Polycyclic aromatic compounds

Abstract

Providing a compound useful as a material for organic devices such as organic electroluminescent elements. 【Solution means】A polycyclic aromatic compound represented by formula (1). TIFF2026047189000248.tif41170 (The A ring to C ring are aryl rings, and Y 1 is B, and X 1 is N, and X 2 is >N-R NX where R NX is a substituted or unsubstituted aryl, provided that at least one of the two X 2 is >N-R NX where R NX is a group represented by formula (1J), and R NX may each be bonded to the A ring or C ring by a linking group or a single bond, * represents the bonding position to N, the J ring is an aryl ring, and R J is a substituted or unsubstituted aryl or alkyl, two adjacent A rings may be bonded by a single bond, and n is an integer of 1 or more. )

Description

[Technical Field]

[0001] The present invention relates to polycyclic aromatic compounds. The present invention also relates to materials for organic devices, organic electroluminescent devices, and display devices and lighting devices containing the above-mentioned polycyclic aromatic compounds. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been studied extensively due to their potential for power saving and miniaturization. Furthermore, organic electroluminescent elements made from organic materials have been actively investigated because they are easily made lighter and larger. In particular, the development of organic materials with luminescence properties such as blue, one of the three primary colors of light, and the development of organic materials with charge transport capabilities (potentially becoming semiconductors or superconductors) have been actively researched, regardless of whether they are polymer compounds or low molecular weight compounds.

[0003] An organic electroluminescent device has a structure consisting of a pair of electrodes, an anode and a cathode, and one or more layers containing an organic compound, disposed between the pair of electrodes. The layers containing the organic compound include light-emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] In particular, Patent Documents 1 and 2 disclose that polycyclic aromatic compounds containing boron are useful as materials for organic electroluminescent devices and the like. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] International Publication No. 2015 / 102118 [Patent Document 2] International Publication No. 2020 / 80528 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] As described above, various materials have been developed for use in organic EL elements, but in order to increase the range of materials for organic EL elements, the development of materials composed of novel compounds is desired. The object of this invention is to provide novel compounds that are useful as materials for organic devices such as organic EL elements. [Means for solving the problem]

[0007] The inventors of the present invention have diligently studied to solve the above problems and have succeeded in producing a novel polycyclic aromatic compound having specific luminescence properties, as a polycyclic aromatic compound having a structure similar to the compounds described in Patent Documents 1 and 2. Furthermore, they have found that an excellent organic EL element can be obtained by arranging a layer containing this polycyclic aromatic compound between a pair of electrodes to construct an organic EL element, thus completing the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further, materials for organic devices containing the following polycyclic aromatic compounds.

[0008] <1> A polycyclic aromatic compound represented by formula (1). [ka]

[0009] (In formula (1), Rings A, B, and C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. Y 1 Each of these is independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl. X 1 These are, independently, N or CR C1X And R C1X These are substituted or unsubstituted aryls, substituted or unsubstituted alkyls, or substituted or unsubstituted cycloalkyls. X 2is, independently of each other, >O, >N-R NX , >C(-R CX )2, >Si(-R IX )2, >S, or >Se, and R NX , R CX , and R IX are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two Rs of >C(-R CX )2 may be bonded to each other to form a ring, and the two Rs of >Si(-R CX )2 may be bonded to each other to form a ring, R IX , at least one R IX , and at least one R NX may each be bonded to one or two of the rings to which X CX containing the R IX is bonded, by a linking group or a single bond, respectively, provided that at least one of the two X NX , R CX , or R IX is the >N-R 2 group in which R is represented by formula (1J), 2 where in formula (1J), NX * represents the bonding position to N, NX J ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, where in formula (1J), * represents the bonding position to N,[[ID= 49]] J ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, R J is a substituent, R J may be bonded to the J ring via another single bond or linking group, when X 1 is N, some or all of the two adjacent A rings may be bonded to each other by a single bond, n is an integer of 1 or more, At least one selected from the group consisting of an aryl ring and a heteroaryl ring in formula (1) may be condensed with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one —CH2— in the cycloalkane may be replaced by —O—. In formula (1), at least one hydrogen may be replaced by deuterium, and at least one nitrogen may be replaced by nitrogen-15 ( 15 N), at least one sulfur may be replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen may be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon may be replaced by carbon-13 ( 13 C), and at least one boron may be replaced by boron-11 ( 11 B).)

[0010] <2> R J is a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, R J may be bonded to the J ring via another single bond or linking group, and is the polycyclic aromatic compound according to <1>.

[0011] <3> The group represented by formula (1J) is represented by formula (1J-1), and is the polycyclic aromatic compound according to <1> or <2>.

Chemical formula

[0012] <4> Z J1 , Z J2 , Z J3 , Z J4 Each of them independently performs -C(-R ZJ )= and Z J1 and Z J3 In at least one of the following, R ZJ is a substituent, <3> The polycyclic aromatic compounds described above. <5> Two X 2 However, each is independent >NR NX That is, <1> ~ <4> A polycyclic aromatic compound as described in any of the following. <6> Two R's NX These are all bases represented by formula (1J), <5> The polycyclic aromatic compounds described above. <7> Y 1 B is <1> ~ <6> A polycyclic aromatic compound as described in any of the following. <8> Rings A, B, and C are each independently substituted or unsubstituted benzene rings. <1> ~ <7> A polycyclic aromatic compound as described in any of the following.

[0013] <9> Represented by one of the following structural formulas: <1> The polycyclic aromatic compounds described above. [ka]

[0014] [ka]

[0015] [ka]

[0016] <10> It has a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes, wherein the organic layer <1> ~ <9> An organic electroluminescent element containing a polycyclic aromatic compound as described in any of the above. <11> The aforementioned organic layer is a light-emitting layer. <10> Organic electroluminescent device as described above. <12> The light-emitting layer comprises a host material, a thermally activated delayed phosphor or phosphorescent material as an assisting dopant, and the polycyclic aromatic compound as an emitting dopant. <11> Organic electroluminescent device as described above. <13> <10> ~ <12> A display device or lighting device equipped with an organic electroluminescent element as described in any of the above. <14> <1> ~ <9> A wavelength conversion material containing a polycyclic aromatic compound as described in any of the following. <15> An organic photodiode comprising a pair of electrodes and an active layer disposed between the pair of electrodes, wherein the active layer is <1> ~ <9> An organic photodiode comprising a polycyclic aromatic compound as described in any of the following. <16> The active layer consists of the polycyclic aromatic compound. <15> The organic photodiode described above. <17> <1> ~ <9> A solar cell material containing a polycyclic aromatic compound as described in any of the following. [Effects of the Invention]

[0017] The present invention provides novel polycyclic aromatic compounds useful as materials for organic devices such as organic electroluminescent devices. The polycyclic aromatic compounds of the present invention can be used in the manufacture of organic devices such as organic electroluminescent devices. [Brief explanation of the drawing]

[0018] [Figure 1] This is a schematic cross-sectional view showing an example of an organic field light-emitting device.

Best Mode for Carrying Out the Invention

[0019] Hereinafter, the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. Also, in the description of the structural formula in this specification, "hydrogen" means "hydrogen atom (H)". Similarly, "carbon atom (C)" may be referred to as "carbon". In this specification, when referring to "adjacent groups", it means two groups each bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in the structural formula.

[0020] In this specification, "Me" represents methyl, "Et" represents ethyl, "nBu" represents n-butyl (normal butyl), "tBu" represents t-butyl (tertiary butyl), "iBu" represents isobutyl, "secBu" represents secondary butyl, "nPr" represents n-propyl (normal propyl), "iPr" represents isopropyl, "tAm" represents t-amyl, "2EH" represents 2-ethylhexyl, "tOct" represents t-octyl, "Ph" represents phenyl, "Mes" represents mesityl (2,4,6-trimethylphenyl), "Ad" represents 1-adamantyl, "Tf" represents trifluoromethanesulfonyl, "TMS" represents trimethylsilyl, and "D" represents deuterium. In this specification, an organic electroluminescent element may be referred to as an "organic EL element".

[0021] In this specification, chemical structures and substituents are sometimes expressed in terms of carbon number. However, when a substituent is substituted into a chemical structure, or when a substituent is further substituted into another substituent, the carbon number refers to the carbon number of the chemical structure and the substituent itself, and does not refer to the total carbon number of the chemical structure and substituent, or the total carbon number of the substituents. For example, "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B. Also, for example, "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without carbon number limitation)" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B.

[0022] This specification describes numerous structural formulas of aromatic compounds. While aromatic compounds are described using combinations of double and single bonds, in reality, due to the resonance of π electrons, even a single substance can have multiple equivalent resonance structures, such as alternating double and single bonds. This specification describes only one resonance structure per substance, but unless otherwise specified, it is assumed that other organically equivalent resonance structures are also included.

[0023] In this specification, the expression "may be doing" is sometimes used, but it has the same meaning as "either not doing" or "doing."

[0024] <Description of rings and substituents> First, the details of the rings and substituents used in this specification are described below. In this specification, "aryl ring" refers to, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms.

[0025] Specific examples of "aryl rings" include the monocyclic benzene ring, the bicyclic biphenyl ring, the condensed bicyclic naphthalene ring and indene ring, the tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), the condensed tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, and anthracene ring, the condensed tetracyclic triphenylene ring, pyrene ring, naphthalene ring, and chrysene ring, and the condensed pentacyclic perylene ring and pentacene ring. Furthermore, the fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, benzofluorene ring, and cyclopentane ring are spiro-linked, respectively. Furthermore, the fluorene ring, benzofluorene ring, and indene ring also include those in which two of the two hydrogen atoms of the methylene group in their structure are replaced by alkyl groups such as methyl, which will be described later as the first substituent, resulting in the formation of dimethylfluorene ring, dimethylbenzofluorene ring, and dimethylindene ring, respectively.

[0026] In this specification, "heteroaryl rings" include, for example, heteroaryl rings having 2 to 30 carbon atoms, with heteroaryl rings having 2 to 25 carbon atoms being preferred, heteroaryl rings having 2 to 20 carbon atoms being more preferred, heteroaryl rings having 2 to 15 carbon atoms being even more preferred, and heteroaryl rings having 2 to 10 carbon atoms being particularly preferred. In addition, "heteroaryl rings" include, for example, heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, boron, selenium, phosphorus, and tellurium as ring constituent atoms in addition to carbon.

[0027] Specific examples of "heteroaryl rings" include, for example, pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings (such as furazan rings), thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, 1H-benzotriazole rings, quinoline rings, isoquinoline rings, sinnoline rings, quinazoline rings, quinoxaline rings, phthalazine rings, naphthyridine rings, purine rings, pteridine rings, carbazole rings, acridine rings, phenoxatiin rings, phenoxazine rings, phenothiazine rings, phenazine rings, phenazacillin rings, indidine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, and thiophene rings. , benzothiophene ring, dibenzothiophene ring, thianthrene ring, indolocarbazole ring, benzoindocarbazole ring, dibenzoindocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, dioxabora-naphthoanthracene ring (5,9-dioxa-13b-bora-13bH-naphtho[3,2,1-de]anthracene ring, etc.), benzoselenov Examples include the phenyl ring, dibenzoselenophene ring, azacarbazole ring, azadibenzothiophene ring, azadibenzofuran ring, azadibenzoselenophene ring, azatriphenylene ring, imidazoimidazole ring, indoloindole ring, benzoflocarbazole ring, benzothienocarbazole ring, indenocarbazole ring, and selenophenocarbazole ring, spiro[fluorene-9,9'-xanthene] ring, and spirobi[silafluorene] ring. In addition, dihydroacridine rings, xanthene rings, and thioxanthene rings are also preferred in which two of the two hydrogen atoms of the methylene group in their structure are replaced by alkyl groups such as methyl as the first substituent described later, resulting in dimethyldihydroacridine rings, dimethylxanthene rings, and dimethylthioxanthene rings.Furthermore, bicyclic rings such as bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, and tricyclic rings such as terpyridyl rings, bispyridylphenyl rings, and pyridylbiphenyl rings can also be listed as "heteroaryl rings." In addition, pyran rings are also included in the definition of "heteroaryl rings."

[0028] In this specification, substituents may be substituted with further substituents. For example, a particular substituent may be described as "substituted or unsubstituted." This means that the particular substituent is substituted with at least one further substituent, or is not substituted. Similarly, it may be described as "may be substituted." In this specification, the particular substituent in this case may be referred to as the "first substituent," and the further substituent as the "second substituent."

[0029] In this specification, substituent group Zα consists of substituents of substituent group Z and substituents represented by formula (A30) described below.

[0030] In this specification, substituent group Z is, An aryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, A heteroaryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, Diarylaminos which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen (the two aryls may be linked to each other via a linking group), A diheteroarylamino (where two heteroaryls may be linked to each other via a linking group) may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen. An arylheteroarylamino (aryl and heteroaryl may be bonded to each other via linking groups) may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen. Diarylboryls (the two aryls may be bonded together by a single bond or a linking group) may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen. Alkyls which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen, A cycloalkyl group which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen. An alkoxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen, An aryloxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, Arylthio, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, Alkenyls which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, It consists of substituted silyls, cyanos, and halogens. The aryl secondary substituent in each group of substituent group Z may be further substituted with an aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; similarly, the heteroaryl secondary substituent may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen.

[0031] In this specification, the term "substituent" does not particularly limit the type of substituent, but unless otherwise specified, it may be any group selected from substituent group Z. For example, when a group described as "substituted or unsubstituted" is substituted, it is sufficient that the group is substituted with at least one group selected from substituent group Z.

[0032] In this specification, "aryl" means, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, an aryl having 6 to 16 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aryl having 6 to 10 carbon atoms.

[0033] A specific example of "aryl" is a monovalent group obtained by removing one hydrogen atom from the aforementioned "aryl ring." For example, monocyclic phenyl, bicyclic biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), condensed bicyclic naphthyl (1-naphthyl or 2-naphthyl), tricyclic terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl-4-yl), and condensed tricyclic acenaphthylene-(1-, 3-, 4-, or 5 -)yl, fluoren-(1-,2-,3-,4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthren-(1-,2-,3-,4-, or 9-)yl, or anthracene-(1-,2-, or 9-)yl, or the tetracyclic quaterphenylyl(5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl Examples include m-terphenyl-4-yl (or m-quaterphenyl), condensed tetracyclic groups such as triphenylene-(1- or 2-)yl, pyren-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl, or condensed pentacyclic groups such as perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl. Other examples include the monovalent group of spirofluorene.

[0034] Furthermore, the aryl as the second substituent also includes structures in which the aryl is substituted with at least one group selected from the group consisting of aryl groups such as phenyl (specific examples are the groups mentioned above), alkyl groups such as methyl (specific examples are the groups described later), and cycloalkyl groups such as cyclohexyl or adamantyl (specific examples are the groups described later). One example is a group in which the 9th position of fluorenyl, as the second substituent, is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl.

[0035] "Arylene" refers to, for example, arylene having 6 to 30 carbon atoms, preferably arylene having 6 to 20 carbon atoms, arylene having 6 to 16 carbon atoms, arylene having 6 to 12 carbon atoms, or arylene having 6 to 10 carbon atoms. A specific example of "arylene" is a divalent group obtained by removing one hydrogen atom from the aforementioned "aryl" (monovalent group).

[0036] "Heteroaryl" refers to, 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. "Heteroaryl" contains one or more heteroatoms, preferably 1 to 5, selected from oxygen, sulfur, nitrogen, etc., in addition to carbon as ring constituent atoms.

[0037] Specific examples of "heteroaryls" include monovalent groups obtained by removing one hydrogen atom from the "heteroaryl ring" mentioned above. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, sinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, These include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazacylinyl, phenazacylinyl, indolidinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, monovalent group of the benzophosphole oxide ring, monovalent group of the dibenzophosphole oxide ring, flazanil, thianthrenil, indolocarbazolyl, benzoindolocabazolyl, dibenzoindolocabazolyl, imidazolinil, or oxazolinil. Other examples include the monovalent group of spiro[fluorene-9,9'-xanthene], the monovalent group of spirovi[silafluorene], and the monovalent group of benzoselenophene.

[0038] Furthermore, the heteroaryl as the second substituent also includes structures in which the heteroaryl is substituted with at least one group selected from the group consisting of aryl groups such as phenyl (specific examples are the groups mentioned above), alkyl groups such as methyl (specific examples are the groups described later), and cycloalkyl groups such as cyclohexyl or adamantyl (specific examples are the groups described later). One example is a group in which the 9th position of carbazolyl as the second substituent is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. In addition, groups in which nitrogen-containing heteroaryls such as pyridyl, pyrimidinyl, triazinyl, and carbazolyl are further substituted with phenyl or biphenylyl are also included in heteroaryls as the second substituent.

[0039] "Heteroarylene" refers to, for example, heteroarylenes having 2 to 30 carbon atoms, preferably heteroarylenes having 2 to 25 carbon atoms, 2 to 20 carbon atoms, 2 to 15 carbon atoms, or 2 to 10 carbon atoms. Furthermore, "heteroarylene" refers to a divalent group such as a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms. A specific example of a "heteroarylene" is a divalent group obtained by removing one hydrogen atom from the aforementioned "heteroaryl" (a monovalent group).

[0040] A "diarylamino" is an amino acid in which two aryl groups are substituted. For details about these aryl groups, please refer to the explanation of "aryl" above. A "diheteroarylamino" is an amino group substituted with two heteroaryl groups. For details on these heteroaryl groups, please refer to the explanation of "heteroaryl" mentioned above. "Arylheteroarylamino" refers to an amino group substituted with aryl and heteroaryl groups. For details on these aryl and heteroaryl groups, please refer to the explanations of "aryl" and "heteroaryl" mentioned above.

[0041] The two aryl atoms in a diarylamino as the first substituent may be linked to each other via a linking group, the two heteroaryl atoms in a diheteroarylamino as the first substituent may be linked to each other via a linking group, and the aryl and heteroaryl atoms in an arylheteroarylamino as the first substituent may be linked to each other via a linking group. Here, the phrase "linked via a linking group" means, for example, that the two phenyl atoms in diphenylamino form a bond via a linking group, as shown below. This explanation also applies to diheteroarylaminos and arylheteroarylaminos formed from aryl or heteroaryl atoms.

[0042] [ka]

[0043] Specifically, the linking groups are >O and >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 Examples include ), and >Se. X Each of these is independently an alkyl, cycloalkyl, aryl, or heteroaryl, and these may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl. Also, >C(-R X )2, -C(-R X )=C(-R X )-,>Si(-R X )2 in each of the two R X is a single bond or a linking group X Y They may be joined to each other via X to form a ring. Y For example, >O, >NR Y ,>C(-R Y )2, >Si(-R Y )2, >S, >CO, >CS, >SO, >SO2, and >Se are listed, R YEach of these is independently an alkyl, cycloalkyl, aryl, or heteroaryl, and these may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl. However, X Y >C(-R Y )2 and >Si(-R Y )In the case of 2, two R Y They do not bond to form further rings. Furthermore, alkenylenes can also be given as linking groups. Any hydrogen atom of the alkenylene can independently form R 2X It may also be replaced with R 2X Each of these is independently alkyl, cycloalkyl, substituted silyl, aryl, and heteroaryl, and these may be substituted with alkyl, cycloalkyl, substituted silyl, or aryl. -C(-R X )=C(-R X )- Two R X These may bond to each other and, together with the C=C to which they bond, form an aryl ring (such as a benzene ring) or a heteroaryl ring. That is, -C(-R X )=C(-R X )- may be an allerene (such as 1,2-phenylene) or a heteroarylene.

[0044] In this specification, when "diarylamino," "diheteroarylamino," or "arylheteroarylamino" is simply referred to, unless otherwise specified, it is assumed that the following explanations are added: "The two aryls of diarylamino may be linked to each other via a linking group," "The two heteroaryls of the diheteroarylamino may be linked to each other via a linking group," and "The aryl and heteroaryls of the arylheteroarylamino may be linked to each other via a linking group."

[0045] A "diarylboryl" is a boryl in which two aryls are substituted, and for details about these aryls, refer to the explanation of "aryl" above. These two aryls may also be linked by a single bond or by a linking group (e.g., -CH=CH-, -CR=CR-, -C≡C-, >NR, >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). Here, the R in -CR=CR-, >NR, >C(-R)2, >Si(-R), and >B(-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. Also, two adjacent Rs may bond to form a ring, forming cycloalkylene, arylene, and heteroarylene. For details of the substituents listed here, refer to the above-mentioned descriptions of "aryl," "arylene," "heteroaryl," "heteroarylene," and "diarylamino," as well as the later-described descriptions of "alkyl," "alkenyl," "alkynyl," "cycloalkyl," "cycloalkylene," "alkoxy," and "aryloxy." Furthermore, wherever the term "diarylboryl" is used in this specification, unless otherwise specified, it is assumed that the two aryl groups of diarylboryl may be linked to each other by a single bond or by a linking group.

[0046] "Alkyl" can be either a linear or branched alkyl group, for example, a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. Preferably, it is an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 5 carbon atoms (branched alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms), and so on.

[0047] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1 -Methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-di Examples include methylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl.

[0048] "Alkylene" is a divalent group obtained by removing one of the hydrogen atoms of an "alkyl" group, such as methylene, ethylene, and propylene.

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

[0050] Specifically, "alkenyls" include alkenyls having 2 to 30 carbon atoms, with alkenyls having 2 to 20 carbon atoms being preferred, alkenyls having 2 to 10 carbon atoms being more preferred, alkenyls having 2 to 6 carbon atoms being even more preferred, and alkenyls having 2 to 4 carbon atoms being particularly preferred. Preferred alkenyls 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.

[0051] "Alkenylene" is a divalent group obtained by removing one of the hydrogen atoms from "alkenyl," and vinylene is an example of this.

[0052] Regarding "alkynyl," you can refer to the explanation of "alkyl" above. It is a group in which a single C≡C bond in the structure of "alkyl" is replaced with a triple C≡C bond, and it includes not just one but two or more single bonds that are replaced with triple bonds (also called alkadiyne-yl or alkatriyne-yl).

[0053] "Cycloalkyl" refers to, for example, a cycloalkyl group having 3 to 24 carbon atoms, preferably a cycloalkyl group having 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 14 carbon atoms, 3 to 12 carbon atoms, 5 to 10 carbon atoms, 5 to 8 carbon atoms, 5 to 6 carbon atoms, or a cycloalkyl group having 5 carbon atoms.

[0054] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituted derivatives of these with 1-5 or 1-4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, or decahydroazlenyl.

[0055] "Cycloalkylene" refers to, 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. A specific example of a "cycloalkylene" is a structure in which one hydrogen atom is removed from the aforementioned "cycloalkyl" (a monovalent group) to create a divalent group.

[0056] A "cycloalkenyl" is a group that has a structure in which at least one single bond between two carbon atoms in the aforementioned "cycloalkyl" is replaced by a double bond (for example, a group in which -CH2-CH2- is replaced by -CH=CH-), and is not an aryl group. Specifically, examples include 1-cyclohexenyl and 1-cyclopentenyl.

[0057] "Alkoxy" is a group represented as "Alk-O- (where Alk is alkyl)," and for details about this alkyl group, please refer to the explanation of "alkyl" mentioned above.

[0058] "Aryloxy" is a group represented as "Ar-O-" (where Ar is aryl), and for details about this aryl group, please refer to the explanation of "aryl" mentioned above. "Arylthio" is a group represented as "Ar-S- (Ar is aryl)," and for details about this aryl group, refer to the explanation of "aryl" mentioned above.

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

[0060] A "triarylsilyl" is a silyl group substituted with three aryl groups. For details about these aryl groups, please refer to the explanation of "aryl" mentioned above. Specific examples of "triarylsilyls" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, or trinaphthylsilyl.

[0061] "Trialkylsilyl" refers to a silyl group substituted with three alkyl groups. For details about these alkyl groups, please refer to the explanation of "alkyl" mentioned above. Specific examples of "trialkylsilyls" include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, or t-butyldiisopropylsilyl.

[0062] "Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups. For details on these cycloalkyl groups, please refer to the explanation of "cycloalkyl" mentioned above. Specific examples of "tricycloalkylsilyls" include tricyclopentylsilyl or tricyclohexylsilyl.

[0063] A "dialkylcycloalkylsilyl" is a silyl group substituted with two alkyl groups and one cycloalkyl group. For details on these alkyl and cycloalkyl groups, please refer to the explanations of "alkyl" and "cycloalkyl" above.

[0064] "Alkyldicycloalkylsilyl" refers to a silyl group substituted with one alkyl and two cycloalkyl groups. For details on these alkyl and cycloalkyl groups, please refer to the explanations of "alkyl" and "cycloalkyl" above.

[0065] "Halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and even more preferably fluorine.

