Polycyclic aromatic compound, organic electroluminescent element, display device, and lighting device

Abstract

Provided are: a polycyclic aromatic compound which is useful as a material for an organic device such as an organic electroluminescent element; an organic electroluminescent element; a display device; and a lighting device. A polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1); ring A to ring D are substituted or unsubstituted aryl rings or heteroaryl rings (where at least one of ring B and ring C is an aryl ring or heteroaryl ring substituted by a group represented by formula (1E), Re1-Re3, A1 and A2 are hydrogen or substituents, at least one of A1 and A2 is a group represented by formula (tR), Ra-Rc are alkyl groups, and Rc is an alkyl group represented by formula (tR). X1 and X2 are > N-RNX (RNX is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group), the aryl ring or heteroaryl ring in the structure can be condensed by cycloalkanes, and the hydrogen in the structure can be substituted by deuterium. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a polycyclic aromatic compound. In particular, the present invention relates to a polycyclic aromatic compound containing nitrogen and boron. The present invention also relates to an organic device material, an organic electroluminescent element, a display device and a lighting device containing the polycyclic aromatic compound. Background Art

[0002] In the past, display devices using light-emitting elements that perform electroluminescence have been studied in various ways because they can achieve power saving or thinning, and organic electroluminescent elements containing organic materials have been actively studied because they can be easily lightweight or large-scaled. In particular, the development of organic materials having luminous properties such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capabilities including holes, electrons, etc. (having the possibility of becoming semiconductors or superconductors) have been actively studied so far, regardless of whether they are polymer compounds or low molecular weight compounds.

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

[0004] Among them, Patent Documents 1 to 4 disclose that polycyclic aromatic compounds containing boron are effectively used as materials for organic electroluminescent elements and the like.

[0005] [Prior art literature]

[0006] [Patent Document]

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

[0008] [Patent Document 2] International Publication No. 2020 / 251049

[0009] [Patent Document 3] Korean Patent Publication No. 10-2022-0128255

[0010] [Patent Document 4] International Publication No. 2021 / 107680 Summary of the invention

[0011] [Problems to be solved by the invention]

[0012] As described above, various materials have been developed as materials used in organic electroluminescence (EL) elements, but in order to increase the selection of materials for organic EL elements, it is desirable to develop a material including a novel compound. The present invention aims to provide a novel compound that can be effectively used as a material for organic devices such as organic EL elements.

[0013] [Technical means to solve the problem]

[0014] The present inventors have made great efforts to solve the above problems and have successfully produced novel polycyclic aromatic compounds with better luminescent properties among polycyclic aromatic compounds having structures similar to the compounds described in Patent Documents 1 to 4. In addition, it was found that an excellent organic EL element can be obtained by configuring an organic EL element with a layer containing the polycyclic aromatic compound between a pair of electrodes, thereby completing the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further provides materials for organic devices containing the following polycyclic aromatic compounds.

[0015] Specifically, the present invention has the following structures.

[0016] <1> A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1);

[0017] [Chemistry 1]

[0018]

[0019] In formula (1),

[0020] Ring A, Ring B and Ring C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, wherein at least one of Ring B and Ring C in the structure is an aryl ring substituted with at least a group represented by Formula (1E) or a heteroaryl ring substituted with at least a group represented by Formula (1E),

[0021] In formula (1E),

[0022] * is the bond position,

[0023] The D ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, R e1 , R e2 , R e3 , A 1 and A 2 are independently hydrogen or a substituent, wherein A 1 and A 2 At least one of them is a monovalent group represented by formula (tR),

[0024] [Chemistry 2]

[0025]

[0026] In formula (tR),

[0027] R a , R b and R c are each independently an alkyl group having 1 to 24 carbon atoms,

[0028] * is the bonding position to the e-ring,

[0029] X 1 and X 2 are independently >O, >NR NX 、>C(-R CX )2、>Si(-R IX )2.>S or>Se, 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, >C(-R CX )2's two R's CX Can bond to each other to form a ring, >Si(-R IX )2's two R's IX Can bond with each other to form a ring, R NX , at least one R CX , and at least one R IX It may be bonded to at least one of the A ring or the B ring or at least one of the A ring or the C ring via a single bond or a linking group,

[0030] At least one of the aryl ring and the heteroaryl ring in the structure may be condensed by at least one cycloalkane, the cycloalkane may be substituted by at least one substituent, and at least one -CH2- in the cycloalkane may be substituted by -O-.

[0031] In the structure, at least one hydrogen may be replaced by deuterium, and at least one nitrogen may be replaced by nitrogen-15( 15 N) substituted, 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) substituted, at least one carbon may be substituted by carbon-13 ( 13 C) substituted, at least one boron may be substituted by boron-11( 11B) Replacement.

[0032] <2> The polycyclic aromatic compound according to <1>, wherein A 1 and A 2 are independently hydrogen or alkyl, wherein A 1 and A 2 At least one of them is a monovalent group represented by formula (tR).

[0033] <3> The polycyclic aromatic compound according to <1> or <2>, wherein formula (1) is represented by any one of formula (1-A) and formula (1-B);

[0034] [Chemistry 3]

[0035]

[0036] In each of formula (1-A) and formula (1-B),

[0037] Ar 1 and Ar 2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,

[0038] R a1 ~R a3 , R b1 ~R b3 , R c1 ~R c4 and R d1 ~R d5 are independently hydrogen or a substituent,

[0039] R a1 ~R a3 , R b1 ~R b3 , R c1 ~R c4 and R d1 ~R d5 In the formula (A), two adjacent groups on one benzene ring may be bonded to each other and together with the benzene ring form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,

[0040] R e1 , R e2 , R e3 , A 1 and A 2 With R in formula (1E) e1 , R e2 , R e3 , A 1 and A 2They have the same meaning respectively.

[0041] In formula (1-B),

[0042] Z 1 is >O、>NR NZ 、>C(-R CZ )2、>Si(-R IZ )2.>S or>Se, R NZ , R CZ and R IZ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, >C(-R CZ )2's two R's CZ Can bond to each other to form a ring, >Si(-R IZ )2's two R's IZ Can bond to each other to form a ring,

[0043] At least one of the aryl ring and the heteroaryl ring in each of Formula (1-A) and Formula (1-B) 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 substituted with -O-,

[0044] In each of formula (1-A) and formula (1-B), at least one hydrogen may be substituted with deuterium, and at least one nitrogen may be substituted with nitrogen-15( 15 N) substituted, 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) substituted, at least one carbon may be substituted by carbon-13 ( 13 C) substituted, at least one boron may be substituted by boron-11( 11 B) Replacement.

[0045] <4> The polycyclic aromatic compound according to <3>, wherein R a2 is hydrogen or a substituent, as R a2 The substituent is a substituted or unsubstituted alkyl group (except methyl), a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group.

[0046] <5> The polycyclic aromatic compound according to <4>, wherein R a2 It is hydrogen, tert-butyl, or phenyl which may be substituted by tert-butyl.

[0047] <6> The polycyclic aromatic compound according to any one of <3> to <5>, wherein Ar 1 and Ar 2 are each independently a group represented by any one of the formulas selected from the group consisting of formula (ArG-1) to formula (ArG-58);

[0048] [Chemistry 4]

[0049]

[0050] [Chemistry 5]

[0051]

[0052] In formula (ArG-1) to formula (ArG-58), Me is a methyl group, tBu is a tert-butyl group, tAm is a tert-amyl group, and # indicates a bonding position to a nitrogen atom.

[0053] <7> The polycyclic aromatic compound according to <6>, wherein Ar 1 and Ar 2 At least one of them is a group represented by any one of the formulas selected from the group consisting of formula (ArG-1) to formula (ArG-46) and formula (ArG-55) to formula (ArG-58).

[0054] <8> The polycyclic aromatic compound according to any one of <3> to <7>, wherein Z 1 is >O or >C(-R CZ )2.

[0055] <9> The polycyclic aromatic compound according to <8>, which is represented by any of the following formulas;

[0056] [Chemistry 6]

[0057]

[0058] [Chemistry 7]

[0059]

[0060] In the formula, Me is a methyl group and tBu is a tert-butyl group.

[0061] <10> The polycyclic aromatic compound according to <1>, which is represented by any of the following formulas;

[0062] [Chemistry 8]

[0063]

[0064] In the formula, Me is a methyl group and tBu is a tert-butyl group.

[0065] <11> The polycyclic aromatic compound according to <1>, which is represented by any of the following formulas;

[0066] [Chemistry 9]

[0067]

[0068] In the formula, Me is a methyl group and tBu is a tert-butyl group.

[0069] <12> An organic electroluminescent element comprising: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer containing the polycyclic aromatic compound according to any one of <1> to <11>.

[0070] <13> The organic electroluminescent element according to <12>, wherein the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant.

[0071] <14> The organic electroluminescent device according to <13>, wherein the host is an anthracene compound, a fluorene compound or a dibenzo[pi]ne compound. Compound.

[0072] <15> A display device or a lighting device, comprising the organic electroluminescent element according to any one of <12> to <14>.

[0073] [Effects of the Invention]

[0074] According to the present invention, there is provided a novel polycyclic aromatic compound which is effectively used as a material for an organic device such as an organic electroluminescent element. The polycyclic aromatic compound of the present invention can be used to produce an organic device such as an organic electroluminescent element. BRIEF DESCRIPTION OF THE DRAWINGS

[0075] Figure 1 This is a schematic cross-sectional view showing an example of an organic electroluminescent element.

[0076] [Explanation of Symbols]

[0077] 100: Organic electroluminescent element

[0078] 101: Substrate

[0079] 102: Anode

[0080] 103: Hole injection layer

[0081] 104: Hole transport layer

[0082] 105: Luminous layer

[0083] 106: Electron transport layer

[0084] 107: Electron injection layer

[0085] 108: Cathode DETAILED DESCRIPTION

[0086] Hereinafter, the present invention will be described in detail. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In addition, in this specification, the numerical range represented by "~" refers to the range including the numerical values ​​described before and after "~" as the lower limit and the upper limit. In addition, in this specification, the "hydrogen" in the description of the structural formula refers to "hydrogen atom (H)". Similarly, "carbon atom (C)" is sometimes referred to as "carbon".

[0087] In the present specification, "adjacent groups" refer to two groups respectively bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in a structural formula.

[0088] In the present specification, "Me" represents a methyl group, "Et" represents an ethyl group, "nBu" represents a normal butyl group, "tBu" represents a tertiary butyl group, "iBu" represents an isobutyl group, "secBu" represents a secondary butyl group, "nPr" represents a normal propyl group, "iPr" represents an isopropyl group, "tAm" represents a tert-amyl group, "2EH" represents a 2-ethylhexyl group, "tOct" represents a tert-octyl group, "Ph" represents a phenyl group, "Mes" represents mesityl (2,4,6-trimethylphenyl), "Ad" represents a 1-adamantyl group, "Tf" represents a trifluoromethanesulfonyl group, "TMS" represents a trimethylsilyl group, and "D" represents a deuterium group.

[0089] In this specification, an organic electroluminescent element may be referred to as an "organic EL element".

[0090] In this specification, the chemical structure or substituent is sometimes represented by the carbon number, but the carbon number when the chemical structure is substituted with a substituent, or when the substituent is further substituted with a substituent, etc., refers to the carbon number of the chemical structure or the substituent, and does not refer to the total carbon number of the chemical structure and the substituent, or the total carbon number of the substituent and the substituent. For example, the so-called "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B. In addition, for example, the so-called "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without carbon number limitation)" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B.

[0091] In this specification, there are multiple structural formulas of aromatic compounds. Aromatic compounds are recorded by combining double bonds and single bonds, but in fact, due to the resonance of π electrons, there are also equivalent resonance structures such as multiple double bonds and single bonds alternately replaced for a single substance. In this specification, only one resonance structural formula is recorded for a substance, but other resonance structural formulas equivalent to organic chemistry are also included unless otherwise specified.

[0092] In addition, in this specification, "may be" may be expressed, but this has the same meaning as "has not been, or has been".

[0093] <Description of Ring and Substituent>

[0094] First, the details of the rings and substituents used in the present specification are described below.

[0095] Examples of the “aryl ring” in the present specification include 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.

[0096] Specific examples of the "aryl ring" include a benzene ring that is a monocyclic ring system, a biphenyl ring that is a bicyclic ring system, a naphthalene ring and an indene ring that are a condensed bicyclic ring system, a terphenyl ring (meta-terphenyl, o-terphenyl, p-terphenyl) that is a tricyclic ring system, an acenaphthene ring, fluorene ring, phenanthren ring, anthracene ring that are a condensed tricyclic ring system, a triphenylene ring, a pyrene ring, a tetracene ring, The ring is a perylene ring, a pentacene ring, etc. of a condensed five-ring system. In addition, the fluorene ring, the benzofluorene ring, and the indene ring also include structures in which the fluorene ring, the benzofluorene ring, the cyclopentane ring, etc. are spiro-bonded. In addition, the fluorene ring, the benzofluorene ring, and the indene ring also include rings in which two of the two hydrogen atoms of the methylene group in the structure are replaced by alkyl groups such as methyl groups described later as the first substituent to form dimethylfluorene rings, dimethylbenzofluorene rings, dimethylindene rings, etc.

[0097] As the "heteroaryl ring" in the present specification, for example, a heteroaryl ring having 2 to 30 carbon atoms can be mentioned, preferably a heteroaryl ring having 2 to 25 carbon atoms, more preferably a heteroaryl ring having 2 to 20 carbon atoms, further preferably a heteroaryl ring having 2 to 15 carbon atoms, and particularly preferably a heteroaryl ring having 2 to 10 carbon atoms can be mentioned. In addition, as the "heteroaryl ring", for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, boron, selenium, phosphorus, and tellurium as ring-constituting atoms other than carbon can be mentioned.

[0098] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazan ring), a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiol ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, Thiophene ring, benzothiophene ring, dibenzothiophene ring, thianthrene ring, indolecarbazole ring, benzindolecarbazole ring, dibenzoindolecarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, dioxaborinaphthoanthracene ring (5,9-dioxa-13b-bora-13bH-naphtho[3,2,1-de]anthracene) ring, etc.), benzoselenophene ring, dibenzoselenophene ring, azacarbazole ring, azadibenzothiophene ring, azadibenzofuran ring, azadibenzoselenophene ring, azatriphenylene ring, imidazoimidazole ring, indoloindole ring, benzofuranocarbazole ring, benzothiophenocarbazole ring, indenocarbazole ring and selenophenecarbazole ring, spiro[fluorene-9,9'-xanthene] ring, spirobis[siliconfluorene] ring, etc. In addition, among the dihydroacridine ring, xanthene ring and thioxanthene ring, two of the two hydrogen atoms of the methylene group in the structure are preferably substituted with an alkyl group such as a methyl group as described later as the first substituent to form a dimethyldihydroacridine ring, a dimethylxanthene ring, a dimethylthioxanthene ring, etc. In addition, bipyridine ring, phenylpyridine ring, pyridylphenyl ring as a bicyclic ring system, terpyridine ring, bipyridylphenyl ring, pyridylbiphenyl ring as a tricyclic ring system can also be listed as a "heteroaryl ring". In addition, the "heteroaryl ring" also includes a pyran ring.

[0099] In this specification, a substituent may be substituted with a further substituent. For example, a specific substituent may be described as "substituted or unsubstituted". This means that the specific substituent is substituted with at least one further substituent or is unsubstituted. In the same sense, it is sometimes referred to as "substitutable". In this specification, the specific substituent at this time may be referred to as a "first substituent" and the further substituent may be referred to as a "second substituent".

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

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

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

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

[0104] The diarylamino group may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group and a halogen group, and the two aryl groups in the diarylamino group may be bonded to each other via a linking group.

[0105] The diheteroarylamino group may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group and a halogen group, and the two heteroaryl groups in the diheteroarylamino group may be bonded to each other via a linking group.

[0106] The arylheteroarylamino group may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group and a halogen group, and the aryl group and the heteroaryl group in the arylheteroarylamino group may be bonded to each other via a linking group.

[0107] The diarylboryl group may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group and a halogen group, and the two aryl groups in the diarylboryl group may be bonded via a single bond or a linking group.

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

[0109] The cycloalkyl group may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group and a halogen group,

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

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

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

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

[0114] Substituted silyl, cyano and halogen.

[0115] The aryl group as the second substituent in each group of the substituent group Z may be further substituted by an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group or a halogen. Similarly, the heteroaryl group as the second substituent may be substituted by an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group or a halogen.

[0116] In the present specification, when referred to as a "substituent", the type of the substituent is not particularly limited, and unless otherwise specified, any substituent selected from the substituent group Z may be used. For example, when a "substituted or unsubstituted" group is substituted, the group may be substituted with at least one group selected from the substituent group Z.

[0117] In the present specification, the "aryl group" is, for example, an aryl group having 6 to 30 carbon atoms, and preferably an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 16 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

[0118] Specific examples of the "aryl group" include a monovalent group obtained by removing one hydrogen atom from the above-mentioned "aryl ring". For example, it is a phenyl group which is a monocyclic ring, a biphenyl group (2-biphenyl, 3-biphenyl, or 4-biphenyl) which is a bicyclic ring, a naphthyl group (1-naphthyl or 2-naphthyl) which is a condensed bicyclic ring, a terphenyl group (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) which is a tricyclic ring, a condensed tricyclic acenaphthene group (1-, 3-, 4-, or 5- The invention also includes the following: a 1-, 2-, 3-, 4-, or 9-) group, a phenanthren-(1-, 2-, 3-, 4-, or 9-) group, a tetraphenyl group (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl group) having a tetracyclic ring system, a triphenylene-(1-, 2-, or 4-) group, a pyrene-(1-, 2-, or 4-) group, or a tetracene-(1-, 2-, or 5-) group having a condensed tetracyclic ring system, or a perylene-(1-, 2-, or 3-) group, or a pentacene-(1-, 2-, 5-, or 6-) group having a condensed pentacyclic ring system. In addition, a monovalent group of spirofluorene and the like can be mentioned.

[0119] In addition, the aryl group serving as the second substituent also includes a structure in which the aryl group is substituted by at least one group selected from the group consisting of aryl groups such as phenyl (specific examples are the groups described 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).

[0120] As an example thereof, there can be mentioned a group in which the 9-position of the fluorenyl group as the second substituent is substituted with an aryl group such as a phenyl group, an alkyl group such as a methyl group, or a cycloalkyl group such as a cyclohexyl group or an adamantyl group.

[0121] The “arylene group” is, for example, an arylene group having 6 to 30 carbon atoms, and preferably an arylene group having 6 to 20 carbon atoms, an arylene group having 6 to 16 carbon atoms, an arylene group having 6 to 12 carbon atoms, or an arylene group having 6 to 10 carbon atoms.

[0122] Specific examples of the "arylene group" include a divalent group obtained by removing one hydrogen atom from the above-mentioned "aryl group" (monovalent group).

[0123] The “heteroaryl group” is, for example, a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms. The “heteroaryl group” contains, in addition to carbon atoms, one or more, preferably one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0124] Specific examples of "heteroaryl" include monovalent groups formed by removing one hydrogen from the "heteroaryl ring". Examples include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiol, phenoxazinyl, phenanthrolinyl, phenanthroline ... Thiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, a monovalent group of a benzophospholine oxide ring, a monovalent group of a dibenzophospholine oxide ring, furazanyl, thianthrenyl, indolecarbazolyl, benzindolecarbazolyl, dibenzoindolecarbazolyl, imidazolinyl, or oxazolinyl, etc. In addition, a monovalent group of spiro[fluorene-9,9'-xanthene], a monovalent group of spirobis[silicon fluorene], and a monovalent group of benzoselenophene can be mentioned.

[0125] In addition, the heteroaryl group as the second substituent also includes a structure in which the heteroaryl group is substituted by at least one group selected from the group consisting of aryl groups such as phenyl (specific examples are the groups described 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).

[0126] As an example, the 9-position of the carbazolyl group as the second substituent is substituted by an aryl group such as a phenyl group, an alkyl group such as a methyl group, or a cycloalkyl group such as a cyclohexyl group or an adamantyl group. In addition, a nitrogen-containing heteroaryl group such as a pyridyl group, a pyrimidyl group, a triazine group, a carbazolyl group, etc., which is further substituted by a phenyl group or a biphenyl group, is also included in the heteroaryl group as the second substituent.

[0127] The “heteroarylene group” is, for example, a heteroarylene group having 2 to 30 carbon atoms, preferably a heteroarylene group having 2 to 25 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, a heteroarylene group having 2 to 15 carbon atoms, or a heteroarylene group having 2 to 10 carbon atoms. In addition, the “heteroarylene group” is, for example, a divalent group such as a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms in addition to carbon.

[0128] Specific examples of the "heteroarylene group" include a divalent group obtained by removing one hydrogen atom from the above-mentioned "heteroaryl group" (monovalent group).

[0129] The "diarylamino group" is an amino group substituted with two aryl groups, and the description of the above-mentioned "aryl group" can be referred to for details of the aryl group.

