation of the solvent was dissolved in toluene, and heptane was added for reprecipitation, thereby obtaining the compound represented by formula (1-1).

[0625] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 839.64.

[0626] 1 H-NMR(CD2Cl2): δ=8.85(s, 1H), 8.83(s, 1H), 7.58(dd, 1H), 7.44(s, 1H),7.30(dd, 1H), 7.28(dd, 1H), 7.13(s, 2H), 7.12(d, 1H), 6.67(s, 1H), 6.60(s,1H), 6.11(s, 1H), 6.08(s, 1H), 2.06(m, 5H), 1.57(m, 14H), 1.32(s, 9H), 1.11(s, 9H), 0.98(s, 9H), 0.95(s,9H).

[0627] Synthesis Example (2): Synthesis of Compounds (1-2)

[0628] Except for changing compound (T-1-1) to compound (T-1-2), compound (1-2) was obtained by following the same steps as in synthesis example (1).

[0629] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 795.65.

[0630]

[0631] Synthesis Example (3): Synthesis of Compounds (1-5)

[0632] Except for changing compound (T-1-1) to compound (T-1-5), compound (1-5) was obtained by following the same steps as in synthesis example (1).

[0633] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1070.69.

[0634]

[0635] Synthesis Example (4): Synthesis of compounds (1-8)

[0636] Except for changing compound (T-1-1) to compound (T-1-8), compound (1-8) was obtained by following the same steps as in synthesis example (1).

[0637] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1070.69.

[0638]

[0639] Synthetic Example (5): Synthesis of Compounds (1-10)

[0640] Except for changing compound (T-1-1) to compound (T-1-10), compound (1-10) was obtained by following the same steps as in synthesis example (1).

[0641] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 10¹⁰.65.

[0642]

[0643] Synthesis Example (6): Synthesis of Compounds (1-15)

[0644] Except for changing compound (T-1-1) to compound (T-1-15), compound (1-15) was obtained by following the same steps as in synthesis example (1).

[0645] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 942.64.

[0646]

[0647] Synthesis Example (7): Synthesis of Compounds (1-30)

[0648] Except for changing compound (T-1-1) to compound (T-1-30), compound (1-30) was obtained by following the same steps as in synthesis example (1).

[0649] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1094.73.

[0650]

[0651] Synthetic Example (8): Synthesis of Compounds (1-35)

[0652] Except for changing compound (T-1-1) to compound (T-1-35), compound (1-35) was obtained by following the same steps as in synthesis example (1).

[0653] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1134.61.

[0654]

[0655] Synthetic Example (9): Synthesis of Compounds (1-34)

[0656] Except for changing compound (T-1-1) to compound (T-1-34), compound (1-34) was obtained by following the same steps as in synthesis example (1).

[0657] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1182.72.

[0658]

[0659] Synthetic Example (10): Synthesis of Compounds (1-36)

[0660] Except for changing compound (T-1-1) to compound (T-1-36), compound (1-36) was obtained by following the same steps as in synthesis example (1).

[0661] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1006.62.

[0662]

[0663] Synthetic Example (11): Synthesis of Compounds (1-38)

[0664] Except for changing compound (T-1-1) to compound (T-1-38), compound (1-38) was obtained by following the same steps as in synthesis example (1).

[0665] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1172.79.

[0666]

[0667] Synthetic Example (12): Synthesis of Compounds (1-41)

[0668] Except for changing compound (T-1-1) to compound (T-1-41), compound (1-41) was obtained by following the same steps as in synthesis example (1).

[0669] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1061.74.

[0670]

[0671] Synthetic Example (13): Synthesis of Compounds (1-48)

[0672] Except for changing compound (T-1-1) to compound (T-1-48), compound (1-48) was obtained by following the same steps as in synthesis example (1).

[0673] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1029.76.

[0674]

[0675] Synthetic Example (14): Synthesis of Compounds (1-50)

[0676] Except for changing compound (T-1-1) to compound (T-1-50), compound (1-50) was obtained by following the same steps as in synthesis example (1).

[0677] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1208.70.

[0678]

[0679] Synthetic Example (15): Synthesis of Compounds (1-60)

[0680] Except for changing compound (T-1-1) to compound (T-1-60), compound (1-60) was obtained by following the same steps as in synthesis example (1).

[0681] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1044.68.

[0682]

[0683] Synthetic Example (16): Synthesis of Compounds (1-63)

[0684] Except for changing compound (T-1-1) to compound (T-1-63), compound (1-63) was obtained by following the same steps as in synthesis example (1).