[0066] When cyano or halogen substitutes, a mode in which all or some of the hydrogens in aryl or heteroaryl in the structure are replaced by cyano or halogen is also preferred.

[0067] The substituent represented by formula (A30) has the following structure. [Chemical formula]

[0068] In formula (A30), Ak is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl or substituted or unsubstituted cycloalkenyl, and at least one -CH2- in the alkyl, cycloalkyl and cycloalkenyl may be replaced by -O- or -S-. R Ak is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl or substituted or unsubstituted cycloalkyl, and R Ak may be bonded to Ak by a linking group or a single bond, and * is the bonding position.

[0069] In formula (A30), since Ak is the above-mentioned substituent and does not conjugate with the non-bonding electron pair on N, the non-bonding electron pair can be conjugated with the π electrons of the bonding destination, and a larger wavelength change is possible compared to the case where aryl or the like is present at the same position. The same applies to the influence on the multiple resonance effect, and a greater improvement in thermally activated delayed fluorescence (TADF) properties is possible.

[0070] R AkIt is preferably an aryl which may be substituted with alkyl or cycloalkyl, a heteroaryl which may be substituted with alkyl or cycloalkyl, an alkyl or cycloalkyl, more preferably an aryl which may be substituted with alkyl, a heteroaryl which may be substituted with alkyl, an alkyl or cycloalkyl, even more preferably an aryl which may be substituted with alkyl, and particularly preferably a phenyl which may be substituted with methyl.

[0071] 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, even more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group.

[0072] R Ak Ak may be the same or different, but it is preferable that they are different.

[0073] R Ak R may be bonded to Ak by a linking group or a single bond. Examples of such linking groups include >O, >S, or >Si(-R)2. 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. Ak Examples of structures in which Ak is bonded by a linking group or single bond include the following:

[0074] [ka] In each of the above formulas, * indicates a bonding position.

[0075] [When two groups bond to the same atom bond to each other] In this specification, when two groups bonded to the same atom may be bonded to each other to form a ring, they may be bonded by a single bond or a linking group (collectively referred to as a bonding group). Examples of linking groups 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-, and the following structure is an example. 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 which may be substituted with alkyl or cycloalkyl, a heteroaryl which may be substituted with alkyl or cycloalkyl, an alkyl which may be substituted with cycloalkyl, an alkenyl which may be substituted with alkyl or cycloalkyl, an alkynyl which may be substituted with alkyl or cycloalkyl, or a cycloalkyl which may be substituted with alkyl or cycloalkyl. In addition, two adjacent Rs may bond to form a ring, forming a cycloalkylene, arylene, or heteroarylene.

[0076] [ka]

[0077] Preferred bonding groups are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, -C(=O)-, and -Se-; more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(=O)-, and -C(-R)2-; even more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, and -S-; and single bonds are most preferred.

[0078] The positions where the two R groups bond via the bonding group are not particularly limited as long as they are bondable positions, but it is preferable that they bond at the most adjacent positions. For example, if the two groups are phenyl groups, it is preferable that they bond at the ortho (position 2) relative to the bond position (position 1) of the "C" or "Si" in phenyl (see the structural formula above).

[0079] <Stereoisomers, etc.> The polycyclic aromatic compounds of the present invention may exist as enantiomers or diastereomers depending on the type of substituent, etc., but regardless of the structural formula described, any pure form of stereoisomer, any mixture of stereoisomers, racemates, etc., are all included within the scope of the present invention.

[0080] <1. Polycyclic aromatic compounds> <Overall structure> It has already been found that polycyclic aromatic compounds, in which aromatic rings are linked by heteroatoms such as boron, nitrogen, oxygen, and sulfur, have a large HOMO-LUMO gap (band gap Eg in thin films). This is because the six-membered ring containing the heteroatoms has low aromaticity, which suppresses the decrease in the HOMO-LUMO gap associated with the expansion of the conjugated system. Furthermore, it has been found that the HOMO-LUMO gap can be arbitrarily changed depending on the type of heteroatom and the linking method. This is thought to be because the HOMO and LUMO energies can be arbitrarily manipulated depending on the spatial extent and energy of the empty orbitals or lone pairs of the heteroatoms.

[0081] These polycyclic aromatic compounds exhibit a narrow full width at half maximum of the fluorescence emission peak due to the localization of excited SOMO1 and SOMO2 states on each atom through electronic perturbation of heteroatoms. This results in high color purity emission when used as dopants in organic light-emitting diodes (OLEDs). For similar reasons, ΔE S1T1 The reduced size allows it to exhibit thermally activated delayed fluorescence, resulting in high efficiency when used as an emitting dopant for organic EL devices. Furthermore, by introducing substituents, the energies of the HOMO and LUMO can be arbitrarily shifted, so that the ionization potential and electron affinity can be optimized according to the surrounding materials.

[0082] The polycyclic aromatic compound of the present invention corresponds to a polycyclic aromatic compound in which the above aromatic rings are linked by hetero elements such as boron, nitrogen, oxygen, sulfur, etc., and has a structure represented by formula (1).

Chemical formula

[0083] In the present invention, it has been found that an organic EL device using the polycyclic aromatic compound represented by formula (1) exhibits green emission with a narrow half-width. As the polycyclic aromatic compound represented by formula (1), when Y 1 is B (boron), the compound is considered to have a deeper LUMO and a narrower band gap Eg compared to a polycyclic aromatic compound with less B (boron) as Y 1 and shows green emission. Also, it has been found that an organic EL device using the polycyclic aromatic compound represented by formula (1) is highly efficient and long-lived compared to an organic EL device using a similar compound that does not have a group represented by formula (1J) as R NX .

[0084] <Explanation of the ring structure in the compound> In formula (1), "A", "B", and "C" within the circle are symbols indicating the ring structures shown by each circle. The structure represented by formula (1) has a structure in which at least five aromatic rings, namely the A ring, B ring, and C ring, are linked by heteroatoms such as boron, nitrogen, oxygen, sulfur, etc., and further form a ring structure. The formed ring structure includes a condensed ring structure composed of at least nine rings.

[0085] In equation (1), n ​​is an integer greater than or equal to 1, an integer between 1 and 10, an integer between 1 and 5, an integer between 1 and 3, or 1 or 2, preferably 1 or 2, and particularly preferably 1. The same explanation applies to n in equation (1-A) described later.

[0086] In equation (1), when n is 1, for example, the following structures can be given. Each sign in each structural formula has the same definition as the corresponding sign in equation (1). Also, in the following example, Y 1 B, X 1 N, X 2 One of them is >NR NX , the other side is >NR NX While an example of >O was shown, other combinations of options also exist. Similarly, examples exist where two adjacent A rings (or "all adjacent A rings" when n is 1) are joined by a single bond.

[0087] [ka]

[0088] In equation (1), when n is 2, for example, the following structures can be given. Each sign in each structural formula has the same definition as the corresponding sign in equation (1). Also, in the following example, Y 1 B, X 1 N, X 2 One of them is >NR NX , the other side is >NR NX While examples of >O have been shown, other combinations of options also exist. Furthermore, examples where some or all adjacent A rings are connected by a single bond also exist.

[0089] [ka]

[0090] In equation (1), X 1When n is N, some or all of two adjacent A rings may be connected by a single bond, and in such cases, it is preferable that all two adjacent A rings are connected by a single bond. "Some or all" means "some locations" or "all locations" in which, when n is 2 or greater, there are 3 or more A rings, and there are 2 or more places where two adjacent A rings are connected.

[0091] In equation (1), rings A, B, and C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0092] The A ring forms a trivalent group with bonds to three consecutive atoms (preferably carbon) on the aryl or heteroaryl ring in its structure. Each of these three bonds forms a Y group. 1 , X 1 , and X 2 It is bonded to the above. In ring A, the ring having atoms with the above three bonds as ring constituent atoms is preferably a 5-membered ring or a 6-membered ring. This ring may be further fused with other rings. Examples of 6-membered rings include benzene rings, pyridine rings, pyrimidine rings, and pyrazine rings. Examples of 6-membered rings that are further fused with other rings include naphthalene rings, anthracene rings, quinoline rings, isoquinoline rings, quinazoline rings, dibenzofuran rings, dibenzothiophene rings, and carbazole rings. Examples of 5-membered rings include furan rings, thiophene rings, pyrrole rings, and thiazole rings. Examples of 5-membered rings that are further fused with other rings include benzofuran rings, benzothiophene rings, and indole rings. An indene ring can also be given as a fused ring. The aryl ring or heteroaryl ring in ring A is preferably a benzene ring, a pyridine ring, a naphthalene ring, a dibenzofuran ring, or a dibenzothiophene ring, with the benzene ring being more preferred.

[0093] The B ring forms a trivalent group with bonds to three consecutive atoms (preferably carbon) on the aryl or heteroaryl ring in its structure. Each of these three bonds forms two Y groups. 1 and X 1 It is bonded to the above. In the B ring, the ring whose constituent atoms have the above three bonds is preferably a 5-membered ring or a 6-membered ring. This ring may be further fused with other rings. Examples of 6-membered rings include benzene rings, pyridine rings, pyrimidine rings, and pyrazine rings. Examples of 6-membered rings that are further fused with other rings include naphthalene rings, anthracene rings, quinoline rings, isoquinoline rings, quinazoline rings, dibenzofuran rings, dibenzothiophene rings, and carbazole rings. Examples of 5-membered rings include furan rings, thiophene rings, pyrrole rings, and thiazole rings. Examples of 5-membered rings that are further fused with other rings include benzofuran rings, benzothiophene rings, and indole rings. An indene ring can also be given as a fused ring. The aryl ring or heteroaryl ring in ring B is preferably a benzene ring or a pyridine ring, with a benzene ring being more preferred.

[0094] Each C ring forms a divalent group with bonds to two adjacent atoms (preferably carbon) on the aryl or heteroaryl ring in its structure. 1 and X 2It is bonded to the above. In each ring of the C ring, the ring whose constituent atoms have the above two bonding hands is preferably a 5-membered ring or a 6-membered ring. This ring may be further fused with other rings. Examples of 6-membered rings include benzene rings, pyridine rings, pyrimidine rings, and pyrazine rings. Examples of 6-membered rings that are further fused with other rings include naphthalene rings, anthracene rings, phenanthrene rings, pyrene rings, quinoline rings, benzofuran rings, benzothiophene rings, indole rings, benzoselenophen rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, dibenzoselenophen rings, phenothiazine rings, phenoxazine rings, and dihydroacridine rings. Examples of 5-membered rings include furan rings, thiophene rings, pyrrole rings, thiazole rings, and selenofen rings. Examples of 5-membered rings that are further fused with other rings include benzofuran rings, benzothiophene rings, indole rings, and benzoselenophen rings. Indene rings can also be cited as examples of fused rings.

[0095] The aryl ring or heteroaryl ring in the C ring is preferably, independently, a benzene ring, a pyridine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, an indene ring, a benzofuran ring, a benzothiophene ring, a benzoselenophene ring, an indole ring, a phenothiazine ring, a phenoxazine ring, or a dihydroacridine ring, more preferably a benzene ring, a pyridine ring, an indene ring, a benzofuran ring, or a benzothiophene ring.

[0096] In substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings in rings A, B, and C, the substituent referred to as "substituted or unsubstituted" is at least one substituent selected from substituent group Zα. The substituent may also be a substituted or unsubstituted diarylphosphinone such as diphenylphosphinone, or a substituted or unsubstituted diarylphosphinyl such as diphenylphosphinyl. When multiple substituents are present, they may be identical or different from each other. Preferred substituents are substituted or unsubstituted alkyls, substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, substituted or unsubstituted diarylaminos, cyanos, or halogens, and more preferably phenyls, t-butyls, diphenylaminos, substituted or unsubstituted carbazolyls, or halogens, which may be substituted with t-butyl or halogens. The group represented by formula (1J) is also listed as a preferred substituent. For other preferred substituents, refer to the description in <Preferred Substituents> below.

[0097] <Y 1 > Y in equation (1) 1 Each of these is independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl. In the case of P=O, P=S, Si-R, or Ge-R, the atom bonded to the A, B, or C ring is P, Si, or Ge. 1 The material is preferably B, P, P=O, P=S, or Si-R, with B being particularly preferred. This explanation is for Y in equation (1-A) 1 But it's the same.

[0098] <X 1 > X in equation (1) 1 These are, independently, N or CR C1X And R C1XR is a substituted or unsubstituted aryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl. C1X Particularly preferred are aryl groups with 6 to 12 carbon atoms or aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl groups with 1 to 6 carbon atoms or alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyl groups with 3 to 16 carbon atoms (e.g., bicyclooctyl, adamantyl, etc.). CR C1X In this case, the atom bonded to rings A and B is carbon (C). X 1 N is particularly preferred. This explanation is for X in equation (1-A) 1 But it's the same.

[0099] <X 2 > In equations (1) and (1-A), X 2 These are, independently, >O and >NR. NX ,>C(-R CX )2, >Si(-R IX )2, >S, or >Se, R NX , R CX , and R IX Each is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and >C(-R CX )2 of 2 CX They may bond to each other to form a ring, >Si(-R IX )2 of 2 IX They may bond to each other to form a ring, R NX , at least one R CX , and at least one R IX Each of these is connected by a linking group or a single bond, and the R NX , R CX , or R IX X including 1 or X 2 It may be bonded to one or two of the rings to which it is bonded.

[0100] R NXA substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl is preferred. CX R is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or a substituted or unsubstituted alkyl, and more preferably a substituted or unsubstituted phenyl or methyl. IX The aryl group is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and more preferably a substituted or unsubstituted phenyl group or a methyl group.

[0101] In the polycyclic aromatic compound represented by formula (1), two X 2 At least one of them is R NX The base is represented by formula (1J) >NR NX X 2 Either one is >NR NX And the other is >NR NX Preferably, the other is >S, >O, or >Se, and the other is >NR NX It is more preferable that it be >S or >O. 2 All of these are >NR NX It is particularly preferable that this be the case.

[0102] <X 2 Explanation of changes in ring structure due to bonding with other rings> X 2 R inside NX , R CX and R IX Each of these is X including itself. 2 X may be bonded to one or two rings by a single bond or a linking group. Specifically, in formula (1), X 2 R inside NX , R CX and R IX It may be bonded to at least one of the A ring or the C ring by a single bond or a linking group. R bonded to the A or C ring NX The base may be represented by formula (1J). However, in this case, R NX is R JIt binds to the A or C ring at other sites.

[0103] R NX , R CX and R IXExamples of linking groups when each of these groups is bonded to a ring include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -Se(=O)-, -Se(=O)2-, -P(=O)-, -B(-R)-, -Si(-R)2-, or -Se-. Of these, from the viewpoint of compound stability (related to the device lifespan) and ease of manufacture, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -Se(=O)-, -Se (=O)2-, -P(=O)-, -B(-R)-, or -Se- is preferred, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- is more preferred, -CH=CH-, -CR=CR-, -N(-R)-, -O-, and -S- is even more preferred, and -CR=CR-, -N(-R)-, -O-, and -S- is particularly preferred. 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 which may be substituted with alkyl or cycloalkyl, a heteroaryl which may be substituted with alkyl or cycloalkyl, an alkyl which may be substituted with alkyl or cycloalkyl, an alkenyl which may be substituted with alkyl or cycloalkyl, an alkynyl which may be substituted with alkyl or cycloalkyl, or a cycloalkyl which may be substituted with alkyl or cycloalkyl. Furthermore, two Rs bonded to the same atom may bond together to form a ring. In addition, two adjacent Rs may bond together to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring. These rings may also be substituted with alkyl or cycloalkyl.

[0104] >NRNX R inside NX Examples of fused rings formed by bonding with a benzene ring as an aryl ring in the A or C ring include a carbazole ring (where R is phenyl). NX (bonded by a single bond), phenoxazine ring (phenyl R) NX (bonded by -O-), phenothiazine ring (phenyl R) NX (bonded by -S-), acridone ring (phenyl R) NX (bonded by -C(=O)-), 5,10-dihydrophenazine ring (phenyl R) NX The ring is bonded by -N(-R)- (where R is hydrogen or a substituent), or the dibenzoazepine ring (where R is phenyl). NX One example is the bond between -CH=CH-.

[0105] Furthermore, the following substructure (A10) may be formed by the above-described connection. [ka]

[0106] In formula (A10), R A1 ~R A4 Each of these is independently hydrogen, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R A1 ~R A4 Any 2 to 4 of them may be linked to each other by linking groups or single bonds, and X at the two * positions. 2 One of the two rings that are joined is bonded to the other ring at the position of **. That is, N in equation (A10) is X 2 ga>NR NX >NR NXThis is N. The atoms on the ring bonded at the two * positions can be adjacent atoms (carbon atoms are preferred). The substructure represented by formula (A10) contains an NC bond with a weak bond dissociation energy (BDE), but the presence of another bond forming the ring promotes the reverse reaction (recombination reaction) even when the NC bond is broken, resulting in a more stable structure. Therefore, it is expected that organic EL devices manufactured using polycyclic aromatic compounds having such a structure will have a longer device lifespan. When a polycyclic aromatic compound contains the structure represented by formula (A10), there can be one or two (preferably one) such structures.

[0107] In formula (A10), R A1 ~R A4 Any two to four of these may be linked to one another by linking groups or single bonds. R A1 ~R A4 are any two (R A1 and R A4 , R A1 and R A4 Furthermore, R A2 and R A3 , R A1 and R A2 , R A3 and R A4 , R A1 and R A2 Furthermore, R A3 and R A4 It is preferable that the ) are linked to each other by a linking group or a single bond, R A1 and R A4It is more preferable that the groups are bonded to each other by linking groups or single bonds. Examples of divalent groups formed by bonding to each other include alkylenes. At least one hydrogen in the alkylene may be substituted with an alkyl or cycloalkyl group, and at least one (preferably one) -CH2- in the alkylene may be substituted with -O- and -S-. As divalent groups formed by bonding to each other, linear alkylenes having 2 to 5 carbon atoms are preferred, linear alkylenes having 3 or 4 carbon atoms are more preferred, and linear alkylenes having 4 carbon atoms (-(CH2)4-) are even more preferred. It is particularly preferable that the linear alkylenes having 4 carbon atoms (-(CH2)4-) are unsubstituted.

[0108] The remaining R that is not involved in linking groups or single bond linkages A1 ~R A4 Each of these is preferably independently hydrogen or an optionally substituted alkyl group, more preferably an optionally substituted C1-C6 alkyl group, even more preferably an unsubstituted C1-C6 alkyl group, and most preferably methyl in all cases. In other words, the substructure represented by formula (A10) is preferably the structure represented by formula (A11).

[0109] [ka] In formula (A11), Me is methyl, and X is present at the two * positions. 2 It is bonded to one of the two rings at the position of **, and to the other ring.

[0110] <Base represented by formula (1J)> The polycyclic aromatic compound represented by formula (1) is X 2 It is >NR NX R NX It includes at least one group represented by the following formula (1J). [ka]

[0111] In formula (1J), the J ring is a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring, and R J R is a substituent (for example, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted alkyl (substituted alkyl, methyl, ethyl, unsubstituted alkyl with 3 to 24 carbon atoms, etc.), or substituted or unsubstituted cycloalkyl). J The J ring may be further bonded to it via another single bond or linking group. * is >NR NX This shows the bond position to N.

[0112] The polycyclic aromatic compound of the present invention is R NX By having a group represented by formula (1J), the purity of the green color is higher compared to similar compounds that do not have this group. Although not bound by any particular theory, it is thought that the emission spectrum with high color purity is achieved by introducing a group represented by formula (1J) into a highly planar molecular structure formed from at least two A rings, at least one B ring, and two C rings, thereby reducing the proportion of structures on the same plane in the entire molecule and reducing intermolecular stacking. Furthermore, it is thought that the vapor deposition properties of the compound can also be ensured by reducing intermolecular stacking. In addition, in this invention, R NX It was found that the presence of the group represented by formula (1J) resulted in higher efficiency and longer lifespan compared to similar compounds that lack this group. This is thought to be due to increased stability of the compound.

[0113] In formula (1J), the "J" in the circle is a symbol indicating a ring structure represented by the circle, and the J ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. The J ring forms a divalent group with bonds to two adjacent atoms (preferably carbon) on the aryl or heteroaryl ring in its structure, and R is bonded between the two bonds. J and >NR NX It is bonded to the N of. That is, if the J ring is a benzene ring, R J It is located in the ortho position of the bond site (*).

[0114] The J ring is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, or a substituted or unsubstituted carbazole ring; more preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted dibenzothiophene ring, or a substituted or unsubstituted dibenzofuran ring; and even more preferably a substituted or unsubstituted benzene ring.

[0115] In a substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in the J ring, the substituent referred to as "substituted or unsubstituted" is preferably at least one substituent selected from the substituent group Zα.

[0116] In equation (1J), R J R is a substituent, and it is preferable that it is a substituent with a bulk height of methyl or greater. JSpecifically, preferred are substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, substituted or unsubstituted arylthios, substituted or unsubstituted heteroarylthios, substituted or unsubstituted aryloxys, substituted or unsubstituted heteroaryloxys, substituted or unsubstituted alkyls, or substituted or unsubstituted cycloalkyls; more preferred are substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, substituted or unsubstituted alkyls, or substituted or unsubstituted cycloalkyls; even more preferred are substituted or unsubstituted aryls, substituted or unsubstituted alkyls, or substituted or unsubstituted cycloalkyls; and particularly preferred are substituted or unsubstituted aryls or substituted or unsubstituted alkyls. From the viewpoint of ease of synthesis, R J It is preferable that the compound is methyl, t-butyl, or phenyl.

[0117] R J The J ring may be further bonded to it via another single bond or linking group. Examples of such linking groups include >NR, >O, >S, >CO, >C=S, >S=O, >S(=O)2, >Se(=O), >Se(=O)2, >P(=O), >B(-R), >C(-R)2, >Si(-R)2, >Se, -CH=CH-, -CR=CR-, or -C≡C-. Here, the R in >NR, R in >B(-R), R in >C(-R)2, >Si(-R)2, and R in -CR=CR- are each independently aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in these groups may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Furthermore, the two R atoms in >C(-R)2 may bond to each other to form a ring, and the two R atoms in >Si(-R)2 may bond to each other to form a ring. Two adjacent R atoms may bond to each other to form a ring, creating cycloalkylenes, arylenes, and heteroarylenes.

[0118] A preferred example of a group represented by formula (1J) is the group represented by formula (1J-1). [ka]

[0119] In formula (1J-1), R J R in equation (1J) J It is synonymous with the same thing, and the preferred range is also the same. In formula (1J-1), Z J1 , Z J2 , Z J3 , Z J4 Each of these can be used independently of -C(-R ZJ ) = or -N = and R ZJ Each is independently either a hydrogen atom or a substituent, and R ZJ Adjacent groups among them may bond together with the j ring to form an aryl ring or heteroaryl ring, and the formed ring may be substituted with at least one substituent selected from the substituent group Zα. ZJ When R is a substituent, the substituent can be any substituent selected from the substituent group Zα. ZJ Examples of rings formed by the bonding of adjacent groups together with the j-ring include naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, and dibenzothiophene rings.

[0120] In formula (1J-1), Z J1 , Z J2 , Z J3 , Z J4 Both are -C(-R ZJ ) = is preferable. ZJPreferably, is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted arylthio, a substituted or unsubstituted heteroarylthio, a substituted or unsubstituted aryloxy, a substituted or unsubstituted heteroaryloxy, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; more preferably is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; more preferably is hydrogen, a substituted or unsubstituted aryl, or a substituted or unsubstituted alkyl; and preferably is hydrogen, methyl, or phenyl. Z J1 , Z J2 , Z J3 , Z J4 Of these, Z J2 and Z J4 It is preferable that -C(-H)= in all cases.

[0121] Z J1 and Z J3 Both are -C(-R ZJ )= and R ZJ Each of these substituents is preferably hydrogen or one of the substituents selected from substituent group Zα, and is preferably hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and more preferably hydrogen, a substituted or unsubstituted phenyl, t-butyl, methyl, cyclohexyl, or adamantyl. Z J1 and Z J3 At least one of them is R ZJ -C(-R) ZJ It is preferable that ) = .

[0122] From the viewpoint of making it easier to reduce intermolecular stacking of the compound represented by formula (1), in formula (1J-1), Z J1 , Z J2 , Z J3 , Z J4 Each of them independently performs -C(-RZJ )= and Z J1 and Z J3 In at least one of the following, R ZJ It is preferable that Z is a substituent, J1 , Z J2 , Z J3 , Z J4 Each of them independently performs -C(-R ZJ )= and Z J1 and Z J3 In both cases, R ZJ It is more preferable that the substituent is.