[0130] The "diheteroarylamino group" is an amino group substituted with two heteroaryl groups, and the description of the "heteroaryl group" can be referred to for details of the heteroaryl group.

[0131] The "arylheteroarylamino group" is an amino group substituted with an aryl group or a heteroaryl group, and the description of the above-mentioned "aryl group" and "heteroaryl group" can be cited for the details of the above-mentioned aryl group and heteroaryl group.

[0132] The two aryl groups in the diarylamino group as the first substituent may be bonded to each other via a linking group, the two heteroaryl groups in the diheteroarylamino group as the first substituent may be bonded to each other via a linking group, and the aryl and heteroaryl groups in the arylheteroarylamino group as the first substituent may be bonded to each other via a linking group. Here, the description of "bonding via a linking group" is as shown below, for example, it means that the two phenyl groups of the diphenylamino group form a bond through a linking group. In addition, the description is also applicable to the diheteroarylamino group and the arylheteroarylamino group formed by aryl or heteroaryl groups.

[0133] [Chemistry 10]

[0134]

[0135] (* indicates the bond position)

[0136] Specific examples of the linking group include: >O, >NR X 、>C(-R X )2. -C(-R X )=C(-R X)-、>Si(-R X )2,>S,>CO,>CS,>SO,>SO2,>SeO,>SeO2,>PO,>B(-R X ) and >Se. R X are independently alkyl, cycloalkyl, aryl, or heteroaryl, which may be substituted by alkyl, cycloalkyl, aryl, or heteroaryl. X )2. -C(-R X )=C(-R X )-、>Si(-R X )2 Each of the two R X Can be linked to the group X via a single bond or Y bond with each other to form a ring. Y , can be listed as >O, >NR Y 、>C(-R Y )2、>Si(-R Y )2, >S, >CO, >CS, >SO, >SO2, and >Se, R Y are independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted by alkyl, cycloalkyl, aryl or heteroaryl. Y is>C(-R Y )2 and>Si(-R Y )2, the two R Y The alkylene group may be substituted with an alkylene group. 2X Replacement, R 2X are independently alkyl, cycloalkyl, substituted silyl, aryl and heteroaryl, which may be substituted by alkyl, cycloalkyl, substituted silyl or aryl. X )=C(-R X )-The two Rs in X They may be bonded to each other and to form an aryl ring (such as a benzene ring) or a heteroaryl ring together with the C=C to which they are bonded. X )=C(-R X )- can be an arylene group (such as 1,2-phenylene) or a heteroarylene group.

[0137] In addition, when simply describing “diarylamino”, “diheteroarylamino” or “arylheteroarylamino” in the present specification, unless otherwise specified, descriptions such as “two aryl groups in the diarylamino group may be bonded to each other via a linking group”, “two heteroaryl groups in the diheteroarylamino group may be bonded to each other via a linking group” and “the aryl and heteroaryl groups in the arylheteroarylamino group may be bonded to each other via a linking group” are respectively added.

[0138] "Diarylboryl" is a boron group substituted with two aryl groups, and the details of the aryl group can be referred to the description of the "aryl group". In addition, the two aryl groups may be bonded via a single bond or a linking group (for example, -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, R of -CR=CR-, R of >NR, R of >C(-R)2, R of >Si(-R), and R of >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 by an aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. In addition, two adjacent Rs may be bonded to each other to form a ring, thereby forming a cycloalkylene, arylene, and heteroarylene. For details of the substituents listed here, the descriptions of the "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" and the descriptions of the "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" described later may be cited. In the present specification, when simply describing a "diarylboryl group", unless otherwise specified, it is assumed that "two aryl groups in the diarylboryl group may be bonded to each other via a single bond or a linking group" is included.

[0139] "Alkyl" can be any of straight chain and branched chain, for example, a straight chain alkyl group with 1 to 24 carbon atoms or a branched chain alkyl group with 3 to 24 carbon atoms, preferably an alkyl group with 1 to 18 carbon atoms (branched chain alkyl group with 3 to 18 carbon atoms), an alkyl group with 1 to 12 carbon atoms (branched chain alkyl group with 3 to 12 carbon atoms), an alkyl group with 1 to 6 carbon atoms (branched chain alkyl group with 3 to 6 carbon atoms), an alkyl group with 1 to 5 carbon atoms (branched chain alkyl group with 3 to 5 carbon atoms), an alkyl group with 1 to 4 carbon atoms (branched chain alkyl group with 3 to 4 carbon atoms), etc.

[0140] Specific examples of “alkyl” include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, 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-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-icosyl.

[0141] The "alkylene group" is a divalent group obtained by removing any hydrogen atom from an "alkyl group", and examples thereof include a methylene group, an ethylene group, and a propylene group.

[0142] Regarding the "alkenyl group", please refer to the description of the "alkyl group". It is a group in which the CC single bond in the structure of the "alkyl group" is replaced by a C=C double bond, and also includes a group in which not only one but more than two single bonds are replaced by double bonds (also called a diene group or a triene group).

[0143] Specific examples of the "alkenyl group" include alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, further preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups are ethenyl, 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.

[0144] The "alkenylene group" is a divalent group obtained by removing any hydrogen atom of an "alkenyl group", and examples thereof include a vinylene group.

[0145] Regarding the “alkynyl group”, reference may be made to the description of the “alkyl group”, which is a group in which the C-C single bond in the structure of the “alkyl group” is replaced by a C≡C triple bond, and also includes a group in which not only one but two or more single bonds are replaced by triple bonds (also called a di-alkynyl group or a tri-alkynyl group).

[0146] The “cycloalkyl group” is, for example, a cycloalkyl group having 3 to 24 carbon atoms, preferably a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, or a cycloalkyl group having 5 carbon atoms.

[0147] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituents having 1 to 5 carbon atoms or 1 to 4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, or decahydroazulyl.

[0148] The “cycloalkylene group” is, for example, a cycloalkylene group having 3 to 24 carbon atoms, preferably a cycloalkylene group having 3 to 20 carbon atoms, a cycloalkylene group having 3 to 16 carbon atoms, a cycloalkylene group having 3 to 14 carbon atoms, a cycloalkylene group having 3 to 12 carbon atoms, a cycloalkylene group having 5 to 10 carbon atoms, a cycloalkylene group having 5 to 8 carbon atoms, a cycloalkylene group having 5 to 6 carbon atoms, or a cycloalkylene group having 5 carbon atoms.

[0149] Specific examples of the "cycloalkylene group" include a structure in which one hydrogen atom is removed from the above-mentioned "cycloalkyl group" (monovalent group) to give a divalent group.

[0150] The "cycloalkenyl group" includes a group having a structure in which at least one set of single bonds between two carbon atoms in the "cycloalkyl group" becomes a double bond (for example, a group in which -CH2-CH2- is substituted with -CH=CH-), and a group that is not equivalent to an aryl group. Specifically, 1-cyclohexenyl, 1-cyclopentenyl, etc. can be mentioned.

[0151] The "alkoxy group" is a group represented by "Alk-O-(Alk is an alkyl group)", and the description of the "alkyl group" can be cited for details of the alkyl group.

[0152] The "aryloxy group" is a group represented by "Ar-O-(Ar is an aryl group)", and the description of the "aryl group" can be cited for details of the aryl group.

[0153] The "arylthio group" is a group represented by "Ar-S-(Ar is an aryl group)", and the description of the "aryl group" can be cited for details of the aryl group.

[0154] The “substituted silyl group” is, for example, a silyl group substituted with at least one of an aryl group, an alkyl group, and a cycloalkyl group, and is preferably a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, or an alkyldicycloalkylsilyl group.

[0155] The "triarylsilyl group" is a silyl group substituted with three aryl groups, and the description of the "aryl group" can be cited for details of the aryl groups.

[0156] Specific examples of the “triarylsilyl group” include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl groups.

[0157] The "trialkylsilyl group" is a silyl group substituted with three alkyl groups, and the description of the "alkyl group" can be referred to for details of the alkyl group.

[0158] Specific examples of “trialkylsilyl” include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, methyldiethylsilyl, n-propyldimethylsilyl, tert-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, sec-butyldi-n-propylsilyl, tert-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, sec-butyldiisopropylsilyl, or tert-butyldiisopropylsilyl.

[0159] The "tricycloalkylsilyl group" is a silyl group substituted with three cycloalkyl groups, and the description of the "cycloalkyl group" can be cited for details of the cycloalkyl group.

[0160] Specific examples of the “tricycloalkylsilyl group” include tricyclopentylsilyl and tricyclohexylsilyl groups.

[0161] The "dialkylcycloalkylsilyl group" is a silyl group substituted with two alkyl groups and one cycloalkyl group, and the description of the "alkyl group" and the "cycloalkyl group" can be cited for details of the alkyl group and the cycloalkyl group.

[0162] The "alkyldicycloalkylsilyl group" is a silyl group substituted with one alkyl group and two cycloalkyl groups, and the description of the "alkyl group" and the "cycloalkyl group" can be cited for details of the alkyl group and the cycloalkyl group.

[0163] The "halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, further preferably fluorine.

[0164] When substituted with a cyano group or a halogen, it is also preferred that all or part of the hydrogen atoms in the aryl group or heteroaryl group in the structure are substituted with a cyano group or a halogen.

[0165] The substituent represented by formula (A30) has the following structure.

[0166] [Chemistry 11]

[0167]

[0168] In formula (A30),

[0169] Ak is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl or substituted or unsubstituted cycloalkenyl, at least one -CH2- in the alkyl, cycloalkyl and cycloalkenyl may be substituted by -O- or -S-,

[0170] R Ak is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl or a substituted or unsubstituted cycloalkyl, R Ak It can be bonded to Ak through a linking group or a single bond, and * is the bonding position.

[0171] In formula (A30), Ak is the substituent, and is not conjugated with the non-covalent electron pair on N, so that the non-covalent electron pair can be conjugated with the π electron of the bonding target, and a larger wavelength change can be achieved compared to the case where an aromatic group or the like exists at the same position. In addition, the same is true for the influence on the multiple resonance effect, and a greater improvement in the thermally activated delayed fluorescence (TADF) property can be achieved.

[0172] R Ak Preferred is an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, more preferably an aryl group which may be substituted by an alkyl group, a heteroaryl group which may be substituted by an alkyl group, an alkyl group or a cycloalkyl group, further preferably an aryl group which may be substituted by an alkyl group, and particularly preferably a phenyl group which may be substituted by a methyl group.

[0173] 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, further preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group.

[0174] R Ak It may be the same as or different from Ak, but is preferably different.

[0175] R Ak It can be bonded to Ak via a linking group or a single bond. Examples of the linking group include >O, >S, or >Si(-R)2. R of >Si(-R)2 is hydrogen, an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. Ak Examples of the structure bonded to Ak via a linking group or a single bond include the following structures.

[0176] [Chemistry 12]

[0177]

[0178] In the above formulas, * represents the bonding position.

[0179] [When two groups bonded to the same atom bond to each other]

[0180] In the present specification, when it is mentioned that two groups bonded to the same atom can be bonded to each other to form a ring, they can be bonded via a single bond or a linking group (these are also collectively referred to as a bonding group). Examples of the linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -Se(=O)-, -Se(=O)2-, -P(=O)-, -B(-R)- or -Se-. For example, the following structures can be mentioned. In addition, the R of -CHR-CHR-, the R of -CR2-CR2-, the R of -CR=CR-, the R of -N(-R)-, the R of -C(-R)2-, the R of -B(-R)-, and the R of -Si(-R)2- are independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl which may be substituted by cycloalkyl, alkenyl which may be substituted by alkyl or cycloalkyl, alkynyl which may be substituted by alkyl or cycloalkyl, or cycloalkyl which may be substituted by alkyl or cycloalkyl. In addition, two adjacent Rs may be bonded to each other to form a ring, and may form a cycloalkylene group, an arylene group, or a heteroarylene group.

[0181] [Chemistry 13]

[0182]

[0183] As the bonding group, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, -C(=O)-, and -Se- are preferred as the linking group; a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(=O)-, and -C(-R)2- are more preferred as the linking group; a single bond, -CR=CR-, -N(-R)-, -O-, and -S- are further preferred as the linking group; and a single bond is most preferred.

[0184] The position at which the two Rs are bonded via a bonding group is not particularly limited as long as it is a position at which bonding is possible, but it is preferred that the two Rs are bonded at the most adjacent position. For example, when the two groups are phenyl groups, it is preferred that the two Rs are bonded to each other at the ortho position (position 2) based on the bonding position (position 1) of "C" or "Si" in the phenyl group (refer to the structural formula).

[0185] <Stereoisomers, etc.>

[0186] The polycyclic aromatic compound of the present invention may exist as enantiomers or diastereomers depending on the type of substituents, but any stereoisomer in any pure form, any mixture of stereoisomers, racemates, etc. are all included in the scope of the present invention regardless of the structural formula described.

[0187] <1. Polycyclic aromatic compounds>

[0188] <Overall structure>

[0189] It has been found that polycyclic aromatic compounds formed by linking aromatic rings using hetero elements such as boron, nitrogen, oxygen, and sulfur have a large highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gap (band gap Eg in the film). The reason is that the aromaticity of the 6-membered ring containing the hetero element is low, and the reduction of the HOMO-LUMO gap accompanying the expansion of the conjugated system is suppressed. In addition, it has been found that the HOMO-LUMO gap can be arbitrarily changed according to the type of hetero element and the method of connection. It is believed that the reason is that the energy of HOMO and LUMO can be arbitrarily changed according to the spatial expansion and energy of the empty orbital or lone pair of the hetero element.

[0190] These polycyclic aromatic compounds cause the excited state singly occupied molecular orbital (SOMO) 1 and SOMO 2 to be localized on each atom due to the electronic disturbance of the heteroelement, thereby narrowing the half-value width of the fluorescence emission peak, and thus obtaining high color purity emission when used as a dopant for an organic EL element. S1T1 It becomes smaller and exhibits thermally activated delayed fluorescence. When used as an emitting dopant in an organic EL element, high efficiency can be obtained.

[0191] Furthermore, by introducing a substituent, the energies of HOMO and LUMO can be arbitrarily changed, and thus the ionization potential and the electron affinity can be optimized according to the surrounding materials.

[0192] In the present invention, it was found that a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) containing a group represented by formula (1E) (hereinafter sometimes referred to as "polycyclic aromatic compound containing structural units represented by formula (1)") can produce organic electroluminescent elements with longer life and higher luminous efficiency compared with polycyclic aromatic compounds of similar structures.

[0193] [Chemistry 14]

[0194]

[0195] The following describes in detail the polycyclic aromatic compound including the structural unit represented by formula (1).

[0196] <Description of Ring Structure in Compound>

[0197] In formula (1), "A", "B", and "C" in the circle are symbols representing the ring structure represented by each circle. The structure represented by formula (1) has a structure in which at least three aromatic rings as the A ring, the B ring, and the C ring are connected by boron and nitrogen to form a ring structure. The formed ring structure is a condensed ring structure composed of at least 5 rings.

[0198] The A ring, the B ring and the C ring are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. The polycyclic aromatic compound comprising the structural unit represented by formula (1) comprises at least one aryl ring substituted with at least one group represented by formula (1E) or at least one heteroaryl ring substituted with at least one group represented by formula (1E) as the B ring or the C ring.

[0199] Ring A forms a trivalent group having bonds on three consecutive elements (preferably carbon) on the aryl ring or heteroaryl ring in its structure. 1, X 1 and X 2 Bond. The ring in which the element having the three bonding bonds is set as the ring constituent element in ring A is preferably a 5-membered ring or a 6-membered ring. The ring may be further condensed with other rings. As an example of a 6-membered ring, a benzene ring may be cited. As an example of a 6-membered ring further condensed with other rings, there may be cited: a naphthalene ring, an anthracene ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, etc. As an example of a 5-membered ring, there may be cited: a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, etc. As an example of a 5-membered ring further condensed with other rings, there may be cited: a benzofuran ring, a benzothiophene ring, an indole ring, etc. In addition, as a condensed ring, an indene ring may also be cited.

[0200] The aryl ring or heteroaryl ring in the A ring is preferably a benzene ring.

[0201] Ring B and ring C each form a divalent group having a bond on two adjacent elements (preferably carbon) on the aryl ring or heteroaryl ring in the structure. 1 , and X 1 or X 2 Bond. The ring in which the element having the two bonding bonds is set as the ring constituent element in each ring of the B ring and the C ring is preferably a 5-membered ring or a 6-membered ring. The ring may be further condensed with other rings. Examples of 6-membered rings include benzene rings, pyridine rings, etc. Examples of 6-membered rings that are further condensed with other rings include: naphthalene rings, quinoline rings, benzofuran rings, benzothiophene rings, indole rings, benzoselenophene rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, dibenzoselenophene rings, etc. Examples of 5-membered rings include: furan rings, thiophene rings, pyrrole rings, thiazole rings, selenophene rings, etc. Examples of 5-membered rings that are further condensed with other rings include: benzofuran rings, benzothiophene rings, indole rings, benzoselenophene rings, etc. In addition, as condensed rings, indene rings may also be mentioned.

[0202] As the aryl ring or heteroaryl ring in the B ring and the C ring, it is preferably a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, an indene ring, a benzofuran ring, a benzothiophene ring, a benzoselenophene ring or an indole ring, respectively and independently, and more preferably a benzene ring, an indene ring, a benzofuran ring or a benzothiophene ring. It is further preferred that the B ring is a benzene ring, and the C ring is a benzene ring, an indene ring, a benzofuran ring or a benzothiophene ring, and it is particularly preferred that the B ring is a benzene ring, and the C ring is an indene ring, a benzofuran ring or a benzothiophene ring.

[0203] In the substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in the A ring, the B ring and the C ring, as the substituent when referring to "substituted or unsubstituted (substituted or unsubstituted)", at least one substituent selected from the substituent group Zα can be listed. In addition, the substituent may also be a substituted or unsubstituted diarylphosphino group such as a diphenylphosphino group. When there are multiple substituents, the multiple substituents may be the same or different from each other. As the substituent, preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, or a halogen, and more preferably a phenyl group, a tert-butyl group, a diphenylamino group, a substituted or unsubstituted carbazolyl group, or a halogen which may be substituted with a tert-butyl group or a halogen. As preferred substituents other than these, reference may be made to the description in <Preferred Substituents> described later.

[0204] <Group represented by formula (1E)>

[0205] In the polycyclic aromatic compound containing the structural unit represented by formula (1), at least one of the rings selected from the group consisting of the B ring and the C ring is an aryl ring or heteroaryl ring having at least a group represented by formula (1E) as a substituent. In the polycyclic aromatic compound containing the structural unit represented by formula (1), the aryl ring or heteroaryl ring having the group represented by formula (1E) is preferably one. In addition, the aryl ring or heteroaryl ring having the group represented by formula (1E) is preferably a benzene ring having the group represented by formula (1E). In the benzene ring, the group represented by formula (1E) is preferably in the para position with respect to boron.

[0206] In formula (1E), ring D is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. Ring D forms a monovalent group having a bond on an element (preferably carbon) on the ring of the aryl ring or heteroaryl ring in its structure, and is bonded to nitrogen through the bond. The ring in which the element having the bond is set as a ring constituent element in ring A is preferably a 5-membered ring or a 6-membered ring. The ring may further condense with other rings. As an example of a 6-membered ring, a benzene ring may be cited. As an example of a 6-membered ring further condensed with other rings, naphthalene ring, anthracene ring, quinoline ring, isoquinoline ring, quinazoline ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, etc. may be cited. As an example of a 5-membered ring, furan ring, thiophene ring, pyrrole ring, thiazole ring, etc. may be cited. As an example of a 5-membered ring further condensed with other rings, benzofuran ring, benzothiophene ring, indole ring, etc. may be cited. In addition, as a condensed ring, an indene ring may also be cited.

[0207] The aryl ring or heteroaryl ring in the D ring is preferably a benzene ring.

[0208] In the substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in the D ring, as the substituent when "substituted or unsubstituted (substituted or unsubstituted)" is mentioned, at least one substituent selected from the substituent group Zα can be listed. In addition, the substituent may also be a substituted or unsubstituted diarylphosphino group such as a diphenylphosphino group. When there are multiple substituents, the multiple substituents may be the same or different from each other. As the substituent, preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group, more preferably a tert-butyl group, a diphenylamino group, or a substituted or unsubstituted carbazolyl group. As preferred substituents other than these, reference may be made to the description in <Preferred Substituents> described later.

[0209] As the monovalent group formed by the D ring, an unsubstituted phenyl group or a phenyl group substituted at the para position with an unsubstituted alkyl group (particularly a tert-butyl group) or a halogen is particularly preferred.

[0210] In formula (1E), R e1 , R e2 , R e3 , A 1 and A 2 are independently hydrogen or a substituent, wherein A 1 and A 2 At least one of them is a monovalent group (tertiary alkyl group) represented by the formula (tR) described later. The details of the formula (tR) will be described later.

