Polycyclic aromatic compound and organic electroluminescent element

Abstract

The present application provides a polycyclic aromatic compound and an organic electroluminescent element, the polycyclic aromatic compound according to an embodiment of the present application is represented by the following formula (1): In formula (1), A ring, B ring, C ring, D ring and E ring are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring, wherein at least one of A ring, B ring, C ring, D ring and E ring is represented by one of formula (Ar-1), formula (Ar-2), formula (Ar-3) and formula (Ar-4), X 1 , X 2 , X 3 and X 4 are each independently N-Ar, O, S or Se, in formula (Ar-1), formula (Ar-2), formula (Ar-3) and formula (Ar-4), Z is each independently -C(-R Z )= or -N=, R Z is hydrogen or a substituent.

Description

Technical Field

[0001] This invention relates to polycyclic aromatic compounds. It also relates to materials for organic devices, organic electroluminescent elements, and display and lighting devices comprising said polycyclic aromatic compounds. Background Technology

[0002] Previously, display devices using light-emitting elements that emit light through electroluminescence have been extensively studied due to their ability to achieve power savings or thinner designs. Consequently, organic electroluminescence elements (sometimes referred to as "organic EL elements" or simply "elements" in this specification) containing organic materials have been actively researched due to their ease of lightweighting or scaling up. In particular, the development of organic materials with light-emitting properties such as blue, one of the three primary colors of light, and the development of organic materials with charge transport capabilities including holes and electrons (possessing the potential to become semiconductors or superconductors), have been actively studied to date, with both high-molecular-weight and low-molecular-weight compounds being researched.

[0003] Organic EL devices have a structure comprising: a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing an organic compound. Within the organic compound-containing layers (sometimes referred to as "organic layers" in this specification), there may be a light-emitting layer, or a charge transport / injection layer for transporting or injecting charges such as holes or electrons, and various organic materials suitable for these layers have been developed.

[0004] Patent Document 1 discloses that polycyclic aromatic compounds formed by linking aromatic rings with heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur can be effectively used as materials for organic electroluminescent elements. Regarding these polycyclic aromatic compounds, it is reported that they possess a large highest occupied molecular orbital (HOMO) - lowest unoccupied molecular orbital (LUMO) gap and a high lowest excited triplet energy level (ET), and exhibit thermally activated delayed fluorescence, thus making them particularly effective as fluorescent materials for organic electroluminescent elements.

[0005] Prior art literature

[0006] Patent documents

[0007] Patent Document 1: International Publication No. 2015 / 102118 Summary of the Invention

[0008] The technical problem to be solved

[0009] As described above, various materials have been developed for use in organic EL devices, but to increase the selection of materials for organic EL devices, it is desirable to develop a material containing compounds different from those previously used. The objective of this invention is to provide a novel material that can be effectively used as a material for organic devices such as organic EL devices.

[0010] Another objective of this invention is to provide an organic electroluminescent device using a combination of novel materials. A particular objective of this invention is to provide an organic EL device with high external quantum efficiency.

[0011] Technical solutions for solving the problem

[0012] The inventors conducted diligent research to solve the aforementioned problems, and successfully manufactured a new compound as a polycyclic aromatic compound formed by linking aromatic rings using heteroelements such as boron, oxygen, nitrogen, and sulfur. Furthermore, they discovered that by arranging a layer containing the aforementioned polycyclic aromatic compound between a pair of electrodes to construct an organic EL device, excellent organic EL devices can be obtained, thus completing the present invention. In other words, the present invention provides a polycyclic aromatic compound as described below, and further provides materials for organic devices containing such polycyclic aromatic compounds.

[0013] <1> A polycyclic aromatic compound, represented by the following formula (1):

[0014]

[0015] In equation (1),

[0016] Rings A, B, C, D, and E are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring, wherein at least one of rings A, B, C, D, and E is represented by one of formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-4).

[0017] X 1 X 2 X 3 and X 4 They are independently N-Ar, O, S, or Se.

[0018] In N-Ar, Ar can be hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group.