[0123] Preferred examples of a base represented by formula (1J-1) include the following: [ka]

[0124] Another preferred example of a group represented by formula (1J) is the group represented by formula (1J-2). [ka]

[0125] In formula (1J-2), R J R in equation (1J) J It is synonymous with and the preferred range is the same. jj Each of these can be used independently of -C(-R jj ) = or -N = and R jj Each of these is independently a hydrogen atom or one of the substituents selected from the substituent group Zα, and the two R jjThe rings may be bonded to each other to form an aryl or heteroaryl ring with the j ring, and the formed ring may be substituted with at least one substituent selected from substituent group Zα. X is >NR, >O, or >S, where R in >NR is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl. R in >NR is preferably a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, and more preferably an unsubstituted aryl (particularly an unsubstituted phenyl).

[0126] In equation (1J-2), Z jj Both are -C(-R jj It is preferable that ) = two R jj It is preferable that the two R rings are bonded to each other and form an aryl ring or heteroaryl ring together with the j ring. jj The ring formed by the bonding of these rings together with the j-ring is preferably a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring, and more preferably an unsubstituted benzofuran ring, an unsubstituted benzothiophene ring, or an unsubstituted indole ring.

[0127] >NR in polycyclic aromatic compounds of the present invention NX R NX The number of elements represented by formula (1J) as is 1 or 2, and preferably 2. In formula (1), X 2 All of them are >NR NX And two R NX It is particularly preferable that all of these are groups represented by formula (1J).

[0128] <Polycyclic aromatic compounds represented by formula (1-A)> A preferred example of a polycyclic aromatic compound represented by formula (1) is the polycyclic aromatic compound represented by formula (1-A).

[0129] [ka]

[0130] In formula (1), the A, B, and C rings are the a ring and its multiple substituents R in formula (1-A), respectively. a1 ~R a3 , the b-ring and its multiple substituents R b1 ~R b3 , the c ring and its multiple substituents R c1 ~R c4 This corresponds to the structure in equation (1) where "a ring A to C having a 6-membered ring" is selected as the A to C rings in equation (1). In that sense, each ring in equation (1) is represented by lowercase letters a to c.

[0131] In formula (1-A), when n is 1, for example, the following structures can be given. The signs in each structural formula are the same as the definitions above, and R a1 ~R a3 , R b1 ~R b3 , and R c1 ~R c4 Furthermore, >NR NX R NX Substituents in (substituents on the phenyl group in the following formulas) have been omitted. Also, in the following example, Y 1 B, X 1 N, X 2 One of them is >NR NX , the other side is >NR NX While an example of >O was shown, other combinations of options also exist. Similarly, examples also exist where two adjacent a-rings (or "all adjacent a-rings" when n is 1) are joined by a single bond.

[0132] [ka]

[0133] The following is >NR NX R NX This shows an example where a phenyl group (in the formula) is bonded to a c-ring (or a ring). While single bonds or -O- bonds are shown as the bonding group, other options are equally available. [ka]

[0134] In general formula (2), when n is 2, for example, the following structures can be given. The signs in each structural formula are the same as the definitions above, and R a1 ~R a3 , R b1 ~R b3 , and R c1 ~R c4 Furthermore, >NR NX R NX Substituents on the phenyl group (in the formula) are omitted. Also, in the following example, Y 1 B, X 1 N, X 2 >O or >NR NX While this example was given, other combinations of options also exist. Furthermore, examples where some or all adjacent a-rings are connected by a single bond also exist. [ka] The following is >NR NX R NX This shows an example where a phenyl group (in the formula) is bonded to a c-ring (or a ring). While single bonds or -O- bonds are shown as the bonding group, other options are equally available.

[0135] [ka]

[0136] In formula (1-A), R a1 ~R a3 , R b1 ~R b3 , and R c1 ~R c4 Each is independently a hydrogen atom or a substituent, and R a1 ~R a3 Of these, two adjacent groups, R b1 ~R b3 Two adjacent groups among them, and R c1 ~R c4Two adjacent groups may bond to each other, forming a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring with the two carbon atoms to which they are bonded.

[0137] R a1 ~R a3 , R b1 ~R b3 , and R c1 ~R c4 When is a substituent, the substituent and the substituent on the formed ring above include at least one substituent selected from substituent group Zα, and at least one substituent selected from substituent group Z is preferred, and substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted diarylamino are preferred. Examples of preferred substituents described later can also be seen. a1 ~R a3 , R b1 ~R b4 , and R c1 ~R c4 When some of these substituents are substituents, those substituents may be the same or different.

[0138] R a1 ~R a3 , R b1 ~R b3 , and R c1 ~R c4 The ring formed when two adjacent groups bond to each other, along with the two carbon atoms to which they bond, is not particularly limited, but examples include benzene rings, naphthalene rings, indene rings, fluorene rings, pyridine rings, furan rings, thiophene rings, pyrrole rings, benzofuran rings, benzothiophene rings, indole rings, selenophene rings, and benzoselenophene rings.

[0139] R a1 ~R a3 In R, a2 is hydrogen or a substituent, and R a1 and R a3It is preferable that each of them is hydrogen. a2 When R is a substituent, preferred substituents are substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted diarylamino, more preferably t-butyl, t-amyl, optionally substituted with methyl adamantyl, optionally substituted with alkyl, optionally substituted with alkyl diarylamino, or optionally substituted with alkyl carbazolyl, even more preferably t-butyl, optionally substituted with methyl adamantyl, optionally substituted with methyl or t-butyl phenyl, optionally substituted with methyl or t-butyl diphenylamino, or optionally substituted with methyl or t-butyl carbazolyl, and particularly preferred t-butyl or optionally substituted with t-butyl phenyl. a2 They may be the same or different from one another. R a1 ~R a3 It is particularly preferable that all of them be hydrogen.

[0140] R b1 ~R b3 In R, b2 is hydrogen or a substituent, and R b1 and R b3 It is preferable that each of them is hydrogen. b2When R is a substituent, preferred substituents are substituted or unsubstituted alkyls, substituted or unsubstituted cycloalkyls, substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, or substituted or unsubstituted diarylaminos; more preferably methyl, t-butyl, t-amyl, adamantyl which may be substituted with methyl, aryl which may be substituted with alkyl, diarylamino which may be substituted with alkyl, or carbazolyl which may be substituted with alkyl; even more preferably methyl, t-butyl, adamantyl which may be substituted with methyl, or phenyl which may be substituted with methyl or t-butyl, diphenylamino which may be substituted with methyl or t-butyl, or carbazolyl which may be substituted with methyl or t-butyl; and particularly preferred methyl. b2 Multiple R when there are multiple b2 They may be the same or different from each other. b2 It is also preferable that the base is represented by formula (1J). R b1 ~R b3 It is particularly preferable that all of them be hydrogen.

[0141] R c1 ~R c4 Each of these is independently either a hydrogen atom or a substituent. c1 ~R c4 Two adjacent groups may bond to each other, forming a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring with the two carbon atoms to which they are bonded. c1 ~R c4 When is a substituent, the substituent and the substituent on the formed ring above include at least one substituent selected from substituent group Zα, and at least one substituent selected from substituent group Z is preferred. c1 ~R c4When multiple of these are substituents, the substituents may be the same or different. The ring formed by two adjacent groups bonding to each other and together with the two carbon atoms to which they are bonded is not particularly limited, but examples include a benzene ring, naphthalene ring, indene ring, fluorene ring, pyridine ring, furan ring, thiophene ring, pyrrole ring, benzofuran ring, benzothiophene ring, indole ring, selenophene ring, and benzoselenophene ring.

[0142] R c1 ~R c4 In R, c3 Preferably, is hydrogen or a substituent, and the others are each hydrogen. c3 When R is a substituent, preferred substituents are substituted or unsubstituted alkyls, substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, or substituted or unsubstituted diarylaminos, more preferably unsubstituted alkyls or substituted or unsubstituted phenyls, and even more preferably methyls. c3 It is also preferable that the base is represented by formula (1J). Multiple R c3 They may be the same or different from one another.

[0143] <Preferred substituents> In polycyclic aromatic compounds used as emitting dopants (and in other compounds used as dopants), a tertiary alkyl group represented by the following formula (tR) (a monovalent group represented by formula (tR)) is particularly preferred as a substituent containing "alkyl". This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Furthermore, substituents in which the tertiary alkyl group represented by formula (tR) is substituted with another substituent as a second substituent are also preferred. Specifically, examples include diarylamino compounds substituted with the tertiary alkyl group represented by formula (tR), carbazolyl compounds substituted with the tertiary alkyl group represented by formula (tR) (preferably N-carbazol), or benzocarbazoll compounds substituted with the tertiary alkyl group represented by formula (tR) (preferably N-benzocarbazol). Substitutions of the (tR) group on diarylamino, carbazolyl, and benzocarbazolyl groups include cases where some or all of the hydrogen atoms in the aryl or benzene ring of these groups are replaced by the (tR) group.

[0144] [ka]

[0145] In the formula (tR), R a , R b , and R c Each of these is an alkyl group having 1 to 24 carbon atoms. a , R b , and R c Each of these groups consists of one or more non-adjacent -CH2- groups in an alkyl group having 1 to 24 carbon atoms, where any -CH2- not in the terminal CH3 group is replaced by an -O-. The group represented by formula (tR) has * as the bond position.

[0146] R a , R b and R cThe "alkyl group having 1 to 24 carbon atoms" can be either linear or branched. Examples include linear 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).

[0147] R in equation (tR) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0148] R a , R b , and R c Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 Examples include -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-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0149] Examples of groups represented by formula (tR) include t-butyl, t-amyl, 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- Examples include 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, and 1,1-dimethylhexyl. Of these, t-butyl and t-amyl are preferred.

[0150] Substituents represented by formula (A30) are also preferred.

[0151] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the substituent structure of the compound used as a dopant (assisting dopant or emitting dopant). Preferably, the group is represented by the following structural formula, and more preferably, methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butyl The components are rucarbazolyl and phenoxy, and more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and tribenzoazepinyl. From the viewpoint of ease of synthesis, greater steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

[0152] In the structural formula below, * represents a bond position. [ka]

[0153] [ka]

[0154] [ka]

[0155]

change

[0156]

change

[0157]

change

[0158]

change

[0159]

change

[0160]

change

[0161]

change

[0162]

change

[0163]

change

[0164]

change

[0165]

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[0166] The polycyclic aromatic compound represented by formula (1) preferably has a structure containing at least one tertiary alkyl (such as t-butyl or t-amyl), neopentyl, or adamantyl represented by formula (tR) above, and preferably contains a tertiary alkyl (such as t-butyl or t-amyl) represented by formula (tR). This is because such bulky substituents increase the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Diarylaminos are also preferred as substituents. Furthermore, diarylaminos substituted with the group of formula (tR), carbazolyls (preferably N-carbazol) substituted with the group of formula (tR), or benzocarbazolls (preferably N-benzocarbazol) substituted with the group of formula (tR) are also preferred. Examples of substitution forms of the group of formula (tR) on diarylaminos, carbazolyls, and benzocarbazolls include cases in which some or all of the hydrogens of the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0167] In the case of substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings in the A, B, and C rings of the polycyclic aromatic compound represented by formula (1), substituted or unsubstituted N-carbazolyl is also preferred as the substituent when referring to "substituted or unsubstituted (substituted or unsubstituted)". When a compound having N-carbazolyl as a substituent is used as a dopant in the light-emitting layer, an organic EL device with a longer lifetime and lower drive voltage can be obtained. It is thought that by having N-carbazolyl as a substituent, the HOMO of the compound becomes deeper, the hole trapping ability decreases, and the drive voltage becomes lower. In addition, it is thought that carrier recombination on the dopant becomes less likely to occur, the dopant is less likely to enter the T1 state, and the lifetime is extended. Here, when N-carbazolyl has a substituent, it is preferable to select the substituent from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, and substituted or unsubstituted cycloalkyl. As for substituted or unsubstituted N-carbazolyl, unsubstituted N-carbazolyl or 3,6-di(t-butyl)N-carbazolyl are particularly preferred.

[0168] In the case of substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings in the A, B, and C rings of the polycyclic aromatic compound represented by formula (1), substituted or unsubstituted 1,3,5-triazinyl is also preferred as the substituent when referring to "substituted or unsubstituted (substituted or unsubstituted)". When a substituted or unsubstituted 1,3,5-triazinyl is included as a substituent, it is particularly preferred that the substituted or unsubstituted 1,3,5-triazinyl is a substituent in the A ring. It is preferable that the substituted or unsubstituted 1,3,5-triazinyl has substituents at positions 2 and 4. The substituents at positions 2 and 4 may be the same or different, but it is preferable that they be the same. Examples of substituents include phenyl and N-carbazolyl.

[0169] In a structure consisting of one or more structural units represented by formula (1), the substituents of the aryl ring or heteroaryl ring may be substituents represented by the following formula (A20). [ka]

[0170] The substituent represented by formula (A20) is bonded by two * to two adjacent atoms on the aryl or heteroaryl ring, respectively. In formula (A20), L is >NR, >O, >Si(-R)2, or >S, where R in >NR is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and R in >Si(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and may be bonded to each other by a linking group or a single bond, and at least one of the >NR and the R in >Si(-R)2 may be bonded to the aryl or heteroaryl ring by a linking group or a single bond. r is an integer from 1 to 4, R A Each of these is independently hydrogen, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and any R A is any other R A They may be bonded to each other by linking groups or single bonds.

[0171] Examples of the substituents mentioned above include substituents represented by any of the following: [ka]

[0172] In each formula, the asterisk (*) indicates that the atom is bonded to two or three adjacent atoms on any of the aryl or heteroaryl rings.

[0173] <Cycloalkane condensation> At least one of the aryl rings and heteroaryl rings in the polycyclic aromatic compound represented by formula (1) may be condensed with at least one cycloalkane.

[0174] The cycloalkane can be any cycloalkane having 3 to 24 carbon atoms. In this case, at least one hydrogen atom in the cycloalkane may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane may be substituted with an -O-.

[0175] The cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, wherein at least one hydrogen atom in the cycloalkane may be substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 22 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

[0176] Examples of "cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0177] 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, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl), halogen (especially fluorine), and deuterium-substituted compounds of these compounds having 1 to 5 carbon atoms.

[0178] Among the examples above, structures having at least one substituent on the α-carbon of the cycloalkane (the carbon adjacent to the carbon at the condensation site in a cycloalkane condensed to an aryl ring or heteroaryl ring), such as shown in the structural formula below, are preferred, structures having two substituents on the α-carbon are more preferred, and structures where both α-carbons each have two substituents (a total of four substituents) are even more preferred. Examples of these substituents include alkyl groups (especially methyl), halogens (especially fluorine), and deuterium, having 1 to 5 carbon atoms. In particular, structures in which a substructure represented by the following formula (B11) or (B12) is bonded to an adjacent carbon atom in the aryl ring or heteroaryl ring are preferred, and structures in which a substructure represented by the following formula (B11) is bonded are more preferred.

[0179] [ka] In equations (B11) and (B12), * indicates a bonding position.

[0180] The number of cycloalkanes condensed to a single aryl 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 to a single benzene ring (phenyl). * indicates the bonding position, and this position may be any carbon that constitutes the benzene ring but not the cycloalkane. Condensed cycloalkanes may also be condensed together, as in formulas (Cy-1-4) and (Cy-2-4). The same applies when the ring (group) to be condensed is an aryl or heteroaryl ring other than a benzene ring (phenyl), and when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

[0181] [ka]

[0182] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows a cycloalkane condensed to a single benzene ring (phenyl) in which one or more -CH2- groups are substituted with -O-. The same applies when the condensed ring (group) is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0183] [ka]

[0184] Cycloalkanes may be substituted with at least one substituent, which can be any substituent selected from substituent group Z. Among these substituents, alkyl (e.g., alkyls with 1 to 6 carbon atoms) and cycloalkyl (e.g., cycloalkyls with 3 to 14 carbon atoms) are preferred. It is also preferred that one of the hydrogen atoms is replaced with a halogen (e.g., fluorine) or deuterium. Furthermore, when a cycloalkyl is substituted, the substitution may form a spiro structure, for example, an example in which a spiro structure is formed on a cycloalkane condensed with one benzene ring (phenyl) is shown below. In each structural formula, * means that if it is a benzene ring, it is a benzene ring included in the backbone structure of the compound, and if it is a phenyl, it means a bond that is substituted on the backbone structure of the compound.

[0185] [ka]

[0186] The forms of cycloalkane condensation include, firstly, a form in which an aryl ring or heteroaryl ring in any of the A, B, or C rings of a polycyclic aromatic compound represented by formula (1) is condensed with a cycloalkane, and secondly, a form in which an aryl ring or heteroaryl ring in the J ring is condensed with a cycloalkane, and thirdly, X 2It is >NR NX R NX Examples include a form in which the aryl ring or heteroaryl ring is condensed with a cycloalkane, and a form in which the aryl ring or heteroaryl ring is condensed with a cycloalkane, where one of the other substituents is a group containing an aryl ring or heteroaryl ring.

[0187] Furthermore, by introducing a cycloalkane structure to the polycyclic aromatic compound represented by formula (1), a further reduction in the melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost indispensable as a purification method for organic devices such as organic EL elements that require high purity, purification can be performed at relatively low temperatures, thus avoiding thermal decomposition of the material. The same applies to the vacuum deposition process, which is a powerful means of fabricating organic devices such as organic EL elements, as the process can be carried out at relatively low temperatures, thus avoiding thermal decomposition of the material and resulting in the acquisition of high-performance organic devices. In addition, 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.

[0188] <Replacement with heavier stable isotopes> In the polycyclic aromatic compounds represented by formula (1), each element is present in naturally occurring isotopes in their natural abundances unless otherwise specified. However, all or some of the elements in each structural formula may be present in amounts exceeding their natural abundances (for example, boron-11( 11 B) may contain heavy stable isotopes at 90 atom percent or more. In this specification, this is simply referred to as "replacing" with "heavy stable isotopes". More specifically, at least one hydrogen can be replaced with deuterium, and at least one nitrogen can be replaced with nitrogen-15. 15 N) can be replaced with at least one sulfur, sulfur-33( 33 S), Sulfur-34( 34 S) or sulfur-36( 36S) can be replaced with at least one oxygen, oxygen-17( 17 O) or oxygen-18( 18 It can be replaced with O), and at least one carbon is carbon-13 ( 13 C) can be replaced with at least one boron, boron-11( 11 It can be replaced with B). The same applies to the structure represented by formula (1-A), and the following explanation also applies to the polycyclic aromatic compound represented by formula (1-A). By replacing at least some elements with heavier stable isotopes, in particular at least one boron can be replaced with boron-11( 11 By substituting with B), the lifespan of an organic electroluminescent device using a polycyclic aromatic compound represented by formula (1) as a dopant can be extended.

[0189] For example, in the polycyclic aromatic compound represented by formula (1), the hydrogen atoms in the A, B, and C rings and their substituents can be replaced with deuterium, and among these, embodiments in which all or some of the hydrogen atoms in the aryl or heteroaryl rings are replaced with deuterium are also possible. Furthermore, from the viewpoint of durability, it is also preferable that all or some of the hydrogen atoms in the polycyclic aromatic compound represented by formula (1) are deuterated. For example, hydrogen atoms in substituents on the aryl or heteroaryl rings in the A, B, and C rings, or X 2 In R NX , R CX or R IX It is also preferable that the hydrogen atoms in the substituents of the substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl are deuterated. An example of such substituent is CD3 (deuterated methyl).

[0190] <Specific examples of polycyclic aromatic compounds> Specific examples of polycyclic aromatic compounds represented by formula (1) include any of the following compounds. However, polycyclic aromatic compounds represented by formula (1) are not limited to the following specific examples.

[0191]

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[0193]

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[0201]

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[0203]

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[0206]

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[0207]

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[0208]

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[0223] [ka]

[0224] [ka]

[0225] [ka]

[0226] [ka]

[0227] <Applications of polycyclic aromatic compounds to polymers> The polycyclic aromatic compounds of the present invention can be used as materials for organic devices, such as materials for organic field-effect light-emitting devices, materials for organic field-effect transistors, materials for organic thin-film solar cells, or wavelength conversion filters, whether as polymer compounds obtained by polymerizing reactive compounds in which reactive substituents are substituted (the monomers used to obtain these polymer compounds have polymerizable substituents), or as crosslinked polymers obtained by further crosslinking the polymer compounds (the polymer compounds used to obtain these crosslinked polymers have crosslinkable substituents), or as pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound (the reactive compound used to obtain these pendant-type polymer compounds has reactive substituents), or as crosslinked pendant-type polymers obtained by further crosslinking the pendant-type polymer compounds (the pendant-type polymer compounds used to obtain these crosslinked polymers have crosslinkable substituents).

[0228] The reactive substituents described above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant-type polymer, and hereinafter simply referred to as "reactive substituents") are not particularly limited as substituents that can increase the molecular weight of the polycyclic aromatic compound, substituents that can further crosslink the polymer compound obtained in this way, and substituents that can undergo a pendant reaction with the main chain polymer, but substituents with the following structures are preferred. * in each structural formula indicates the bond position. [ka]

[0229] Z is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, a C1-C12 alkylene, a C1-C12 oxyalkylene, and a C1-C12 polyoxyalkylene. Among the above substituents, groups represented by formula (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17) are preferred, and groups represented by formula (XLS-1), (XLS-3), or (XLS-17) are more preferred.

[0230] Such polymer compounds, polymer crosslinks, pendant-type polymer compounds, and pendant-type polymer crosslinks may also contain, in addition to the repeating units of the polycyclic aromatic compounds according to the present invention, at least one compound selected from the group consisting of substituted or unsubstituted triarylamines, substituted or unsubstituted fluorenes, substituted or unsubstituted anthracenes, substituted or unsubstituted tetracenes, substituted or unsubstituted triazines, substituted or unsubstituted carbazoles, substituted or unsubstituted tetraphenylsilanes, substituted or unsubstituted spirofluorenes, substituted or unsubstituted triphenylphosphines, substituted or unsubstituted dibenzothiophenes, and substituted or unsubstituted dibenzofurans as a repeating unit.

[0231] Examples of substituents in these repeating units include at least one substituent selected from substituent group Z.

[0232] <Method for producing polycyclic aromatic compounds> Polycyclic aromatic compounds represented by formula (1) basically involve first bonding each aromatic ring to a bonding group (X 1 Ya X 2 An intermediate can be produced by bonding the benzene rings with a group containing boron (first reaction), and then the final product can be produced by bonding the fused rings containing each benzene ring with a bonding group (a group containing boron) (second reaction). In the first reaction, for example, if it is an etherification reaction, general reactions such as nucleophilic substitution reactions and Ullmann reactions can be used, and if it is an amination reaction, general reactions such as the Buchwald-Hartwig reaction, nucleophilic substitution reactions and Goldberg amination can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (a series of aromatic electrophilic substitution reactions, the same applies below) can be used. The desired compound can be produced by using a starting material having the desired fused ring at some point in the reaction process, or by adding a ring condensation step.

[0233] Among the polycyclic aromatic compounds represented by formula (1), compound (1a) in which Y is boron can be produced by referring to, for example, the methods described in International Publication No. 2015 / 102118, International Publication No. 2020 / 80528, and Chem. Soc. Rev., 2024, 53, 1624.

[0234] The following scheme (1) describes the borylation of intermediate-2, which has a halogen atom. After metallation by reacting the halogen atom of intermediate-1 with an organometallic reagent such as t-butyllithium, a boron-metal exchange reaction is carried out by reacting it with a boron reagent such as boron trichloride, boron tribromide, or boron triiodide, and then a Brønsted base such as diisopropylethylamine is added to obtain the compound represented by formula (1a) as desired.

[0235] [ka]

[0236] The following scheme (2-1) is a method for synthesizing compound (1a) from intermediate-2 which contains a halogen atom. By reacting intermediate-2 with a boron reagent such as boron triiodide, intermediate-3 is obtained. Then, in the presence of a nickel catalyst such as [1,2-bis(diphenylphosphin)ethane]dichloronickel(II) (NiCl2(dppe)), a reducing agent such as sodium hydroborate is reacted to convert the halogen atom to a hydrogen atom, thereby obtaining the compound represented by formula (1a).

[0237] [ka]

[0238] Furthermore, by applying Suzuki coupling reactions, Buchwald coupling reactions, etc., it is possible to convert intermediate-3 obtained in scheme (2-1) into compound (1b) and compound (1c). For example, as shown in scheme (2-2), compound (1b) can be obtained by reacting it with an arylboronic acid, and as shown in scheme (2-3), compound (1c) can be obtained by reacting it with an arylamine.

[0239] [ka]

[0240] By appropriately selecting the raw materials to be used, polycyclic aromatic compounds having substituents at desired positions can be synthesized.