[0211] A 1 and A 2 are all tertiary alkyl groups represented by formula (tR), or only A 1 is a tertiary alkyl group represented by formula (tR), or only A 2 A is a tertiary alkyl group represented by the formula (tR). 1 and A 2 The other group other than the group represented by the formula (tR) is hydrogen or a substituent. From the viewpoint of being able to produce an organic electroluminescent element with a longer lifetime and higher luminous efficiency, it is preferably hydrogen or an unsubstituted alkyl group, more preferably hydrogen, methyl or tert-butyl, and still more preferably hydrogen.

[0212] As R e1 , R e2 and R e3When it is a substituent, the substituent may be at least one substituent selected from the substituent group Zα. When there are multiple substituents, the multiple substituents may be the same or different from each other. As a substituent, preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group, more preferably an unsubstituted alkyl group, and further preferably a tert-butyl group. As other preferred substituents, reference may be made to the description in <Preferred Substituents> described later.

[0213] Preferably R e1 , R e2 and R e3 are hydrogen, or R e1 and R e3 is hydrogen and R e2 is tert-butyl, more preferably R e1 , R e2 and R e3 All are hydrogen.

[0214] <X 1 and X 2 >

[0215] In formula (1), X 1 and X 2 are independently >O, >NR NX 、>C(-R CX )2、>Si(-R IX )2.>S or>Se, 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, >C(-R CX )2 two R CX Can bond to each other to form a ring, >Si(-R IX )2 two R IX Can bond with each other to form a ring, R NX , at least one R CX , and at least one R IX can be connected to the R NX , R CX or R IX X 1 or X 2 One or both of the bonded rings are bonded.

[0216] R NX Preferably, R is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. NXPreferred examples include Ar in formula (1-A) and formula (1-B): 1 and Ar 2 The example described later. CX It 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 methyl group. IX Preferred is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and more preferred is a substituted or unsubstituted phenyl group or methyl group.

[0217] In the polycyclic aromatic compound containing a structural unit represented by formula (1) used as an emissive dopant in the light-emitting layer of an organic EL device, X 1 and X 2 Each independently preferably is >NR NX , >S, >O or >Se, more preferably >NR NX , >O or >S, and more preferably >NR NX or >S, particularly preferably >NR NX .

[0218] <By X 1 or X 2 Explanation of changes in ring structure caused by bonding with the ring>

[0219] X 1 and X 2 R NX , R CX and R IX can be connected to X by a single bond or a linking group 1 or X 2 Specifically, in formula (1), X 1 R NX , R CX and R IX It may be bonded to at least one of the A ring and the B ring via a single bond or a linking group, 2 R NX , R CX and R IX It may be bonded to at least one of the A ring or the C ring via a single bond or a linking group.

[0220] As R NX , R CX and R IXThe linking groups when bonded to the ring respectively 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-, etc. Among these, -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-, more preferably -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S- and -C(-R)2-, further preferably -CH=CH-, -CR=CR-, -N(-R)-, -O- and -S-, particularly preferably -CR=CR-, -N(-R)-, -O- and -S-. The R of "-CHR-CHR-", the R of "-CR2-CR2-", the R of "-CR=CR-", the R of "-N(-R)-", the R of "-C(-R)2-", the R of "-B(-R)-", and the R of "-Si(-R)2-" are independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl which may be substituted by alkyl or cycloalkyl, alkenyl which may be substituted by alkyl or cycloalkyl, alkynyl which may be substituted by alkyl or cycloalkyl, or cycloalkyl which may be substituted by alkyl or cycloalkyl. In addition, two R bonded to the same atom may bond to each other to form a ring. Furthermore, two adjacent R may bond to each other to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring. In addition, these rings may also be substituted by alkyl or cycloalkyl.

[0221] As >NR NX R NX Examples of the condensed ring formed by bonding with the benzene ring as an aryl ring in the A ring, the B ring, or the C ring (c ring) include: a carbazole ring (where R is a phenyl group); NX through a single bond), a phenoxazine ring (a phenyl group R NX through -O-bonding), phenothiazine ring (phenyl R NX through -S-bonding), or acridone ring (R NX through a -C(=O)- bond).

[0222] From the viewpoint of obtaining a highly efficient element, it is preferably >NR NX R NX A structure that is bonded to the ring in ring A via a single bond.

[0223] In addition, the following partial structure (A10) may be formed by the connection as described above.

[0224] [Chemistry 15]

[0225]

[0226] In formula (A10), R A1 ~R A4 are independently hydrogen, alkyl or cycloalkyl, R A1 ~R A4 Any two to four of the above may be bonded to each other via a linking group or a single bond, and may be bonded to X at the two * positions. 1 and X 2 One of the two rings bonded is bonded to the other ring at the ** position. That is, N in formula (A10) is X 1 or X 2 NR NX When>NR NX N. The atoms on the ring that are bonded at the two * positions only need to be adjacent atoms (preferably carbon atoms). The partial structure represented by formula (A10) includes a NC bond with a weak bond dissociation energy (BDE), but the presence of another bond that forms the ring also promotes the reverse reaction (rebonding reaction) when the NC bond breaks, thus becoming a more stable structure. Therefore, in an organic EL element manufactured using a polycyclic aromatic compound having such a structure, it can be expected that the element life will be extended. When the structure represented by formula (A10) is included in the polycyclic aromatic compound, the number thereof can be one or two (preferably one).

[0227] In formula (A10), R A1 ~R A4 Any two to four of may be linked to each other via a linking group or a single bond.

[0228] R A1 ~R A4 Preferably, any two (R A1 and R A4 , R A1 and R A4 and R A2 and R A3 , R A1 and R A2 , RA3 and R A4 , R A1 and R A2 and R A3 and R A4 ) are bonded to each other through a linking group or a single bond, and more preferably R A1 and R A4 They are bonded to each other through a linking group or a single bond. As a divalent group formed by mutual bonding, an alkylene group can be cited. At least one hydrogen in the alkylene group can be substituted by an alkyl group or a cycloalkyl group, and at least one (preferably one) -CH2- in the alkylene group can be substituted by -O- and -S-. As a divalent group formed by mutual bonding, a straight-chain alkylene group having 2 to 5 carbon atoms is preferred, a straight-chain alkylene group having 3 or 4 carbon atoms is more preferred, and a straight-chain alkylene group having 4 carbon atoms (-(CH2)4-) is further preferred. The straight-chain alkylene group having 4 carbon atoms (-(CH2)4-) is particularly preferably unsubstituted.

[0229] The remaining R not involved in the linking group or single bond A1 ~R A4 Preferably, they are each independently hydrogen or an optionally substituted alkyl group, more preferably an optionally substituted alkyl group having 1 to 6 carbon atoms, further preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, and most preferably, they are all methyl groups.

[0230] That is, the partial structure represented by formula (A10) is preferably a structure represented by the following formula (A11).

[0231] [Chemistry 16]

[0232]

[0233] In formula (A11), Me is a methyl group, and at the two * positions, it is connected to X 1 and X 2 One of the two rings bonded is bonded to the other ring at the ** position.

[0234] <Structure composed of one or two or more structural units>

[0235] The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1). As a polycyclic aromatic compound having a structure composed of one of the structural units, a polycyclic aromatic compound represented by formula (1) can be cited. As a polycyclic aromatic compound having a structure composed of two or more of the structural units represented by formula (1), a compound equivalent to a polymer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1) can be cited. The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer can be any form as long as it has a plurality of the structural units in one compound, and can be a form in which any ring contained in the structural unit is bonded in a manner that is shared by a plurality of structural units, or can be a form in which any ring contained in the structural unit is bonded by condensation with each other. In addition, the structural unit may be bonded to a plurality of groups using a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, or the like. Of these, a bonded group in a shared ring is preferred. The two or more structural units in the polycyclic aromatic compound having a structure composed of two or more structural units represented by formula (1) may be the same or different from each other.

[0236] An aryl ring or a heteroaryl ring substituted with a group represented by the formula (1E) may be contained in each structural unit, but it is sufficient that at least one is contained as the polycyclic aromatic compound as a whole.

[0237] <Polycyclic aromatic compound represented by formula (1-A) or formula (1-B)>

[0238] Preferred examples of the polycyclic aromatic compound containing the structural unit represented by formula (1) include polycyclic aromatic compounds represented by formula (1-A) or formula (1-B).

[0239] [Chemistry 17]

[0240]

[0241] In each of formula (1-A) and formula (1-B), R e1 , R e2 , R e3 , A 1 and A 2 With R in formula (1E) e1 , R e2 , R e3 , A 1 and A 2 They have the same meanings and the preferred ranges are also the same.

[0242] In each of formula (1-A) and formula (1-B), R a1 ~R a3 , R b1 ~R b3 , R c1 ~R c4 , and R d1 ~R d5 are independently hydrogen or a substituent, R a1 ~R a3 The two adjacent bases in R b1 ~R b3 The two adjacent bases in R c1 ~R c4 The two adjacent bases in R d1 ~R d5 Two adjacent groups in the group may be bonded to each other and, together with the two carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0243] As R a1 ~R a3 , R b1 ~R b3 , R c1 ~R c4 , and R d1 ~R d5 The substituent when it is a substituent and the substituent for the ring formed above include at least one substituent selected from the substituent group Zα, preferably at least one substituent selected from the substituent group Z, and more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group. The examples of preferred substituents described below can also be referred to. R a1 ~R a3 and R b1 ~R b4 When a plurality of "" are substituents, the substituents may be the same or different.

[0244] As R a1 ~R a3 , R b1 ~R b3 , R c1 ~R c4 and R d1 ~R d5 The ring formed by two adjacent groups in the ring being bonded to each other and the two carbon atoms to which they are bonded is not particularly limited, and examples thereof include a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a pyridine ring, a furan ring, a thiophene ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, an indole ring, a selenophene ring, a benzoselenophene ring, and the like.

[0245] In R a1 ~R a3 In the above examples, R a2 is hydrogen or a substituent, and R a1 and R a3 As R a2 When it is a substituent, the substituent is preferably a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or a substituted or unsubstituted diarylamino, more preferably a tert-butyl, a tert-amyl, an adamantyl group which may be substituted with a methyl group, an aryl group which may be substituted with an alkyl group, a diarylamino group which may be substituted with an alkyl group, or a carbazolyl group which may be substituted with an alkyl group, further preferably a tert-butyl, an adamantyl group which may be substituted with a methyl group, a phenyl group which may be substituted with a methyl group or a tert-butyl group, a diphenylamino group which may be substituted with a methyl group or a tert-butyl group, or a carbazolyl group which may be substituted with a methyl group or a tert-butyl group, and particularly preferably a tert-butyl group or a phenyl group which may be substituted with a tert-butyl group. In the research conducted by the present inventors, it was found that when R a2 The compound represented by formula (1-A) or formula (1-B) wherein R is methyl a2 The organic EL device in which the compound represented by the formula (1-B) having a methyl group is used as a dopant material tends to have a shorter lifespan. Although not being bound by a specific theory, it is believed that the reason is that the carbon-hydrogen bond energy at the benzyl position is small and is easily cut. Therefore, it is preferred that R a2 Not methyl.

[0246] Preferably R b1 ~R b3 All are hydrogen.

[0247] R c1 ~R c4 R are independently hydrogen or a substituent. c1 ~R c4 The two adjacent groups in the formula (R) may be bonded to each other and, together with the two carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. c1 ~R c4 The substituent when it is a substituent and the substituent for the ring formed above include at least one substituent selected from the substituent group Zα, preferably at least one substituent selected from the substituent group Z. c1 ~R c4 The substituents in the case of a plurality of substituents may be the same or different. The ring formed by two adjacent groups bonded to each other and the two carbon atoms to which they are bonded is not particularly limited, and examples thereof include: a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a pyridine ring, a furan ring, a thiophene ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, an indole ring, a selenophene ring, a benzoselenophene ring, and the like.

[0248] In R c1 ~R c4 In the above examples, R c2 or R c3 is hydrogen or a substituent, and the others are hydrogen, more preferably R c2 or R c3 is a substituent, and the others are hydrogen. c2 or R c3 When it is a substituent, the substituent is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group, more preferably an unsubstituted alkyl group or a phenyl group which may be substituted with an unsubstituted alkyl group, and further preferably a tert-butyl group or a phenyl group which may be substituted with a tert-butyl group.

[0249] Also preferably R c1 ~R c4 Two adjacent bases in (e.g. R c2 and R c3 >) are bonded to each other and together with the carbon atoms to which they are bonded form a cycloolefin. The structure is equivalent to R c1 ~R c4 The structure of a cycloalkane condensed on the bonded benzene ring. In particular, R c1 ~R c4 The structure in which two adjacent groups are bonded to each other to form a partial structure represented by the formula (B11) or formula (B12) described later is taken as an example. 1 When >S, R is preferred c2 and R c3 The reason is that, as shown in the examples, especially in this structure, when R a2 When it is a methyl group, the life of the device tends to be shortened.

[0250] R d1 ~R d5 R are independently hydrogen or a substituent. d1 ~R d5 The two adjacent groups in the formula (R) may be bonded to each other and, together with the two carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. d1 ~R d5 The substituent when it is a substituent and the substituent for the ring formed above include at least one substituent selected from the substituent group Zα, preferably at least one substituent selected from the substituent group Z. d1 ~R d5The substituents in the case of a plurality of substituents may be the same or different. The ring formed by two adjacent groups bonded to each other and the two carbon atoms to which they are bonded is not particularly limited, and examples thereof include: a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a pyridine ring, a furan ring, a thiophene ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, an indole ring, a selenophene ring, a benzoselenophene ring, and the like.

[0251] In R d1 ~R d5 In the above examples, R d3 is hydrogen or a substituent, and the others are each hydrogen. d3 When it is a substituent, the substituent is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group, more preferably an unsubstituted alkyl group, and still more preferably a tert-butyl group.

[0252] In formula (1-B), Z 1 is >O、>NR NZ 、>C(-R CZ )2、>Si(-R IZ )2.>S or>Se, R NZ , R CZ and R IZ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two R CZ Can bond to each other to form a ring, two R IZ They may bond with each other to form a ring. NZ , preferably a substituted or unsubstituted aryl group, more preferably a phenyl group which may be substituted by an alkyl group. CZ , preferably methyl or phenyl. IZ , preferably methyl or phenyl.

[0253] Z 1 It is preferably >O, >C(-CH3)2 or >S. From the viewpoint of high luminescence quantum yield (photoluminescence quantum yield (PLQY)), it is more preferably >O or >C(-CH3)2.

[0254] In each of formula (1-A) and formula (1-B), Ar 1 and Ar 2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

[0255] Ar 1and Ar 2 Each of the above groups is independently preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, or a substituted or unsubstituted dibenzofuranyl group, further preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted dibenzofuranyl group, and particularly preferably a phenyl group which may be substituted with an alkyl group, a cycloalkyl group, or a halogen group, a biphenyl group which may be substituted with an alkyl group, a cycloalkyl group, or a halogen group, a 4-p-terphenyl group which may be substituted with an alkyl group, a cycloalkyl group, or a halogen group, a 4′-m-terphenyl group which may be substituted with an alkyl group, a cycloalkyl group, or a halogen group, or an unsubstituted dibenzofuranyl group (particularly a 4-dibenzofuranyl group). It is also preferred that at least one selected from the group consisting of an aryl ring and a heteroaryl ring contained in the above structure is condensed with a cycloalkane as described later.

[0256] Preferably Ar 1 and Ar 2 At least one of the groups is a substituted or unsubstituted biphenyl group (particularly a substituted or unsubstituted 2-biphenyl group), a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0257] In formula (1), as Ar 1 and Ar 2 Specific examples of include monovalent groups represented by any one of the following formulae (ArG-1) to (ArG-58) independently of one another. By using any of these groups, a material having high heat resistance that sublimates at a low sublimation temperature can be provided.

[0258] [Chemistry 18]

[0259]

[0260] [Chemistry 19]

[0261]

[0262] In formula (ArG-1) to formula (ArG-58), # represents the bonding position to the nitrogen atom. 1 and Ar 2 In each of Formula (ArG-1) to Formula (ArG-58), a group represented by a formula in which one or two or more hydrogen atoms are replaced by halogen atoms (particularly fluorine atoms) is also preferred.

[0263] Among the polycyclic aromatic compounds containing the structural unit represented by formula (1), Ar is preferred from the viewpoint of improving the stability of the compound while improving the horizontal orientation, thereby achieving both high device efficiency and long device life. 1 and Ar 2 All of them are groups represented by any one of the formulas selected from the group consisting of formula (ArG-1) to formula (ArG-58). From the same viewpoint, Ar 1 and Ar 2 At least any one of them is a group represented by any one of the formulas selected from the group consisting of formula (ArG-1) to formula (ArG-46) and formula (ArG-55) to formula (ArG-58), and more preferably at least any one of them is a group represented by any one of the formulas selected from the group consisting of formula (ArG-1) to formula (ArG-15) and formula (ArG-20) to formula (ArG-46).

[0264] <Preferred substituents>

[0265] In the polycyclic aromatic compounds used as emissive dopants (and in the compounds used as dopants), as a substituent containing an "alkyl group", a tertiary alkyl group represented by the following formula (tR) (a monovalent group represented by the formula (tR)) is one of the particularly preferred groups. The reason is that by such a bulky substituent, the intermolecular distance increases, and thus the luminescence quantum yield (PLQY) is improved. In addition, it is also preferred that the tertiary alkyl group represented by the formula (tR) is substituted as a second substituent on other substituents. Specifically, a diarylamino group substituted with a tertiary alkyl group represented by the formula (tR), a carbazolyl group substituted with a tertiary alkyl group represented by the formula (tR) (preferably an N-carbazolyl group), or a benzocarbazolyl group substituted with a tertiary alkyl group represented by the formula (tR) (preferably an N-benzocarbazolyl group) can be listed. Examples of substitution forms of the group of formula (tR) for the diarylamino group, carbazolyl group and benzocarbazolyl group include a case where a part or all of the hydrogen atoms of the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0266] [Chemistry 20]

[0267]

[0268] In the formula (tR), R a , R b and R c are each independently an alkyl group having 1 to 24 carbon atoms. a , R b and R c Each of them may be one or two or more non-adjacent alkyl groups having 1 to 24 carbon atoms, and the -CH2- in the terminal CH3 is not substituted by -O-. The group represented by the formula (tR) has * as the bonding position.

[0269] As R a , R b and R c The "alkyl group having 1 to 24 carbon atoms" may be any of a straight chain and a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms).

[0270] R in the formula (tR) a , R b and R c The total number of carbon atoms in the moiety is preferably 3 to 20, particularly preferably 3 to 10.

[0271] As R a , R b and R c Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-icosyl.

[0272] Examples of the group represented by the formula (tR) include a tert-butyl group, a tert-amyl group, a 1-ethyl-1-methylpropyl group, a 1,1-diethylpropyl group, a 1,1-dimethylbutyl group, a 1-ethyl-1-methylbutyl group, a 1,1,3,3-tetramethylbutyl group, a 1,1,4-trimethylpentyl group, a 1,1,2-trimethylpropyl group, a 1,1-dimethyloctyl group, a 1,1-dimethylpentyl group, a 1,1-dimethylheptyl group, a 1,1,5-trimethylhexyl group, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, tert-butyl and tert-pentyl are preferred.

[0273] As the substituent, a substituent represented by formula (A30) is also preferred.

[0274] The emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the substituent possessed by the compound used as a dopant (assisting dopant or emitting dopant). The group represented by the following structural formula is preferred, and a methyl group, a tert-butyl group, a tert-amyl group, a tert-octyl group, a neopentyl group, an adamantyl group, a phenyl group, an o-tolyl group, a p-tolyl group, a 2,4-xylyl group, a 2,5-xylyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group, a 3,6-di-tert-butylcarbazolyl group, and a phenoxy group are more preferred. A methyl group, a tert-butyl group, a tert-amyl group, a tert-octyl group, a neopentyl group, an adamantyl group, a phenyl group, an o-tolyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group, a 3,6-di-tert-butylcarbazolyl group, and a tribenzazepinyl group are further preferred. From the viewpoint of ease of synthesis, a group with large steric hindrance is preferred because selective synthesis can be performed. Specifically, a tert-butyl group, a tert-amyl group, a tert-octyl group, an adamantyl group, an o-tolyl group, a p-tolyl group, a 2,4-xylyl group, a 2,5-xylyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a 3,6-dimethylcarbazolyl group, and a 3,6-di-tert-butylcarbazolyl group are preferred.

[0275] In the following structural formulas, * indicates a bonding position.