[0685] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 966.52.

[0686]

[0687] Synthetic Example (17): Synthesis of Compounds (1-75)

[0688] Except for changing compound (T-1-1) to compound (T-1-75), compound (1-75) was obtained by following the same steps as in synthesis example (1).

[0689] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1111.84.

[0690]

[0691] Synthetic Example (18): Synthesis of Compounds (1-78)

[0692] Except for changing compound (T-1-1) to compound (T-1-78), compound (1-78) was obtained by following the same steps as in synthesis example (1).

[0693] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 876.63.

[0694]

[0695] Synthetic Example (19): Synthesis of Compounds (1-82)

[0696] Except for changing compound (T-1-1) to compound (T-1-82), compound (1-82) was obtained by following the same steps as in synthesis example (1).

[0697] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1159.76.

[0698]

[0699] Synthetic Example (20): Synthesis of Compounds (1-83)

[0700] Except for changing compound (T-1-1) to compound (T-1-83), compound (1-83) was obtained by following the same steps as in synthesis example (1).

[0701] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1170.74.

[0702]

[0703] Synthetic Example (21): Synthesis of Compounds (1-85)

[0704] Except for changing compound (T-1-1) to compound (T-1-85), compound (1-85) was obtained by following the same steps as in synthesis example (1).

[0705] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 987.56.

[0706]

[0707] Synthetic Example (22): Synthesis of Compounds (1-87)

[0708] Except for changing compound (T-1-1) to compound (T-1-87), compound (1-87) was obtained by following the same steps as in synthesis example (1).

[0709] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1277.75.

[0710]

[0711] Synthetic Example (23): Synthesis of Compounds (1-90)

[0712] Except for changing compound (T-1-1) to compound (T-1-90), compound (1-90) was obtained by following the same steps as in synthesis example (1).

[0713] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1070.64.

[0714]

[0715] Synthetic Example (24): Synthesis of Compounds (1-95)

[0716] Except for changing compound (T-1-1) to compound (T-1-95), compound (1-95) was obtained by following the same steps as in synthesis example (1).

[0717] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 890.51.

[0718]

[0719] Synthetic Example (25): Synthesis of Compounds (1-96)

[0720] Except for changing compound (T-1-1) to compound (T-1-96), compound (1-96) was obtained by following the same steps as in synthesis example (1).

[0721] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 882.48.

[0722]

[0723] Synthesis Example (26): Synthesis of Compound (1-101)

[0724] Except for changing compound (T-1-1) to compound (T-1-101), compound (1-101) was obtained by following the same steps as in synthesis example (1).

[0725] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 916.42.

[0726]

[0727] Synthetic Example (27): Synthesis of Compound (1-102)

[0728] Except for changing compound (T-1-1) to compound (T-1-102), compound (1-102) was obtained by following the same steps as in synthesis example (1).

[0729] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 914.41.

[0730]

[0731] Synthetic Example (28): Synthesis of Compound (1-103)

[0732] Except for changing compound (T-1-1) to compound (T-1-103), compound (1-103) was obtained by following the same steps as in synthesis example (1).

[0733] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 917.42.

[0734]

[0735] Synthetic Example (29): Synthesis of Compound (1-105)

[0736] Except for changing compound (T-1-1) to compound (T-1-105), compound (1-105) was obtained by following the same steps as in synthesis example (1).

[0737] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 860.48.

[0738]

[0739] Synthetic Example (30): Synthesis of Compound (1-107)

[0740] Except for changing compound (T-1-1) to compound (T-1-107), compound (1-107) was obtained by following the same steps as in synthesis example (1).

[0741] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 886.53.

[0742]

[0743] Synthetic Example (31): Synthesis of Compounds (1-110)

[0744] Except for changing compound (T-1-1) to compound (T-1-110), compound (1-110) was obtained by following the same steps as in synthesis example (1).

[0745] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1306.75.

[0746]

[0747] Synthetic Example (32): Synthesis of Compound (1-111)

[0748] Except for changing compound (T-1-1) to compound (T-1-111), compound (1-111) was obtained by following the same steps as in synthesis example (1).

[0749] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1340.75.

[0750]

[0751] Synthesis Example (33): Synthesis of Compound (1-112)

[0752] Except for changing compound (T-1-1) to compound (T-1-112), compound (1-112) was obtained by following the same steps as in synthesis example (1).

[0753] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1258.70.

[0754]

[0755] Synthetic Example (34): Synthesis of Compounds (1-115)

[0756] Except for changing compound (T-1-1) to compound (T-1-115), compound (1-115) was obtained by following the same steps as in synthesis example (1).