[0241] A Lewis acid such as aluminum trichloride may be added to accelerate the reaction. Furthermore, the halogen atoms (Hal) in intermediates 1 to 3 of schemes (1), (2-1) to (2-3) may be F, Cl, Br, or I, may be the same, or may be independently different, and can be appropriately selected considering the reactivity of the substrate.

[0242] Examples of organometallic reagents used in the above scheme (1) include alkyllithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; isopropylmagnesium chloride; isopropylmagnesium bromide; phenylmagnesium chloride; phenylmagnesium bromide; and lithium chloride complexes of isopropylmagnesium chloride, which are known as turbogrignard reagents.

[0243] In addition to the reagents listed above, organometallic reagents used in the above scheme (1) include organoalkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium tetramethylpiperidinylmagnesium chloride-lithium chloride complex, and lithium tri-n-butylmagnesate.

[0244] Furthermore, when alkyllithium is used as an organometallic reagent, additives that can accelerate the reaction include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethylpropylene urea.

[0245] Furthermore, Lewis acids used in the schemes described above include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, BI3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3. These Lewis acids can also be used in a similar manner when supported on a solid.

[0246] Furthermore, examples of Brønsted acids used in the schemes described above include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, and hydrogen fluoride. Examples of solid Brønsted acids include Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and TeikaCure (trade name: Teika Corporation).

[0247] Furthermore, amines that may be added to the scheme described above include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, and 2,6-di-t-butylamine.

[0248] Furthermore, solvents used in the schemes described above include o-dichlorobenzene, chlorobenzene, toluene, benzene, mesitylene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl-t-butyl ether, tert-butanol, N,N-dimethylacetamide, and N,N-dimethylformamide.

[0249] In the above scheme, a Brønsted base or Lewis acid may be used to accelerate the tandem hetero-Friedel-Crafts reaction. However, when using boron halides such as boron trifluoride, boron trichloride, boron tribromide, or boron triiodide, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction progresses, so the use of a Brønsted base to capture the acids is effective. On the other hand, when using boron amination halides or boron alkoxyides, amines and alcohols are generated as the aromatic electrophilic substitution reaction progresses, so in most cases, it is not necessary to use a Brønsted base. However, because the leaving ability of aminos and alkoxys is low, the use of a Lewis acid to promote their elimination is effective.

[0250] Furthermore, the polycyclic aromatic compounds of the present invention include compounds in which at least some of the hydrogen atoms are replaced by deuterium, and compounds in which various substituents are substituted. Such compounds can be synthesized in the same manner as described above by using starting materials in which the desired positions are deuterated or derivatized.

[0251] <2. Organic Devices> The polycyclic aromatic compounds of the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, and organic thin-film solar cells.

[0252] The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, and organic thin-film solar cells, but organic field-light-emitting devices are preferred. The polycyclic aromatic compounds according to the present invention are preferably organic field-light-emitting materials, more preferably materials for light-emitting layers (light-emitting materials), and most preferably dopant materials for light-emitting layers.

[0253] <2-1. Organic electroluminescent element> <2-1-1. Structure of an organic electroluminescent element> Figure 1 is a schematic cross-sectional view showing an example of an organic EL element. The organic EL element 100 shown in Figure 1 comprises a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light-emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light-emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0254] The organic EL element 100 may also be configured by reversing the manufacturing order, for example, by having a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emissive layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emissive layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0255] Not all of the above layers are necessarily required; the minimum configuration unit consists of an anode 102, a light-emitting layer 105, and a cathode 108, and the hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are optional layers. Furthermore, each of the above layers may consist of a single layer or multiple layers.

[0256] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode" configurations, other configurations of layers constituting an organic EL element include "substrate / anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron injection layer / cathode", and "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport The configuration may also be "transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron transport layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / cathode", or "substrate / anodode / emissive layer / electron injection layer / cathode".

[0257] <2-1-2. Light-emitting layer in organic electroluminescent devices> The polycyclic aromatic compounds of the present invention are preferably used as materials for forming one or more organic layers in an organic electroluminescent device, and more preferably as materials for forming a light-emitting layer. The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 with electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 can be any compound that emits light when excited by the recombination of holes and electrons (luminescent compound), and it is preferable that the compound can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state.

[0258] The light-emitting layer may consist of a single layer or multiple layers, each formed from a light-emitting layer material (host material, dopant material). The host material and dopant material may each be of one type or a combination of multiple types. The dopant material may be contained throughout the host material or partially contained within it. As for the doping method, it can be formed by co-deposition with the host material, but it may also be mixed with the host material beforehand and then deposited simultaneously.

[0259] The amount of host material used varies depending on the type of host material and should be determined according to the characteristics of that host material. A guideline for the amount of host material used is preferably 50 to 99.999% by mass of the total mass of the light-emitting layer material, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass. If the host material is a combination of a hole-transporting host material and an electron-transporting host material, the amount of host material used is the combined mass of the hole-transporting host material and the electron-transporting host material. The ratio of the amounts of hole-transporting host material to electron-transporting host material should be 1:9 to 9:1 by mass, preferably 4:6 to 6:4, and more preferably approximately 1:1.

[0260] The amount of dopant material used varies depending on the type of dopant material and should be determined according to the characteristics of that dopant material. A guideline for the amount of dopant material used is preferably 0.001 to 50% by mass of the total mass of the light-emitting layer material, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass. Within this range, for example, it is preferable in that it can prevent density quenching.

[0261] As the dopant material, both an emitting dopant and an assisting dopant material may be used. As the assisting dopant material, both a thermally activated delayed fluorescence material and a phosphorescent material can be preferably used. In an organic electroluminescent device using an assisting dopant material, a low concentration of the emitting dopant material is preferable in that it can prevent concentration quenching. A high concentration of the assisting dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic electroluminescent device using a thermally activated delayed fluorescence assisting dopant material, a lower concentration of the emitting dopant material is preferable compared to the amount of the assisting dopant material in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant material.

[0262] When assisting dopant materials are used, the approximate amounts of host material, assisting dopant material, and emitting dopant material used are 40-99% by mass, 59-1% by mass, and 20-0.001% by mass, respectively, based on the total mass of the material for the light-emitting layer. Preferably, these amounts are 60-95% by mass, 39-5% by mass, and 10-0.01% by mass, respectively, and more preferably 70-90% by mass, 29-10% by mass, and 5-0.05% by mass.

[0263] The polycyclic aromatic compounds of the present invention are more preferably used as materials for forming a light-emitting layer, and more preferably as dopants. Polycyclic aromatic compounds containing the structural unit represented by formula (1) can be used as emitting dopants for TTF devices that utilize the phenomenon of triplet-triplet fusion (TTF), in which a singlet exciton is generated from multiple triplet excitons.

[0264] Furthermore, the polycyclic aromatic compounds of the present invention may be used as "thermally activated delayed phosphors" and as emitting dopants for organic EL devices exhibiting thermally activated delayed fluorescence (TADF) (hereinafter sometimes referred to as "TADF devices"). In "thermally activated delayed phosphors," by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, reverse intersystem cross-transition from the lowest excited triplet state to the lowest excited singlet state, which normally has a low transition probability, is efficiently generated, and emission from the singlet state (thermally activated delayed fluorescence, TADF) is produced. In normal fluorescence emission, 75% of the triplet excitons generated by electric excitation pass through the thermal deactivation pathway and cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, enabling the realization of highly efficient organic EL devices.

[0265] The polycyclic aromatic compound of the present invention can be used as an emitting dopant for a "TADF element," as an emitting dopant for an organic electroluminescent element (TAF element) that uses another thermally activated delayed phosphor as an assisting dopant, and as an emitting dopant for an organic electroluminescent element (PSF element) that uses a phosphorescent material as an assisting dopant. From the viewpoint that the fewer materials used in the element, the easier it is to manufacture, it is preferable to use it as an emitting dopant for a TADF element, and the former is more preferable. From the viewpoint of efficiency, it is preferable to use it as an emitting dopant for both a TAF element and a PSF element, and it is more preferable to use it as an emitting dopant for a TAF element.

[0266] Generally, a faster delayed fluorescence (TADF) indicates superior TADF properties. Specifically, when an emissive material with a delayed fluorescence lifetime of 20 μsec or less is used as an emitting dopant in a light-emitting device, it can provide high device efficiency and a long device lifetime. A delayed fluorescence lifetime of less than 20 μsec is preferred, 10 μsec or less is more preferred, and 5 μsec or less is most preferred.

[0267] Also, generally speaking, ΔE S1T1 The smaller the value of ΔE, the better the TADF performance. S1T1This is the lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 This is the energy difference with ). Specifically, ΔE S1T1 The value of is preferably 0.20 eV or less, more preferably 0.15 eV or less, and particularly preferably 0.10 eV or less.

[0268] <Host Materials> Examples of host materials include condensed ring derivatives such as anthracene and pyrene, which have been known as luminescent materials for some time; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; benzofluorene derivatives; N-phenylcarbazole derivatives; carbazonitrile derivatives; and dibenzochrysene derivatives. Other examples include compounds represented by any of the formulas (H1), (H2), and (H3), hole-transporting host materials (HH), electron-transporting host materials (EH), and bipolar host materials. From the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms in the host material are deuterated. Furthermore, it is also preferable to construct the light-emitting layer by combining a host compound in which some or all of the hydrogen atoms are deuterated with a dopant compound in which some or all of the hydrogen atoms are deuterated.

[0269] The lowest excited triplet energy level of the host material (E T1 ) is chosen from the viewpoint of promoting the generation of TADF within the light-emitting layer without inhibiting it, and is the highest E within the light-emitting layer. T1 E of a dopant or assisting dopant T1 It is preferable that it be higher than the E of the host material. Specifically, the E of the host material T1 E is the dopant or assisting dopant mentioned above. T1 It is preferable that it is 0.01 eV or more higher than, more preferably 0.03 eV or more higher, and even more preferably 0.1 eV or more higher than. Also, the E of the host material T1The voltage is preferably 2.70 eV or higher, more preferably 2.73 eV or higher, and even more preferably 2.80 eV or higher. A TADF-active compound may be used as the host material.

[0270] The host material may be a single type or a combination of multiple types. If multiple types are used, a combination of a hole-transporting host material and an electron-transporting host material is preferred.

[0271] [Compounds represented by any of the following formulas: (H1), (H2), and (H3)] As the host material, for example, a compound represented by any of the following formulas (H1), (H2), and (H3) can be used. [ka]

[0272] In equations (H1), (H2), and (H3), L 1 L is a divalent group containing a single bond or at least an arylene or heteroarylene. Specifically, L 1 It can be a single bond, or a divalent group formed by linking any two of the following with -O-, -S-, -CH2-, -Si(-Arx)2- (Arx is aryl), or cycloalkylene. 1 The arylene used is preferably one with 6 to 16 carbon atoms, more preferably one with 6 to 12 carbon atoms, and particularly preferably one with 6 to 10 carbon atoms. Specifically, divalent groups such as benzene rings, biphenyl rings, terphenyl rings, and fluorene rings are used. 1The heteroarylenes included are preferably heteroarylenes having 2 to 24 carbon atoms, more preferably heteroarylenes having 2 to 20 carbon atoms, even more preferably heteroarylenes having 2 to 15 carbon atoms, and particularly preferably heteroarylenes having 2 to 10 carbon atoms. Specifically, these include pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings (such as furazan rings), thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, and isoindole rings. Examples of divalent groups include 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, 1H-benzotriazole rings, quinoline rings, isoquinoline rings, sinnoline rings, quinazoline rings, quinoxaline rings, phthalazine rings, naphthyridine rings, purine rings, pteridine rings, carbazole rings, acridine rings, phenoxatiin rings, phenoxazine rings, phenothiazine rings, phenazine rings, indidine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, thiophene rings, benzothiophene rings, dibenzothiophene rings, and thianthlene rings. At least one hydrogen atom in each of the compounds represented by the above formulas may be substituted with at least one group selected from substituent group Z or with deuterium, for example, with an alkyl, cyano, halogen or deuterium having 1 to 6 carbon atoms.

[0273] Preferred examples include compounds represented by any of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen atom may be substituted with a halogen, cyano, a C1-C4 alkyl group (e.g., methyl or t-butyl), phenyl, or naphthyl.

[0274] [ka]

[0275] [ka]

[0276] [ka]

[0277] [ka]

[0278] [Anthracene compounds] Examples of anthracene compounds that can serve as hosts include the compound represented by formula (3-H) and the compound represented by formula (3-H2). [ka]

[0279] In formula (3-H), X and Ar 4 Each is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, an optionally substituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted alkyl, an optionally substituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl, and all X and Ar 4 They cannot become hydrogen at the same time. At least one hydrogen atom in the compound represented by formula (3-H) may be substituted with a halogen, cyano, deuterium, or an optionally substituted heteroaryl.

[0280] Furthermore, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded together via X, and X may be a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., which are groups having a divalent bond value).

[0281] Preferred embodiments of the above anthracene compound are described below. The definitions of the symbols in the following structures are the same as those described above. [ka]

[0282] In formula (3-H), each X is independently a group represented by formula (3-X1), formula (3-X2), or formula (3-X3), and the groups represented by formula (3-X1), formula (3-X2), or formula (3-X3) bond to the anthracene ring of formula (3-H) at *. Preferably, two Xs do not simultaneously become the group represented by formula (3-X3). More preferably, two Xs do not simultaneously become the group represented by formula (3-X2).

[0283] Furthermore, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded together via X, and X may be a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., which are groups having a divalent bond value).

[0284] The naphthylene moieties in formulas (3-X1) and (3-X2) may be condensed with a single benzene ring. The resulting structure is as follows: [ka]

[0285] Ar 1 and Ar 2 Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 If the group is represented by formula (A), then the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at its *.

[0286] Ar 3 This refers to phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). Note that Ar 3 If the group is represented by formula (A), then the group represented by formula (A) bonds with the single bond represented by the line in formula (3-X3) at its *. That is, the anthracene ring of formula (3-H) and the group represented by formula (A) bond directly.

[0287] Also, Ar 3 It may have substituents, Ar 3 At least one hydrogen in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a crisenyl group, a triphenylenyl group, a pyrenyl group, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl groups). Note that Ar 3 If the substituent on is the group represented by formula (A), then the group represented by formula (A) is the Ar in formula (3-X3) in its *3 It combines with it.

[0288] Ar 4 These are silyls that are independently substituted with hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or C1-C4 alkyl (methyl, ethyl, t-butyl, etc.) and / or C5-C10 cycloalkyl.

[0289] Furthermore, the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with the group represented by formula (A). When substituted with the group represented by formula (A), the group represented by formula (A) substitutes for at least one hydrogen atom in the compound represented by formula (3-H) at that *.

[0290] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have. [ka]

[0291] In equation (A), Y is -O-, -S-, or >NR 29 And R 21 ~R 28 Each is independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an optionally substituted amino, a halogen, a hydroxyl, or a cyano, and R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, R 29 is hydrogen or an aryl that may be substituted. In equation (A), Y is preferably -O-.

[0292] R 21 ~R 28 Examples of "substituted amino acids" in "amino acids that may be substituted" include diarylamino acids, diheteroarylamino acids, and arylheteroarylamino acids.

[0293] Y as ">NR" 29 R in " 29 is hydrogen or an aryl that may be substituted.

[0294] R 21 ~R 28 Adjacent groups may bond to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group that does not form a ring is represented by formula (A-1) below, while the group that does form a ring is represented by formulas (A-2) to (A-14) below, for example. At least one hydrogen in any of the groups represented by formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (the two aryls may be bonded to each other via a linking group)-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano.

[0295] [ka]

[0296] Examples of rings formed by the bonding of adjacent groups include the cyclohexane ring in the case of hydrocarbon rings, and the aforementioned R in the case of aryl rings and heteroaryl rings. 21 ~R 28 Examples include the ring structures described as "aryl" and "heteroaryl" in formula (A-1), where these rings are formed to condense with one or two benzene rings.

[0297] The group represented by formula (A) is the group obtained by removing one hydrogen atom from any position in formula (A), where * indicates the position. In other words, the group represented by formula (A) may have any position as its bonded position. For example, either carbon atom on the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 Among them, any atom on a ring formed by the bonding of adjacent groups to each other, or as Y in the structure of formula (A), ">NR 29 R in " 29 Any position in the middle, or ">NR 29 N(R) in " 29 It can be a group that directly bonds with (which forms a bonding site). The same applies to the group represented by any of formulas (A-1) to (A-14).

[0298] Examples of the group represented by formula (A) include any of the groups represented by formulas (A-1) to (A-14), with groups represented by any of formulas (A-1) to (A-5) and formulas (A-12) to (A-14) being preferred, groups represented by any of formulas (A-1) to (A-4) being more preferred, groups represented by any of formulas (A-1), (A-3), and (A-4) being even more preferred, and the group represented by formula (A-1) being particularly preferred.

[0299] Examples of groups represented by formula (A) include the following. The definitions of Y and * in the formula are the same as above. [ka]

[0300] [ka]

[0301] In the compound represented by formula (3-H), the group represented by formula (A) is the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and the Ar in formula (3-X3). 3A form in which it is combined with one of the following is preferred.

[0302] Furthermore, all or part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be deuterium.

[0303] The anthracene compound used as a host may be, for example, a compound represented by the following formula (3-H2). [ka]

[0304] In formula (3-H2), Ar c R is an optionally substituted aryl or optionally substituted heteroaryl, c is hydrogen, alkyl, or cycloalkyl, and Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 , and Ar 18 Each of these is independently a hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino (the two aryls may be linked to each other via a linking group), an optionally substituted diheteroarylamino (the two heteroaryls may be linked to each other via a linking group), an optionally substituted arylheteroarylamino (the aryl and heteroaryl may be linked to each other via a linking group), an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, or an optionally substituted silyl, wherein at least one hydrogen in the compound represented by formula (3-H2) may be substituted with a halogen, cyano, or deuterium.

[0305] The "aryl group that may be substituted" is preferably a group represented by any of the following formulas (3-H2-X1) to (3-H2-X8).

[0306] [ka]

[0307] In equations (3-H2-X1) to (3-H2-X8), * indicates the bond position. In equations (3-H2-X1) to (3-H2-X3), Ar 21 Ar 22 , and Ar 23 Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In the explanation of formula (3-H2), the group represented by formula (A) is the same as that explained for the anthracene compound represented by formula (3-H).

[0308] 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 of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). In addition, one or more hydrogens 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 t-butyl).

[0309] Furthermore, preferred examples of "optionally substituted aryls" include terpheniryl (in particular m-terphenyl-5'-yl), which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, crisenyl, triphenylenyl, pyrenyl, and the group represented by formula (A).

[0310] Examples of "optionally substituted heteroaryls" include the group represented by formula (A). Other specific examples of "optionally substituted aryls" and "optionally substituted heteroaryls" include dibenzofuryl, naphthobenzofuryl, and phenyl-substituted dibenzofuryl.

[0311] At least one hydrogen atom in the compound represented by formula (3-H2) may be substituted with a halogen, cyanopropyl alcohol, or deuterium. Examples of halogens 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.

[0312] In formula (3-H2), R c The element is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen. In formula (3-H2), Ar 11 ~Ar 18 Preferably, at least two of the substituents are optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0313] Anthracene compounds represented by formula (3-H2) are Ar 11 ~Ar 18It is more preferable that two of the substituents are optionally substituted aryl or optionally substituted heteroaryl, and the other six substituents are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. In other words, it is more preferable that the anthracene compound represented by formula (3-H2) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0314] Anthracene compounds represented by formula (3-H2) are Ar 11 ~Ar 18 It is more preferable that any two of the elements are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or t-butyl.

[0315] Furthermore, in equation (3-H2), R c is hydrogen and Ar 11 ~Ar 18 It is preferable that any six of them are hydrogen.

[0316] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formulas: (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E). [ka]

[0317] In formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E), Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18Each of the following groups is independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when both the hydrogen of the methylene group in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyl groups may be bonded to each other by single bonds. c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 The carbon atoms of the anthracene ring that are not bonded may have methyl or t-butyl atoms bonded to them instead of hydrogen atoms.

[0318] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 When each of these is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl, it is preferable that the group is represented by any of the above formulas (3-H2-X1) to (3-H2-X8).

[0319] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18Each of the groups is more preferably independently phenyl, biphenylyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenylyl (especially m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or any of the above formulas (A-1) to (A-4), in which case at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or any of the above formulas (A-1) to (A-4).

[0320] 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, cyano, or deuterium. Deuterated forms are preferred, and forms in which the entire anthracene ring is deuterated, or forms in which all hydrogen atoms are deuterated, are preferred.

[0321] Particularly preferred anthracene compounds represented by the formula (3-H2) include the anthracene compounds represented by the following formula (3-H2-Aa). [ka]

[0322] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15Each of the following groups is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or any of the above formulas (A-1) to (A-11), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or any of the above formulas (A-1) to (A-11). Here, when both the hydrogen of the methylene group in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyl groups may be bonded to each other by single bonds. Also, Ar c ', Ar 14 ', and Ar 15 Carbon atoms on an anthracene ring that are not bonded to a ' group may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with a halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with deuterium.

[0323] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15 Each of the groups is preferably independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4) above, and at least one hydrogen in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4).

[0324] In the compound represented by formula (3-H2-Aa), at least the carbon at position 10 of the anthracene ring (Ar cIt is preferable that the hydrogen bonded to the carbon atom to which the ' is attached (with the carbon atom at position 9) is substituted with deuterium. That is, the compound represented by formula (3-H2-Aa) is preferably the compound represented by the following formula (3-H2-Ab). In formula (3-H2-Ab), D is deuterium, and Ar c ', Ar 14 ', and Ar 15 ' is the same as the definition in formula (3-H2-Aa). In formula (3-H2-Ab), D indicates that at least this position is deuterium, and one or more of the other hydrogens in formula (3-H2-Ab) may also be deuterium, and it is also preferable that all of the hydrogens in formula (3-H2-Ab) are deuterium.

[0325] [ka]

[0326] Specific examples of anthracene compounds include, for example, the 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), and (3-600) to (3-605), and (3-606-Y) to (3-626-Y). The hydrogen atoms in these formulas may be partially or entirely substituted with deuterium, but particularly preferred forms of deuterium substitution are listed separately. In the formulas, Y represents -O-, -S-, >NR. 29 (R 29 (This is the same definition as above) or >C(-R 30 )2(R 30 R may be either an aryl or alkyl group that is linked, 29 For example, phenyl, R 30 For example, methyl. The formula numbering is as follows: for example, if Y is O, formula (3-131-Y) becomes formula (3-131-O), and Y is -S- or >NR. 29 In these cases, the equations are (3-131-S) or (3-131-N), respectively.

[0327]

change

[0328]

change

[0329]

change

[0330]

change

[0331]

change

[0332]

change

[0333]

change

[0334]

change

[0335]

change

[0336]

change

[0337]

change

[0338] [ka]

[0339] [ka]

[0340] [ka]

[0341] [ka]

[0342] [ka]

[0343] [ka]

[0344] [ka]

[0345] [ka]

[0346] [ka] In the above formula, D is deuterium.

[0347] Among these compounds, formulas (3-131-Y)~(3-134-Y), formula (3-138-Y), formula (3-140-Y)~(3-143-Y), formula (3-150-Y), formula (3-153-Y)~(3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173-Y), formula (3-177-Y), formula (3-180-Y)~(3-183-N), formula (3-185-Y), formula (3-190-Y), formula (3-223-Y), formula (3-241- Compounds represented by formulas (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) are preferred. Furthermore, Y is -O- or >NR 29 It is preferable that it is -O-, and more preferably that it is deuterium-substituted. The deuterium substitution form is also preferred.

[0348] The above anthracene compounds include compounds having a reactive group at a desired position on the anthracene skeleton, and anthracene compounds represented by formula (3-H), where X and Ar 4 The compounds can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions, using compounds having reactive groups in substructures such as the structure of formula (A) as starting materials. Examples of reactive groups in these reactive compounds include halogens and boronic acids. For specific production methods, refer to the synthesis methods in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725, for example.

[0349] [Fluorene compounds] The compound represented by formula (4-H) basically functions as a host. [ka]

[0350] In formula (4-H), R 1 From R 10 Each of these is independently a hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in formula (4-H) via a single bond or a linking group), diarylamino (the two aryls may be bonded to each other via a linking group), diheteroarylamino (the two heteroaryls may be bonded to each other via a linking group), arylheteroarylamino (the aryl and heteroaryl may be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 Each of these may be independently bonded to form a fused ring or spiro ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a single bond or a linking group), diarylamino (the two aryls may be bonded to each other via a linking group), diheteroarylamino (the two heteroaryls may be bonded to each other via a linking group), arylheteroarylamino (the aryl and heteroaryl may be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (4-H) may be substituted with a halogen, cyano, or deuterium.