[0276] [Chemistry 21]

[0277]

[0278] [Chemistry 22]

[0279]

[0280] [Chemistry 23]

[0281]

[0282] [Chemistry 24]

[0283]

[0284] [Chemistry 25]

[0285]

[0286] [Chemistry 26]

[0287]

[0288] [Chemistry 27]

[0289]

[0290] [Chemistry 28]

[0291]

[0292] [Chemistry 29]

[0293]

[0294] [Chemistry 30]

[0295]

[0296] [Chemistry 31]

[0297]

[0298] [Chemistry 32]

[0299]

[0300] [Chemistry 33]

[0301]

[0302] [Chemistry 34]

[0303]

[0304] The polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1) is preferably a structure comprising at least one tertiary alkyl group (tert-butyl or tert-amyl, etc.), neopentyl or adamantyl represented by the formula (tR), and more preferably a tertiary alkyl group (tert-butyl or tert-amyl, etc.) represented by the formula (tR). The reason is that the intermolecular distance is increased by such a bulky substituent, so the luminescence quantum yield (PLQY) is improved. In addition, as a substituent, a diarylamino group is also preferred. Furthermore, a diarylamino group substituted by a base of formula (tR), a carbazolyl group substituted by a base of formula (tR) (preferably N-carbazolyl) or a benzocarbazolyl group substituted by a base of formula (tR) (preferably N-benzocarbazolyl) is also preferred. As a substitution form of the base of formula (tR) for diarylamino, carbazolyl and benzocarbazolyl, examples of hydrogen substitution of part or all of the hydrogen of the aryl ring or benzene ring in these groups by the base of formula (tR) can be cited.

[0305] In the structure composed of one or more structural units represented by formula (1), the substituent of the aryl ring or heteroaryl ring may be a substituent represented by the following formula (A20).

[0306] [Chemistry 35]

[0307]

[0308] The substituent represented by formula (A20) is bonded to two adjacent atoms on the aryl ring or heteroaryl ring at two * positions. In formula (A20), L is >NR, >O, >Si(-R)2 or >S, R of the >NR is a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl or substituted or unsubstituted cycloalkyl, R of the >Si(-R)2 is hydrogen, a substitutable aryl, a substitutable alkyl or a substitutable cycloalkyl, and they may be bonded to each other via a linking group, and at least one of R of the >NR and the >Si(-R)2 may be bonded to the aryl ring or heteroaryl ring via a linking group or a single bond,

[0309] r is an integer from 1 to 4,

[0310] R A are independently hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted cycloalkyl, any R A Can be connected to any other R through a linking group or a single bond A Mutually bonded.

[0311] Examples of the substituent include substituents represented by any of the following.

[0312] [Chemistry 36]

[0313]

[0314] In each formula, the * only needs to be bonded to two or three consecutive (adjacent) atoms on any aryl ring or heteroaryl ring.

[0315] <Cycloalkane condensation>

[0316] In the polycyclic aromatic compound having a structure consisting of one or two of the structural units represented by formula (1), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane.

[0317] The cycloalkane may be a cycloalkane having 3 to 24 carbon atoms. At least one hydrogen in the cycloalkane may be substituted by 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 by -O-.

[0318] The cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, wherein at least one hydrogen in the cycloalkane may be substituted by 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.

[0319] Examples of the “cycloalkane” include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0320] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.2]octane, adamantane, diadamantane, decahydronaphthalene and decahydroazulene, and alkyl (especially methyl)-substituted, halogen (especially fluorine)-substituted and deuterium-substituted products thereof having 1 to 5 carbon atoms.

[0321] Among the examples, a structure having at least one substituent on the carbon at the α position of the cycloalkane (a carbon adjacent to the carbon at the condensation site in the cycloalkane condensed to an aryl ring or a heteroaryl ring) is preferred, for example, as shown in the following structural formula, a structure having two substituents on the carbon at the α position is more preferred, and a structure having two substituents on both carbons at the α position is further preferred (having a total of four substituents). As the substituent, alkyl groups (especially methyl) having 1 to 5 carbon atoms, halogens (especially fluorine) and deuterium are listed. Particularly preferred is a structure in which a partial structure represented by the following formula (B11) or the following formula (B12) is bonded to adjacent carbon atoms in an aryl ring or a heteroaryl ring, and more preferred is a structure in which a partial structure represented by the following formula (B11) is bonded to adjacent carbon atoms in an aryl ring or a heteroaryl ring.

[0322] [Chemistry 37]

[0323]

[0324] In each of formula (B11) and formula (B12), * represents a bonding position.

[0325] The number of cycloalkanes condensed on one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are condensed on a benzene ring (phenyl). * represents the bonding position, which can be any of the carbons that constitute the benzene ring and do not constitute the cycloalkane. The cycloalkanes condensed as in formula (Cy-1-4) and formula (Cy-2-4) can also be condensed with each other. This is true whether the condensed ring (base) is an aryl ring or heteroaryl ring other than the benzene ring (phenyl), or whether the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0326] [Chemistry 38]

[0327]

[0328] At least one -CH2- in the cycloalkane may be substituted with -O-. For example, the following shows an example in which one or more -CH2- in the cycloalkane condensed on a benzene ring (phenyl) is substituted with -O-. This is true whether the condensed ring (base) is an aryl ring or heteroaryl ring other than the benzene ring (phenyl), or whether the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0329] [Chemistry 39]

[0330]

[0331] The cycloalkane may be substituted with at least one substituent, and as the substituent, any substituent selected from the substituent group Z can be cited. Among these substituents, alkyl groups (e.g., alkyl groups having 1 to 6 carbon atoms) and cycloalkyl groups (e.g., cycloalkyl groups having 3 to 14 carbon atoms) are preferred. In addition, it is also preferred that any hydrogen group is substituted with a halogen (e.g., fluorine) or deuterium. In addition, when a cycloalkyl group is substituted, it may be a substitution form that forms a spiro ring structure. For example, the following shows an example in which a spiro ring structure is formed in a cycloalkane condensed on a benzene ring (phenyl). Regarding the * in each structural formula, in the case of a benzene ring, it refers to a benzene ring contained in the skeletal structure of the compound, and in the case of a phenyl group, it refers to a bond that is substituted in the skeletal structure of the compound.

[0332] [Chemistry 40]

[0333]

[0334] Examples of the cycloalkane condensation include: a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) in which an aryl ring or heteroaryl ring in any of rings A, B and C is condensed with a cycloalkane; a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) in which an aryl ring or heteroaryl ring in ring D is condensed with a cycloalkane; 1 or X 2 NR NX R NX A form in which the aryl ring or heteroaryl ring in is condensed with a cycloalkane; and a form in which the aryl ring or heteroaryl ring is condensed with a cycloalkane when any of the other substituents is a group containing an aryl ring or a heteroaryl ring.

[0335] In addition, by introducing a cycloalkane structure into a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1), a further reduction in the melting point or sublimation temperature can be expected. The situation means that in the sublimation purification, which is almost indispensable as a purification method for organic devices such as organic EL elements requiring high purity, since the purification can be carried out at a lower temperature, the thermal decomposition of the material can be avoided. In addition, the situation is also the same for the vacuum evaporation process, which is a powerful means for making organic devices such as organic EL elements. The process can be implemented at a lower temperature, so the thermal decomposition of the material can be avoided, and a high-performance organic device can be obtained as a result. In addition, since the solubility in the organic solvent is improved by introducing the cycloalkane structure, it can also be applied to the production of components using a coating process. Among them, the present invention is not particularly limited to these principles.

[0336] <Substitution with heavy stable isotopes>

[0337] Each element in the polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) is an element containing multiple isotopes that occur naturally in a natural occurrence ratio unless otherwise specified. All or part of the elements in each structural formula may contain more than the natural occurrence ratio (for example, in the case of boron-11 ( 11 In the present specification, it is referred to as "replaced 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), at least one sulfur may be substituted with sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36( 36 S), at least one oxygen may be substituted with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon may be substituted with carbon-13 (13 C), at least one boron may be formed from boron-11 ( 11 By replacing at least a portion of the elements with heavy stable isotopes, in particular by replacing at least one boron with boron-11 ( 11 B), the life of the organic electroluminescent device using the polycyclic aromatic compound represented by the formula (1) can be prolonged.

[0338] <Substitution using deuterium>

[0339] All or part of the hydrogen in the polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) may be deuterium. From the viewpoint of device life and high efficiency, it is more preferable that the hydrogen in the polycyclic aromatic compound is substituted with deuterium.

[0340] For example, in a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1), 1 ~R 11 Any hydrogen in 1 or X 2 NR NX R NX The hydrogen in the formula (1) may be substituted with deuterium, and among these, all or part of the hydrogen in the aryl or heteroaryl group may be substituted with deuterium. In addition, from the viewpoint of durability, it is also preferred that all or part of the hydrogen in the polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) is deuterated.

[0341] <Specific examples of polycyclic aromatic compounds>

[0342] As specific examples of polycyclic aromatic compounds having a structure composed of one or more structural units represented by formula (1), any of the following compounds can be cited. However, the polycyclic aromatic compounds having a structure composed of one or more structural units represented by formula (1) are not limited to the following specific examples.

[0343] [Chemistry 41]

[0344]

[0345] [Chemistry 42]

[0346]

[0347] [Chemistry 43]

[0348]

[0349] [Chemistry 44]

[0350]

[0351] [Chemistry 45]

[0352]

[0353] [Chemistry 46]

[0354]

[0355] [Chemistry 47]

[0356]

[0357] [Chemistry 48]

[0358]

[0359] [Chemistry 49]

[0360]

[0361] [Chemistry 50]

[0362]

[0363] [Chemistry 51]

[0364]

[0365] [Chemistry 52]

[0366]

[0367] [Chemistry 53]

[0368]

[0369] [Chemistry 54]

[0370]

[0371] [Chemistry 55]

[0372]

[0373] [Chemistry 56]

[0374]

[0375] [Chemistry 57]

[0376]

[0377] [Chemistry 58]

[0378]

[0379] [Chemistry 59]

[0380]

[0381] [Chemistry 60]

[0382]

[0383] [Chemistry 61]

[0384]

[0385] [Chemistry 62]

[0386]

[0387] [Chemistry 63]

[0388]

[0389] [Chemistry 64]

[0390]

[0391] [Chemistry 65]

[0392]

[0393] [Chemistry 66]

[0394]

[0395] [Chemistry 67]

[0396]

[0397] [Chemistry 68]

[0398]

[0399] [Chemistry 69]

[0400]

[0401] [Chemistry 70]

[0402]

[0403] [Chemistry 71]

[0404]

[0405] [Chemistry 72]

[0406]

[0407] [Chemistry 73]

[0408]

[0409] [Chemistry 74]

[0410]

[0411] [Chemistry 75]

[0412]

[0413] [Chemistry 76]

[0414]

[0415] [Chemistry 77]

[0416]

[0417] [Chemistry 78]

[0418]

[0419] [Chemistry 79]

[0420]

[0421] [Chemistry 80]

[0422]

[0423] [Chemistry 81]

[0424]

[0425] [Chemistry 82]

[0426]

[0427] [Chemistry 83]

[0428]

[0429] [Chemistry 84]

[0430]

[0431] [Chemistry 85]

[0432]

[0433] [Chemistry 86]

[0434]

[0435] [Chemistry 87]

[0436]

[0437] [Chemistry 88]

[0438]

[0439] [Chemistry 89]

[0440]

[0441] [Chemistry 90]

[0442]

[0443] [Chemistry 91]

[0444]

[0445] [Chemistry 92]

[0446]

[0447] [Chemistry 93]

[0448]

[0449] [Chemistry 94]

[0450]

[0451] [Chemistry 95]

[0452]

[0453] [Chemistry 96]

[0454]

[0455] [Chemistry 97]

[0456]

[0457] [Chemistry 98]

[0458]

[0459] [Chemistry 99]

[0460]

[0461] [Chemical 100]

[0462]

[0463] <Application of polycyclic aromatic compounds in polymers>

[0464] The polycyclic aromatic compound of the present invention can also be used in materials for organic devices, such as materials for organic electroluminescent elements, materials for organic field effect transistors, materials for organic thin-film solar cells, or wavelength conversion filters, as the following polymer compound (the monomer used to obtain the polymer compound has a polymerizable substituent), or a polymer crosslinked body (the polymer compound used to obtain the polymer crosslinked body has a crosslinkable substituent), or the following pendant polymer compound (the reactive compound used to obtain the pendant polymer compound has a reactive substituent), or a pendant polymer crosslinked body (the pendant polymer compound used to obtain the pendant polymer crosslinked body has a crosslinkable substituent), wherein the polymer compound is obtained by polymerizing the reactive compound substituted with a reactive substituent in the polycyclic aromatic compound of the present invention as a monomer, the polymer crosslinked body is obtained by further crosslinking the polymer compound, the pendant polymer compound is obtained by reacting a main chain polymer with the reactive compound, and the pendant polymer crosslinked body is obtained by further crosslinking the pendant polymer compound.

[0465] The reactive substituent (including the polymerizable substituent, the cross-linkable substituent, and the reactive substituent for obtaining the pendant type polymer, hereinafter also referred to as "reactive substituent") is not particularly limited as long as it is a substituent that can make the polycyclic aromatic compound high molecular weight, a substituent that can further cross-link the polymer compound obtained in this way, and a substituent that can undergo a pendant reaction in the main chain type polymer, but preferably a substituent of the following structure. * in each structural formula represents a bonding position.

[0466] [Chemistry 101]

[0467]

[0468] Z is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene group having 1 to 12 carbon atoms, an oxyalkylene group having 1 to 12 carbon atoms, and a polyoxyalkylene group having 1 to 12 carbon atoms. Among the substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10), or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3), or formula (XLS-17) is more preferred.

[0469] Such polymer compounds, polymer crosslinked bodies, pendant polymer compounds, and pendant polymer crosslinked bodies may contain, in addition to the repeating units of the polycyclic aromatic compounds of 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 tetracene, substituted or unsubstituted triazines, substituted or unsubstituted carbazoles, substituted or unsubstituted tetraphenylsilanes, substituted or unsubstituted spirofluorenes, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofurans as repeating units.

[0470] As the substituent in these repeating units, for example, at least one substituent selected from the substituent group Z can be mentioned.

[0471] <Method for producing polycyclic aromatic compounds>

[0472] The polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) is basically firstly formed by a bonding group (X 1 and X 2 ) makes the condensed ring containing each benzene ring and X bond, thus manufactures intermediate (first reaction), thereafter, utilizes bonding group (base containing boron) to make the condensed ring containing each benzene ring bond, thus can manufacture final product (second reaction).In the first reaction, for example, if it is etherification reaction, then can utilize general reactions such as nucleophilic substitution reaction, Ullmann reaction (Ullmann Reaction), if it is amination reaction, then can utilize general reactions such as Buchwald-Hartwig reaction (Buchwald-Hartwig Reaction), nucleophilic substitution reaction, Goldberg amination (Goldberg Amination).In addition, in the second reaction, can utilize tandem hetero-Friedel-Crafts reaction (Tandem Hetero-Friedel-Crafts Reaction) (continuous aromatic electrophilic substitution reaction, the same below).Can manufacture target compound by using raw material with desired condensed ring somewhere in reaction process or appending the process that ring is condensed.

[0473] [Production method via intermediate 1]

[0474] The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each of the following steps, reference can be made to the description of International Publication No. 2015 / 102118.

[0475] The following reaction is described, which includes the following reaction steps: synthesizing the following intermediate from a halogenated precursor, reacting X in the following intermediate 1 with an organic base compound,1 With X 2 and using a reagent selected from the group consisting of boron halides, boron amide halides (e.g., BCl3, BBr3, or BI3, etc.), boron alkoxides, and boron aryloxides to exchange the metal with boron; and using a Brünster base to use the boron to replace R 4 ~R 7 The condensed ring bonded to R 8 ~R 11 The halogen atom (Hal) in the formula may be any one of F, Cl, Br, and I, and may be the same or independently different, and may be appropriately selected in consideration of the reactivity of the substrate.

[0476] [Chemistry 102]

[0477]

[0478] Examples of the metallating reagent used in the halogen-metal exchange reaction in the process described so far include alkyl lithiums such as methyl lithium, n-butyl lithium, sec-butyl lithium, and tert-butyl lithium, isopropyl magnesium chloride, isopropyl magnesium bromide, phenyl magnesium chloride, phenyl magnesium bromide, and a lithium chloride complex of isopropyl magnesium chloride known as Turbo Grignard reagent.

[0479] In addition, as the metallating reagent used in the ortho-metal exchange reaction in the process described so far, in addition to the above reagents, organic base compounds such as lithium diisopropylamide, lithium tetramethylpiperidinide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium chloride tetramethylpiperidinyl magnesium-lithium chloride complex, and tri-n-butyl lithium magnesiumate can also be listed.

[0480] Furthermore, examples of additives that promote the reaction when using alkyl lithium as the metallizing agent include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethylpropyleneurea.

[0481] In addition, examples of the Lewis acid used in the process described so far include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, BI3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, CoBr3, etc. In addition, substances obtained by supporting these Lewis acids on a solid may also be used in the same manner.

[0482] In addition, examples of the Brønsted acid used in the process described so far include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboxylic acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride, etc. In addition, examples of solid Brønsted acid include Amberlist (trade name: Dow Chemical), Nafion (trade name: Dupont), zeolite, Taycacure (trade name: Tayca Co., Ltd.), etc.

[0483] In addition, examples of amines that can be added in the processes 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-tert-butylamine.

[0484] In addition, examples of the solvent used in the processes described so far include o-dichlorobenzene, chlorobenzene, toluene, benzene, dichloromethane, chloroform, dichloroethylene, benzotrifluoride, decahydronaphthalene, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, and methyl-tert-butyl ether.

[0485] In the process, in order to promote the tandem hetero Friedel-Crafts reaction, a Brünster base or a Lewis acid may also be used. Wherein, in the case of using boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide, as the aromatic electrophilic substitution reaction proceeds, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated, so it is effective to use a Brünster base that captures the acid. On the other hand, in the case of using boron amination halides and boron alkoxylates, as the aromatic electrophilic substitution reaction proceeds, amines and alcohols are generated, so in most cases, there is no need to use a Brünster base, but because the ability of amino or alkoxy to dissociate is low, it is effective to use a Lewis acid that promotes its dissociation.

[0486] The polycyclic aromatic compound of the present invention also includes compounds in which at least a portion of hydrogen is substituted with deuterium or with various substituents, and such compounds can be synthesized in the same manner as above by using raw materials deuterated or derivatized at desired positions.

[0487] <2. Organic devices>

[0488] The polycyclic aromatic compound of the present invention can be used as a material for organic devices, such as organic electroluminescent elements, organic field effect transistors, and organic thin-film solar cells.

[0489] The polycyclic aromatic compound of the present invention can be used as a material for an organic device. Examples of organic devices include organic electroluminescent elements, organic field effect transistors, and organic thin-film solar cells, and are preferably organic electroluminescent elements. The polycyclic aromatic compound of the present invention is preferably a material for an organic electroluminescent element, more preferably a material for a light-emitting layer (light-emitting material), and most preferably a dopant material for a light-emitting layer.

[0490] <2-1. Organic electroluminescent element>

[0491] <2-1-1. Structure of organic electroluminescent element>

[0492] Figure 1 This is a schematic cross-sectional view showing an example of an organic EL element.

[0493] Figure 1 The organic EL element 100 shown includes: a substrate 101, an anode 102 arranged on the substrate 101, a hole injection layer 103 arranged on the anode 102, a hole transport layer 104 arranged on the hole injection layer 103, a light-emitting layer 105 arranged on the hole transport layer 104, an electron transport layer 106 arranged on the light-emitting layer 105, an electron injection layer 107 arranged on the electron transport layer 106, and a cathode 108 arranged on the electron injection layer 107.

[0494] In addition, the organic EL element 100 can also reverse the production order to form a structure such as the following, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

[0495] The above-mentioned layers are not all indispensable layers, and the minimum structural unit is set to a structure including an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that can be set arbitrarily. In addition, the above-mentioned layers may each include a single layer or a plurality of layers.

[0496] The morphology of the layers constituting the organic EL element may be, in addition to the structural morphology of “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron injection layer / cathode”. The structural morphology of the substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", and "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0497] <2-1-2. Light-emitting layer in organic electroluminescent element>

[0498] The polycyclic aromatic compound of the present invention is preferably used as a material for forming any one or more organic layers in an organic electroluminescent element, and is more preferably used as a material for forming a light-emitting layer. The light-emitting layer 105 is a layer that emits light by recombination of holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. As a material for forming the light-emitting layer 105, any compound (luminescent compound) that is excited to emit light by recombination of holes and electrons can be used, and preferably a compound that can form a stable thin film shape and shows strong light-emitting (fluorescence) efficiency in a solid state. The polycyclic aromatic compound of the present invention can be used as a material for the light-emitting layer, as a dopant material, or as a host material, but is preferably used as a material for the light-emitting layer, and is more preferably used as a dopant material.

[0499] In addition, there are examples where an assist dopant and an emitting dopant are used together as a dopant, but in this specification, when simply described as a "dopant", it means an emitting dopant when an assist dopant is not used.

[0500] The polycyclic aromatic compound including the structural unit represented by the formula (1) can be used as an emitting dopant for a TTF device utilizing a phenomenon in which a singlet exciton is generated from a plurality of triplet excitons (Triplet-Triplet Fusion (TTF)).