[0757] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1324.77.

[0758]

[0759] Synthetic Example (35): Synthesis of Compounds (1-116)

[0760] Except for changing compound (T-1-1) to compound (T-1-116), compound (1-116) was obtained by following the same steps as in synthesis example (1).

[0761] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1242.72.

[0762]

[0763] Synthetic Example (36): Synthesis of Compounds (1-117)

[0764] Except for changing compound (T-1-1) to compound (T-1-117), compound (1-117) was obtained by following the same steps as in synthesis example (1).

[0765] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1090.47.

[0766]

[0767] Synthetic Example (37): Synthesis of Compound (1-121)

[0768] Except for changing compound (T-1-1) to compound (T-1-121), compound (1-121) was obtained by following the same steps as in synthesis example (1).

[0769] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 765.42.

[0770]

[0771] Synthetic Example (38): Synthesis of Compounds (1-123)

[0772] Except for changing compound (T-1-1) to compound (T-1-123), compound (1-123) was obtained by following the same steps as in synthesis example (1).

[0773] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1003.67.

[0774]

[0775] Synthetic Example (39): Synthesis of Compounds (1-124)

[0776] Except for changing compound (T-1-1) to compound (T-1-124), compound (1-124) was obtained by following the same steps as in synthesis example (1).

[0777] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 915.66.

[0778]

[0779] Synthetic Example (40): Synthesis of Compound (1-127)

[0780] Except for changing compound (T-1-1) to compound (T-1-127), compound (1-127) was obtained by following the same steps as in synthesis example (1).

[0781] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1040.67.

[0782]

[0783] Synthetic Example (41): Synthesis of Compounds (1-130)

[0784] Except for changing compound (T-1-1) to compound (T-1-130), compound (1-130) was obtained by following the same steps as in synthesis example (1).

[0785] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1004.68.

[0786]

[0787] Synthetic Example (42): Synthesis of Compound (1-132)

[0788] Except for changing compound (T-1-1) to compound (T-1-132), compound (1-132) was obtained by following the same steps as in synthesis example (1).

[0789] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1050.57.

[0790]

[0791] Synthetic Example (43): Synthesis of Compounds (1-135)

[0792] Except for changing compound (T-1-1) to compound (T-1-135), compound (1-135) was obtained by following the same steps as in synthesis example (1).

[0793] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1002.59.

[0794]

[0795] Synthetic Example (44): Synthesis of Compounds (1-138)

[0796] Except for changing compound (T-1-1) to compound (T-1-138), compound (1-138) was obtained by following the same steps as in synthesis example (1).

[0797] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 800.51.

[0798]

[0799] Synthetic Example (45): Synthesis of Compounds (1-142)

[0800] Except for changing compound (T-1-1) to compound (T-1-142), compound (1-142) was obtained by following the same steps as in synthesis example (1).

[0801] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1326.85.

[0802]

[0803] Synthetic Example (46): Synthesis of Compounds (1-144)

[0804] Except for changing compound (T-1-1) to compound (T-1-144), compound (1-144) was obtained by following the same steps as in synthesis example (1).

[0805] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 995.51.

[0806]

[0807] Synthetic Example (47): Synthesis of Compounds (1-148)

[0808] Except for changing compound (T-1-1) to compound (T-1-148), compound (1-148) was obtained by following the same steps as in synthesis example (1).

[0809] The m / z(M+) value was determined by MS (MALDI-TOF MS) to be 1476.97.

[0810]

[0811] <<Fabrication and Evaluation of Vapor Deposited Organic Electron Components>>

[0812] Next, the fabrication and evaluation of organic EL elements using the polycyclic aromatic compounds of the present invention will be described.

[0813] <Structure of Organic EL Components>

[0814] Organic EL elements are manufactured using the polycyclic aromatic compounds of the present invention.

[0815] The material structures of each layer in the organic EL elements of Examples B1 to B5 and Comparative Examples B1 to B5 are shown in Table 1 below.

[0816] Table 1

[0817]

[0818] The following shows the chemical structural formulas of “HI”, “HAT-CN”, “HT-1”, “HT-2”, “ET-1”, “ET-2”, “BH”, “Liq”, and “Comparative Compounds (1) to (5)” as described in Japanese Patent Application Publication No. 2022-065644.

[0819]

[0820]

[0821] <Components of Example B1>

[0822] A 26mm × 28mm × 0.7mm glass substrate (manufactured by Opto Science Co., Ltd.) with an ITO film thickness of 180nm ground to 150nm 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 Co., Ltd.), and molybdenum vapor deposition boats containing HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET-1, and ET-2, respectively, and aluminum nitride vapor deposition boats containing Liq, LiF, and aluminum, respectively, were installed.