[0351] Furthermore, as specific examples of heteroaryls, monovalent groups can also be given, which are represented by removing any one hydrogen atom from the compounds of the following formulas: (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5).

[0352] [ka]

[0353] In equations (4-Ar1) to (4-Ar5), Y 1 Each of these is independently O, S, or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulas (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0354] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via single bonds or linking groups. That is, the fluorene skeleton in formula (4-H) and the heteroaryls may not only be directly bonded, but may also be bonded to each other via linking groups. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0355] Also, R in equation (4-H) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 Each of them independently bonds to form a fused ring, R 9 and R 10 They may be bonded together to form a spiro ring. 1From R 8 The condensed ring formed by this process is a ring that condenses with the benzene ring in formula (4-H), and is either an aliphatic or aromatic ring. Preferably, it is an aromatic ring, and examples of structures including the benzene ring in formula (4-H) include naphthalene rings and phenanthrene rings. 9 and R 10 The spiro ring formed by this process is a ring that spirobonds to the 5-membered ring in formula (4-H), and is either an aliphatic or aromatic ring. Preferably, it is an aromatic ring, such as a fluorene ring.

[0356] The compound represented by formula (4-H) is preferably a compound represented by the following formulas (4-H-1), (4-H-2), or (4-H-3), where in each case R in formula (4-H) 1 and R 2 A compound in which a benzene ring formed by the bonding of R is condensed, in formula (4-H). 3 and R 4 A compound in which a benzene ring formed by the bonding of R is condensed, in formula (4-H). 1 From R 8 It is a compound in which none of the following are bonded.

[0357] [ka]

[0358] R in equations (4-H-1), (4-H-2), and (4-H-3) 1 From R 10 The definition of is the corresponding R in equation (4-H). 1 From R 10 This is the same as R in equations (4-H-1) and (4-H-2). 11 From R 14 The definition of R in equation (4-H) is also 1 From R 10 It is the same as this.

[0359] The compound represented by formula (4-H) is more preferably the compound represented by the following formulas (4-H-1A), (4-H-2A), or (4-H-3A), where R is present in formulas (4-H-1), (4-H-2), or (4-H-3), respectively. 9 and R 10 This is a compound in which a spirofluorene ring is formed by the bonding of two molecules.

[0360] [ka]

[0361] R in equations (4-H-1A), (4-H-2A), and (4-H-3A) 2 From R 7 The definition of is the corresponding R in equations (4-H-1), (4-H-2), and (4-H-3). 2 From R 7 This is the same as R in equations (4-H-1A) and (4-H-2A). 11 From R 14 The definition of R in equations (4-H-1) and (4-H-2) is also 11 From R 14 It is the same as this.

[0362] Furthermore, in the compound represented by formula (4-H), all or part of the hydrogen atoms may be substituted with halogens, cyanosides, or deuterium.

[0363] A more specific example of a fluorene compound as a host in the present invention is the compound represented by the following structural formula. [ka]

[0364] [Dibenzochrysene compounds] Dibenzochrysene compounds used as hosts are, for example, compounds represented by the following formula (5-H). [ka]

[0365] In formula (5-H), R 1 From R 16 Each of these is independently a hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzochrysene skeleton in formula (5-H) via a single bond or linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and R 1 From R 16 Adjacent groups may bond to each other to form a fused ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a single bond or a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (5-H) may be substituted with a halogen, cyano, or deuterium.

[0366] Examples of alkenyls in the definition of formula (5-H) include alkenyls having 2 to 30 carbon atoms, with alkenyls having 2 to 20 carbon atoms being preferred, alkenyls having 2 to 10 carbon atoms being more preferred, alkenyls having 2 to 6 carbon atoms being even more preferred, and alkenyls having 2 to 4 carbon atoms being particularly preferred. Preferred alkenyls 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.

[0367] Furthermore, as specific examples of heteroaryls, monovalent groups can also be represented by removing any one hydrogen atom from the compounds of the following formulas: (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5).

[0368] [ka]

[0369] In equations (5-Ar1) to (5-Ar5), Y 1 Each of these is independently O, S, or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulas (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0370] These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via single bonds or linking groups. That is, the dibenzochrysene skeleton in formula (5-H) and the heteroaryls may not only be directly bonded, but may also be bonded to each other via linking groups. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0371] 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 is hydrogen. In this case, R in equation (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R15 Preferably, each of these is independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having this structure may be bonded to the dibenzochrysene skeleton in formula (5-H) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-), methyl, ethyl, propyl, or butyl.

[0372] 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 is hydrogen. In this case, R in equation (5-H) 3 , R 6 , R 11 and R 14 At least one (preferably one or two, more preferably one) of the groups is a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, and the other groups (i.e., the positions other than those substituted by the monovalent group having the aforementioned structure) are hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, wherein at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0373] Also, R in equation (5-H)2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 If a monovalent group having a structure represented by formulas (5-Ar1) to (5-Ar5) is selected, then at least one hydrogen in that structure is R in formula (5-H). 1 From R 16 It may also bond with either of them to form a single bond.

[0374] A more specific example of a dibenzochrysene compound as a host in the present invention is the compound represented by the following structural formula. [ka]

[0375] [ka]

[0376] [Hole-transporting host materials (HH) and electron-transporting host materials (EH)] The host material may be a single type or a combination of multiple types. If multiple types are used, a combination of a hole-transporting host material and an electron-transporting host material is preferred. Hole-transporting host materials (HH) and electron-transporting host materials (EH) satisfy the following relationship with respect to HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital). The homeosphere of a hole-transporting host material (HH) is shallower than that of an electron-transporting host material (EH), and the lumen-luminosity of an electron-transporting host material (EH) is deeper than that of a hole-transporting host material (HH). Furthermore, it is preferable that the HOMO of the emitting dopant is shallower than the HOMO of the hole-transporting host material (HH), or that the LUMO of the emitting dopant is deeper than the LUMO of the electron-transporting host material (EH).

[0377] Furthermore, the lowest excited triplet energy level (E) of hole-transporting host materials (HH) and electron-transporting host materials (EH) T1 ) is chosen from the viewpoint of promoting the generation of TADF within the light-emitting layer without inhibiting it, and is the highest E within the light-emitting layer. T1 Emitting dopant or assisting dopant having E T1 It is preferable that it be higher than the E of the host material. Specifically, the E of the host material T1 This refers to the E of the above-mentioned emitting dopant or assisting dopant. T1 It is preferable that it is 0.01 eV or more higher than, more preferably 0.03 eV or more higher, and even more preferably 0.1 eV or more higher than. Also, the E of the host material T1 The voltage is preferably 2.47 eV or higher, more preferably 2.49 eV or higher, and even more preferably 2.56 eV or higher.

[0378] Furthermore, it is preferable to use a hole-transporting host material in the hole transport layer adjacent to the light-emitting layer, and also to use an electron-transporting host material in the electron transport layer adjacent to this light-emitting layer. This is because carrier leakage and energy leakage from the light-emitting layer to adjacent layers are less likely to occur, resulting in a highly efficient organic EL device. The host material in the light-emitting layer (hole-transporting host material) and the hole transport layer material may be the same or different. Similarly, the host material in the light-emitting layer (electron-transporting host material) and the electron transport layer material may be the same or different.

[0379] [Hole-transporting host material (HH)] Examples of preferred hole-transporting host materials (HH) include compounds represented by formula (HH-1) or having a substructure represented by formula (HH-1) and comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. Preferably, these compounds do not contain any imine structure (-N=C-; including a heteroaryl ring substructure), boron (>B-), or cyano (CN).

[0380] [ka]

[0381] In equation (HH-1), Q is either >O, >S, or >NA H And, In formula (HH-1), the carbon atom adjacent to the carbon atom to which Q is bonded in each of the two phenyl molecules may be bonded to each other by L. L is a single bond, >O, >S, or >C(-A) H )2, A H is hydrogen, aryl, or heteroaryl, and >C(-A H )2 A H They may be bound to each other.

[0382] When a hole-transporting host material contains a substructure represented by formula (HH-1), it may contain one substructure, but it is also preferable to contain two or more. If it contains two or more substructures, the two or more substructures may be the same or different. The two or more substructures may be bonded to each other by single bonds, bonded so as to share any ring contained in the substructure, or bonded so as to be condensed between any rings contained in the substructure. The substructures may further have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy.

[0383] Compounds represented by the above formula (HH-1), or having a substructure represented by the formula (HH-1), have a structure containing at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings is preferably 6 or more, more preferably 8 or more. It is also preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of monorings; for fused rings, it refers to the number of monorings constituting the fused ring.

[0384] The hole-transporting host material is preferably a compound containing one or more substructures selected from the group consisting of a triarylamine structure, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a condensed polycyclic ring containing phenoxazine or phenothiazine. The hole-transporting host material may contain one such substructure, but it is also preferable to contain two or more. If it contains two or more substructures, the two or more substructures may be the same or different from each other.

[0385] Specific examples of hole-transporting host materials include the following compounds. [ka]

[0386] [ka]

[0387] [ka]

[0388] [ka]

[0389] [ka]

[0390] [ka]

[0391] [ka]

[0392] [ka]

[0393] [ka]

[0394] [ka]

[0395] [ka]

[0396] [ka]

[0397] [ka]

[0398] Of the above, HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1-20 to HH-1-24, HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92, HH-1-106 to HH-1-108, and HH-1-109 to HH-1-115 are preferred.

[0399] [Electron-transporting host materials (EH)] Examples of electron-transporting host materials (EH) include compounds represented by formulas (EH-1A) to (EH-1D), or compounds having a substructure represented by formulas (EH-1A) to (EH-1D) and containing at least three rings selected from the group consisting of aryl rings and heteroaryl rings.

[0400] [ka]

[0401] In equations (EH-1A) to (EH-1D), Ar is a heteroaryl ring that contains N=C as a substructure constituting the ring. Z is a single bond, -O-, -S-, or -N(-A) E )- and, A is bonded to the carbon atom adjacent to the carbon atom that is bonded to Z. E These can be connected by L, L is a single bond, >O, >S or >C(-A E )2, A E is an aryl, heteroaryl, or triarylsilyl, and in formula (EH-1C), any one of the A's is present. E It may also be a diarylamino, Two A atoms bonded to the same atom E They may be connected to each other by L, X is C, P, or S. When X is C, n=2 and m=1, When X is P, n=3 and m=1, When X is S, n=2 and m=1 to 2.

[0402] Compounds represented by the above formulas (EH-1A) to (EH-1D), or compounds having substructures represented by the above formulas (EH-1A) to (EH-1D), have a structure containing at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. It is also preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of monorings; for fused rings, it refers to the number of monorings constituting the fused ring.

[0403] When an electron-transporting host material contains a substructure represented by formulas (EH-1A) to (EH-1D), it may contain one substructure, but it is also preferable to contain two or more. If it contains two or more substructures, they may be the same or different from each other. The two or more substructures may be bonded to each other by single bonds, bonded so as to share any ring contained in the substructure, or bonded so as to be fused to any ring contained in the substructure. The substructures may further have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy.

[0404] The following compounds are specific examples of electron-transporting host materials. [ka]

[0405] [ka]

[0406] [ka]

[0407] [ka]

[0408] [ka]

[0409] [ka]

[0410] [ka]

[0411] [ka]

[0412] [ka]

[0413] Another preferred example of an electron-transporting host material (a compound having a substructure represented by formula (EH-1)) is a polycyclic aromatic compound represented by the following formula (EH-1b), or a polymer of a polycyclic aromatic compound having multiple structures represented by the following formula (EH-1b). [ka]

[0414] In equation (EH-1b), R 1 , R 2 , R 3 , R 4 and R 5 (Hereinafter referred to as “R 1 Each of these (also called "etc.") is independently either a hydrogen atom or a substituent. This substituent can be any substituent selected from substituent group Z. In equation (EH-1b), X 1 and X 2These are, independently, >NR (amine nitrogen), >O, >C(-R)2, >S, or >Se, and X 1 and X 2 It is not possible for both to be >C(-R)2. In >NR and >C(-R)2, R is independently hydrogen or a substituent selected from substituent group Z, and may further be substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above are secondary substituents), and R in >NR and >C(-R)2 may independently be bonded to at least one of the a, b, and c rings by a linking group or a single bond. Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 (hereafter, "Y 1 Each of these (also called "etc.") is independently either =C(-R)- or =N- (pyridine nitrogen), and at least one is =N- (pyridine nitrogen), In the above-mentioned =C(-R)-, R is independently selected from hydrogen or the substituent group Z. The aforementioned R 1 , R 2 , R 3 , R 4 and R 5 , and also, the Y 1 ~Y 6 As =C(-R)-, adjacent R groups may bond together to form an aryl ring or heteroaryl ring with at least one of the a, b, and c rings, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy (the above are the first substituents), and at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above are the second substituents). At least one hydrogen atom in the compound and structure represented by formula (EH-1b) may be substituted with cyano, halogen, or deuterium.

[0415] In equation (EH-1b), R 1 , R 2 , R 3 , R 4 and R 5 Both are hydrogen, or R 3 and R 4 Both are hydrogen, and R 1 , R 2 and R 5 Preferably, one or more substituents selected from the group consisting of are other than hydrogen, and the others are hydrogen. Preferred substituents are alkyl, aryl which may be substituted with alkyl or heteroaryl, heteroaryl which may be substituted with alkyl or aryl, or diarylamino which may be substituted with alkyl or aryl. In this case, preferred alkyl is a C1-C6 alkyl (methyl, t-butyl, etc.), preferred aryl is phenyl or biphenyl, and preferred heteroaryl is triazinyl, carbazolyl (2-carbazolyl, 3-carbazolyl, 9-carbazolyl, etc.), pyrimidinyl, pyridinyl, dibenzofuranyl, or dibenzothienyl. Specific examples include phenyl, biphenyl, diphenyltriazinyl, carbazolyltriazinyl, monophenylpyrimidinyl, diphenylpyrimidinyl, carbazolyltriazinyl, pyridinyl, dibenzofuranyl, and dibenzothienyl.

[0416] Y 1 Each of these is independently =C(-R)- or =N-, and at least one of them is =N-. 1 ~Y 6 Either of these can be =N-. Preferably, Y 1 and Y 6 ga = N-(a ring is a pyrimidine ring), Y 1 or Y 6 ga = N-(a ring is a pyridine ring), Y 2 and Y5 ga = N-(b-ring and c-ring are pyridine rings), Y 3 and Y 4 ga = N-(b-ring and c-ring are pyridine rings), Y 2 ~Y 5 ga = N-(b-ring and c-ring are pyrimidine rings), Y 1 , Y 3 , Y 4 and Y 6 ga = N - (a ring is a pyrimidine ring, b ring and c ring are pyridine rings), Y 1 , Y 2 , Y 5 and Y 6 ga = N - (a ring is a pyrimidine ring, b ring and c ring are pyridine rings), Y 1 ~Y 6 ga = N - (a, b, and c rings are pyrimidine rings), Y 2 or Y 5 The formula is N-(where the b-ring or c-ring is a pyridine ring).

[0417] In addition to the above arrangement relationships of =N-, X 1 and X 2 It is preferable that >O, and that the polycyclic aromatic compound contains a substructure represented by any of the following formulas. [ka]

[0418] In particular, polycyclic aromatic compounds containing the substructure represented by formula (EH-1b-N1) have a higher E ratio compared to structures without N. S1 , high E T1 , small ΔE S1T1 It holds. Specific examples of polycyclic aromatic compounds represented by formula (EH-1b) are shown below.

[0419] [ka]

[0420] [ka]

[0421] [ka]

[0422] [ka]

[0423] [ka]

[0424] [ka]

[0425] Of the above, EH-1-1 to EH-1-4, EH-1-10, EH-1-21 to EH-1-25, EH-1-32, EH-1-33, EH-1-51 to EH-1-59, EH-1-61, EH-1-66, EH-1-68, EH-1-71, EH-1-72, EH-1-90, EH-1-94 to EH-1-99, EH-1-100, EH-1-101, EH-1-104, EH-1-115, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127 to EH-1-130 are preferred.

[0426] [Combination of hole-transporting host material and electron-transporting host material] The combination of hole-transporting host material and electron-transporting host material results in the HOMO, LUMO, and lowest excited triplet energy levels (E) of the hole-transporting host material, electron-transporting host material, and dopant material. T1 ) is selected by. With respect to HOMO and LUMO, a combination is selected in which the HOMO(HH) of the hole-transporting host material is shallower than the HOMO(EH) of the electron-transporting host material, and the LUMO(EH) of the electron-transporting host material is deeper than the LUMO(HH) of the hole-transporting host material. More specifically, a combination in which HOMO(HH) is 0.10 eV or more shallower than HOMO(EH) and LUMO(HH) is 0.10 eV or more deeper than HOMO(EH) is preferred, a combination in which HOMO(HH) is 0.20 eV or more shallower than HOMO(EH) and LUMO(HH) is 0.20 eV or more deeper than HOMO(EH) is more preferred, and a combination in which HOMO(HH) is 0.25 eV or more shallower than HOMO(EH) and LUMO(HH) is 0.25 eV or more deeper than HOMO(EH) is even more preferred.

[0427] The hole-transporting host material and the electron-transporting host material may be in combinations that form an aggregate called an exciplex. It is generally known that exciplexes are easily formed between a material with a relatively deep LUMO level and a material with a shallow HOMO level. The interaction between the hole-transporting host material and the electron-transporting host material, specifically whether or not an exciplex is formed, can be determined by forming a monolayer film consisting only of the hole-transporting host material and the electron-transporting host material under the same conditions as for forming the emissive layer, measuring the emission spectrum (fluorescence, phosphorescence spectrum), and comparing the obtained emission spectrum with the emission spectra shown by the hole-transporting host material and the electron-transporting host material individually. This can be determined by whether the spectrum of the mixed film containing the hole-transporting host material and the electron-transporting host material shows an emission wavelength different from both the spectrum of the hole-transporting host material film and the spectrum of the electron-transporting host material film. Specifically, a difference of 10 nm or more in the peak wavelength of the spectra can be used as an indicator.

[0428] The following are specific examples of combinations of hole-transporting host materials and electron-transporting host materials that do not form an excyplex: HOMO, LUMO and E T1To satisfy the physical properties, in hole-transporting host materials, compounds having carbazole, dibenzofuran, dibenzothiophene, triarylamine, indolocarbazole, and benzooxazinophenoxazine as substructures are preferred, compounds having carbazole, dibenzofuran, and dibenzothiophene as substructures are more preferred, and compounds having carbazole as a substructure are even more preferred. Similarly, in electron-transporting host materials, compounds having pyridine, triazine, phosphine oxide, benzoflopyridine, and dibenzooxacillin as substructures are preferred, compounds having triazine, phosphine oxide, benzoflopyridine, and dibenzooxacillin as substructures are more preferred, and compounds having triazine are even more preferred.

[0429] More specifically, the hole-transporting host material is preferably selected from the group consisting of HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1-20 to HH-1-24, HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92 and HH-1-106 to HH-1-108, and the electron-transporting host material is preferably EH-1-1 to EH-1-4, EH It is preferable to select from the group consisting of EH-1-10, EH-1-21 to EH-1-25, EH-1-32, EH-1-33, EH-1-51 to EH-1-59, EH-1-61, EH-1-71, EH-1-72, EH-1-90, EH-1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127 to EH-1-130. Preferred combinations include compound HH-1-1 and compound EH-1-22, compound HH-1-1 and compound EH-1-23, compound HH-1-1 and compound EH-1-24, compound HH-1-2 and compound EH-1-22, compound HH-1-2 and compound EH-1-23, compound HH-1-2 and compound EH-1-24, or compound HH-1-1 and compound EH-1-128.

[0430] The following are specific examples of combinations of hole-transporting host materials and electron-transporting host materials that form an excyplex: HOMO, LUMO, and E T1 To satisfy the physical properties, in hole-transporting host materials, compounds having carbazole, triarylamine, indolocarbazole, and benzoxazinophenoxazine as substructures are preferred, compounds having triarylamine, indolocarbazole, and benzoxazinophenoxazine as substructures are more preferred, and compounds having triarylamine as a substructure are even more preferred. Similarly, in electron-transporting host materials, compounds having pyridine, triazine, phosphine oxide, and benzoflopyridine as substructures are preferred, compounds having triazine, phosphine oxide, benzoflopyridine, and dibenzoxacillin as substructures are more preferred, and compounds having phosphine oxide and triazine are even more preferred.

[0431] More specifically, the hole-transporting host material is preferably selected from the group consisting of HH-1-1, HH-1-2, HH-1-11, HH-1-12, HH-1-17, HH-1-18, HH-1-23, HH-1-24, and HH-1-115, and the electron-transporting host material is preferably EH-1-1 to EH-1-4, EH-1-21 to EH-1-25, and EH-1-5 It is preferable to select from the group consisting of 1 to EH-1-57, EH-1-59, EH-1-66, EH-1-68, EH-1-90, EH-1-94, EH-1-99, EH-1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127 to EH-1-130. Preferred combinations include compound HH-1-1 and compound EH-1-21, compound HH-1-2 and compound EH-1-21, compound HH-1-12 and compound EH-1-94, compound HH-1-12 and compound EH-1-117, compound HH-1-1 and compound EH-1-130, compound HH-1-33 and compound EH-1-117, compound HH-1-48 and compound EH-1-117, compound HH-1-49 and compound EH-1-117, or compound HH-1-115 and compound EH-1-99.

[0432] For further information on specific combinations of hole-transporting and electron-transporting host materials, please refer to: Organic Electronics 66(2019)227-24, Advanced Functional Materials 25(2015)361-366, Advanced Materials 26(2014)4730-4734, ACS Applied Materials and Interfaces 8(2016)32984-32991, ACS Applied Materials and Interfaces 2016,8,9806-9810, ACS Applied Materials and Interfaces 2016,8,32984-32991, Journal of Materials Chemistry C,2018,6,8784-8792, Angewante Chemie International Edition.2018,57,12380-12384, Advanced Functional Materials,24,2014,3970,Advanced See also the descriptions in Materials, 26, 2014, 5684, Synthetic Metals, 201, 2015, 49, and Nature Photonics, 16, 212-218 (2022).

[0433] [Bipolar host material] As the host material, a bipolar host material having structural or energetic characteristics of both a hole-transporting host material and an electron-transporting host material may be used. In the case of multiple combinations, either or both of the hole-transporting host material or the electron-transporting host material can be replaced with the bipolar host material. However, when replacing a hole-transporting host material with a bipolar host material, the bipolar host material used as the hole-transporting host material has a shallower energy than the HOMO of the electron-transporting host material, and when replacing an electron-transporting host material with a bipolar host material, the bipolar host material used as the electron-transporting host material has a deeper energy than the LUMO of the hole-transporting host material. When replacing a bipolar host material with a hole-transporting host material or an electron-transporting host material, a combination of a hole-transporting host material and a bipolar host material, or a bipolar host material and an electron-transporting host material, is preferable. Furthermore, it is preferable that the HOMO of the emitting dopant is shallower than the HOMO of the bipolar host material used as the hole-transporting host material (HH), or that the LUMO of the emitting dopant is deeper than the LUMO of the bipolar host material used as the electron-transporting host material (EH).

[0434] Furthermore, the lowest excited triplet energy level (E) of the bipolar host material T1 ) is chosen from the viewpoint of promoting the generation of TADF within the light-emitting layer without inhibiting it, and is the highest E within the light-emitting layer. T1 Emitting dopant or assisting dopant having E T1 It is preferable that it be higher than the E of the host material. Specifically, the E of the host material T1 Follow the instructions provided. The following compounds are specific examples of bipolar host materials.

[0435] [ka]

[0436] [High molecular compounds, etc.] The host materials described above can also be used as materials for the light-emitting layer as polymer compounds obtained by polymerizing reactive compounds in which reactive substituents are substituted as monomers, or as polymer crosslinks thereof, or as pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or as pendant-type polymer crosslinks thereof. In this case, the explanation for the polycyclic aromatic compound represented by formula (1) can be referenced for the reactive substituent.

[0437] <Dopant Materials> Besides the polycyclic aromatic compounds of the present invention, known compounds can be used as dopant materials, and various materials can be selected according to the desired emission color.Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene; benzoxazole derivatives; benzothiazole derivatives; benzimidazole derivatives; benzotriazole derivatives; oxazole derivatives; oxadiazole derivatives; thiazole derivatives; imidazole derivatives; thiadiazole derivatives; triazole derivatives; pyrazoline derivatives; stilbene derivatives; thiophene derivatives; and tetraphenylbutadiene. Derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (Japanese Patent Publication No. 1-245087), bisstyrylarylene derivatives (Japanese Patent Publication No. 2-247278), diazindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobenzofuran, and other isobenzofuran derivatives. Coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. Examples include conductors, fluorescein derivatives, pyrylium derivatives, carbostyryl derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, phlopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

[0438] As the dopant material, it is also preferable to use a boron-containing polycyclic aromatic compound as described in International Publication No. 2015 / 102118, International Publication No. 2020 / 162600, paragraphs 0097 to 0269 of Japanese Patent Publication No. 2021-077890, etc. The dopant materials described above can also be used as materials for the light-emitting layer as polymer compounds obtained by polymerizing reactive compounds in which reactive substituents are substituted as monomers, or as polymer crosslinks thereof, or as pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or as pendant-type polymer crosslinks thereof. In this case, the explanation for the polycyclic aromatic compound represented by formula (1) can be referenced for the reactive substituent.