[0501] In addition, a polycyclic aromatic compound containing a structural unit represented by formula (1) can be used as an emitting dopant of a TADF element as a "thermally active delayed phosphor". In a "thermally active delayed phosphor", by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, an inverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, which usually has a low transition probability, is efficiently generated, thereby showing luminescence from the singlet state (thermally active delayed fluorescence, TADF). In normal fluorescent luminescence, 75% of the triplet excitons generated by current excitation pass through the thermal deactivation path and therefore cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescent luminescence, which can achieve a highly efficient organic EL element.

[0502] The light-emitting layer may be a single layer or may include multiple layers, either of which may be used, and each of which is formed by a light-emitting layer material (main material, dopant material). The main material and the dopant material may be one type or a combination of multiple types, either of which may be used. The dopant material may be contained in the entire main material or in part of the main material, either of which may be used. As a doping method, it may be formed by a co-evaporation method with the main material, or it may be pre-mixed with the main material and then evaporated simultaneously. The following shows a specific example of a dopant combined with the compound of the present invention when the dopant is set to a combination of multiple types.

[0503] [Chemistry 103]

[0504]

[0505] [Chemistry 104]

[0506]

[0507] [Chemistry 105]

[0508]

[0509] [Chemistry 106]

[0510]

[0511] [Chemistry 107]

[0512]

[0513] From the viewpoint of durability, it is also preferred that a part or all of the hydrogen atoms of the dopant material be deuterated.

[0514] The amount of the host material used varies depending on the type of the host material and can be determined by matching the characteristics of the host material. The base amount of the host material used is preferably 50% to 99.999% by mass of the total mass of the material for the light-emitting layer, more preferably 80% to 99.95% by mass, and further preferably 90% to 99.9% by mass.

[0515] The amount of the dopant material used varies depending on the type of the dopant material, and can be determined by matching the characteristics of the dopant material. The basis for the amount of the dopant material used is preferably 0.001% to 50% by mass of the total mass of the material for the light-emitting layer, more preferably 0.05% to 20% by mass, and further preferably 0.1% to 10% by mass. If it is within the above range, it is preferred, for example, in terms of preventing concentration quenching.

[0516] On the other hand, in an organic EL element using a thermally active delayed fluorescence dopant material, it is preferred that the amount of the dopant material used is low in terms of preventing the concentration quenching phenomenon, but it is preferred that the amount of the dopant material used is high in terms of the efficiency of the thermally active delayed fluorescence mechanism. Furthermore, in an organic EL element using a thermally active delayed fluorescence auxiliary dopant material, it is preferred that the amount of the auxiliary dopant material used is low in terms of the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant material compared to the amount of the dopant material used. The polycyclic aromatic compound of the present invention can be used as a dopant (also referred to as an emission dopant) in an organic EL element using a thermally active delayed fluorescence auxiliary dopant material.

[0517] When an auxiliary dopant material is used, the usage amounts of the host material, the auxiliary dopant material and the dopant material are 40% to 99.999% by mass, 59% to 1% by mass and 20% to 0.001% by mass, respectively, based on the total amount of the material for the light-emitting layer, preferably 60% to 99.99% by mass, 39% to 5% by mass and 10% to 0.01% by mass, respectively, and more preferably 70% to 99.95% by mass, 29% to 10% by mass and 5% to 0.05% by mass, respectively.

[0518] <Main material>

[0519] Examples of the host material include anthracene, pyrene, dibenzo[pi]ne, and or condensed ring derivatives such as fluorene, bistyryl derivatives such as bistyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, and the like.

[0520] In addition, from the viewpoint of durability, it is also preferred that part or all of the hydrogen atoms of the host material are deuterated. Furthermore, it is also preferred that a host compound in which part or all of the hydrogen atoms are deuterated is combined with a dopant compound in which part or all of the hydrogen atoms are deuterated to form the light-emitting layer.

[0521] [Compound represented by any one of formula (H1), formula (H2) and formula (H3)]

[0522] As the host material, for example, a compound represented by any of the following formula (H1), formula (H2), and formula (H3) can be used.

[0523] [Chemistry 108]

[0524]

[0525] In formula (H1), formula (H2) and formula (H3), L1 is a single bond, or a divalent group containing at least an arylene group or a heteroarylene group. 1 L may be a single bond, or an arylene group having 6 to 24 carbon atoms, a heteroarylene group having 2 to 24 carbon atoms, a heteroarylene arylene group having 6 to 24 carbon atoms, or an arylene heteroarylene group having 6 to 24 carbon atoms, or a divalent group formed by linking any two of these groups by -O-, -S-, -CH2-, -Si(-Arx)2- (Arx is an aryl group) or a cycloalkylene group. 1 The arylene group in is preferably an arylene group having 6 to 16 carbon atoms, more preferably an arylene group having 6 to 12 carbon atoms, and particularly preferably an arylene group having 6 to 10 carbon atoms. Specifically, divalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, and a fluorene ring can be mentioned. 1 The heteroarylene group in the formula (I) is preferably a heteroarylene group having 2 to 24 carbon atoms, more preferably a heteroarylene group having 2 to 20 carbon atoms, further preferably a heteroarylene group having 2 to 15 carbon atoms, and particularly preferably a heteroarylene group having 2 to 10 carbon atoms. Specifically, examples thereof include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazan ring), a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, divalent groups such as isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiol ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, and thianthrene ring. At least one hydrogen in the compounds represented by the above formulas may be substituted with at least one group selected from the substituent group Z or deuterium, for example, alkyl having 1 to 6 carbon atoms, cyano, halogen or deuterium.

[0526] As preferred specific examples, compounds represented by any of the following structural formulas can be cited. In addition, in the following structural formulas, at least one hydrogen can be substituted by halogen, cyano, alkyl having 1 to 4 carbon atoms (such as methyl or tert-butyl), phenyl or naphthyl.

[0527] [Chemistry 109]

[0528]

[0529] [Chemistry 110]

[0530]

[0531] [Chemistry 111]

[0532]

[0533] [Chemistry 112]

[0534]

[0535] [Anthracene compounds]

[0536] Examples of the main anthracene compound include compounds represented by formula (3-H) and compounds represented by formula (3-H2).

[0537] [Chemistry 113]

[0538]

[0539] In formula (3-H),

[0540] X and Ar 4 are each independently hydrogen or selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, optionally substituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, optionally substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio or substituted silyl, all of X and Ar 4 It will not become hydrogen at the same time.

[0541] At least one hydrogen in the compound represented by formula (3-H) may be substituted with a halogen, a cyano group, a deuterium group or an optionally substituted heteroaryl group.

[0542] In addition, the structure represented by formula (3-H) can also be used as a unit structure to form a polymer (preferably a dimer). In the case, for example, the unit structures represented by formula (3-H) are bonded to each other via X, and as the X, a single bond, an arylene group (phenylene, biphenylene and naphthylene, etc.) and a heteroarylene group (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring and phenyl-substituted carbazole ring, etc., having a divalent bonding valence) can be listed.

[0543] Preferred embodiments of the anthracene compound are described below. The definitions of the symbols in the following structures are the same as those described above.

[0544] [Chemistry 114]

[0545]

[0546] In formula (3-H), X is independently a group represented by formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3-H) at *. Preferably, two Xs are not simultaneously represented by formula (3-X3). More preferably, two Xs are not simultaneously represented by formula (3-X2).

[0547] In addition, the structure represented by formula (3-H) can also be used as a unit structure to form a polymer (preferably a dimer). In the case, for example, the unit structures represented by formula (3-H) are bonded to each other via X, and as the X, a single bond, an arylene group (phenylene, biphenylene and naphthylene, etc.) and a heteroarylene group (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring and phenyl-substituted carbazole ring, etc., having a divalent bonding valence) can be listed.

[0548] The naphthylene moiety in formula (3-X1) and formula (3-X2) can be condensed with one benzene ring. The structure formed by condensation in this manner is shown below.

[0549] [Chemistry 115]

[0550]

[0551] Ar 1 and Ar 2 are independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, phenyl, triphenylene, pyrene, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 In the case of a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0552] Ar 3 is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, phenyl, triphenylene, pyrene, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 3 In the case of a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by the straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (3-H) is directly bonded to the group represented by formula (A).

[0553] In addition, Ar 3 It may have a substituent, Ar 3At least one hydrogen in the alkyl group may be replaced by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, substituted with a phenyl group, a triphenylene group, a pyrene group, or a group represented by formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). 3 When the substituent is a group represented by formula (A), the group represented by formula (A) is in the position * and Ar in formula (3-X3) 3 Bond.

[0554] Ar 4 Each independently represents hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or a silyl group substituted with an alkyl group having 1 to 4 carbon atoms (such as methyl, ethyl, and tert-butyl) and / or a cycloalkyl group having 5 to 10 carbon atoms.

[0555] In addition, the hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may also be replaced by a group represented by formula (A). In the case of replacement by a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3-H) at the *.

[0556] The group represented by formula (A) is one of substituents that the anthracene compound represented by formula (3-H) may have.

[0557] [Chemistry 116]

[0558]

[0559] In formula (A), Y is -O-, -S- or >NR 29 , R 21 ~R 28 are each independently hydrogen, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, an optionally substituted amino group, a halogen group, a hydroxyl group or a cyano group, and R 21 ~R 28 The adjacent groups in the group may be bonded to each other to form a hydrocarbon ring, an aromatic ring or a heteroaromatic ring. 29 is hydrogen or an aryl group which may be substituted.

[0560] Y in formula (A) is preferably -O-.

[0561] As R 21 ~R 28 Examples of the “substituted amino group” in the “amino group which may be substituted” include diarylamino, diheteroarylamino, and arylheteroarylamino.

[0562] As Y's ">NR 29 "R" 29 is hydrogen or an aryl group which may be substituted.

[0563] R 21 ~R 28 The adjacent groups in can be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where a ring is not formed is a group represented by the following formula (A-1). As the case where a ring is formed, for example, the groups represented by the following formulas (A-2) to (A-14) can be listed. In addition, at least one hydrogen in the group represented by any one of formulas (A-1) to (A-14) can be substituted by an alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (two aryl groups can be bonded to each other via a linking group) substituted amino, diheteroaryl substituted amino, arylheteroaryl substituted amino, halogen, hydroxyl or cyano.

[0564] [Chemistry 117]

[0565]

[0566] Examples of the ring formed by mutually bonding adjacent groups include a hydrocarbon ring such as a cyclohexane ring, and examples of the aryl ring or heteroaryl ring include the above R 21 ~R 28 The ring structure described in the "aryl" or "heteroaryl" in formula (A-1) is formed by condensing with one or two benzene rings.

[0567] The group represented by formula (A) is a group obtained by removing a hydrogen atom at any position of formula (A), and * represents the position. That is, the group represented by formula (A) can be bonded at any position. For example, it can be bonded to any carbon atom on the two benzene rings in the structure of formula (A), R 21 ~R 28 The atoms on any ring formed by bonding the adjacent groups in the formula (A) to each other, or the ">NR" as Y in the structure of the formula (A) 29 "R 29 Any position in or ">NR 29 "N(R 29 The same applies to the group represented by any one of formulae (A-1) to (A-14).

[0568] As the group represented by formula (A), for example, a group represented by any one of formulas (A-1) to (A-14) can be listed, preferably a group represented by any one of formulas (A-1) to (A-5) and (A-12) to (A-14), more preferably a group represented by any one of formulas (A-1) to (A-4), further preferably a group represented by any one of formulas (A-1), (A-3) and (A-4), and particularly preferably a group represented by formula (A-1).

[0569] Examples of the group represented by formula (A) include the following groups: Y and * in the formula have the same meanings as described above.

[0570] [Chemistry 118]

[0571]

[0572] [Chemistry 119]

[0573]

[0574] In the compound represented by formula (3-H), the group represented by formula (A) is preferably in a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3) and Ar in formula (3-X3). 3 The form of any bond in .

[0575] In addition, all or part of the hydrogen atoms in the chemical structure of the anthracene compound represented by the formula (3-H) may be deuterium atoms.

[0576] The anthracene compound serving as a host may be, for example, a compound represented by the following formula (3-H2).

[0577] [Chemistry 120]

[0578]

[0579] In formula (3-H2), Ar c is an aryl group which may be substituted or a heteroaryl group which may be substituted, R c is hydrogen, alkyl, or cycloalkyl, Ar 11 ,Ar 12 ,Ar 13 ,Ar 14 ,Ar 15 , A 16 ,Ar 17 and Ar 18Each of the above groups is independently hydrogen, a substitutable aryl group, a substitutable heteroaryl group, a substitutable diarylamino group (two aryl groups may be bonded to each other via a linking group), a substitutable diheteroarylamino group (two heteroaryl groups may be bonded to each other via a linking group), a substitutable arylheteroarylamino group (aryl and heteroaryl groups may be bonded to each other via a linking group), a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable alkenyl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable arylthio group, or a substitutable silanyl group. At least one hydrogen in the compound represented by the formula (3-H2) may be substituted by halogen, cyano or deuterium.

[0580] As the "aryl group which may be substituted", a group represented by any one of the following formulas (3-H2-X1) to (3-H2-X8) is also preferred.

[0581] [Chemistry 121]

[0582]

[0583] In formula (3-H2-X1) to formula (3-H2-X8), * represents a bonding position. In formula (3-H2-X1) to formula (3-H2-X3), Ar 21 ,Ar 22 and Ar 23 are independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, In the description of formula (3-H2), the group represented by formula (A) is the same as the group described in the anthracene compound represented by formula (3-H).

[0584] In formula (3-H2-X4) to formula (3-H2-X8), Ar 24 ,Ar 25 ,Ar 26 ,Ar 27 ,Ar 28 ,Ar 29 , and Ar 30 are independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, In addition, any one or two or more hydrogen atoms in each of the groups represented by formula (3-H2-X1) to formula (3-H2-X8) may be substituted by an alkyl group having 1 to 6 carbon atoms (preferably a methyl group or a tert-butyl group).

[0585] Furthermore, preferred examples of the "aryl group which may be substituted" include phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, fluorenyl, A terphenyl group (particularly m-terphenyl-5′-group) substituted with one or more substituents selected from the group consisting of a terphenyl group, a triphenylene group, a pyrene group, and a group represented by formula (A).

[0586] Examples of the "optionally substituted heteroaryl group" include groups represented by formula (A). In addition, specific examples of the "optionally substituted aryl group" and the "optionally substituted heteroaryl group" include dibenzofuranyl, naphthobenzofuranyl, and phenyl-substituted dibenzofuranyl.

[0587] At least one hydrogen in the compound represented by formula (3-H2) may be substituted by halogen, cyano or deuterium. Examples of the "halogen" in the above case include fluorine, chlorine, bromine, and iodine. Particularly preferred are compounds in which all hydrogens in the compound represented by formula (3-H2) are substituted by deuterium.

[0588] In formula (3-H2), R c It is hydrogen, alkyl or cycloalkyl, preferably hydrogen, methyl or tert-butyl, more preferably hydrogen.

[0589] In the formula (3-H2), Ar is preferably 11 ~Ar 18 At least two of them are substituted aryl groups or substituted heteroaryl groups. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of substituted aryl groups and substituted heteroaryl groups are bonded to the anthracene ring.

[0590] Among the anthracene compounds represented by formula (3-H2), Ar 11 ~Ar 18 Two of the anthracene compounds are substituted aryl groups or substituted heteroaryl groups, and the other six are hydrogen, substituted alkyl groups, substituted cycloalkyl groups, substituted alkenyl groups or substituted alkoxy groups. That is, the anthracene compound represented by formula (3-H2) is more preferably a structure having three substituents selected from the group consisting of substituted aryl groups and substituted heteroaryl groups bonded to the anthracene ring.

[0591] Among the anthracene compounds represented by formula (3-H2), Ar 11 ~Ar 18 Any two of them are aryl or heteroaryl, and the other six are hydrogen, methyl or tert-butyl.

[0592] Furthermore, in the formula (3-H2), R c is hydrogen, and Ar 11 ~Ar 18 Any six of them are hydrogen.

[0593] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D), or formula (3-H2-E).

[0594] [Chemistry 122]

[0595]

[0596] In formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D) or formula (3-H2-E), Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 ' and Ar 18 'are independently phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, phenyl, triphenylene, pyrenyl, or a group represented by formula (A), at least one hydrogen in these groups may be replaced by phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, Here, when the hydrogen atoms of the methylene groups in the fluorenyl group and the benzofluorenyl group are substituted by phenyl groups, these phenyl groups may be bonded to each other via single bonds. c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 ' and Ar 18 The carbon atom of the anthracene ring of ' may be bonded with a methyl group or a tert-butyl group in place of hydrogen.

[0597] When Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 ' and Ar 18 When ' and ' are respectively substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl, they are preferably a group represented by any one of the formulas (3-H2-X1) to (3-H2-X8).

[0598] Ar c '、Ar 11'、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 ' and Ar 18 'More preferably, they are independently phenyl, biphenyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenyl (especially m-terphenyl-5'-yl), naphthyl, phenanthrenyl, fluorenyl, or a group represented by any one of the formulas (A-1) to (A-4). In this case, at least one hydrogen in these groups may be substituted by a phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, or a group represented by any one of the formulas (A-1) to (A-4).

[0599] In addition, at least one hydrogen in the compound represented by Formula (3-H2-A), Formula (3-H2-B), Formula (3-H2-C), Formula (3-H2-D) or Formula (3-H2-E) may be substituted by halogen, cyano, or deuterium. In addition, a deuterated form is preferred, and a form in which all anthracene rings are deuterated, or a form in which all hydrogen atoms are deuterated is preferred.

[0600] Particularly preferred anthracene compounds represented by formula (3-H2) include anthracene compounds represented by the following formula (3-H2-Aa).

[0601] [Chemistry 123]

[0602]

[0603] In the formula (3-H2-Aa), Ar c '、Ar 14 ' and Ar 15 'are independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, A group represented by any one of the formulae (A-1) to (A-11), wherein at least one hydrogen in these groups may be replaced by a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, Here, when the hydrogen atoms of the methylene groups in the fluorenyl group and the benzofluorenyl group are substituted by phenyl groups, these phenyl groups may be bonded to each other via single bonds. c '、Ar 14 ' and Ar 15 The carbon atom of the anthracene ring of ' may be substituted with a methyl group or a tert-butyl group instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with a halogen or a cyano group, and at least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with deuterium.

[0604] In the formula (3-H2-Aa), Ar c '、Ar 14 ' and Ar 15 'Preferably, they are independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the formulas (A-1) to (A-4), and at least one hydrogen in these groups may be substituted by a phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the formulas (A-1) to (A-4).

[0605] In the compound represented by the formula (3-H2-Aa), it is preferred that the carbon atom bonded to at least the 10-position of the anthracene ring (Ar c The hydrogen at the carbon to which the bond is attached is substituted with deuterium. That is, the compound represented by the formula (3-H2-Aa) is preferably a compound represented by the following formula (3-H2-Ab). In the formula (3-H2-Ab), D is deuterium, Ar c '、Ar 14 ' and Ar 15 ' is the same as the definition in formula (3-H2-Aa). D in formula (3-H2-Ab) means that at least the position is deuterated, and any one or more other hydrogens in formula (3-H2-Ab) may be deuterated at the same time, and it is also preferred that all hydrogens in formula (3-H2-Ab) are deuterated.

[0606] [Chemistry 124]

[0607]

[0608] Specific examples of anthracene compounds include compounds represented by formula (3-131-Y) to (3-182-Y), formula (3-183-N), formula (3-184-Y) to (3-284-Y), and compounds represented by formula (3-500) to (3-557), and formula (3-600) to (3-605), and formula (3-606-Y) to (3-626-Y). The hydrogen atoms in these formulas may be partially or completely substituted with deuterium, but particularly preferred forms of deuterium substitution are listed separately. Y in the formula may be -O-, -S-, >NR 29 (R 29 The definition is the same as above) or>C(-R 30 )2(R 30 is any one of an aryl group or an alkyl group that can be linked, R 29 For example, phenyl, R 30 For example, methyl group. Regarding the formula number, for example, when Y is O, the formula (3-131-Y) is the formula (3-131-O), and when Y is -S- or >NR 29In the case of, set it to formula (3-131-S) or formula (3-131-N) respectively.

[0609] [Chemistry 125]

[0610]

[0611] [Chemistry 126]

[0612]

[0613] [Chemistry 127]

[0614]

[0615] [Chemistry 128]

[0616]

[0617] [Chemistry 129]

[0618]

[0619] [Chemistry 130]

[0620]

[0621] [Chemistry 131]

[0622]

[0623] [Chemistry 132]

[0624]

[0625] [Chemistry 133]

[0626]

[0627] [Chemistry 134]

[0628]

[0629] [Chemistry 135]

[0630]

[0631] [Chemistry 136]

[0632]

[0633] [Chemistry 137]

[0634]

[0635] [Chemistry 138]

[0636]

[0637] [Chemistry 139]

[0638]

[0639] [Chemistry 140]

[0640]

[0641] [Chemistry 141]

[0642]

[0643] [Chemistry 142]

[0644]

[0645] [Chemistry 143]

[0646]

[0647] [Chemistry 144]

[0648]

[0649] In the above formula, D is deuterium.