[0019] In X 3In the case of N-Ar, Ar can be bonded to at least one of the A and B rings via a single bond or a linker group, in the X 4 In the case of N-Ar, Ar can be bonded to at least one of the A and C rings via a single bond or a linker group, in the X 1 In the case of N-Ar, Ar can be bonded to at least one of the B and D rings via a single bond or a linker group, in the X 2 In the case of N-Ar, Ar can be bonded to at least one of the C and E rings via a single bond or a linker group.

[0020] In formula (1), at least one of the groups selected from aryl rings and heteroaryl rings can be condensed by at least one cycloalkane, the cycloalkane can be substituted by at least one substituent, and at least one -CH2- in the cycloalkane can be substituted by -O-.

[0021] In equations (Ar-1), (Ar-2), (Ar-3), and (Ar-4),

[0022] Any two or three consecutive Z's are contraction positions, and all other Z's are independently -C(-R). Z = or -N=,

[0023] Z=Z can be independently set to >O and >NR respectively. NX >C(-R CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2 or >Se,

[0024] The R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted.

[0025] When rings A, B, C, D, and E are all represented by equation (Ar-1), at least one of Z in equation (Ar-1) is -N=.

[0026] In formula (1), at least one hydrogen atom may be replaced by deuterium, halogen, or cyano, and at least one nitrogen atom may be replaced by nitrogen-15 ( 15 (N) can be replaced, and at least one boron can be replaced by boron-11 (N). 11 B) Replacement.

[0027] <2> according to <1> The polycyclic aromatic compounds described herein, wherein at least one of the B ring, D ring, and E ring is represented by one of the formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-4), wherein the formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-4) are selected from at least one of the following formulas (Ar-1) to (Ar-1-3), (Ar-2-1) to (Ar-2-9), (Ar-3-1) to (Ar-3-6), and (Ar-4-1) to (Ar-4-4):

[0028]

[0029] In equations (Ar-1-1) to (Ar-1-3), equations (Ar-2-1) to (Ar-2-9), equations (Ar-3-1) to (Ar-3-6), and equations (Ar-4-1) to (Ar-4-4), And # represents B and X 1 X 2 or X 3 The bond position.

[0030] <3> according to <1> The polycyclic aromatic compounds described herein, wherein the A ring is represented by one of the formulas (Ar-1), (Ar-2), and (Ar-3), wherein the formulas (Ar-1), (Ar-2), and (Ar-3) are selected from the following formulas (Ar-5-1) to (Ar-5-4):

[0031]

[0032] In equations (Ar-5-1) to (Ar-5-4), # indicates the bond position to B, and # indicates the bond position to X. 3 or X 4 The bond position.

[0033] <4> according to <1> The polycyclic aromatic compounds described herein, wherein formula (1) is represented by the following formulas (1-1) to (1-74):

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] In equations (1-1) to (1-74), X 1 X 2 X 3 and X 4 Independently with X in equation (1) 1 X 2 X 3 and X 4 With the same definition, Za, Zb, Zc, Zd, and Ze are each independently -C(-R). Z )= or -N=, the R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted, with Za=Za, Zb=Zb, Zc=Zc, Zd=Zd, and Ze=Ze being independently >O, >NR, respectively. NX >C(-R CX )2、>Si(-R SiX )2、>S、>CO、>SO、>SO2 or>Se, where at least one of Za, Zb, Zc, Zd and Ze in equation (1-1) is -N=.

[0040] <5> according to <1> The polycyclic aromatic compounds recorded in it, X 3 and X 4 They are N-Ar, respectively.

[0041] <6> according to <1> The polycyclic aromatic compounds described herein, wherein formula (1) is represented by the following formulas (2-1) to (2-74):

[0042]

[0043]

[0044]

[0045]

[0046]

[0047] In equations (2-1) to (2-74), X 1 and X 2 Independently with X in equation (1) 1 and X 2 The definitions are the same, N-Ar 1 Ar in 1 and N-Ar 2 Ar 2Each of these is independently defined as Ar in N-Ar of equation (1), and Za, Zb, Zc, Zd, and Ze are independently -C(-R). Z )= or -N=, the R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted, with Za=Za, Zb=Zb, Zc=Zc, Zd=Zd, and Ze=Ze being independently >O, >NR, respectively. NX >C(-R CX )2、>Si(-R SiX )2、>S、>CO、>SO、>SO2 or>Se, where at least one of Za, Zb, Zc, Zd and Ze in equation (2-1) is -N=.