[0439] <Assisting dopant (thermally activated delayed phosphor or phosphorescent material)> The light-emitting layer may also preferably contain an assisting dopant along with the emitting dopant and host material. A thermally activated delayed phosphor or phosphorescent material is preferred as the assisting dopant. The polycyclic aromatic compounds of the present invention can preferably be used as emitting dopants in TAF elements or PSF elements.

[0440] In this embodiment, known host compounds can be used, for example, compounds having at least one of a carbazole ring and a furan ring, and among these, it is preferable to use a compound in which at least one of furanyl and carbazolyl is bonded to at least one of arylene and heteroarylene. Specific examples include mCP (1,3-bis(N-carbazole-9-yl)benzene) and mCBP (3,3'-di(9H-carbazole-9-yl)-1,1'-biphenyl). In addition, TADF-active compounds may be used as host compounds. In this embodiment, it is also preferable to use a combination of a hole-transporting host material and an electron-transporting host material (for example, compounds HH-1-115 and EH-1-99) as the host.

[0441] The lowest excited triplet energy level E(1,T,Sh), determined from the short-wavelength peak shoulder of the phosphorescence spectrum of the host compound, is preferably higher than the lowest excited triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitter or assisting dopant having the highest lowest excited triplet energy level in the light-emitting layer, from the viewpoint of promoting rather than inhibiting the generation of TADF in the light-emitting layer. Specifically, 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 than E(2,T,Sh) and E(3,T,Sh). Furthermore, the lowest excited triplet energy level E of the host material is preferably 2.70 eV or higher, more preferably 2.73 eV or higher, and even more preferably 2.80 eV or higher.

[0442] [Thermally activated delayed phosphors] A "thermally activated delayed fluorescence" refers to a compound that absorbs thermal energy to undergo reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and then radiatively deactivates from that lowest excited singlet state to emit delayed fluorescence. However, "thermally activated delayed fluorescence" also includes compounds that undergo a higher-order triplet state during the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, see the paper by Monkman et al. from the University of Durham (NATURE COMMUNICATIONS, 7:13680, DOI: 10.1038 / ncomms13680), the paper by Hosokai et al. from the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3: e1603282), the paper by Sato et al. from Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-05007-7), and also from Kyoto University. Examples include a presentation by Sato et al. at an academic conference (98th Annual Meeting of the Chemical Society of Japan, presentation number: 2I4-15, "Mechanism of high-efficiency luminescence in organic electroluminescence using DABNA as a luminescent molecule," Graduate School of Engineering, Kyoto University), a review by Bui et al. (DOI: 10.3762 / bjoc.14.18), a review by Duan et al. (DOI: 10.1063 / 1.5143501), a review by Ding et al. (DOI: 10.1088 / 1674-4926 / 42 / 5 / 050201), and a review by Xie et al. (DOI: 10.1002 / adom.202002204). In this invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300K, the observation of a slow fluorescence component is used to determine that the target compound is a "thermally activated delayed phosphor." Here, a slow-fluorescent component refers to one with a fluorescence lifetime of 0.1 μsec or longer. Fluorescence lifetime can be measured, for example, using a fluorescence lifetime analyzer (Hamamatsu Photonics, C11367-01).

[0443] In a light-emitting layer further containing a "thermally activated delayed phosphor" as an assisting dopant, the polycyclic aromatic compound of the present invention can function as an emitting dopant. That is, the "thermally activated delayed phosphor" can function as an assisting dopant that assists the luminescence of the polycyclic aromatic compound of the present invention. In this specification, an organic electroluminescent device that uses a thermally activated delayed phosphor as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device). In TAF devices, a "host compound" refers to a compound whose lowest excitation singlet energy level, determined from the short-wavelength shoulder of the fluorescence spectrum peak, is higher than that of the thermally activated delayed phosphor acting as the assisting dopant, and also higher than that of the emitting dopant.

[0444] The thermally activated delayed phosphor (TADF compound) used in TAF elements is preferably a donor-acceptor type thermally activated delayed phosphor (DA-type TADF compound), which is designed to enable efficient reverse intersystem crossing by localizing the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) within the molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors.

[0445] Herein, in this specification, "electron-donating substituent" (donor) means substituents and substructures in which the HOMO is localized in a thermally activated delayed phosphor molecule, and "electron-accepting substituent" (acceptor) means substituents and substructures in which the LUMO is localized in a thermally activated delayed phosphor molecule.

[0446] Generally, thermally activated delayed phosphors using donors and acceptors have large spin-orbit coupling (SOC) and small exchange interaction between the HOMO and LUMO due to their structure, resulting in a ΔE S1T1 Because of its small size, a very fast reverse intersystem crossover rate can be obtained. By using the polycyclic aromatic compound of the present invention as an emitting dopant and a thermally activated delayed phosphor (TADF material) as an assisting dopant, it is possible to provide a device that satisfies any or all of the following: high efficiency, high color purity, and long lifetime. The thermally activated delayed phosphor is a compound whose emission spectrum overlaps at least partially with the absorption spectrum of the polycyclic aromatic compound of the present invention. The polycyclic aromatic compound and the TADF compound of the present invention may both be contained in the same layer, or they may be contained in adjacent layers or other nearby layers.

[0447] As a thermally activated delayed phosphor in a TAF element, for example, a compound in which the donor and acceptor are directly or via a spacer can be used. As the electron-donating group (donor structure) and electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazacillin.Acceptor structures include sulfonyl dibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonite, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracendione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorange carbonite, triphenyltriazine, pyrazinedicarbonite, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonite, dibenzoquinoxalinedicarbonite, bis(phenylsulfonyl)benzene, dimethylthioxanthone dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. In particular, the compounds having thermally activated delayed fluorescence in the TAF element are preferably compounds having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a substructure.

[0448] The compound used as the assisting dopant in the light-emitting layer of a TAF device is preferably a thermally activated delayed phosphor whose emission spectrum overlaps at least partially with the absorption peak of the emitting dopant. Examples of compounds that can be used as thermally activated delayed phosphors in the light-emitting layer of a TAF device are given below. However, the compounds that can be used as thermally activated delayed phosphors in a TAF device are not limited to the following example compounds.

[0449] [ka]

[0450] [ka]

[0451] [ka]

[0452] [ka]

[0453] [ka]

[0454] Furthermore, as a thermally activated delayed phosphor, a compound represented by any of the following formulas (AD1), (AD2), and (AD3) can also be used. [ka]

[0455] In the above 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 substructure and the height of the lowest excited singlet energy level and the lowest excited triplet energy level. J is a spacer structure that separates the donor substructure and the acceptor substructure, and is independently an arylene having 6 to 18 carbon atoms, and is preferably an arylene having 6 to 12 carbon atoms from the viewpoint of the magnitude of conjugation that leaches from the donor substructure and the acceptor substructure. More specifically, phenylene, methylphenylene, and dimethylphenylene are examples. Q is independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of the shallowness of the LUMO of the formed substructure and the height of the lowest excited singlet energy level and the lowest excited triplet energy level. Ar is independently hydrogen, a C6-C24 aryl, a C2-C24 heteroaryl, a C1-C12 alkyl, or a C3-C18 cycloalkyl, and is preferably hydrogen, a C6-C12 aryl, a C2-C14 heteroaryl, a C1-C4 alkyl, or a C6-C10 cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, ditert-butylcarbazolyl, benzimidazolyl, or phenylbenzimidazolyl, and even more preferably hydrogen, phenyl, or carbazolyl. m is 1 or 2. n is an integer less than or equal to (6-m), and is preferably an integer from 4 to (6-m) from the viewpoint of steric hindrance. Furthermore, at least one hydrogen atom in each of the above formulas may be substituted with a halogen or deuterium.

[0456] 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.

[0457] The compound used as the second component of the light-emitting layer in the TAF element may be a donor-acceptor type TADF compound represented by DA, in which one donor D and one acceptor A are directly bonded or bonded via a linking group. However, it is preferable to have a structure represented by the following formula (DAD1), in which multiple donor Ds are directly bonded or bonded via linking groups to one acceptor A, because this results in better characteristics of the organic electroluminescent element. (D 1 -L 1 )nA 1 (DAD1) Formula (DAD1) includes compounds represented by the following formula (DAD2). D 2 -L 2 -A 2 -L 3 -D 3 (DAD2) In equations (DAD1) and (DAD2), D 1 , D 2 and D 3 Each of these independently represents a donor group. The donor structure described above can be used as the donor group. A 1 and A 2 Each of these independently represents an acceptor group. The above acceptor structure can be used as the acceptor group. 1 , L 2 and L 3Each of these independently represents a single bond or a conjugated linkage group. The conjugated linkage group is a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene having 6 to 18 carbon atoms, and more preferably an arylene having 6 to 12 carbon atoms. 1 , L 2 and L 3 It is even more preferable that each of them is independently phenylene, methylphenylene, or dimethylphenylene. In formula (DAD1), n ​​is 2 or more, and A 1 n represents an integer less than or equal to the maximum number of substitutions possible. n can be selected, for example, from 2 to 10 or from 2 to 6. When n is 2, the compound is represented by formula (DAD2). n D 1 They may be the same or different, and n L 1 These may be the same or different. Preferred specific examples of the compounds represented by formulas (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, but the second component that can be used in the present invention is not limited to these compounds.

[0458] [ka]

[0459] [Phosphorescent materials] In the light-emitting layer, a phosphorescent material may be used as an assisting dopant. In this specification, an organic electroluminescent element that uses a phosphorescent material as an assisting dopant is sometimes referred to as a phosphorescent assist element, a phosphor-sensitized fluorescent (PSF) element, or a phosphorescent material. The phosphorescent material utilizes intramolecular spin-orbit interaction (heavy atom effect) by metal atoms to obtain light emission from an excited triplet state. For example, a luminescent metal complex can be used as such a phosphorescent material. Examples of luminescent metal complexes include compounds represented by the following formulas (B-1) and (B-2).

[0460] [ka]

[0461] In equation (B-1), M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu, n is an integer from 1 to 3, and "XY" are each independent bidentate ligands. In equation (B-2), M is at least one selected from the group consisting of Pt, Re, and Cu, and "WXYZ" is a tetradentate ligand. In formula (B-1), from the viewpoint of efficiency and lifespan, M is preferably Ir and n is preferably 3. In equation (B-2), Pt is preferred for M from the viewpoint of efficiency and lifespan. In equation (B-1), ligand (XY) has at least one ligand selected from the group consisting of the following. In equation (B-2), ligand (WXYZ) has at least one ligand selected from the group consisting of the following as part of it.

[0462] [ka]

[0463] During the ceremony, --- is bonded to the central metal M, Y is independent of 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 And, Each aromatic carbon CH in the ring may be independently substituted with N. R e and R f These may optionally condense or bond to form a ring. R a , R b , R c , and Rd Each of these can be substituted independently, either without substitution or with 1 to the maximum number of substitutions possible. R a , R b , R c , R d , R e , and R f However, each is independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or a combination thereof. However, R a , R b , R c , and R d Any two adjacent substituents in may condense or bond to form a ring or a multidentate ligand.

[0464] 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), 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.

[0465] Other compounds represented by formula (B-1) include, for example, the following compounds. [ka]

[0466] [ka]

[0467] [ka]

[0468] Alternatively, iridium complexes described in Japanese Patent Publication No. 2006-089398, Japanese Patent Publication No. 2006-080419, Japanese Patent Publication No. 2005-298483, Japanese Patent Publication No. 2005-097263, and Japanese Patent Publication No. 2004-111379, U.S. Patent Application Publication No. 2019 / 0051845, etc., or platinum complexes described in Advanced Materials, 26: 7116-7121, NPG Asia Materials 13, 53 (2021), Applied Physics Letters, 117, 253301 (2020), Light-Emitting Diode - An Outlook On the Empirical Features and Its Recent Technological Advancements, Chapter 5 may be used.

[0469] <2-1-3. Substrates in Organic Electroluminescent Devices> The substrate 101 is a support for the organic EL element 100, and is typically made of quartz, glass, metal, or plastic. The substrate 101 is formed in the form of a plate, film, or sheet depending on the purpose, and can be made of glass, metal, metal foil, plastic film, or plastic sheet, for example. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used, and the thickness only needs to be sufficient to maintain mechanical strength, for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it is better to have fewer ions eluted from the glass, but soda-lime glass with a barrier coating such as SiO2 is also commercially available and can be used. Furthermore, to enhance the gas barrier properties, the substrate 101 may be provided with a gas barrier film, such as a dense silicon oxide film, on at least one side. It is particularly preferable to provide a gas barrier film when using a synthetic resin plate, film, or sheet with low gas barrier properties as the substrate 101.

[0470] <2-1-4. Anode in an Organic Electroluminescent Device> The anode 102 plays the role of injecting holes into the light-emitting layer 105. If either the hole injection layer 103 or the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes will be injected into the light-emitting layer 105 via these layers.

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

[0472] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light, but from the viewpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, an ITO substrate with a resistance of 300 Ω / □ or less will function as an element electrode, but since substrates of about 10 Ω / □ are now available, it is particularly desirable to use a low-resistance product of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

[0473] <2-1-5. Hole injection layer and hole transport layer in organic electroluminescent devices> The hole injection layer 103 plays the role of efficiently injecting holes moving from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays the role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of hole injection / transport materials and a polymer binder. Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0474] For hole-injecting and transporting materials, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes under an applied electric field. Therefore, it is desirable to have high hole injection efficiency and efficient transport of the injected holes. To achieve this, it is preferable to have a low ionization potential, high hole mobility, excellent stability, and a material that does not easily generate trapping impurities during manufacturing and use.

[0475] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from among compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (4,4',4”-tris(N-carbazol)triphenylamine, polymers having aromatic tertiary amino acids in 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-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’Triphenylamine derivatives such as -tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc., stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Examples include conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrine), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymer systems, polycarbonates, styrene derivatives, polyvinylcarbazoles, and polysilanes having the monomers in their side chains are preferred, but the compound is not particularly limited as long as it can form a thin film necessary for fabricating a light-emitting device, allow holes to be injected from the anode, and transport holes.

[0476] Furthermore, the conductivity of organic semiconductors is known to be strongly influenced by doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, "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 an electron transfer process in the electron-donating base material (hole transporter). The conductivity of the base material changes considerably depending on the number and mobility of holes. Examples of matrix materials having hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (Japanese Patent Publication No. 2005-167175). The polycyclic aromatic compounds of the present invention may be used as materials for forming hole injection layers or hole transport layers.

[0477] <2-1-6. Electron blocking layer in organic electroluminescent devices> An electron blocking layer may be provided between the hole injection / transport layer and the light-emitting layer to prevent the diffusion of electrons from the light-emitting layer. For forming the electron blocking layer, any compound represented by one of the above formulas (H1), (H2), and (H3) can be used. The polycyclic aromatic compounds of the present invention may also be used as materials for forming electron blocking layers.

[0478] <2-1-7. Electron injection layer and electron transport layer in organic electroluminescent devices> The electron injection layer 107 plays the role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays the role of efficiently transporting 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 each formed by laminating and mixing one or more types of electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0479] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them. It is desirable for this layer to have high electron injection efficiency and to efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and to be a material that does not easily generate trapping impurities during manufacturing and use. However, when considering the balance between hole and electron transport, if the main role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, then even if the electron transport capacity is not very high, the effect of improving luminescence efficiency will be equivalent to that of a material with high electron transport capacity. Therefore, the electron injection and transport layer in this embodiment may also include the function of a layer that can efficiently prevent the movement of holes.

[0480] The material used to form the electron transport layer 106 or electron injection layer 107 (electron transport material) can be arbitrarily selected from compounds conventionally used as electron transfer compounds in photoconductive materials, and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0481] The materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their fused ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, examples include fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used individually or in combination with different materials.

[0482] Furthermore, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, and benzoquinone derivatives. Examples include phosphorus derivatives (such as 2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazole-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(2,2':6',2”-terpyridine-4'-yl)benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridine-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0483] Furthermore, metal complexes containing electron-accepting nitrogen can also be used, such as quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0484] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0485] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0486] The polycyclic aromatic compounds of the present invention may be used as materials for forming electron injection layers or electron transport layers.

[0487] The electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. This reducing substance can be any substance having a certain reducing property; for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0488] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), or Ba (2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Of these, alkali metals K, Rb, or Cs are more preferred reducing substances, Rb or Cs are even more preferred, and Cs is the most preferred. These alkali metals have particularly high reducing ability, and their addition in relatively small amounts to materials forming electron transport layers or electron injection layers can improve the luminescence brightness and extend the lifespan of organic EL devices. Furthermore, combinations of two or more alkali metals are also preferred as reducing substances with a work function of 2.9 eV or less, and combinations including Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs, Na, and K, are particularly preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or electron injection layer, improvements in luminescence brightness and extended lifespan can be achieved in organic EL devices.

[0489] <2-1-8. Cathode in Organic Electroluminescent Devices> The cathode 108 plays the role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0490] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum), are preferred. To increase electron injection efficiency and improve device characteristics, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, a method is known in which the organic layer is doped with trace amounts of lithium, cesium, or magnesium to use electrodes with high stability. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0491] Furthermore, for electrode protection, it is preferable to laminate metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. The method for fabricating these electrodes is not particularly limited as long as conductivity can be achieved, such as resistance heating, electron beam deposition, sputtering, ion plating, and coating.

[0492] <2-1-9. Binding agents that may be used in each layer> The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer described above can form each layer individually, but they can also be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethylcellulose, vinyl acetate resins, ABS resins, and polyurethane resins, or in curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins as polymer binders.

[0493] <2-1-10. Method for fabricating organic electroluminescent devices> Each layer constituting an organic EL element can be formed by thinning the material to be composed of each layer using methods such as vapor deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, spin coating or casting, or coating. There are no particular limitations on the thickness of each layer formed in this way, and it can be set appropriately according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The thickness can usually be measured with a quartz crystal oscillating film thickness measuring device. When thinning using vapor deposition, the deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Generally, the deposition conditions are a boat heating temperature of +50 to +400°C and a vacuum of 10°C. -6 ~10 -3 It is preferable to appropriately set the Pa, deposition rate to 0.01 to 50 nm / second, substrate temperature to -150 to +300°C, and film thickness to 2 nm to 5 μm.

[0494] When applying a DC voltage to the organic EL element obtained in this way, the voltage should be applied with the anode as + and the cathode as -. When a voltage of approximately 2 to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, this organic EL element will also emit light when a pulsed current or alternating current is applied. The waveform of the applied AC current can be arbitrary.

[0495] Next, as an example of a method for fabricating an organic EL device, we will describe a method for fabricating an organic EL device consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode.

[0496] <Vapor deposition method> An anode is fabricated by forming a thin film of anode material on a suitable substrate using a vapor deposition method, and then thin films of a hole injection layer and a hole transport layer are formed on this anode. A host material and a dopant material are co-deposited on this to form a thin film that serves as the light-emitting layer, and then an electron transport layer and an electron injection layer are formed on this light-emitting layer. Finally, a thin film made of cathode material is formed using a vapor deposition method to form the cathode, thereby obtaining the desired organic EL element. In addition, in the fabrication of the organic EL element described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order.

[0497] <Wet film formation method> The wet film deposition method is carried out by preparing a liquid organic layer-forming composition containing low-molecular-weight compounds capable of forming each organic layer of an organic EL device. If a suitable organic solvent for dissolving these low-molecular-weight compounds is not available, the organic layer-forming composition may be prepared from polymer compounds obtained by polymerizing the low-molecular-weight compounds with other monomers or main-chain polymers that have solubility properties, by substituting reactive substituents on the low-molecular-weight compounds.

[0498] Wet film formation generally involves a coating step of applying an organic layer-forming composition to a substrate and a drying step of removing the solvent from the applied organic layer-forming composition to form a coating film. If the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), this drying step further crosslinks it to form a polymer crosslinked body. Depending on the coating step, methods using a spin coater are called spin coating, methods using a slit coater are called slit coating, methods using a plate are called gravure, offset, reverse offset, and flexographic printing, methods using an inkjet printer are called inkjet printing, and methods spraying in a mist are called spraying. Drying methods include air drying, heating, and vacuum drying. The drying step may be performed only once, or multiple times using different methods and conditions. In addition, different methods may be used in combination, such as firing under reduced pressure.

[0499] Wet deposition is a method of forming thin films using a solution, such as certain printing methods (inkjet printing), spin coating or casting, and coating methods. Unlike vacuum deposition, wet deposition does not require expensive vacuum deposition equipment and can be performed under atmospheric pressure. In addition, wet deposition allows for large-area deposition and continuous production, leading to reduced manufacturing costs.

[0500] On the other hand, compared to vacuum deposition, wet deposition can be difficult for layering. When fabricating layered films using wet deposition, it is necessary to prevent the upper layer's composition from dissolving the lower layer, and techniques such as controlled solubility of the composition, crosslinking of the lower layer, and orthogonal solvents (solvents that do not mix with each other) are employed. However, even with these techniques, it can be difficult to use wet deposition for coating all films.

[0501] Therefore, a common approach is to fabricate organic EL elements using a wet deposition method for only a few layers, and a vacuum deposition method for the rest.

[0502] For example, the procedure for fabricating an organic EL element by partially applying a wet film deposition method is shown below. (Step 1) Film deposition by vacuum deposition of the anode (Step 2) Wet deposition of a hole injection layer-forming composition containing hole injection layer material. (Step 3) Wet deposition of a hole transport layer forming composition containing a hole transport layer material. (Step 4) Wet deposition of a light-emitting layer-forming composition containing a host material and a dopant material. (Step 5) Deposition of electron transport layer by vacuum deposition (Step 6) Deposition of electron injection layer by vacuum deposition (Step 7) Deposition of film by vacuum deposition of cathode By following this procedure, an organic EL element is obtained consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode. Of course, the electron transport layer and electron injection layer may also be formed by a wet deposition method using a layer-forming composition containing the electron transport layer material and the electron injection layer material, respectively. In this case, it is preferable to use means to prevent the dissolution of the lower light-emitting layer, or to deposit the film from the cathode side, in the opposite direction to the procedure described above.

[0503] <Other film formation methods> Laser heating and deposition (LITI) can be used to form organic layer-forming compositions. LITI is a method of heating and depositing a compound attached to a substrate using a laser, and organic layer-forming compositions can be used as the material coated onto the substrate.

[0504] <Optional steps> Appropriate processing steps, cleaning steps, and drying steps may be appropriately inserted before and after each film formation step. Examples of processing steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for creating a bank may also be included.

[0505] Photolithography can be used to create the resist bank. Positive and negative resist materials can be used as the resist bank material for photolithography. Patternable printing methods such as inkjet, gravure offset printing, reverse offset printing, and screen printing can also be used. Permanent resist materials can also be used in these cases.

[0506] Materials used in the bank include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of ethylenic monomers having hydroxyls, biopolymers, polyacryloyl compounds, polyesters, polystyrene, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetates, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

[0507] <Compositions for forming organic layers used in wet film deposition methods> The organic layer-forming composition is obtained by dissolving a low-molecular-weight compound capable of forming each organic layer of an organic EL element, or a high-molecular-weight compound obtained by polymerizing the low-molecular-weight compound, in an organic solvent. For example, the light-emitting layer-forming composition contains, as a first component, at least one polycyclic aromatic compound (or its high-molecular-weight compound) which is a dopant material, as a second component, at least one host material, and as a third component, at least one organic solvent. The first component functions as a dopant component of the light-emitting layer obtained from the composition, and the second component functions as a host component of the light-emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and during application, the controlled evaporation rate of the third component itself provides a smooth and uniform surface shape.

[0508] <organic solvents> The organic layer-forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, the film-forming properties, the presence or absence of defects in the coating film, surface roughness, and smoothness can be controlled and improved. Furthermore, when forming films using an inkjet method, the meniscus stability at the pinholes of the inkjet head can be controlled, thereby controlling and improving ejection performance. In addition, by controlling the drying rate of the film and the orientation of derivative molecules, the electrical properties, luminescence properties, efficiency, and lifespan of an organic EL element having an organic layer obtained from the organic layer-forming composition can be improved.