[0650] Among these compounds, preferred are compounds of formula (3-131-Y) to (3-134-Y), formula (3-138-Y), formula (3-140-Y) to (3-143-Y), formula (3-150-Y), formula (3-153-Y) to (3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173-Y), formula (3-177-Y), formula (3-180-Y) to (3-183-N), formula (3-185-Y), formula (3-190-Y), formula (3-223-Y), formula (3-224-Y), -241-Y), formula (3-250-Y), formula (3-252-Y) to formula (3-254-Y), formula (3-270-Y) to formula (3-284-Y), formula (3-501), formula (3-507), formula (3-508), formula (3-509), formula (3-513), formula (3-514), formula (3-519), formula (3-521), formula (3-538) to formula (3-547) or formula (3-600) to formula (3-605), and formula (3-606-Y) to formula (3-626-Y). In addition, Y is preferably -O- or >NR 29 , more preferably -O-. In addition, a deuterium-substituted form is also preferred.

[0651] The anthracene compound may be a compound having a reactive group at a desired position of the anthracene skeleton, and in the case of an anthracene compound represented by formula (3-H), a compound having a reactive group at a desired position of the anthracene skeleton, 4 and a compound having a reactive group in a partial structure such as the structure of formula (A) as a starting material, and applying Suzuki coupling, Negishi coupling, or other known coupling reactions to manufacture. As the reactive group of the reactive compound, halogen or boric acid can be cited. As a specific manufacturing method, for example, reference can be made to the synthesis method of paragraphs

[0089] to

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

[0652] [Fluorene compounds]

[0653] The compound represented by formula (4-H) basically functions as a main body.

[0654] [Chemistry 145]

[0655]

[0656] In formula (4-H),

[0657] R 1 To R 10 are independently 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 (two aryl groups may be bonded to each other via a linking group), diheteroarylamino (two heteroaryl groups may be bonded to each other via a linking group), arylheteroarylamino (aryl and heteroaryl groups may be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen in these groups may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group, and R 1 With R 2 , R 2 With R 3 , R 3 With R 4 , R 5 With R 6 , R 6 With R 7 , R 7 With R 8 or R 9 With R 10They may be independently bonded to form a condensed ring or a spiro ring, and at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the formed ring via a single bond or a linking group), a diarylamino group (two aryl groups may be bonded to each other via a linking group), a diheteroarylamino group (two heteroaryl groups may be bonded to each other via a linking group), an arylheteroarylamino group (aryl and heteroaryl groups may be bonded to each other via a linking group), an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group or an aryloxy group, and at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, and at least one hydrogen in the compound represented by formula (4-H) may be substituted by a halogen, a cyano group or a deuterium group.

[0658] In addition, specific examples of heteroaryl groups include monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4) or (4-Ar5).

[0659] [Chemistry 146]

[0660]

[0661] In Formula (4-Ar1) to Formula (4-Ar5), Y 1 are independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, and at least one hydrogen in the structures of Formula (4-Ar1) to (4-Ar5) may be substituted by phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0662] These heteroaryl groups may be bonded to the fluorene skeleton in formula (4-H) via a single bond or a linking group. That is, the fluorene skeleton in formula (4-H) may be bonded not only directly to the heteroaryl group, but also bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0663] In addition, R in formula (4-H) 1 With R 2 , R 2 With R 3 , R 3 With R 4 , R 5 With R 6 , R 6 With R 7 or R 7 With R 8 can independently bond and form a condensed ring, R 9 With R 10 Can bond and form a spiro ring.1 To R 8 The condensed ring formed is a ring condensed on the benzene ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and examples of the structure containing the benzene ring in formula (4-H) include a naphthalene ring and a phenanthrene ring. 9 With R 10 The spiro ring formed is a ring spiro-bonded to the 5-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and examples thereof include a fluorene ring.

[0664] The compound represented by formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2) or formula (4-H-3), and R in formula (4-H) is 1 With R 2 The compound formed by condensation of the benzene ring formed by bonding, R in formula (4-H) 3 With R 4 The compound formed by condensation of the benzene ring formed by bonding, in formula (4-H) R 1 To R 8 A compound in which neither of is bonded.

[0665] [Chemistry 147]

[0666]

[0667] R in formula (4-H-1), formula (4-H-2) and formula (4-H-3) 1 To R 10 The definition of is the same as that of R in formula (4-H) 1 To R 10 The same, R in formula (4-H-1) and formula (4-H-2) 11 To R 14 The definition of is also the same as R in formula (4) 1 To R 10 same.

[0668] The compound represented by formula (4-H) is preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A) or formula (4-H-3A), and R in formula (4-H-1), formula (4-H-2) or formula (4-H-3) is 9 With R 10 A compound that is bonded to form a spiro-fluorene ring.

[0669] [Chemistry 148]

[0670]

[0671] R in formula (4-H-1A), formula (4-H-2A) and formula (4-H-3A)2 To R 7 The definition is the same as that of R in formula (4-H-1), formula (4-H-2) and formula (4-H-3) 2 To R 7 The same, and R in formula (4-H-1A) and formula (4-H-2A) 11 To R 14 The definition of is also the same as R in formula (4-H-1) and formula (4-H-2) 11 To R 14 same.

[0672] In addition, all or part of hydrogen in the compound represented by formula (4-H) may be substituted by halogen, cyano or deuterium.

[0673] More specific examples of the fluorene compound that is the subject of the present invention include compounds represented by the following structural formulas.

[0674] [Chemistry 149]

[0675]

[0676] [Dibenzo Compound]

[0677] Dibenzoylmethane as the main The compound is, for example, a compound represented by the following formula (5-H).

[0678] [Chemistry 150]

[0679]

[0680] In formula (5-H), R 1 To R 16 are independently hydrogen, aryl, heteroaryl (the heteroaryl may be connected to the dibenzoylmethane in formula (5-H) via a single bond or a linking group skeleton bond), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen in these groups may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, and R 1 To R 16 The adjacent groups in the formula (5-H) may be bonded to each other to form a condensed ring, and at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the formed ring via a single bond or a linking group), a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group or an aryloxy group, and at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, and at least one hydrogen in the compound represented by the formula (5-H) may be substituted by a halogen, a cyano group or a deuterium group.

[0681] Examples of the alkenyl group in the definition of formula (5-H) include alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, further preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0682] In addition, specific examples of the heteroaryl group include a monovalent group represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5).

[0683] [Chemistry 151]

[0684]

[0685] In formula (5-Ar1) to formula (5-Ar5), Y 1 are independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, and at least one hydrogen in the structures of Formula (5-Ar1) to (5-Ar5) may be substituted by phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0686] These heteroaryl groups may be linked to the dibenzoylmethane in formula (5-H) via a single bond or a linking group. That is, the dibenzo The skeleton and the heteroaryl group may be bonded not only directly but also via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0687] The compound represented by formula (5-H) is preferably 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 In the above case, R in formula (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R15 Preferably, each of them is independently hydrogen, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the monovalent group having the above structure can be connected with the dibenzofuran in formula (5-H) via phenylene, biphenylene, naphthylene, anthracenyl, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-) backbone bond), methyl, ethyl, propyl, or butyl.

[0688] 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 In the above case, R in formula (5-H) 3 , R 6 , R 11 , R 14 At least one (preferably one or two, more preferably one) of the above is a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) with an intervening single bond, phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O- or -OCH2CH2O-, and other than the above at least one (i.e., other than the position replaced by the monovalent group having the above structure) is hydrogen, phenyl, biphenylene, naphthyl, anthracene, methyl, ethyl, propyl or butyl, and at least one of the hydrogens may be substituted by phenyl, biphenylene, naphthyl, anthracene, methyl, ethyl, propyl or butyl.

[0689] In addition, as R in the formula (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 In the case of selecting a monovalent group having a structure represented by formula (5-Ar1) to formula (5-Ar5), at least one hydrogen in the structure can react with R in formula (5-H) 1 To R 16 to form a single bond.

[0690] The dibenzoylmethane as the subject of the present invention More specific examples of the compound include compounds represented by the following structural formulas.

[0691] [Chemistry 152]

[0692]

[0693] [Chemistry 153]

[0694]

[0695] The light-emitting layer material (host material and dopant material) can also be used in the light-emitting layer material as the following polymer compound or its polymer crosslinked product, or the following pendant polymer compound or its pendant polymer crosslinked product, wherein the polymer compound is obtained by polymerizing a reactive compound substituted with a reactive substituent in the light-emitting layer material (host material and dopant material) as a monomer, and the pendant polymer compound is obtained by reacting a main chain polymer with the reactive compound. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by formula (1) can be cited.

[0696] <Assisted dopant (thermally active delayed phosphor or phosphorescent material)>

[0697] The light-emitting layer in the organic electroluminescent element may contain a host compound as a first component, an auxiliary dopant as a second component, and an emission dopant as a third component. The polycyclic aromatic compound of the present invention is preferably used as an emission dopant. As the auxiliary dopant (compound), a thermally active delayed fluorescent substance or a phosphorescent material can be used.

[0698] In the following description, an organic electroluminescent element using a thermally activated delayed fluorescent substance as an auxiliary dopant is sometimes referred to as a "TAF element" (Thermal Activated Delayed Fluorescence (TADF) Assisting Fluorescence element). In addition, an organic electroluminescent element using a phosphorescent material as an auxiliary dopant is sometimes referred to as a PSF element (phosphorescence assisting element: phosphor-sensitized fluorescent element).

[0699] In this embodiment, the light-emitting layer may be a single layer or may include multiple layers, either of which is acceptable. In addition, the main compound, the auxiliary dopant and the polycyclic aromatic compound of the present invention may be contained in the same layer, or may include at least one component in multiple layers. The main compound, the auxiliary dopant and the polycyclic aromatic compound of the present invention contained in the light-emitting layer may be one type or a combination of multiple types, either of which is acceptable. The auxiliary dopant and the emission dopant may be contained in the entire main compound as a matrix, or may be contained in a part of the main compound as a matrix. The light-emitting layer doped with the auxiliary dopant and the emission dopant may be formed by the following methods: a method of forming a film of the main compound, the auxiliary dopant and the emission dopant by a ternary co-evaporation method; a method of pre-mixing the main compound, the auxiliary dopant and the emission dopant and then evaporating them simultaneously; a wet film-forming method of applying a composition (coating) for forming a light-emitting layer prepared by dissolving the main compound, the auxiliary dopant and the emission dopant in an organic solvent, etc.

[0700] The amount of the main compound used varies depending on the type of the main compound, and can be determined according to the characteristics of the main compound. The basis for the amount of the main compound used is preferably 40% to 99% by mass of the total mass of the light-emitting layer material, more preferably 50% to 98% by mass, and further preferably 60% to 95% by mass. If it is within the above range, it is preferred, for example, in terms of efficient charge transport and efficient energy transfer toward the dopant.

[0701] The amount of the auxiliary dopant used varies depending on the type of the auxiliary dopant, and can be determined based on the characteristics of the auxiliary dopant. The basis for the amount of the auxiliary dopant used is preferably 1% to 60% by mass of the total mass of the light-emitting layer material, more preferably 2% to 50% by mass, and further preferably 5% to 30% by mass. If it is within the above range, it is preferred, for example, in terms of efficiently moving energy to the emission dopant.

[0702] The amount of the emission dopant (compound having a boron atom) used varies depending on the type of the emission dopant, and can be determined based on the characteristics of the emission dopant. The basis for the amount of the emission dopant used is preferably 0.001% to 30% by mass of the total mass of the light-emitting layer material, more preferably 0.01% to 20% by mass, and further preferably 0.1% to 10% by mass. If it is within the above range, it is preferred, for example, in terms of preventing concentration quenching.

[0703] In terms of preventing concentration quenching, it is preferred that the amount of the emitting dopant used is low. In terms of the efficiency of the thermally activated delayed fluorescence mechanism, it is preferred that the amount of the auxiliary dopant used is high. Furthermore, in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the auxiliary dopant, it is preferred that the amount of the emitting dopant used is low compared to the amount of the auxiliary dopant used.

[0704] In this embodiment, as the host compound, a known compound can be used.

[0705] From the viewpoint of promoting rather than inhibiting the generation of TADF in the light-emitting layer, the lowest excited triplet energy level E(1, T, Sh) of the host compound obtained from the shoulder peak on the short-wavelength side of the peak of the phosphorescence spectrum is preferably higher than the lowest excited triplet energy levels E(2, T, Sh) and E(3, T, Sh) of the emitting dopant or the auxiliary dopant having the highest lowest excited triplet energy level 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 more, more preferably 0.03 eV or more, and further preferably 0.1 eV or more, compared to E(2, T, Sh) and E(3, T, Sh). In addition, a TADF-active compound may be used as the host compound.

[0706] The “host compound” in the TAF element refers to a compound having a lower lowest excited singlet energy level as determined from the shoulder peak on the short-wavelength side of the peak of the fluorescence spectrum than the thermally activated delayed phosphor as the second component and the emitting dopant as the third component.

[0707] As the main compound, for example, a compound having at least one of a carbazole ring and a furan ring can be cited, wherein a compound formed by bonding at least one of a furanyl group and a carbazole group to at least one of an arylene group and a heteroarylene group is preferred. As the main compound, for example, a compound represented by any one of the formulas (H1), (H2) and (H3) can be used, more specifically, mCP or mCBP can be used.

[0708] [Thermally activated delayed phosphor (auxiliary dopant)]

[0709] The so-called "thermally activated delayed fluorescence" refers to a compound that absorbs thermal energy and undergoes reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and is radiatively deactivated from the lowest excited singlet state, thereby emitting delayed fluorescence. The so-called "thermally activated delayed fluorescence" also includes the case where a higher-order triplet state is passed during the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, there are the papers published by Monkman et al. of Durham University (Nature Communications (7: 13680, digital object identifier (DOI) : 10.1038 / ncomms13680)), the papers published by Hosokai et al. of the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Science Advances (Sci. Adv.) (2017; 3: e1603282)), and the papers published by Sato et al. of Kyoto University (Scientific Reports (2017)). Reports)" (7: 4820, DOI: 10.1038 / s41598-017-05007-7)), and also a society publication by Sato et al. of Kyoto University (98th Spring Annual Meeting of the Chemical Society of Japan, publication number: 2I4-15, "Mechanism of high-efficiency luminescence in organic electroluminescence using diazaboranaphthoanthracene (DABNA) as a luminescent molecule", Graduate School of Engineering, Kyoto University), etc. In the present invention, with respect to a sample containing a target compound, the target compound is determined to be a "thermally active delayed fluorescent substance" based on the observation of a slow fluorescent component when the fluorescence lifetime is measured at 300K. Here, the so-called slow fluorescent component refers to a component with a fluorescence lifetime of more than 0.1μsec. The measurement of the fluorescence lifetime can be carried out, for example, using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics, C11367-01).

[0710] The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "thermally activated delayed phosphor" can function as an assisting dopant that assists the light emission of the polycyclic aromatic compound of the present invention.

[0711] The thermally active delayed phosphor (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally active delayed phosphor (DA-type TADF compound): it is designed to use an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to localize the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in the molecule to produce efficient reverse intersystem crossing. Here, in this specification, the so-called "electron-donating substituent" (donor) refers to a substituent and a partial structure that are localized in the HOMO of the thermally active delayed phosphor molecule, and the so-called "electron-accepting substituent" (acceptor) refers to a substituent and a partial structure that are localized in the LUMO of the thermally active delayed phosphor molecule.

[0712] Generally speaking, due to the structure, the thermally active delayed phosphor using a donor or acceptor has a large spin orbit coupling (SOC: Spin Orbit Coupling), a small exchange interaction between HOMO and LUMO, and a small ΔE(ST), so a very fast reverse intersystem crossing speed can be obtained. By using the polycyclic aromatic compound of the present invention as an emission dopant and using a thermally active delayed phosphor (TADF material) as an auxiliary dopant, a device that satisfies any or all of high efficiency, high color purity and long life can be provided.

[0713] The thermally active delayed phosphor can be any 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 of the present invention and the thermally active delayed phosphor can be contained in the same layer or in adjacent layers or other adjacent layers.

[0714] As the thermally active delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer can be used. As the electron-donating group (donor structure) and the electron-accepting group (acceptor structure) used in the thermally active delayed phosphor of the present invention, for example, the structure described in "Chemistry of Materials" (2017, 29, 1946-1963) can be used. Examples of the donor structure include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothiophenocarbazole, phenyldihydroindolecarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazole-based amine, tetraphenylcarbazole-based diamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridine diamine, tetramethyl-dihydro-indenoacridine and diphenyl-dihydrodibenzazasilin, etc. Examples of the acceptor structure include sulfonyldiphenyl, benzophenone, phenylenebis(phenyl ketone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, terephthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthrone, anthracene dione, 5H-cyclopenta[1,2-b:5,4-b′]bipyridine, fluorene dicarbonitrile, triphenyltriazine, pyrazine dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tri(dimethylphenyl)borane. In particular, the compound having thermally activated delayed fluorescence in the TAF element is preferably a compound having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, oxadiazole, thiadiazole and benzophenone as a partial structure.

[0715] As the second component of the light-emitting layer in the TAF element, it is preferred that the light-emitting spectrum of the light-emitting dopant overlaps at least partially with the absorption peak of the light-emitting dopant. The following are examples of compounds that can be used as the second component (thermally active delayed phosphor) of the light-emitting layer in the TAF element. However, the compounds that can be used as the thermally active delayed phosphor in the TAF element are not to be interpreted in a limiting sense by the following example compounds.

[0716] [Chemistry 154]

[0717]

[0718] [Chemistry 155]

[0719]

[0720] [Chemistry 156]

[0721]

[0722] [Chemistry 157]

[0723]

[0724] [Chemistry 158]

[0725]

[0726] Furthermore, as the thermally activated delayed phosphor, a compound represented by any one of the following formula (AD1), formula (AD2), and formula (AD3) may be used.

[0727] [Chemistry 159]

[0728]

[0729] In the formula (AD1), formula (AD2) and formula (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 partial structure formed 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 partial structure from the acceptor partial structure, and is independently an arylene group having 6 to 18 carbon atoms, and is preferably an arylene group having 6 to 12 carbon atoms from the viewpoint of the size of the conjugation that oozes out from the donor partial structure and the acceptor partial structure. More specifically, phenylene, methylphenylene and dimethylphenylene can be listed. Q is independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of the shallowness of the LUMO of the partial structure formed and the height of the lowest excited singlet energy level and the lowest excited triplet energy level. Ar is independently hydrogen, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 18 carbon atoms. From the viewpoint of the depth of the HOMO of the partial structure formed and the height of the lowest excited singlet energy level and the lowest excited triplet energy level, preferably hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 14 carbon atoms, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazine, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazolyl, or phenylbenzimidazolyl, and further preferably hydrogen, phenyl, or carbazolyl. m is 1 or 2. n is an integer of (6-m) or less, and from the viewpoint of steric hindrance, preferably an integer of 4 to (6-m). Furthermore, at least one hydrogen atom in the compounds represented by the above formulae may be substituted by a halogen or deuterium.

[0730] More specifically, the compound used as the second component of the light-emitting layer in the TAF element is 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.

[0731] The compound used as the second component of the light-emitting layer in the TAF element can be a donor-acceptor type TADF compound represented by DA in which a donor D is directly bonded to an acceptor A or is bonded via a linking group. The compound having a structure represented by the following formula (DAD1) in which multiple donors D are directly bonded to an acceptor A or are bonded via a linking group is a compound with better characteristics of the organic electroluminescent element and is therefore preferred.

[0732] (D 1 -L 1 )n 1 (DAD1)

[0733] Formula (DAD1) includes a compound represented by the following formula (DAD2).

[0734] D 2 -L 2 -A 2 -L 3 -D 3 (DAD2)

[0735] In formula (DAD1) and formula (DAD2), D 1 , D 2 and D 3 Each independently represents a donor group. As the donor group, the above-mentioned donor structure can be adopted. 1 and A 2 Each independently represents an acceptor group. As the acceptor group, the above-mentioned acceptor structure can be adopted. 1 , L 2 and L 3 Each independently represents a single bond or a conjugated linking group. The conjugated linking group is a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene group having 6 to 18 carbon atoms, and more preferably an arylene group having 6 to 12 carbon atoms. 1 , L 2 and L 3 Furthermore, it is preferred that each is independently phenylene, methylphenylene or dimethylphenylene. In formula (DAD1), n ​​is 2 or more and represents an integer less than the maximum number of substitutions that can be made by A1. n can be selected, for example, in the range of 2 to 10, or in the range of 2 to 6. When n is 2, it is a compound represented by formula (DAD2). n D 1 Can be the same or different, n L 1 Preferred specific examples of the compounds represented by formula (DAD1) and formula (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.