[0823] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 5 × 10⁻⁶. -4 First, HI is heated and vapor-deposited to a thickness of 40 nm. Next, HAT-CN is heated and vapor-deposited to a thickness of 5 nm. Then, HT-1 is heated and vapor-deposited to a thickness of 45 nm. Finally, HT-2 is heated and vapor-deposited to a thickness of 10 nm to form a hole layer comprising four layers. Next, BH and compound (1-1) are simultaneously heated and vapor-deposited to a thickness of 25 nm to form a light-emitting layer. The vapor deposition rate is adjusted to maintain a BH to compound (1-1) mass ratio of approximately 97:3. Then, ET-1 is heated and vapor-deposited to a thickness of 5 nm. Next, ET-2 and Liq are simultaneously heated and vapor-deposited to a thickness of 25 nm to form an electron layer comprising two layers. The vapor deposition rate is adjusted to maintain an ET-2 to Liq mass ratio of approximately 50:50. The evaporation rate of each layer is 0.01 nm / s to 1 nm / s. Subsequently, LiF is heated and evaporation is performed at a rate of 0.01 nm / s to 0.1 nm / s to achieve a film thickness of 1 nm. Then, aluminum is heated and evaporation is performed to achieve a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0824] <Components of Examples B2-B5 and Comparative Examples B1-B5>

[0825] Except for using the compounds listed in Tables 2 and 3 instead of compound (1-1) as dopant materials, the organic EL elements of Examples B2 to B5 and Comparative Examples B1 to B5 were prepared in the same manner as in Example B1.

[0826] <Evaluation of Organic EL Properties>

[0827] For the organic EL devices of Examples B1 to B5 and Comparative Examples B1 to B5, the ITO electrode was set as the anode and the LiF / aluminum electrode was set as the cathode. A DC voltage was applied, and the flow rate was measured at 1000 cd / m². 2 The driving voltage during light emission, external quantum efficiency, and device lifetime. Furthermore, the device lifetime is measured in terms of 1000 cd / m². 2 The duration for which the initial brightness is maintained at more than 95% while continuously driven by the voltage during emission. The results are shown in Tables 2 and 3.

[0828] 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.

[0829] The method for measuring external quantum efficiency is 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 observed wavelength region 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.

[0830] Table 2

[0831]

[0832] When comparing Example B1 with Comparative Example B1, Example B2 with Comparative Example B2, Example B3 with Comparative Example B3, Example B4 with Comparative Example B4, and Example B5 with Comparative Example B5, it is found that by deuterating the hydrogen at the α-position of the cycloalkyl ring of Formula (G-1), the luminous efficiency of the organic electroluminescent element can be improved and its lifetime can be extended.

[0833] Industrial applicability

[0834] The polycyclic aromatic compounds of the present invention are effectively used as materials for organic devices, particularly as materials for light-emitting layers in the formation of light-emitting layers of organic electroluminescent elements. Specifically, by using the polycyclic aromatic compounds of the present invention containing cycloalkyl groups with deuterium-substituted α-hydrogens as dopants for light-emitting layers, organic electroluminescent elements with long lifetimes or high-efficiency light emission can be obtained.