[0509] (1) Physical properties of organic solvents The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. A boiling point higher than 130°C is preferable from the viewpoint of inkjet ejection performance. A boiling point lower than 300°C is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoint of good inkjet ejection performance, film formation, smoothness, and low residual solvent, a composition containing two or more organic solvents is more preferable. On the other hand, depending on the circumstances, the composition may be in a solid state by removing the solvent from the organic layer-forming composition, taking into consideration transportability, etc.

[0510] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) GS ) is the boiling point (BP) of a poor solvent (PS) PS A configuration that is lower than ) is particularly preferable. By adding a high-boiling-point poor solvent, the low-boiling-point good solvent volatilizes first during film formation, increasing the concentration of the constituents in the composition and the concentration of the poor solvent, thus promoting rapid film formation. As a result, a coating film with fewer defects, low surface roughness, and high smoothness can be obtained.

[0511] Difference in solubility (S GS -S PS The difference in boiling points (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS The temperature is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0512] The organic solvent is removed from the coating film after film formation by drying processes such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to heat at a temperature of at least one solute's glass transition temperature (Tg) + 30°C or lower from the viewpoint of improving coating film formation. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at a temperature of at least one solute's glass transition temperature (Tg) - 30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. In addition, drying may be performed multiple times at different temperatures, or multiple drying methods may be used in combination.

[0513] (2) Specific examples of organic solvents Organic solvents used in compositions for forming organic layers include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decane-2-ol, dodecane-2-ol, and cyclohexanol. Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzo trifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenethole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1- Examples of solvents include, but are not limited to, thylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-vitrill, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, and benzyloctyl ether. Furthermore, the solvent may be used individually or in mixtures.

[0514] <Optional ingredients> The organic layer-forming composition may contain optional components as long as they do not impair its properties. Examples of optional components include binders and surfactants.

[0515] (1) Binder The organic layer-forming composition may contain a binder. The binder forms a film during film formation and also bonds the resulting film to the substrate. It also plays a role in dissolving, dispersing, and binding other components within the organic layer-forming composition.

[0516] Examples of binders used in organic layer-forming compositions include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0517] The binder used in the organic layer-forming composition may be a single type or a mixture of multiple types.

[0518] (2) Surfactants The organic layer-forming composition may contain surfactants, for example, to control the uniformity of the film surface, the hydrophilicity and liquid repellency of the film surface. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic groups, and further classified into alkyl, silicone, and fluorine based on the structure of their hydrophobic groups. They are also classified into monomolecular systems with relatively small molecular weights and simple structures, and polymeric systems with large molecular weights and side chains or branching, based on their molecular structure. Furthermore, they are classified into single systems and mixed systems containing two or more surfactants and a substrate, based on their composition. All types of surfactants can be used in the organic layer-forming composition.

[0519] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (product name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, and BYK. 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (product name, manufactured by Big Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (product name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (product name, manufactured by Seimi Chemical Co., Ltd.), Futergent 222F, Futergent 251, FTX-218 (product name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerin tetrakis(fluoroalkyl polyoxyethylene ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene noni Examples include tetraphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonate, and alkyldiphenyl ether disulfonate.

[0520] Furthermore, a single surfactant may be used, or two or more may be used in combination.

[0521] <Composition and physical properties of organic layer-forming compositions> The content of each component in the organic layer-forming composition is determined considering the good solubility, storage stability, and film-forming properties of each component in the organic layer-forming composition, as well as the good film quality of the coating obtained from the organic layer-forming composition, good ejection properties when using an inkjet method, and good electrical properties, luminescence properties, efficiency, and lifespan of the organic EL element having an organic layer made using the composition. For example, in the case of a light-emitting layer-forming composition, it is preferable that the first component is present in an amount of 0.0001% to 2.0% by mass of the total mass of the light-emitting layer-forming composition, the second component in an amount of 0.0999% to 8.0% by mass of the total mass of the light-emitting layer-forming composition, and the third component in an amount of 90.0% to 99.9% by mass of the total mass of the light-emitting layer-forming composition.

[0522] More preferably, the first component is present in an amount of 0.005% to 1.0% by mass relative to the total mass of the light-emitting layer forming composition, the second component in an amount of 0.095% to 4.0% by mass relative to the total mass of the light-emitting layer forming composition, and the third component in an amount of 95.0% to 99.9% by mass relative to the total mass of the light-emitting layer forming composition. Even more preferably, the first component is present in an amount of 0.05% to 0.5% by mass relative to the total mass of the light-emitting layer forming composition, the second component in an amount of 0.25% to 2.5% by mass relative to the total mass of the light-emitting layer forming composition, and the third component in an amount of 97.0% to 99.7% by mass relative to the total mass of the light-emitting layer forming composition.

[0523] The organic layer-forming composition can be produced by appropriately selecting and performing stirring, mixing, heating, cooling, dissolving, dispersion, etc., on the above-mentioned components using known methods. Furthermore, after preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement / sealing treatment may be performed as appropriate.

[0524] Regarding the viscosity of the organic layer-forming composition, a higher viscosity results in better film formation and good ejection when using an inkjet method. On the other hand, a lower viscosity makes it easier to form thin films. For this reason, the viscosity of the organic layer-forming composition is preferably 0.3 to 3 mPa·s at 25°C, and more preferably 1 to 3 mPa·s. In this invention, viscosity is a value measured using a cone-plate type rotational viscometer.

[0525] A lower surface tension in the organic layer-forming composition results in better film formation and a defect-free coating. On the other hand, a higher surface tension results in better inkjet ejection performance. For this reason, the organic layer-forming composition preferably has a surface tension of 20 to 40 mN / m at 25°C, and more preferably 20 to 30 mN / m. In this invention, the surface tension is a value measured using the suspension drop method.

[0526] <Cross-linkable polymer compounds: Compounds represented by formula (XLP-1)> Next, we will explain the case where the above-mentioned polymer compound has a crosslinkable substituent. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1). [ka] In equation (XLP-1), Each MU is a divalent group, independently represented by removing any two hydrogen atoms from an aromatic compound, and each EC is a monovalent group, independently represented by removing any one hydrogen atom from an aromatic compound, where two hydrogens in MU are substituted with EC or MU, and k is an integer between 2 and 50000. However, the compound represented by formula (XLP-1) has at least one crosslinking substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having the crosslinking substituent is 0.1 to 80% by mass of the molecule.

[0527] More specifically, MU is independently allylene, heteroarylene, dialylenearylamino, dialylenearylboryl, oxavorin-diyl, and azavorin-diyl. Each EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy. At least one hydrogen in MU and EC may further be substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl groups. k is an integer between 2 and 50000. k is preferably an integer between 20 and 50000, and more preferably an integer between 100 and 50000.

[0528] At least one hydrogen atom in MU and EC in formula (XLP-1) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen, or deuterium. Furthermore, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-. Any -CH2- in the alkyl group, except for the -CH2- directly connected to EC in formula (XLP-1), may be substituted with an arylene group having 6 to 24 carbon atoms. Any hydrogen atom in the alkyl group may be substituted with fluorine.

[0529] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds. [ka]

[0530] More specifically, divalent groups represented by one of the following structures are included. In these, MU binds to another MU or EC at *.

[0531] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0532] Furthermore, ECx can be a monovalent group represented by one of the following structures, for example. In these structures, EC binds to MU at *.

[0533] [ka] [ka]

[0534] From the viewpoint of solubility and coating film-forming properties, the compound represented by formula (XLP-1) preferably has 10 to 100% of the total number of MU (k) in the molecule being alkyl groups with 1 to 24 carbon atoms, more preferably has 30 to 100% of the total number of MU (k) in the molecule being alkyl groups with 1 to 18 carbon atoms (branched alkyl groups with 3 to 18 carbon atoms), and even more preferably has 50 to 100% of the total number of MU (k) in the molecule being alkyl groups with 1 to 12 carbon atoms (branched alkyl groups with 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MU (k) in the molecule be alkyl groups with 7 to 24 carbon atoms, and more preferably has 30 to 100% of the total number of MU (k) in the molecule being alkyl groups with 7 to 24 carbon atoms (branched alkyl groups with 7 to 24 carbon atoms).

[0535] The content of monovalent or divalent aromatic compounds having crosslinkable substituents is preferably 0.5 to 50% by mass, and more preferably 1 to 20% by mass.

[0536] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the polymer compound described above, but substituents with the following structures are preferred. The asterisk (*) in each structural formula indicates the bond position. [ka]

[0537] L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, a C1-C12 alkylene, a C1-C12 oxyalkylene, and a C1-C12 polyoxyalkylene. Among the above substituents, groups represented by formula (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17) are preferred, and groups represented by formula (XLS-1), (XLS-3), or (XLS-17) are more preferred.

[0538] Examples of divalent aromatic compounds having crosslinkable substituents include compounds having the following substructure. * in the following structural formulas indicates a bond position. [ka] [ka] [ka] [ka]

[0539] <Method for producing polymer compounds and crosslinked polymer compounds> Methods for producing polymer compounds and crosslinkable polymer compounds will be explained using the compound represented by the above formula (XLP-1) as an example. These compounds can be synthesized by appropriately combining known production methods.

[0540] Solvents used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, and ether-based solvents, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

[0541] The reaction may also be carried out in a two-phase system. If the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as needed.

[0542] The compound represented by formula (XLP-1) may be produced in a single step or in multiple steps. Furthermore, it may be produced by a batch polymerization method, where all the raw materials are placed in the reaction vessel before the reaction begins; by a dropwise polymerization method, where the raw materials are added dropwise to the reaction vessel; or by a precipitation polymerization method, where the product precipitates as the reaction progresses. These methods can be combined as appropriate. For example, when synthesizing the compound represented by formula (XLP-1) in a single step, the target product is obtained by adding monomers with polymerizable groups attached to monomer units (MU) and monomers with polymerizable groups attached to end-cap units (EC) to the reaction vessel and carrying out the reaction. Alternatively, when synthesizing the compound represented by formula (XLP-1) in multiple steps, the target product is obtained by polymerizing monomers with polymerizable groups attached to monomer units (MU) to the desired molecular weight, and then adding monomers with polymerizable groups attached to end-cap units (EC) and reacting them. By adding monomers with polymerizable groups attached to different types of monomer units (MU) in multiple steps and carrying out the reaction, a polymer with a concentration gradient in the monomer unit structure can be produced. Furthermore, after preparing a precursor polymer, the target polymer can be obtained by a subsequent reaction.

[0543] Furthermore, the primary structure of the polymer can be controlled by selecting the polymerizable groups of the monomer unit (MU). For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize polymers with random primary structures (synthesis scheme 1), polymers with regular primary structures (synthesis schemes 2 and 3), etc., which can be used in appropriate combinations depending on the target product. Moreover, by using monomers having three or more polymerizable groups, hyperbranched polymers and dendrimers can be synthesized. [ka]

[0544] Monomers that can be used in the present invention can be synthesized according to the methods described in Japanese Patent Publication No. 2010-189630, International Publication No. 2012 / 086671, International Publication No. 2013 / 191088, International Publication No. 2002 / 045184, International Publication No. 2011 / 049241, International Publication No. 2013 / 146806, International Publication No. 2005 / 049546, International Publication No. 2015 / 145871, Japanese Patent Publication No. 2010-215886, Japanese Patent Publication No. 2008-106241, International Publication No. 2016 / 031639, and Japanese Patent Publication No. 2011-174062.

[0545] Furthermore, for specific polymer synthesis procedures, refer to the methods described in Japanese Patent Publication No. 2012-036388, International Publication No. 2015 / 008851, Japanese Patent Publication No. 2012-36381, Japanese Patent Publication No. 2012-144722, International Publication No. 2015 / 194448, International Publication No. 2013 / 146806, International Publication No. 2015 / 145871, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, and International Publication No. 2011 / 049241.

[0546] <2-1-11. Application Examples of Organic Electroluminescent Devices> Organic EL elements can also be applied to display devices or lighting equipment. A display device or lighting device equipped with an organic EL element can be manufactured by known methods, such as connecting the organic EL element to a known driving device, and can be driven using known driving methods such as DC driving, pulse driving, or AC driving as appropriate.

[0547] 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 Publication No. 10-335066, Japanese Patent Publication No. 2003-321546, and Japanese Patent Publication No. 2004-281086). Examples of display methods include either matrix or segment displays. Matrix and segment displays may coexist on the same panel.

[0548] In a matrix display, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and characters or images are displayed using a collection of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on personal computers, monitors, and televisions, square pixels with sides of 300 μm or less are usually used, while for large displays such as display panels, pixels with sides on the order of millimeters are used. For monochrome displays, pixels of the same color can be arranged, but for color displays, red, green, and blue pixels are arranged side by side. In this case, there are typically delta type and stripe type displays. The matrix can be driven by either a line-sequential drive method or an active matrix. Line-sequential drive has the advantage of a simpler structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is necessary to choose the appropriate method depending on the application.

[0549] In segment-based displays, a pattern is formed to display predetermined information, and a designated area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cooktops, and panel displays in automobiles.

[0550] Examples of lighting devices include lighting devices such as indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, and Japanese Patent Publication No. 2004-119211). Backlights are mainly used to improve the visibility of non-self-illuminating display devices and are used in liquid crystal displays, clocks, audio equipment, automobile panels, display boards, and signs. In particular, for liquid crystal displays, especially backlights for personal computers where miniaturization is a challenge, conventional methods using fluorescent lamps or light guide plates make miniaturization difficult. Therefore, backlights using organic EL elements are characterized by their thinness and light weight.

[0551] <2-2. Other Organic Devices> The polycyclic aromatic compounds according to the present invention can be used not only for the organic field-light-emitting device described above, but also for the fabrication of organic field-effect transistors, organic thin-film solar cells, or organic photodiodes (organic photodetectors).

[0552] An organic field-effect transistor (OCT) is a type of transistor that controls current using an electric field generated by a voltage input. In addition to source and drain electrodes, it has a gate electrode. When a voltage is applied to the gate electrode, an electric field is generated, allowing the current to be controlled by arbitrarily blocking the flow of electrons (or holes) between the source and drain electrodes. Compared to simple transistors (bipolar transistors), OTCs are easier to miniaturize and are frequently used as components in integrated circuits.

[0553] The structure of an organic field-effect transistor typically includes a source electrode and a drain electrode in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode further separated by an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following: (1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode (3) Substrate / Organic semiconductor active layer / Source electrode / Drain electrode / Insulator layer / Gate electrode (4) Substrate / Source electrode / Drain electrode / Organic semiconductor active layer / Insulator layer / Gate electrode Organic field-effect transistors configured in this way can be applied as pixel driving switching elements in active-matrix driven liquid crystal displays and organic electroluminescent displays.

[0554] Organic thin-film solar cells have a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode 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 compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer, depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in organic thin-film solar cells. In addition to the above, organic thin-film solar cells may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. Organic thin-film solar cells can be appropriately selected and combined with known materials used in organic thin-film solar cells.

[0555] An organic photodiode is a mechanism that uses organic materials to convert light into electrical signals, and is used, for example, as an organic photodetector or organic photodetector. An organic photodiode has a sandwich structure in which an organic layer containing a light absorber is sandwiched between electrodes as an active layer.

[0556] The polycyclic aromatic compounds of the present invention can be used to form the active layer of an organic photodiode. Generally, the active layer contains a donor compound (electron-donating compound) and an acceptor compound (electron-accepting compound). After light is absorbed by the active layer, an excited state moves to the interface of the donor-acceptor compound, inducing charge separation. Subsequently, the generated holes and electrons are collected at their respective electrodes, generating an electric current. On the other hand, the polycyclic aromatic compounds of the present invention that exhibit multiple resonance effects can form an active layer as a single component as a light absorber (Adv. Mater. 2024, 2414465). That is, the active layer can be formed solely from the polycyclic aromatic compounds of the present invention.

[0557] Furthermore, the polycyclic aromatic compounds of the present invention can also be used as donor compounds or acceptor compounds in the active layer by selecting substituents. In this case, the acceptor or donor compound to be combined may be a polymer material, an ionic compound, a metal complex, or an inorganic material, and in the case of a polymer material, a crosslinking agent may be added.

[0558] Examples of donor compounds to be combined with the polycyclic aromatic compound of the present invention include tetrathianaphthalene, and examples of polymer materials include F8BT (poly(9,9-di-n-octylfluorenyl-2,7-diyl)-co-1,4-benzo-(2,1,3)-thiadiazole) and PFO (poly(9,9-din-octylfluorene)). Inorganic materials can include alkali metals, alkaline earth metals, rare earth metals, or metals belonging to Group 13 of the periodic table, as well as their oxides and carbonates, such as lithium, cesium, magnesium, calcium, indium, ytterbium, lithium oxide, and cesium carbonate.

[0559] Examples of acceptor compounds to be combined with the polycyclic aromatic compound of the present invention include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (F4-TCNQ) and tetrachloro-1,4-benzoquinone (chloranil). In addition, inorganic materials such as molybdenum oxide, tin oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide can be used.

[0560] When the active layer contains both donor and acceptor compounds, methods such as dissolving and mixing them together (bulk heterojunction) or joining them in a planar manner (parallel heterojunction) are used, and the method is selected considering the properties of the compounds used. It is also possible to mix materials that act as quantum dots to form a nanocomposite active layer (Adv. Mater. 2016, 28, 2043-2048).

[0561] An organic photodiode may have a hole-blocking layer and an electron-blocking layer in addition to a pair of electrodes and an active layer placed between the pair of electrodes. Typically, a hole-blocking layer and an electron-blocking layer are provided above and below the active layer in contact with it, and an anode electrode and a cathode electrode may be provided further. Examples of such structures include the following. Depending on the characteristics of the active layer, the hole-blocking layer or electron-blocking layer may be omitted, and a layer that functions as an electron transport layer or hole transport layer may be added. (1) Substrate / Anode electrode / Electron blocking layer / Active layer / Hole blocking layer / Cathode electrode (2) Substrate / Cathode electrode / Hole blocking layer / Active layer / Electron blocking layer / Anode electrode

[0562] Inorganic materials or polymeric materials may be used for the electron blocking layer and hole blocking layer. Examples of polymeric materials include PEDOT / PSS (Poly3,4-EthyleneDiOxyThiophene / Poly4-StyreneSulfonate).

[0563] For organic photodiodes, in addition to the above, you can also refer to Adv. Mater. 2016, 28, 4766, Adv. Opt. Mater. 2024, 12, 2303216, Adv. Mater. 2016, 28, 2043, Nat.Commun. 2020, 11, 2871, Nano Lett. 2017, 17, 1995, Adv. Mater. 2017, 29, 1702184, Chem. Mater. 2021, 33, 5147, etc.

[0564] <3. Wavelength conversion materials> The polycyclic aromatic compounds of the present invention can be used as wavelength conversion materials. Currently, there is much research into applying multi-color technology using color conversion methods to liquid crystal displays, organic EL displays, and lighting. Color conversion refers to the conversion of light emitted from a light source to longer wavelength light, for example, converting ultraviolet light or blue light into green light or red light. By creating a film of a wavelength conversion material with this color conversion function and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, i.e., to extract white light. By using such a white light source, which combines 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 drive unit and a color filter, it becomes possible to manufacture a full-color display. Furthermore, if the liquid crystal drive unit is not required, it can be used as a white light source as is, and can be applied as a white light source for LED lighting, for example. In addition, 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, it becomes possible to manufacture a full-color organic EL display without using a metal mask. Furthermore, by using a blue microLED as a light source in combination with a wavelength conversion film that converts blue light into green and red light, it becomes possible to create low-cost full-color microLED displays.

[0565] The polycyclic aromatic compounds of the present invention can be used as wavelength conversion materials. Using a wavelength conversion material containing the polycyclic aromatic compounds of the present invention, light from light sources and light-emitting elements that generate ultraviolet light or shorter wavelength blue light can be converted into blue or green light with high color purity suitable for use in display devices (display devices using organic EL elements or liquid crystal displays). The color to be converted can be adjusted by appropriately selecting substituents on the polycyclic aromatic compounds of the present invention, binder resins used in the wavelength conversion composition described later, etc. The wavelength conversion material can be prepared as a wavelength conversion composition containing the polycyclic aromatic compounds of the present invention. Alternatively, a wavelength conversion film may be formed using this wavelength conversion composition.

[0566] The wavelength conversion composition may contain, in addition to the polycyclic aromatic compound of the present invention, a binder resin, other additives, and a solvent. As the binder resin, for example, those described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283 can be used. As the other additive, compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283 can be used. As the solvent, refer to the description of solvents included in the above-mentioned light-emitting layer forming composition.

[0567] The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. Known film formation methods can be used as a method for producing the wavelength conversion layer from the wavelength conversion composition. The wavelength conversion film may consist solely of a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, or it may include other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light to green or red light, or a wavelength conversion layer that converts blue or green light to red light). Furthermore, the wavelength conversion film may include a substrate layer and a barrier layer to prevent degradation of the color conversion layer due to oxygen, moisture, or heat. [Examples]

[0568] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0569] <<Example of synthesis>> Synthesis Example (1): Synthesis of Compound (1-1) [ka]

[0570] [First step] Compound (S-1) (391 mg, 0.51 mmol) was dissolved in 1,2-dichlorobenzene (5.0 mL), and boron triiodide (776 mg, 2.0 mmol) was added at 0°C. The mixture was stirred at 80°C for 2 hours. Then, the temperature was raised to 150°C and the mixture was stirred for 19 hours. After cooling to room temperature, phosphate buffer solution (pH=6.8, 10 mL) and saturated sodium thiosulfate aqueous solution (10 mL) were added to the reaction mixture to stop the reaction. The mixture was then extracted with dichloromethane (20 mL, 3 times), and the organic layer was dried over anhydrous sodium sulfate. Next, the solvent was removed by distillation, and toluene (10 mL) and acetic acid (10 mL) were added. The mixture was stirred at 80°C for 2 hours. After cooling again to room temperature, saturated sodium bicarbonate aqueous solution (20 mL) was added to stop the reaction. The mixture was then extracted with dichloromethane (20 mL, 3 times), and the organic layer was dried over anhydrous sodium sulfate. The crude product obtained was subjected to silica gel column chromatography (eluent: hexane / dichloromethane = 5 / 1), and washed with acetonitrile (15 mL) to obtain 31.1 mg of compound (S-2).

[0571] [Second process] To the compound (S-2) obtained in the first step, [1,2-bis(diphenylphosphinofino)ethane]dichloronickel(II) (NiCl2(dppe), 4.33 mg, 0.008 mmol) and sodium borohydride (7.10 mg, 0.19 mmol) were added, and the mixture was dissolved in N,N-dimethylacetamide (1 mL) and stirred at 110°C for 18 hours. After cooling to room temperature, 5 mL of aqueous ammonium chloride solution was added to stop the reaction, and the organic layer was extracted with toluene (15 mL, 5 times). The organic layer was then dried using anhydrous sodium sulfate. Subsequently, silica gel column chromatography (eluent: dichloromethane) was performed, and the crude product obtained was washed with acetonitrile (15 mL) to obtain compound (1-1) (22.0 mg, 0.03 mmol) as an orange solid.

[0572] [ka]

[0573] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (495MHz, CDCl3): δ=1.74(s,6H), 2.04(s,6H), 2.39(s,6H), 2.47(s,6H), 2.68(s,3H), 6.24(d,J=8.22Hz,2H), 6.60(s,2H), 7. 13(s,2H), 7.18(d,J=7.65Hz,2H), 7.20(s,2H), 7.29(t,J=8.22Hz,2H), 7.88(d,J=7.94Hz,2H), 8.66(s,2H), 8.69(d,J=7.65Hz,2H).

[0574] Synthesis Example (2): Synthesis of Compounds (1-2) [ka]

[0575] [First step] Using compound (S-3) (1.95 g, 25.0 mmol), 1,2-dichlorobenzene (250 mL), and boron triiodide (39.1 g, 100.0 mmol), 1.97 g (2.63 mmol) of compound (S-4) was obtained by performing the same procedure as in the first step of synthesis example (1).

[0576] [Second process] Using the compound (S-4) (37.4 mg, 0.05 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 5.3 mg, 0.01 mmol), sodium borohydride (7.56 mg, 0.20 mmol), and N,N-dimethylacetamide (1 mL), the compound represented by formula (1-2) (25.4 mg, 0.037 mmol) was obtained by performing the same procedure as in the second step of synthesis example (1).

[0577] [ka]

[0578] Synthesis Example (3): Synthesis of Compounds (1-3) [ka]

[0579] Under a nitrogen atmosphere, a flask containing compound (S-4) (30.0 mg, 0.04 mmol) obtained in the first step of synthesis example (2), 2-biphenylboronic acid (compound (T-1), 39.8 mg, 0.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 3.3 mg, 0.0036 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 3.4 mg, 0.0084 mmol), tert-butoxypotassium (26.9 mg, 0.24 mmol), tert-butanol (2 ml), and toluene (2 ml) was heated to 80°C and stirred for 24 hours. The reaction solution was cooled to room temperature and extracted with water and toluene. The solvent was then removed by distillation to obtain the crude product. The crude product obtained was washed with methanol, and then subjected to silica gel column chromatography (eluent: dichloromethane) to obtain compounds (1-3) (19.6 mg).