[0736] [Chemistry 160]

[0737]

[0738] [Phosphorescent materials (auxiliary dopants)]

[0739] In the light-emitting layer, a phosphorescent material can be used as an auxiliary dopant. The phosphorescent material utilizes the intramolecular spin-orbit interaction (heavy atom effect) caused by the metal atom to obtain luminescence from the excited triplet state. As such a phosphorescent material, for example, a luminescent metal complex can be used. As the luminescent metal complex, for example, compounds represented by the following formula (B-1) and the following formula (B-2) can be cited.

[0740] [Chemistry 161]

[0741]

[0742] In formula (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 of 1 to 3, and "XY" are each independently a bidentate ligand.

[0743] In formula (B-2), M is at least one selected from the group consisting of Pt, Re and Cu, and "WXYZ" is a tetradentate ligand.

[0744] In formula (B-1), M is preferably Ir and n is preferably 3 from the viewpoint of efficiency and life.

[0745] In formula (B-2), M is preferably Pt from the viewpoint of efficiency and life.

[0746] The ligand (XY) in formula (B-1) has at least one ligand selected from the group consisting of: The ligand (WXYZ) in formula (B-2) has at least one ligand selected from the group consisting of: as a part thereof.

[0747] [Chemistry 162]

[0748]

[0749] In the formula,

[0750] It is bonded to the central metal M at ---,

[0751] Y is independently BR e NR e , PR e ,O,S,Se,C=O,S=O,SO2,CR e R f 、SiR e R f , or GeRe R f ,

[0752] The aromatic carbon CH in the ring can be substituted with N independently.

[0753] R e and R f Can be condensed or bonded to form a ring,

[0754] R a , R b , R c and R d Each independently is unsubstituted or substituted to a range from 1 to the maximum number of substitutions possible,

[0755] R a , R b , R c , R d , R e , and R f are independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thiol or a combination thereof,

[0756] Among them, R a , R b , R c , and R d Any two adjacent substituents in the group may be condensed or bonded to form a ring, or may form a multidentate ligand.

[0757] Examples of the compound represented by formula (B-1) include Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), and fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium(III)(fac-tris(2-(3-p-xylyl)phenyl)pyridinium(III)), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq )2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(2-phq)3, Ir( BT)2(acac), Ir(DMP)3, Ir(Mphq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)( Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, etc.

[0758] Examples of the compound represented by formula (B-1) include the following compounds in addition to the above.

[0759] [Chemistry 163]

[0760]

[0761] [Chemistry 164]

[0762]

[0763] [Chemistry 165]

[0764]

[0765] In addition, iridium complexes described in Japanese Patent Laid-Open No. 2006-089398, Japanese Patent Laid-Open No. 2006-080419, Japanese Patent Laid-Open No. 2005-298483, Japanese Patent Laid-Open No. 2005-097263, and Japanese Patent Laid-Open No. 2004-111379, U.S. Patent Application Publication No. 2019 / 0051845, or Advanced Materials (26: 7116-7121), Nature Asia Materials (NPG Asia Materials) (13, 53 (2021)), Applied Physics Letters (Applied Physics Letters) (117, 253301 (2020)), Light-Emitting Diode-An Outlook On the Empirical Features and Its Recent Technological Progress Outlook (Light-Emitting Diode-An Outlook On the Empirical Features and Its Recent Technological Progress Outlook) can also be used. The platinum complex described in "Technological Advances" (Chapter 5).

[0766] <2-1-3. Substrate in organic electroluminescent element>

[0767] The substrate 101 is a support of the organic EL element 100, and quartz, glass, metal, plastic, etc. can be generally used. The substrate 101 is formed into a plate, film or sheet according to the purpose, for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. can be used. Among them, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, polysulfone, etc. are preferably used. If it is a glass substrate, soda-lime glass or alkali-free glass can be used. In addition, the thickness can be sufficient to maintain the mechanical strength, so for example, it can be more than 0.2 mm. As the upper limit of the thickness, for example, it is less than 2 mm, preferably less than 1 mm. Regarding the material of the glass, since the dissolved ions from the glass are preferably less, it is preferably alkali-free glass. Since soda-lime glass with a barrier coat (barrier coat) of SiO2 or the like is also commercially available, the soda-lime glass can be used. In addition, in order to improve the gas barrier properties, a gas barrier film such as a fine silicon oxide film may be provided on at least one surface of the substrate 101. When a plate, film or sheet made of a synthetic resin with low gas barrier properties is used as the substrate 101, it is particularly preferred to provide a gas barrier film.

[0768] <2-1-4. Anode in organic electroluminescent element>

[0769] The anode 102 plays a role of injecting holes into the light-emitting layer 105. When 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 are injected into the light-emitting layer 105 via these layers.

[0770] As materials for forming the anode 102, inorganic compounds and organic compounds can be cited. As inorganic compounds, for example, metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (Indium Tin Oxide, ITO), indium-zinc oxide (Indium Zinc Oxide, IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass or Nesa glass, etc. As organic compounds, for example, polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline, etc. can be cited. In addition, it can be appropriately selected from the substances used as the anode of the organic EL element for use.

[0771] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light emission of the light emitting element, but from the perspective of the power consumption of the light emitting element, a low resistance is ideal. For example, if it is an ITO substrate of less than 300Ω / Y, it functions as an element electrode, but now it is also possible to supply a substrate of about 10Ω / Y, so it is particularly ideal to use a low resistance product such as 100Ω / Y to 5Ω / Y, preferably 50Ω / Y to 5Ω / Y. The thickness of ITO can be arbitrarily selected in accordance with the resistance value, but is usually used between 50nm and 300nm.

[0772] <2-1-5. Hole injection layer and hole transport layer in organic electroluminescent element>

[0773] The hole injection layer 103 plays a role in efficiently injecting holes migrated from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role in 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 formed by stacking or mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. In addition, an inorganic salt such as iron (III) chloride can be added to the hole injection / transport material to form a layer.

[0774] As a hole injection / transport material, it is necessary to efficiently inject / transmit holes from the positive electrode between electrodes to which an electric field is applied, and it is ideal that the hole injection efficiency is high and the injected holes are efficiently transmitted. Therefore, it is preferred that the material has a small ionization potential, a large hole mobility, and excellent stability, and is not prone to produce impurities that become traps during manufacture and use.

[0775] As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, and known compounds used in hole injection layers and hole transport layers of p-type semiconductors and organic EL elements. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (4,4',4"-tri(N-carbazolyl)triphenylamine, polymers having an aromatic tertiary amino group 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 '-tetrakis([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc. Among polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole and polysilane having the above monomers on the side chain are preferred, but there is no particular limitation as long as it is a compound that can form a thin film required for the production of a light-emitting element and can inject holes from the anode and then transport holes.

[0776] In addition, it is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials contain compounds with good electron donating properties or compounds with good electron accepting properties. In order to dope electron donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known (for example, refer to the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo (M. Pfeiffer , A. Beyer, T. Fritz, K. Leo), "Applied Physics Letters (Appl. Phys. Lett.)", 73(22), 3202-3204 (1998)" and the reference "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo (J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo), "Applied Physics Letters (Appl. Phys. Lett.)", 73(6), 729-731 (1998)"). These so-called holes are generated through the electron migration process of the electron-donating basic material (hole transport material). The conductivity of the basic material varies greatly depending on the number and mobility of the holes. As a host material having hole transport properties, for example, benzidine derivatives (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine, TPD), starburst amine derivatives (4,4',4"-tris(N,N-diphenylamino)triphenylamine (4,4',4"-tris(N,N-diphenylamino)triphenylamine, TDATA), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) (Japanese Patent Publication No. 2005-167175). The polycyclic aromatic compound of the present invention can also be used as a hole injection layer forming material or a hole transport layer forming material.

[0777] <2-1-6. Electron blocking layer in organic electroluminescent element>

[0778] An electron blocking layer may be provided between the hole injection / transport layer and the light-emitting layer to prevent diffusion of electrons from the light-emitting layer. The electron blocking layer may be formed using a compound represented by any one of the formulas (H1), (H2) and (H3). The polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.

[0779] <2-1-7. Electron injection layer and electron transport layer in organic electroluminescent element>

[0780] The electron injection layer 107 plays a role of efficiently injecting electrons migrated from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a 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 respectively formed by stacking or mixing one or more electron transport / injection materials, or are formed by a mixture of an electron transport / injection material and a polymer binder.

[0781] The so-called electron injection / transport layer is a layer responsible for injecting electrons from the cathode and then transmitting electrons, and it is desirable that the electron injection efficiency is high and the injected electrons are transmitted efficiently. Therefore, it is preferably a material with large electron affinity, large electron mobility, excellent stability, and impurities that are not easy to produce when manufacturing and using it. However, considering the transmission balance of holes and electrons, in the case of mainly playing the role of efficiently preventing the holes from the anode from being recombined and flowing to the cathode side, even if the electron transmission ability is not so high, it has the effect of improving luminous efficiency equally with the material with high electron transmission ability. Therefore, the electron injection / transport layer in the present embodiment may also include the function of the layer that can efficiently prevent the migration of holes.

[0782] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transfer compounds in photoconductive materials and known compounds used in electron injection layers and electron transport layers of organic EL elements.

[0783] As the material used in the electron transport layer or the electron injection layer, it is preferably containing at least one selected from the following compounds: a compound containing an aromatic ring or heteroaromatic ring containing one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus; a pyrrole derivative and its condensed ring derivative; and a metal complex with electron-accepting nitrogen. Specifically, it can be listed: condensed ring aromatic ring derivatives such as naphthalene and anthracene, styrene aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl, purple ring ketone derivatives, coumarin derivatives, naphthalene dicarboximide derivatives, quinone derivatives such as anthraquinone or diphenoquinone, phosphine oxide derivatives, aryl nitrile derivatives and indole derivatives. As a metal complex with electron-accepting nitrogen, for example, hydroxyl oxazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes can be listed. These materials can be used alone or mixed with different materials.

[0784] In addition, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzoazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, Biologicals, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tri(N-phenylbenzimidazole-2-yl)benzene, etc.), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2':6',2"-terpyridine-4'-yl)benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, pyrimidine derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, bisphenylvinyl derivatives, silole derivatives and oxazoline derivatives, etc.

[0785] In addition, metal complexes having electron-accepting nitrogen can also be used, examples of which include hydroxyquinoline metal complexes, hydroxyoxazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0786] The materials can be used alone or in combination with different materials.

[0787] Among the materials, preferred are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aromatic nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and oxazoline derivatives.

[0788] The polycyclic aromatic compound of the present invention can also be used as a material for forming an electron injection layer or a material for forming an electron transport layer.

[0789] The electron transport layer or the electron injection layer may further contain a substance that can reduce the material forming the electron transport layer or the electron injection layer. The reducing substance may be a variety of substances as long as it has 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 preferably used.

[0790] As preferred reducing substances, alkali metals such as Na (work function 2.36eV), K (work function 2.28eV), Rb (work function 2.16eV) or Cs (work function 1.95eV) or alkaline earth metals such as Ca (work function 2.9eV), Sr (work function 2.0eV~2.5eV) or Ba (work function 2.52eV) can be listed, and substances with a work function of 2.9eV or less are particularly preferred. Among these, more preferred reducing substances are K, Rb or Cs as alkali metals, and more preferably Rb or Cs, and most preferably Cs. The reducing ability of these alkali metals is particularly high. By adding a relatively small amount of the alkali metal to the material forming the electron transport layer or the electron injection layer, the luminous brightness in the organic EL element can be improved or the life can be prolonged. In addition, as the reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and a combination containing Cs is particularly preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or the electron injection layer, the luminance of the light emission in the organic EL element can be improved or the life can be prolonged.

[0791] <2-1-8. Cathode in organic electroluminescent element>

[0792] The cathode 108 plays a role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

[0793] As the material forming the cathode 108, if it is a substance that can efficiently inject electrons into the organic layer, it is not particularly limited, and the same material as the material forming the anode 102 can be used. Among them, preferably metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.) and the like. In order to improve the efficiency of electron injection to improve the characteristics of the element, lithium, sodium, potassium, cesium, calcium, magnesium or alloys containing these low work function metals are effective. However, generally speaking, these low work function metals are unstable in the atmosphere in most cases. In order to improve this point, it is known that there is a method of doping a trace amount of lithium, cesium or magnesium into the organic layer and using an electrode with high stability. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. Among them, it is not limited to these.

[0794] Furthermore, the following are preferred examples: for protecting the electrodes, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys of these metals, inorganic substances such as silicon dioxide, titanium dioxide and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. are stacked. The method for making these electrodes is not particularly limited as long as it is a method that can achieve conduction such as resistance heating, electron beam evaporation, sputtering, ion plating and coating.

[0795] <2-1-9. Adhesives that can be used in each layer>

[0796] The materials used in the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer and electron injection layer can form each layer separately, or can be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinyl carbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene ether, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, acrylonitrile-butadiene-styrene (ABS) resin, polyurethane resin, etc., or in hardening resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. as a polymer binder.

[0797] <2-1-10. Method for producing organic electroluminescent element>

[0798] Each layer constituting the organic EL element can be formed by making the material to constitute each layer into a thin film using a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular stacking, printing, inkjet, spin coating, casting, coating, etc. The film thickness of each layer formed in the above manner is not particularly limited and can be appropriately set according to the properties of the material, but is generally in the range of 2nm to 5000nm. The film thickness can generally be measured using a quartz oscillation film thickness measuring device or the like. When using the vapor deposition method for thin film formation, the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, etc. The vapor deposition conditions are generally preferably a boat heating temperature of +50°C to +400°C and a vacuum degree of 10 -6 Pa~10 -3 Pa, the vapor deposition rate is 0.01 nm / sec to 50 nm / sec, the substrate temperature is -150°C to +300°C, and the film thickness is appropriately set within the range of 2 nm to 5 μm.

[0799] Next, as an example of a method for making an organic EL element, a method for making an organic EL element including an anode / hole injection layer / hole transport layer / light-emitting layer containing a main material and a dopant material / electron transport layer / electron injection layer / cathode is described. On an appropriate substrate, a thin film of an anode material is formed by a vapor deposition method to make an anode, and a thin film of a hole injection layer and a hole transport layer is formed on the anode. The main material and the dopant material are co-evaporated on the thin film to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and then a thin film containing a cathode material is formed by a vapor deposition method as a cathode, thereby obtaining a target organic EL element. In addition, in the production of the organic EL element, the production order can also be reversed, and the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode are produced in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0800] When a direct current voltage is applied to the organic EL element obtained in the above manner, it can be applied with the anode as + polarity and the cathode as - polarity. If a voltage of about 2V to 40V is applied, light emission can be observed from the transparent or translucent electrode side (anode or cathode, or both). In addition, the organic EL element also emits light when a pulse current or an alternating current is applied. In addition, the waveform of the applied alternating current can be arbitrary.

[0801] <2-1-11. Application examples of organic electroluminescent elements>

[0802] Organic EL elements can also be used in display devices, lighting devices, and the like.

[0803] A display device or lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element to a known driving device, and can be driven using a known driving method such as DC driving, pulse driving, AC driving, etc. as appropriate.

[0804] As the display device, for example, panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. (for example, refer to Japanese Patent Laid-Open No. 10-335066, Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open No. 2004-281086, etc.). In addition, as the display mode of the display, for example, any one of a matrix mode and a segment mode can be listed. In addition, the matrix display and the segment display can coexist in the same panel.

[0805] In a matrix, pixels for display are arranged two-dimensionally in a grid or mosaic shape, etc., so that text or images are displayed by a collection of pixels. The shape or size of a pixel is determined according to the purpose. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with a side of less than 300 μm are usually used. In addition, in the case of large displays such as display screens, pixels with a side of mm are used. In the case of monochrome display, it is sufficient to arrange pixels of the same color. In the case of color display, red, green, and blue pixels are displayed in parallel. In the case, typical ones are triangular and stripe types. Moreover, as a driving method of the matrix, it can be either a line-sequential driving method or an active matrix. Line-sequential driving has the advantage of simple structure, but in the case of considering the operating characteristics, active matrix is ​​sometimes more excellent, so the driving method also needs to be used according to the purpose.

[0806] In the segmented method (type), a pattern is formed in a manner to display predetermined information, and the determined area is illuminated. Examples include: time or temperature display in a digital clock or thermometer, operating status display of audio equipment or induction cookers, and panel display of a car.

[0807] As lighting devices, for example, lighting devices such as indoor lighting, backlight sources of liquid crystal display devices, etc. can be listed (for example, refer to Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, Japanese Patent Publication No. 2004-119211, etc.). Backlight sources are mainly used to improve the visibility of display devices that do not emit light by themselves, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display boards, and logos. In particular, as a backlight source for personal computers, where thinning is becoming a problem in liquid crystal display devices, if it is considered that the existing methods are difficult to be thinned due to the inclusion of fluorescent lamps or light guide plates, the backlight source using organic EL elements has the characteristics of being thin and lightweight.

[0808] <2-2. Other organic devices>

[0809] The polycyclic aromatic compound of the present invention can be used not only in the organic electroluminescent element, but also in the preparation of organic field effect transistors or organic thin film solar cells.

[0810] An organic field effect transistor is a transistor that uses an electric field generated by voltage input to control current. In addition to a source electrode and a drain electrode, a gate electrode is also provided. An organic field effect transistor is a transistor in which an electric field is generated when a voltage is applied to the gate electrode, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. Compared with a single transistor (bipolar transistor), a field effect transistor is easy to miniaturize and is often used as a component constituting an integrated circuit, etc.

[0811] Regarding the structure of an organic field effect transistor, generally, a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and a gate electrode is provided via an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. As an example of its element structure, the following structure can be cited.

[0812] (1) Substrate / gate electrode / insulator layer / source electrode, drain electrode / organic semiconductor active layer

[0813] (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode, drain electrode

[0814] (3) Substrate / organic semiconductor active layer / source electrode, drain electrode / insulator layer / gate electrode

[0815] (4) Substrate / source electrode, drain electrode / organic semiconductor active layer / insulator layer / gate electrode

[0816] The organic field effect transistor configured in this way can be used as a pixel driving switch element of an active matrix driving liquid crystal display or an organic electroluminescent display, etc.

[0817] Organic thin film solar cells have a structure in which an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode of ITO or the like are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compounds of the present invention can be used as materials for hole transport layers, p-type semiconductor layers, n-type semiconductor layers, and electron transport layers according to their physical properties. In organic thin film solar cells, the polycyclic aromatic compounds of the present invention can function as hole transport materials or electron transport materials. In addition to the above layers, organic thin film solar cells may also appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. In organic thin film solar cells, known materials used for organic thin film solar cells can be appropriately selected for use in combination.

[0818] <3. Wavelength conversion materials>

[0819] The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.

[0820] Currently, the application of multicolor technology based on color conversion to liquid crystal displays or organic EL displays, lighting, etc. is being actively studied. The so-called color conversion is to convert the light emitted from the light source into light with a longer wavelength, for example, it means converting ultraviolet light or blue light into green light or red light. The wavelength conversion material with the color conversion function is filmed, for example, combined with a blue light source, so that the three primary colors of blue, green and red can be extracted from the blue light source, that is, white light can be extracted. This white light source composed of a combination of a blue light source and a wavelength conversion film with a color conversion function is used as a light source unit, and combined with a liquid crystal drive part and a color filter, so that a full-color display can be made. In addition, if there is no liquid crystal drive part, it can be directly used as a white light source, for example, it can be used as a white light source for light-emitting diode (LED) lighting, etc. In addition, a blue organic EL element is used as a light source and combined with a wavelength conversion film that converts blue light into green light and red light, so that a full-color organic EL display without using a metal mask can be made. Furthermore, by using a blue micro LED as a light source and combining it with a wavelength conversion film that converts blue light into green light and red light, a low-cost full-color micro LED display can be produced.

[0821] The polycyclic aromatic compound of the present invention can be used as the wavelength conversion material. The wavelength conversion material containing the polycyclic aromatic compound of the present invention can be used to convert ultraviolet light or light from a light source or light-emitting element that generates blue light with a shorter wavelength into blue light or green light with high color purity suitable for use in a display device (a display device or a liquid crystal display device using an organic EL element). The adjustment of the converted color can be carried out by appropriately selecting the substituent of the polycyclic aromatic compound of the present invention, the binder resin used in the wavelength conversion composition described later, etc. The wavelength conversion material is prepared as a wavelength conversion composition containing the polycyclic aromatic compound of the present invention. In addition, the wavelength conversion composition can also be used to form a wavelength conversion film.

[0822] The wavelength conversion composition may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention. As the binder resin, for example, the resins described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283 may be used. As other additives, the compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283 may be used. As the solvent, the description of the solvent contained in the light-emitting layer forming composition may be referred to.

[0823] The wavelength conversion film includes a wavelength conversion layer formed by curing the wavelength conversion composition. As a method for making a wavelength conversion layer from a wavelength conversion composition, reference can be made to a known film formation method. The wavelength conversion film may include only a wavelength conversion layer formed by a composition comprising a polycyclic aromatic compound of the present invention, or may include other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light into green light or red light, a wavelength conversion layer that converts blue light or green light into red light). Furthermore, the wavelength conversion film may also include a substrate layer, or a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[0824] [Example]

[0825] Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

[0826] In the examples, "APCI-MS" refers to atmospheric pressure chemical ionization-mass spectrometry.