Claims

1. A polycyclic aromatic compound having a structure composed of one or more structural units represented by the following formula (1): In equation (1), Rings A, B, and C are each independently a substituted aryl ring or a substituted heteroaryl ring. Y 1 For B, P, P=O, P=S, Al, Ga, As, Si-R s or Ge-R Ge The Si-R S R S and Ge-R Ge R Ge Each can be independently substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. X 1 and X 2 Independently defined as >O and >NR respectively. NX >C(-R CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2 or >Se, wherein >NR NX R NX The >C(-R) CX )2 of R CX and the >Si(-R SiX )2 of R SiX Each of the following can be independently 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. In the X 1 For >N–R NX >C(–R CX )2 or >Si(–R SiX In the case of )2, >N–R NX R NX >C(–R CX )2 of R CX and >Si(–R SiX )2 of R SiX They can independently form rings by using single bonds or linkers as mediators and bonding with A-rings or B-rings. In the X 2 For >N–R NX >C(–R CX )2 or >Si(–R SiX In the case of )2, >N–R NX R NX >C(–R CX )2 of R CX and >Si(–R SiX )2 of R SiX They can independently form rings by using single bonds or linkers as mediators and bonding with A-rings or C-rings. The >C(-R) CX )2 two R CX and the aforementioned >Si(-R SiX )2 two R SiX They can bond together to form a ring. in, At least one ring in the structure selected from the group consisting of rings A, B, and C contains a basis represented by the following formula (G-1), or is composed of R. S R Ge R NX R CX and R SiX At least one of the bases represented includes the base represented by the following equation (G-1). In equation (G-1), P1 ring is a substituted cycloalkyl ring. For the bonding positions with structures other than those in equation (G-1), D represents deuterium. In the structure, at least one of the aryl ring and the heteroaryl ring may be condensed via at least one cycloalkane, and at least one hydrogen atom of the cycloalkane may be substituted. In the structure, each substituent substituted in ring A, ring B, or ring C can form a ring with the substituent-substituted ring A, ring B, or ring C via a single bond or a linker. In the structure, at least one hydrogen atom may be substituted with a cyano group or a halogen group. In the structure, at least one -CH2- can be substituted by -O-. In the structure, at least one hydrogen may be substituted with deuterium, at least one nitrogen may be substituted with nitrogen-15, at least one sulfur may be substituted with sulfur-33, sulfur-34 or sulfur-36, at least one oxygen may be substituted with oxygen-17 or oxygen-18, at least one carbon may be substituted with carbon-13, and at least one boron may be substituted with boron-11.

2. The polycyclic aromatic compound according to claim 1, wherein, Equation (1) is represented by any one of the following equations (1-a) to (1-m): In equations (1-a) to (1-m), X 1 To X 6 Independently with X in equation (1) 1 and X 2 The definitions are the same, Y 1 and Y 2 Independently with Y in equation (1) 1 The definitions are the same. The X 1 To X 6 >NR NX R NX >C(-R CX )2 of R CX and >Si(-R SiX )2 of R SiX It can be linked to one or two Z bonds via a linker base or a single bond. Z is independently equal to C(-R) CCX )- or =N-, the =C(-R CCX )- of R CCX Each of the following can be independently hydrogen, deuterium, cyano, halogen, substituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted diarylamino, or substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, or substituted or unsubstituted diarylboroyl. The two heteroaryl groups of the diarylene-amino group, the aryl and heteroaryl groups of the aryl-heteroaryl-amino group, and the two aryl groups of the diaryleboryl group can be bonded to each other via linker groups. The =C(-R) CCX The two R's of )- CCX They can bond together to form a ring. Wherein, the R CCX R S R Ge R NX R CX and R SiX At least one of the bases represented includes the base represented by equation (G-1).

3. The polycyclic aromatic compound according to claim 1, wherein, The basis represented by equation (G-1) is selected from the basis represented by equations (g-1) to (g-10) below: In equations (g-1) to (g-10), D represents the bonding position with structures other than those in equations (g-1) to (g-10), where D is deuterium.

4. The polycyclic aromatic compound according to claim 1, wherein, The Y 1 The answer is B.

5. The polycyclic aromatic compound according to claim 1, wherein, At least one ring selected from the group consisting of rings A, B, and C contains at least one basis represented by equation (G-1).

6. The polycyclic aromatic compound according to claim 1, wherein, The X 1 and X 2 Each is independently >O or >NR NX , The R NX It contains at least one basis represented by equation (G-1).

7. The polycyclic aromatic compound according to claim 1, wherein, The polycyclic aromatic compound contains at least one group represented by the following formula (G-2): In equation (G-2), P1 ring is a substituted cycloalkyl ring, and P2 ring is a substituted aryl ring or a substituted heteroaryl ring. D represents the bonding position with structures other than those in equation (G-2).

8. The polycyclic aromatic compound according to claim 1, wherein, The polycyclic aromatic compound is represented by any of the following formulas: In the formula, D represents deuterium.

9. A material for organic devices, wherein, Contains a polycyclic aromatic compound as described in any one of claims 1 to 8.

10. An organic electroluminescent element, in, include: A pair of electrodes, consisting of an anode and a cathode; and A light-emitting layer is disposed between the pair of electrodes. The luminescent layer contains a polycyclic aromatic compound according to any one of claims 1 to 8.

11. The organic electroluminescent element according to claim 10, wherein, The light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

12. The organic electroluminescent element according to claim 11, wherein, The main body is anthracene compounds, fluorene compounds, dibenzo[a]benzo[b] ...

13. A display device, wherein, It has an organic electroluminescent element as described in claim 10.

14. A lighting device, wherein, It has an organic electroluminescent element as described in claim 10.

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