[0580] [ka]

[0581] Synthesis Example (4): Synthesis of Compounds (1-6) [ka]

[0582] Under a nitrogen atmosphere, a flask containing the compound (S-4) (37.4 mg, 0.05 mmol) obtained in the first step of synthesis example (2), 9H-carbazole (20.0 mg, 0.12 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 3.3 mg, 0.0036 mmol), tri-tert-butylphosphonium tetrafluoroborate (tBu3P-HBF4, 9.3 mg, 0.032 mmol), tert-butoxysodium (5.7 mg, 0.4 mmol), and toluene (3 ml) was heated to 110°C and stirred for 24 hours. After the reaction solution was cooled to room temperature, toluene (10 mL) was added and the mixture was washed with water (20 mL x 3 times). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane) to obtain compounds (1-6) (23.2 mg, 0.023 mmol).

[0583] [ka]

[0584] Synthesis Example (5): Synthesis of Compounds (1-8) [ka]

[0585] The flask containing compound (S-4) (37.4 mg, 0.05 mmol) obtained in the first step of synthesis example (2), diphenylamine (18.5 mg, 0.11 mmol), bis(di-tert-butyl(3-methyl-2-butenyl)phosphine)dichloropalladium (NECO-296, 1.8 mg, 0.003 mmol), tert-butoxysodium (33.6 mg, 0.3 mmol), and mesitylene (3 ml) was heated to 130°C and stirred for 12 hours. The reaction solution was cooled to room temperature, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane / dichloromethane = 2 / 1), and then washed with ethyl acetate at 80°C to obtain compound (1-8) (16.5 mg, 0.016 mmol).

[0586] [ka]

[0587] Synthesis Example (6): Synthesis of Compounds (1-4) [ka]

[0588] [First step] Compound (S-6) (0.85 g, 1.04 mmol) was obtained by using compound (S-5) (8.0 g, 10.0 mmol), 1,2-dichlorobenzene (100 mL), and boron triiodide (15.6 g, 40.0 mmol) and performing the same procedure as in the first step of synthesis example (1).

[0589] [Second process] Compound (1-4) was obtained (23.9 mg, 0.032 mmol) by using the compound (S-6) (40.9 mg, 0.05 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 4.33 mg, 0.008 mmol), sodium borohydride (7.10 mg, 0.19 mmol), and N,N-dimethylacetamide (1 mL) and performing the same procedure as in the second step of synthesis example (1).

[0590] [ka]

[0591] Synthesis Example (7): Synthesis of Compounds (1-5) [ka]

[0592] Compounds (1-5) were obtained (19.9 mg, 0.019 mmol) by performing the same procedure as in Synthesis Example (3) using compound (S-6) (32.6 mg, 0.04 mmol), 2-biphenylboronic acid (compound (T-1), 39.8 mg, 0.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 3.3 mg, 0.0036 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 3.4 mg, 0.0084 mmol), tert-butoxypotassium (26.9 mg, 0.24 mmol), tert-butanol (2 ml), and toluene (2 ml) obtained in the first step of Synthesis Example (6).

[0593] [ka]

[0594] Synthesis Example (8): Synthesis of Compounds (1-10) [ka]

[0595] Compounds (1-10) were obtained (23.2 mg, 0.023 mmol) by performing the same procedure as in Synthesis Example (4) using the compound (S-6) (40.8 mg, 0.05 mmol) obtained in the first step of Synthesis Example (6), 9H-carbazole (20.0 mg, 0.12 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 3.3 mg, 0.0036 mmol), tri-tert-butylphosphonium tetrafluoroborate (tBu3P-HBF4, 9.3 mg, 0.032 mmol), tert-butoxysodium (38 mg, 0.4 mmol), and toluene (3 mL).

[0596] [ka]

[0597] Synthesis Example (9): Synthesis of Compounds (1-11) [ka]

[0598] [First step] Compound (S-7) was obtained (179 mg, 0.21 mmol) by performing the same procedure as in Synthesis Example (3) using compound (S-4) (300 mg, 0.4 mmol), 2-biphenylboronic acid (compound (T-1), 63 mg, 0.32 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 33 mg, 0.036 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 34 mg, 0.084 mmol), tert-butoxypotassium (72 mg, 0.64 mmol), tert-butanol (10 ml), and toluene (10 ml) obtained in the first step of Synthesis Example (2).

[0599] [Second process] Compound (1-11) was obtained (34.1 mg, 0.041 mmol) by using the compound (S-7) (173 mg, 0.20 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 21.2 mg, 0.04 mmol), sodium borohydride (30.2 mg, 0.80 mmol), and N,N-dimethylacetamide (4 mL) and performing the same procedure as in the second step of synthesis example (1).

[0600] [ka]

[0601] Synthesis Example (10): Synthesis of Compounds (1-12) [ka]

[0602] [First step] Compound (S-8) was obtained (105.1 mg, 0.12 mmol) by performing the same procedure as in Synthesis Example (4) using the compound (S-4) (150 mg, 0.20 mmol) obtained in the first step of Synthesis Example (2), 9H-carbazole (26.7 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 4.5 mg, 0.005 mmol), tri-tert-butylphosphonium tetrafluoroborate (tBu3P-HBF4, 14.5 mg, 0.05 mmol), tert-butoxysodium (22.8 mg, 0.24 mmol), and toluene (5 ml).

[0603] [Second process] Compound (1-12) was obtained (25.4 mg, 0.029 mmol) by using the compound (S-8) (87.9 mg, 0.1 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 10.5 mg, 0.02 mmol), sodium borohydride (7.56 mg, 0.20 mmol), and N,N-dimethylacetamide (3 mL) and performing the same procedure as in the second step of synthesis example (1).

[0604] [ka]

[0605] Synthesis Example (11): Synthesis of Compounds (1-13) [ka]

[0606] [First step] Compound (S-9) was obtained (96.0 mg, 0.109 mmol) by performing the same procedure as in Synthesis Example (5) using compound (S-4) (150 mg, 0.2 mmol) obtained in the first step of Synthesis Example (2), diphenylamine (27.0 mg, 0.16 mmol), bis(di-tert-butyl(3-methyl-2-butenyl)phosphine)dichloropalladium (NECO-296, 6.0 mg, 0.01 mmol), tert-butoxysodium (22.8 mg, 0.24 mmol), and mesitylene (5 ml).

[0607] [Second process] Compound (1-13) was obtained (33 mg, 0.039 mmol) by using the compound (S-9) (88.1 mg, 0.1 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 5.3 mg, 0.01 mmol), sodium borohydride (7.56 mg, 0.20 mmol), and N,N-dimethylacetamide (1 mL) and performing the same procedure as in the second step of synthesis example (1).

[0608] [ka]

[0609] Synthesis Example (12): Synthesis of Compounds (1-14) [ka]

[0610] [First step] Compound (S-10) was obtained (87.8 mg, 0.094 mmol) by performing the same procedure as in Synthesis Example (3) using compound (S-6) (163 mg, 0.2 mmol), 2-biphenylboronic acid (compound (T-1), 31.6 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 16.5 mg, 0.018 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 17 mg, 0.042 mmol), tert-butoxypotassium (22.4 mg, 0.2 mmol), tert-butanol (3 ml), and toluene (3 ml) obtained in the first step of Synthesis Example (6).

[0611] [Second process] Compound (1-14) was obtained (25.2 mg, 0.028 mmol) by using the compound (S-10) (74.7 mg, 0.08 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 5.3 mg, 0.01 mmol), sodium borohydride (7.56 mg, 0.20 mmol), and N,N-dimethylacetamide (2 mL) and performing the same procedure as in the second step of synthesis example (1).

[0612] [ka]

[0613] Synthesis Example (13): Synthesis of Compounds (1-15) [ka]

[0614] [First step] Compound (S-6) (204 mg, 0.25 mmol), obtained in the first step of synthesis example (6), 9H-carbazole (33.3 mg, 0.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 4.5 mg, 0.005 mmol), tri-tert-butylphosphonium tetrafluoroborate (tBu3P-HBF4, 14.5 mg, 0.05 mmol), tert-butoxysodium (22.8 mg, 0.24 mmol), and toluene (5 ml) were used to obtain compound (S-11) (115 mg, 0.12 mmol) by performing the same procedure as in synthesis example (4).

[0615] [Second process] Compound (1-15) was obtained (23.7 mg, 0.026 mmol) by using the compound (S-11) (96.3 mg, 0.1 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 10.6 mg, 0.02 mmol), sodium borohydride (7.56 mg, 0.20 mmol), and N,N-dimethylacetamide (3 mL) and performing the same procedure as in the second step of synthesis example (1).

[0616] [ka]

[0617] Synthesis Example (14): Synthesis of Compounds (1-7) [ka]

[0618] [First step] Using compound (S-12) (12.88 g, 15.0 mmol), chlorobenzene (4 mL), and boron triiodide (23.5 g, 60.0 mmol), 2.75 g (3.15 mmol) of compound (S-13) was obtained by performing the same procedure as in the first step of synthesis example (1).

[0619] [Second process] Using the compound (S-13) (175 mg, 0.2 mmol) obtained in the first step, [1,2-bis(diphenylphosphinole)ethane]dichloronickel(II) (NiCl2(dppe), 21 mg, 0.04 mmol), sodium borohydride (30.3 mg, 0.8 mmol), and N,N-dimethylacetamide (3 mL), the compound represented by formula (1-7) (33.8 mg, 0.042 mmol) was obtained by performing the same procedure as in the second step of synthesis example (1).

[0620] [ka]

[0621] Synthesis Example (15): Synthesis of Compounds (1-16) [ka]

[0622] Compounds (1-16) were obtained (92.6 mg, 0.081 mmol) by performing the same procedure as in Synthesis Example (4) using the compound (S-13) (0.43 g, 0.5 mmol) obtained in the first step of Synthesis Example (14), 9H-carbazole (0.20 mg, 1.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 32.1 mg, 0.035 mmol), tri-tert-butylphosphonium tetrafluoroborate (tBu3P-HBF4, 87.0 mg, 0.3 mmol), tert-butoxysodium (0.45 mg, 4.0 mmol), and mesitylene (10 mL).

[0623] [ka]

[0624] Synthesis Example (16): Synthesis of Compounds (1-17) [ka]

[0625] Compound (S-13) (0.175g, 0.2 mmol), 4-cyanophenylboronic acid (compound (T-2), 0.147g, 1.0 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphin]palladium(II) (PdCl2(amphos) 2、 Compounds (1-17) were obtained (81.0 mg, 0.077 mmol) by using 4 mg, 0.006 mmol, tripotassium phosphate (0.25 g, 1.2 mmol), and N-methylpyrrolidone (NMP, 3 ml) and performing the same procedure as in synthesis example (3).

[0626] [ka]

[0627] Synthesis Example (17): Synthesis of Compounds (1-27) [ka]

[0628] [First step] Under a nitrogen atmosphere, a flask containing the compound (S-13) (0.43 g, 0.5 mmol) obtained in the first step of synthesis example (14), bis(pinacolate)diborone (0.51 g, 2.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 91.6 mg, 0.1 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopyropyrbiphenyl (XPhos, 95.2 mg, 0.2 mmol), potassium acetate (29.4 mg, 3.0 mmol), and N,N-dimethylformamide (DMF) (5 ml) was heated to 80°C and stirred for 36 hours. The reaction solution was cooled to room temperature and extracted with water and toluene. The solvent was then removed by distillation to obtain the crude product. The crude product obtained was purified by silica gel column chromatography (eluent: hexane / dichloromethane = 4 / 1), and after removing the solvent by distillation, it was washed with acetonitrile to obtain compound (S-14) (0.40 g).

[0629] [Second process] Under a nitrogen atmosphere, a flask containing compound (S-14) (105.8 mg, 0.1 mmol) obtained in the first step, 2-bromo-4,6-diphenyl-1,3,5-triazine (compound (T-3), 125.9 mg, 0.4 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 23.2 mg, 0.02 mmol), potassium carbonate (82.9 mg, 0.6 mmol), toluene (4 ml), and water (2 ml) was heated to 100°C and stirred for 12 hours. The reaction solution was cooled to room temperature and extracted with water and toluene. The solvent was then removed by distillation to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane / dichloromethane), and after distillation of the solvent, it was washed with acetonitrile to obtain compound (1-27) (19.0 mg).

[0630] [ka]

[0631] The following compounds were synthesized using methods similar to those described in synthesis examples (1) to (17). [ka]

[0632] [ka]

[0633] The following comparative compounds were synthesized according to the methods described in their respective publications. Compounds (#528-1) and (#528-2) are described in International Publication No. 2020-080528, compound (#666-1) in International Publication No. 2018-203666, compound (#782-1) and (#782-2) in Chinese Patent Application Publication No. 110790782, compound (#790-1) in International Publication No. 2020-135790, and compound (RD1) in Chemical Science (2025), 16(17), 7495-7502.

[0634] [ka]

[0635] The formation of the target substance was confirmed by MALDI-TOF-MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry). [Table 1] TIFF2026047189000233.tif36170

[0636] <<Methods for evaluating basic physical properties>> Sample preparation The basic physical properties of the compound (1-1) synthesized above were evaluated. In this example, PMMA and the compound under evaluation were dissolved in toluene, and then a thin film was formed on a transparent support substrate made of quartz or glass by spin coating to prepare a sample. The concentration of the compound under evaluation in the coating film was 1% by mass.

[0637] Evaluation of luminescence characteristics A coating film formed on a transparent glass support substrate was used as the sample for measurement. The fluorescence spectrum of the sample was measured using a spectrofluorometer (Hitachi High-Tech Corporation, F-7000).

[0638] The fluorescence spectrum was measured by exciting the sample at room temperature. The excitation wavelength in the spectrum measurement was set to 340 nm. The full width at half maximum was determined as the width between the upper and lower wavelengths where the intensity becomes 50% centered on the maximum emission wavelength.

[0639] A sample for measuring the absolute PL quantum yield was prepared by sealing a coating film formed on a transparent support substrate made of quartz with a glass sealing substrate in a nitrogen atmosphere. The fluorescence quantum yield (PLQY) was measured using an absolute PL quantum yield measuring device (manufactured by Hamamatsu Photonics K.K., C9920-02G).

[0640]

Table 2

[0641] <<Manufacture and Evaluation of Vapor Deposition Type Organic EL Devices>> Using each of the synthesized compounds of the present invention and comparative compounds, each of the organic EL devices of TAF and PSF was manufactured.

[0642] <TAF Configuration: Examples T1-1 to Examples T1-9, Examples T2-1 to Examples T2-5, Comparative Examples T1 to Comparative Examples T6> ITO(50nm) / HAT-CN(10nm) / Tris-PCz(30nm) / mCBP(5nm) / PIC-TRZ2:4CzIPN: Each compound described in Table 3 (91:8:1)(30nm) / SF3-TRZ(10nm) / SF3-TRZ:Liq(7:3)(30nm) / Liq(2nm) / Al(100nm)

[0643] A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by OptoSciences Co., Ltd.) on which ITO with a film thickness of 200 nm formed by sputtering was polished to 50 nm was used as the transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boats containing HAT-CN, Tris-PCz, mCBP, PIC-TRZ2, 4CzIPN, each compound described in Table 3, SF3-TRZ, and Liq, and tungsten vapor deposition boats containing aluminum were respectively attached.

[0644] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was evacuated to 5×10 -4 Pa, and first, HAT-CN was heated and vapor-deposited to a thickness of 10 nm to form a hole injection layer. Next, Tris-PCz was heated and vapor-deposited to a thickness of 30 nm to form a hole transport layer 1, and further, mCBP was heated and vapor-deposited to a thickness of 5 nm to form a hole transport layer 2. Next, PIC-TRZ2, 4CzIPN, and each compound described in Table 3 were simultaneously heated and vapor-deposited to a thickness of 30 nm. The deposition rate was adjusted so that the mass ratio of PIC-TRZ2, 4CzIPN, and each compound described in Table 3 was approximately 91:8:1. Next, SF3-TRZ was heated and vapor-deposited to a thickness of 10 nm to form an electron transport layer 1, and further, SF3-TRZ and Liq were heated and vapor-deposited to a thickness of 30 nm to form an electron transport layer 2. The deposition rate was adjusted so that the mass ratio of SF3-TRZ and Liq was approximately 7:3. The deposition rate of each layer was 0.01 - 1 nm / second. Thereafter, Liq was heated and vapor-deposited at a deposition rate of 0.01 - 0.1 nm / second to a thickness of 2 nm, and then, aluminum was heated and vapor-deposited to a thickness of 100 nm to form a cathode, obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to be 1 - 10 nm / second.

[0645] The chemical structures of the compounds used in the manufacture of the above elements are shown below.

[0646]

Chemical formula

[0647] <PSF configuration: Examples P1-1 to P1-9, Examples P2-1 to P2-5, Comparative Examples P1 to P6> ITO (50nm) / HAT-CN (5nm) / NPD (30nm) / TcTa (10nm) / CBP:Ir(ppy)2(acac): Each compound listed in Table 3 (69:30:1) (30nm) / 9Cz46m (10nm) / p-bpPhen (30nm) / LiF (1nm) / Al (100nm)

[0648] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4 The pressure was reduced to Pa, and first, HAT-CN was heated and deposited to a thickness of 5 nm to form a hole injection layer. Next, NPD was heated and deposited to a thickness of 30 nm to form hole transport layer 1, and then TcTa was heated and deposited to a thickness of 10 nm to form hole transport layer 2. Next, CBP, Ir(ppy)2(acac), and each compound listed in Table 3 were heated simultaneously and deposited to a thickness of 30 nm. The deposition rate was adjusted so that the mass ratio of CBP, Ir(ppy)2(acac), and each compound listed in Table 3 was approximately 69:30:1. Next, 9Cz46m was heated and deposited to a thickness of 10 nm to form electron transport layer 1, and then p-bpPhen was heated and deposited to a thickness of 30 nm to form electron transport layer 2. The deposition rate for each layer was 0.01 to 1 nm / second. Subsequently, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to achieve a film thickness of 1 nm. Then, aluminum was heated and deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of the aluminum was adjusted to 1 to 10 nm / second.

[0649] The chemical structures of the compounds used in the manufacture of each of the above elements are shown below.

[0650] [ka]

[0651] [evaluation] The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x,y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum. These evaluation items are, for example, 1000 cd / m². 2 The value at the time of emission can be used.

[0652] The quantum efficiency of a light-emitting device has two components: internal quantum efficiency and external quantum efficiency. Internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the device as electrons (or holes) that is purely converted into photons. External quantum efficiency, on the other hand, is calculated based on the amount of these photons emitted to the outside of the device. Since some of the photons generated in the light-emitting layer are absorbed or reflected within the device and not emitted to the outside, the external quantum efficiency is lower than the internal quantum efficiency.

[0653] The measurement method for spectral radiance (emission spectrum) and external quantum efficiency is as follows: Using an Advantest R6144 voltage / current generator, the device's radiance was 1000 cd / m². 2 A voltage is applied to cause the element to emit light. A TOPCON SR-3AR spectroradiometer is used to measure the spectral radiance in the visible light region from a direction perpendicular to the light-emitting surface. Assuming the light-emitting surface is a perfectly diffusive surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π. Next, the number of photons is integrated across the entire observed wavelength range to obtain the total number of photons emitted from the element. The number of carriers injected into the element is obtained by dividing the applied current value by the elementary charge, and the external quantum efficiency is obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element. The full width at half maximum of the emiss...

Claims

1. A polycyclic aromatic compound represented by formula (1). 【Chemistry 1】 (In formula (1), Rings A, B, and C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. Y １ Each of these is independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl. X １ These are, independently, N or C-R Ｃ１Ｘ And R Ｃ１Ｘ These are substituted or unsubstituted aryls, substituted or unsubstituted alkyls, or substituted or unsubstituted cycloalkyls. X ２ is, independently of each other, >O, >N-R ＮＸ , >C(-R ＣＸ ), ２ , >Si(-R ＩＸ ), ２ , >S, or >Se, and R ＮＸ , R ＣＸ , and R ＩＸ Each is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, >C(-R ＣＸ ) ２ The two R's ＣＸ They may bond to each other to form a ring, >Si(-R ＩＸ ) ２ The two R's ＩＸ They may bond to each other to form a ring, R ＮＸ , at least one R ＣＸ , and at least one R ＩＸ Each of these is connected by a linking group or a single bond, and the R ＮＸ , R ＣＸ , or R ＩＸ X including ２ It may be bonded to one or two of the rings to which it is bonded. However, two X ２ At least one of them is R ＮＸ The group represented by formula (1J) is N-R ＮＸ And, In equation (1J), * indicates the bond position with N. The J ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. R Ｊ is a substituent, R Ｊ The J ring may be further bonded via another single bond or linking group. X １ When N, some or all of two adjacent A rings may be connected by a single bond. n is an integer greater than or equal to 1, At least one selected from the group consisting of aryl rings and heteroaryl rings in formula (1) may be condensed with at least one cycloalkane, and the cycloalkane may be substituted with at least one substituent, and at least one -CH group in the cycloalkane ２ The hyphen can be replaced with -O-, In equation (1), at least one hydrogen may be replaced by deuterium, and at least one nitrogen may be nitrogen-15( １５ N) may be replaced by sulfur-33( ３３ S), Sulfur-34 ( ３４ S) or Sulfur-36 ( ３６ S), at least one oxygen, oxygen-17 ( １７ O) or oxygen-18 ( １８ O), at least one carbon is carbon-13 ( １３ C), at least one boron is boron-11 ( １１ B) can be used as a substitute.

2. R Ｊ is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted arylthio, a substituted or unsubstituted heteroarylthio, a substituted or unsubstituted aryloxy, a substituted or unsubstituted heteroaryloxy, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl. R J The polycyclic aromatic compound according to claim 1, wherein the J ring may be further bonded to the J ring via another single bond or linking group.

3. The polycyclic aromatic compound according to claim 1, wherein the group represented by formula (1J) is represented by formula (1J-1). 【Chemistry 2】 In formula (1J-1), R Ｊ R in equation (1J) Ｊ It is synonymous with, Z Ｊ１ Z Ｊ２ Z Ｊ３ Z Ｊ４ Each of them independently performs -C(-R ＺＪ ) = or -N = and R ＺＪ Each is independently either a hydrogen atom or a substituent, and R ＺＪ Adjacent groups among them may bond together with the j ring to form an aryl ring or a heteroaryl ring, and the formed ring may be substituted with at least one substituent.

4. Z Ｊ１ Z Ｊ２ Z Ｊ３ Z Ｊ４ Each of them independently performs -C(-R ＺＪ ) = and Z Ｊ１ and Z Ｊ３ In at least one of the following, R ＺＪ The polycyclic aromatic compound according to claim 3, wherein is a substituent.

5. Two X ２ However, each is independent > N-R ＮＸ The polycyclic aromatic compound according to claim 1.

6. Two R's ＮＸ The polycyclic aromatic compound according to claim 5, wherein all of the groups are represented by formula (1J).

7. Y １ A polycyclic aromatic compound according to any one of claims 1 to 6, wherein B is [the compound].

8. The polycyclic aromatic compound according to any one of claims 1 to 6, wherein the A ring, B ring, and C ring are each independently substituted or unsubstituted benzene rings.

9. A polycyclic aromatic compound according to claim 1, represented by any of the following structural formulas. 【Transformation 3】 【Chemistry 4】 【Transformation 5】

10. An organic electroluminescent element comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes, wherein the organic layer contains a polycyclic aromatic compound according to any one of claims 1 to 6 and 9.

11. The organic electroluminescent element according to claim 10, wherein the organic layer is a light-emitting layer.

12. The organic electroluminescent element according to claim 11, wherein the light-emitting layer comprises a host material, a thermally activated delayed phosphor or phosphorescent material as an assisting dopant, and the polycyclic aromatic compound as an emitting dopant.

13. A display device or lighting device comprising an organic electroluminescent element as described in claim 10.

14. A wavelength conversion material containing a polycyclic aromatic compound according to any one of claims 1 to 6 and 9.

15. An organic photodiode comprising a pair of electrodes and an active layer disposed between the pair of electrodes, wherein the active layer comprises a polycyclic aromatic compound according to any one of claims 1 to 6 and 9.

16. The organic photodiode according to claim 15, wherein the active layer is made of the polycyclic aromatic compound.

17. A solar cell material containing a polycyclic aromatic compound according to any one of claims 1 to 6 and 9.

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