[0827] <<Synthesis example>>

[0828] Synthesis Example (1): Synthesis of Compound (1-037)

[0829] [Chemistry 166]

[0830]

[0831] Under nitrogen atmosphere, 2-(tert-butyl)aniline (50.0 g), 1-bromo-4-(tert-butyl)benzene (71.4 g), dichlorobis[di-tert-butyl(4-dimethylaminophenyl)phosphino]palladium(II) (Pd-132, 4.74 g) as a palladium catalyst, sodium tert-butoxide (tBuONa, 48.3 g) and toluene (500 ml) were placed in a flask and stirred at reflux temperature for 2 hours. After the reaction was completed, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified using a silica gel short-path column (eluent: toluene / heptane = 1 / 4 (volume ratio)). Further, recrystallization was performed from ethanol to obtain 73.5 g of an intermediate (Int-1-037-1).

[0832] [Chemistry 167]

[0833]

[0834] Under nitrogen atmosphere, the intermediate (Int-1-037-1) (70.0 g), 1-bromo-3-chlorobenzene (47.6 g), Pd-132 (3.52 g) as a palladium catalyst, tBuONa (35.9 g) and toluene (700 ml) were placed in a flask and stirred at 90° C. for 2 hours. After the reaction was completed, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified using a silica gel short-path column (eluent: toluene / heptane = 1 / 9 (volume ratio)) to obtain 67.3 g of the intermediate (Int-1-037-2).

[0835] [Chemistry 168]

[0836]

[0837] Under nitrogen environment, the intermediate (Int-1-037-2) (65.0g), 5-(tert-butyl)-[1,1'-biphenyl]-2-amine (37.4g), Pd-132 (2.35g) as a palladium catalyst, tBuONa (23.9g) and toluene (650ml) were placed in a flask and stirred at reflux temperature for 2 hours. After the reaction was completed, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was refined using a silica gel short-path column (eluent: toluene / heptane = 1 / 4 (volume ratio)). Further, recrystallization was performed from ethanol to obtain 87.7g of the intermediate (Int-1-037-3).

[0838] [Chemistry 169]

[0839]

[0840] Under nitrogen environment, the intermediate (Int-1-037-3) (85.0g), 5-(tert-butyl)-1,2,3-trichlorobenzene (34.8g), Pd-132 (2.07g) as a palladium catalyst, tBuONa (21.1g) and toluene (850ml) were placed in a flask and stirred at reflux temperature for 4 hours. After the reaction was completed, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. After that, the crude product obtained by concentrating the organic layer was refined using a silica gel short-path column (eluent: toluene / heptane = 1 / 9 (volume ratio)). Recrystallization was then performed from ethanol to obtain 87.0g of the intermediate (Int-1-037-4).

[0841] [Chemistry 170]

[0842]

[0843] Under nitrogen atmosphere, 3-bromo-5-phenylbenzofuran (30.0 g), 4-(tert-butyl)aniline (16.4 g), Pd-132 (1.56 g) as a palladium catalyst, tBuONa (15.8 g) and toluene (300 ml) were placed in a flask and stirred at 90° C. for 2 hours. After the reaction was completed, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified using a silica gel short-path column (eluent: toluene / heptane = 1 / 4 (volume ratio)), thereby obtaining an intermediate (Int-1-037-5) (30.8 g).

[0844] [Chemistry 171]

[0845]

[0846] Under nitrogen environment, intermediate (Int-1-037-4) (65.0g), intermediate (Int-1-037-5) (28.4g), Pd-132 (1.18g) as palladium catalyst, tBuONa (12.0g) and toluene (650ml) were placed in a flask and heated at reflux temperature for 3 hours. After the reaction was completed, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was refined using a silica gel short-path column (eluent: toluene / heptane = 1 / 9 (volume ratio)), thereby obtaining 68.3g of intermediate (Int-1-037).

[0847] [Chemistry 172]

[0848]

[0849] Under nitrogen atmosphere, at 0°C, a 1.60M t-butyllithium pentane solution (tBuLi, 74.8ml) was added to a flask containing the intermediate (Int-1-037) (65.0g) and t-butylbenzene (tBu-benzene, 650ml). After the addition was completed, the temperature was raised to 70°C and stirred for 0.5 hours, and components with a boiling point lower than that of t-butylbenzene were removed by vacuum distillation. The mixture was cooled to -50°C and boron tribromide (30.0g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled again to 0°C and N,N-diisopropylethylamine ( i Pr2NEt, 15.5g), stirred at room temperature until the heat stopped, then heated to 80°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled by an ice bath was added, and then toluene was added for liquid separation. After the organic layer was concentrated, it was purified using a silica gel short-path column (eluent: toluene). The obtained crude product was recrystallized from toluene to obtain 8.88g of compound (1-037).

[0850] [Chemistry 173]

[0851]

[0852] APCI-MS observed m / z (M+H) = 1060.72, confirming the formation of the target product.

[0853] Synthesis Example (2): Synthesis of Compound (1-293)

[0854] In the same manner as in Synthesis Example (1), compound (1-293) was obtained from intermediate (Int-1-293).

[0855] [Chemistry 174]

[0856]

[0857] The structure of the obtained compound was confirmed by nuclear magnetic resonance (NMR) measurement, and m / z (M+H) = 1096.80 was observed by APCI-MS, confirming the formation of the target product.

[0858] Synthesis Example (3): Synthesis of Compound (1-294)

[0859] In the same manner as in Synthesis Example (1), compound (1-294) was obtained from intermediate (Int-1-294).

[0860] [Chemistry 175]

[0861]

[0862] APCI-MS observed m / z (M+H) = 1094.82, confirming the formation of the target product.

[0863] Synthesis Example (4): Synthesis of Compound (1-305)

[0864] In the same manner as in Synthesis Example (1), compound (1-305) was obtained from intermediate (Int-1-305).

[0865] [Chemistry 176]

[0866]

[0867] APCI-MS observed m / z (M+H) = 1202.94, confirming the formation of the target product. Synthesis Example (5): Synthesis of Compound (1-061)

[0868] In the same manner as in Synthesis Example (1), compound (1-061) was obtained from intermediate (Int-1-061).

[0869] [Chemistry 177]

[0870]

[0871] APCI-MS observed m / z (M+H) = 1060.68, confirming the formation of the target product. Synthesis Example (6): Synthesis of Compound (1-032)

[0872] In the same manner as in Synthesis Example (1), compound (1-032) was obtained from intermediate (Int-1-032).

[0873] [Chemistry 178]

[0874]

[0875] APCI-MS observed m / z (M+H) = 1080.63, confirming the formation of the target product. Synthesis Example (7): Synthesis of Compound (1-157)

[0876] In the same manner as in Synthesis Example (1), compound (1-157) was obtained from intermediate (Int-1-157).

[0877] [Chemistry 179]

[0878]

[0879] APCI-MS observed m / z (M+H) = 1018.67, confirming the formation of the target product. Synthesis Example (8): Synthesis of Compound (1-151)

[0880] In the same manner as in Synthesis Example (1), compound (1-151) was obtained from intermediate (Int-1-151).

[0881] [Chemistry 180]

[0882]

[0883] APCI-MS observed m / z (M+H) = 1038.56, confirming the formation of the target product. Synthesis Example (9): Synthesis of Compound (1-111)

[0884] In the same manner as in Synthesis Example (1), compound (1-111) was obtained from intermediate (Int-1-111).

[0885] [Chemistry 181]

[0886]

[0887] APCI-MS observed m / z (M+H) = 1080.66, confirming the formation of the target product. Synthesis Example (10): Synthesis of Compound (1-511)

[0888] In the same manner as in Synthesis Example (1), compound (1-511) was obtained from intermediate (Int-1-511).

[0889] [Chemistry 182]

[0890]

[0891] APCI-MS observed m / z (M+H) = 1066.78, confirming the formation of the target product. Synthesis Example (11): Synthesis of Compound (1-429)

[0892] In the same manner as in Synthesis Example (1), compound (1-429) was obtained from intermediate (Int-1-429).

[0893] [Chemistry 183]

[0894]

[0895] APCI-MS observed m / z (M+H) = 1086.72, confirming the formation of the target product. Synthesis Example (12): Synthesis of Compound (1-450)

[0896] In the same manner as in Synthesis Example (1), compound (1-450) was obtained from intermediate (Int-1-450).

[0897] [Chemistry 184]

[0898]

[0899] APCI-MS observed m / z (M+H) = 1198.90, confirming the formation of the target product. Synthesis Example (13): Synthesis of Compound (1-709)

[0900] In the same manner as in Synthesis Example (1), compound (1-709) was obtained from intermediate (Int-1-709).

[0901] [Chemistry 185]

[0902]

[0903] Synthesis Example (14): Synthesis of Compound (1-710)

[0904] In the same manner as in Synthesis Example (1), compound (1-710) was obtained from intermediate (Int-1-710).

[0905] [Chemistry 186]

[0906]

[0907] Synthesis Example (15): Synthesis of Compound (1-906)

[0908] In the same manner as in Synthesis Example (1), compound (1-906) was obtained from intermediate (Int-1-906).

[0909] [Chemistry 187]

[0910]

[0911] APCI-MS observed m / z (M+H) = 1132.81, confirming the formation of the target product. Synthesis Example (16): Synthesis of Compound (1-908)

[0912] In the same manner as in Synthesis Example (1), compound (1-908) was obtained from intermediate (Int-1-908).

[0913] [Chemistry 188]

[0914]

[0915] APCI-MS observed m / z (M+H) = 1130.80, confirming the formation of the target product.

[0916] Synthesis Example (17): Synthesis of Compound (1-955)

[0917] In the same manner as in Synthesis Example (1), compound (1-955) was obtained from intermediate (Int-1-955).

[0918] [Chemistry 189]

[0919]

[0920] APCI-MS observed m / z (M+H) = 842.60, confirming the formation of the target product.

[0921] Synthesis Example (18): Synthesis of Compound (1-960)

[0922] In the same manner as in Synthesis Example (1), compound (1-960) was obtained from intermediate (Int-1-960).

[0923] [Chemistry 190]

[0924]

[0925] APCI-MS observed m / z (M+H) = 728.38, confirming the formation of the target product.

[0926] <<Fabrication and evaluation of vapor deposition type organic EL elements>>

[0927] Next, the preparation and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.

[0928] <Structure of organic EL element>

[0929] An organic EL device is produced using the polycyclic aromatic compound of the present invention.

[0930] The material structures of the respective layers in the organic EL devices of Examples B1 to B18 and Comparative Examples B1 to B4 are shown in Table 1 below.

[0931] [Table 1]

[0932]

[0933] The chemical structural formulas of “HI”, “HAT-CN”, “HT-1”, “HT-2”, “ET-1”, “ET-2”, “BH”, “Liq”, “Comparative Compound (1)” (compound described in the specification of U.S. Patent Application Publication No. 2022 / 0310924), “Comparative Compound (2)” (compound described in the specification of Chinese Patent Application Publication No. 113135935), and “Comparative Compound (3)” and “Comparative Compound (4)” (compound described in International Publication No. 2020 / 076108) in Tables 1, 2 and 3 are shown below.

[0934] [Chemistry 191]

[0935]

[0936] [Chemistry 192]

[0937]

[0938] <Element of Example B1>

[0939] A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) on which ITO film having a thickness of 180 nm formed by sputtering was polished to 150 nm was used as a transparent support substrate. The transparent support substrate was fixed on a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing HI, HAT-CN, HT-1, HT-2, BH, compound (1-037), ET-1, and ET-2, and an aluminum nitride vapor deposition boat containing Liq, LiF, and aluminum, respectively, were installed.

[0940] The following layers were formed in sequence on the ITO film of the transparent supporting substrate. The vacuum chamber was depressurized to 5×10 -4 Pa, first, HI is heated and evaporated in a manner to make the film thickness 40nm, then HAT-CN is heated and evaporated in a manner to make the film thickness 5nm, then HT-1 is heated and evaporated in a manner to make the film thickness 45nm, then HT-2 is heated and evaporated in a manner to make the film thickness 10nm, to form a hole layer including four layers. Then, BH and compound (1-037) are heated at the same time and evaporated in a manner to make the film thickness 25nm to form a light-emitting layer. The evaporation rate is adjusted in a manner such that the mass ratio of BH to compound (1-037) is approximately 97 to 3. Furthermore, ET-1 is heated and evaporated in a manner to make the film thickness 5nm, then ET-2 and Liq are heated at the same time and evaporated in a manner to make the film thickness 25nm to form an electron layer including two layers. The evaporation rate is adjusted in a manner such that the mass ratio of ET-2 to Liq is approximately 50 to 50. The deposition rate of each layer is 0.01 nm / sec to 1 nm / sec. Thereafter, LiF is heated and vapor-deposited at a deposition rate of 0.01 nm / sec to 0.1 nm / sec so as to have a film thickness of 1 nm, and then aluminum is heated and vapor-deposited so as to have a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL element.

[0941] <Elements of Example B2 to Example B18 and Comparative Examples B1 to B4>

[0942] Organic EL devices of Examples B2 to B18 and Comparative Examples B1 to B4 were obtained in the same manner as in Example B1 except that the compounds listed in Tables 2 and 3 were used as the dopant material instead of Compound (1-037).

[0943] <Evaluation of organic EL characteristics>

[0944] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency. The internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the light-emitting element as electrons (or holes) that is purely converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element. A portion of the photons generated in the light-emitting layer are absorbed by the inside of the light-emitting element or continuously reflected without being released to the outside of the light-emitting element, so the external quantum efficiency is lower than the internal quantum efficiency.

[0945] The external quantum efficiency was measured by the following method: Using a voltage / current generator R6144 manufactured by Advantest, a voltage was applied so that the device brightness reached 1000 cd / m 2 The element emits light by applying a voltage of . Using a spectroradiometer SR-3AR manufactured by TOPCON, the spectral radiance brightness in the visible light region is measured from a direction perpendicular to the light-emitting surface. Assuming that the light-emitting surface is a completely diffuse surface, the value of the spectral radiance brightness of each wavelength component measured is divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Then, the number of photons is accumulated in the observed full wavelength region and set as the total number of photons released from the element. The value obtained by dividing the applied current value by the elementary charge is set as the number of carriers injected into the element, and the value obtained by dividing the total number of photons released from the element by the number of carriers injected into the element is the external quantum efficiency.

[0946] For the organic EL devices of Examples B1 to B18 and Comparative Examples B1 to B4, an ITO electrode was used as an anode and a LiF / aluminum electrode was used as a cathode. A DC voltage was applied to measure the 1000 cd / m 2 External quantum efficiency and device life when emitting light. In addition, device life is based on 1000cd / m 2 The voltage during light emission was calculated as the time for which the luminance was maintained at 95% or more of the initial luminance by continuous driving.

[0947] [Table 2]

[0948]

[0949] [Table 3]

[0950]

[0951] The polycyclic aromatic compound of the present invention is effectively used as a material for organic devices, particularly as a material for a light-emitting layer for forming a light-emitting layer of an organic electroluminescent element. By using the polycyclic aromatic compound of the present invention as a dopant for the light-emitting layer, an organic electroluminescent element with a long life and high light efficiency can be obtained.

Claims

1. A polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1); [Chemistry 1] In formula (1), Ring A, Ring B and Ring C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, wherein, At least one of the B ring and the C ring in the structure is an aryl ring substituted with at least a group represented by the formula (1E) or a heteroaryl ring substituted with at least a group represented by the formula (1E), In formula (1E), * is the bond position, The D ring is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, R e1 , R e2 , R e3 , A 1 and A 2 are independently hydrogen or a substituent, wherein A 1 and A 2 At least one of them is a monovalent group represented by formula (tR), [Chemistry 2] In formula (tR), R a , R b and R c are each independently an alkyl group having 1 to 24 carbon atoms, * is the bonding position to the e-ring, X 1 and X 2 are independently >O, >NR NX 、>C(-R CX )2、>Si(-R IX )2.>S or>Se, 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, >C(-R CX )2's two R's CX Can bond to each other to form a ring, >Si(-R IX )2's two R's IX Can bond with each other to form a ring, R NX , at least one R CX , and at least one R IX It may be bonded to at least one of the A ring or the B ring or at least one of the A ring or the C ring via a single bond or a linking group, At least one of the aryl ring and the heteroaryl ring in the structure may be condensed by at least one cycloalkane, the cycloalkane may be substituted by at least one substituent, and at least one -CH2- in the cycloalkane may be substituted by -O-. In the structure, at least one hydrogen may be replaced by deuterium, and at least one nitrogen may be replaced by nitrogen-15( 15 N) substituted, 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) substituted, at least one carbon may be substituted by carbon-13 ( 13 C) substituted, at least one boron may be substituted by boron-11( 11 B) Replacement.

2. The polycyclic aromatic compound according to claim 1, wherein A 1 and A 2 are independently hydrogen or alkyl, wherein A 1 and A 2 At least one of them is a monovalent group represented by formula (tR).

3. The polycyclic aromatic compound according to claim 1, wherein Formula (1) is represented by either formula (1-A) or formula (1-B); [Chemistry 3] In each of formula (1-A) and formula (1-B), Ar 1 and Ar 2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, R a1 ~R a3 , R b1 ~R b3 , R c1 ~R c4 and R d1 ~R d5 are independently hydrogen or a substituent, R a1 ~R a3 , R b1 ~R b3 , R c1 ~R c4 and R d1 ~R d5 In the formula (A), two adjacent groups on one benzene ring may be bonded to each other and together with the benzene ring form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, R e1 , R e2 , R e3 , A 1 and A 2 With R in formula (1E) e1 , R e2 , R e3 , A 1 and A 2 They have the same meaning respectively. In formula (1-B), Z 1 is >O、>NR NZ 、>C(-R CZ )2、>Si(-R IZ )2.>S or>Se, R NZ , R CZ and R IZ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, >C(-R CZ )2's two R's CZ Can bond to each other to form a ring, >Si(-R IZ )2's two R's IZ Can bond to each other to form a ring, At least one of the aryl ring and the heteroaryl ring in each of Formula (1-A) and Formula (1-B) 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 substituted with -O-, In each of formula (1-A) and formula (1-B), at least one hydrogen may be substituted with deuterium, and at least one nitrogen may be substituted with nitrogen-15( 15 N) substituted, 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) substituted, at least one carbon may be substituted by carbon-13 ( 13 C) substituted, at least one boron may be substituted by boron-11( 11 B) Replacement.

4. The polycyclic aromatic compound according to claim 3, wherein R a2 is hydrogen or a substituent, as R a2 The substituent is a substituted or unsubstituted alkyl group (except methyl), a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group.

5. The polycyclic aromatic compound according to claim 4, wherein R a2 It is hydrogen, tert-butyl, or phenyl which may be substituted by tert-butyl.

6. The polycyclic aromatic compound according to claim 4, wherein A 1 and A 2 are independently hydrogen or alkyl, wherein A 1 and A 2 At least one of them is a monovalent group represented by formula (tR).

7. The polycyclic aromatic compound according to claim 3, wherein Ar 1 and Ar 2 are each independently a group represented by any one of the formulas selected from the group consisting of formula (ArG-1) to formula (ArG-58); [Chemistry 4] [Chemistry 5] In formula (ArG-1) to formula (ArG-58), Me is a methyl group, tBu is a tert-butyl group, tAm is a tert-amyl group, and # indicates a bonding position to a nitrogen atom.

8. The polycyclic aromatic compound according to claim 7, wherein Ar 1 and Ar 2 At least one of them is a group represented by any one of the formulas selected from the group consisting of formula (ArG-1) to formula (ArG-46) and formula (ArG-55) to formula (ArG-58).

9. The polycyclic aromatic compound according to claim 3, wherein Z 1 is >O or >C(-R CZ )2.

10. The polycyclic aromatic compound according to claim 9, which is represented by any of the following formulas; [Chemistry 6] [Chemistry 7] In the formula, Me is a methyl group and tBu is a tert-butyl group.

11. The polycyclic aromatic compound according to claim 1, which is represented by any of the following formulas: In the formula, Me is a methyl group and tBu is a tert-butyl group.

12. The polycyclic aromatic compound according to claim 1, which is represented by any of the following formulas: In the formula, Me is a methyl group and tBu is a tert-butyl group.

13. An organic electroluminescent element, comprising: a pair of electrodes, including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer contains the polycyclic aromatic compound according to any one of claims 1 to 12.

14. The organic electroluminescent element according to claim 13, wherein The light-emitting layer includes a host and the polycyclic aromatic compound as a dopant.

15. The organic electroluminescent element according to claim 14, wherein The main body is an anthracene compound, a fluorene compound or a dibenzo Compound.

16. A display device or a lighting device, comprising the organic electroluminescent element according to claim 13.

Images