[0048] <7> according to <1> The polycyclic aromatic compounds recorded in it, X 1 and X 2 At least one of them is O or S.

[0049] <8> according to <6> The polycyclic aromatic compounds recorded in it, Ar 1 and Ar 2 At least one of them is represented by the following formula (o-Ar):

[0050]

[0051] In formula (o-Ar), The F ring represents a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring, and the G ring represents a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted arylthio, a substituted or unsubstituted heteroarylthio, a substituted or unsubstituted aryloxy, a substituted or unsubstituted heteroaryloxy, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl.

[0052] <9> according to <1> ~ <5> , <7> The polycyclic aromatic compounds described in any of the items in X 3 and X 4 In the case of N-Ar, the Ar is the same.

[0053] <10> according to <6> or <8> The polycyclic aromatic compounds described in the document, namely Ar 1 and the Ar 2 same.

[0054] <11> according to <1> The polycyclic aromatic compounds described herein are represented by any of the following formulas:

[0055]

[0056] .

[0057] <12> An organic electroluminescent element includes: a pair of electrodes, comprising an anode and a cathode; and an organic layer disposed between the pair of electrodes, the organic layer comprising, according to... <1> to <11> The polycyclic aromatic compounds recorded in it.

[0058] <13> according to <12> The organic electroluminescent element described herein has an organic layer that is a light-emitting layer.

[0059] <14> according to <13> The organic electroluminescent element described herein includes an luminescent layer comprising at least one selected from the group consisting of auxiliary dopants and phosphorescent materials.

[0060] <15> A display device comprising <12> The electroluminescent element described in the text.

[0061] <16> A lighting device comprising <12> The electroluminescent element described in the text.

[0062] Technical effect

[0063] According to the present invention, a novel polycyclic aromatic compound is provided. The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for a light-emitting layer used to form a light-emitting layer in an organic electroluminescent element. Attached Figure Description

[0064] Figure 1 This is a schematic cross-sectional view illustrating an example of an organic EL element.

[0065] Explanation of reference numerals in the attached figures

[0066] 100: Organic electroluminescent element

[0067] 101: Substrate

[0068] 102: Anode

[0069] 103: Hole Injection Layer

[0070] 104: Hole Transport Layer

[0071] 105: Emissive layer

[0072] 106: Electron Transport Layer

[0073] 107: Electron Injection Layer

[0074] 108: Cathode Detailed Implementation

[0075] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. Furthermore, in this specification, the numerical range indicated by "~" refers to the range including the values ​​described before and after "~" as both the lower and upper limits. Additionally, in this specification, "hydrogen" in the description of the structural formula refers to "hydrogen atom (H)".

[0076] In this specification, when referring to "adjacent base", it means two bases that are bonded to two adjacent atoms (two atoms directly bonded by covalent bonds) in the structural formula.

[0077] In this specification, the number of carbon atoms is sometimes used to represent chemical structures or substituents. However, when a substituent is substituted in a chemical structure, or when a substituent is further substituted on a substituent, the number of carbon atoms refers to the individual carbon atom of the chemical structure or substituent, and not the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituents. For example, "substituent B with carbon atom number X substituted by substituent A with carbon atom number X" means that "substituent A with carbon atom number X" is substituted on "substituent B with carbon atom number Y". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B. Similarly, "substituent B with carbon atom number Y substituted by substituent A" means that "substituent A (without a specified number of carbon atoms) is substituted on "substituent B with carbon atom number Y". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B.

[0078] <Explanation of Substituents>

[0079] First, the details of the substituents used in this specification are explained below.

[0080] In this specification, substituents are sometimes substituted by further substituents. For example, a particular substituent is sometimes described as "substituted or unsubstituted." This means that the particular substituent is substituted by at least one further substituent or is unsubstituted. In the same sense, it is sometimes also referred to as "substitutable." In this specification, the particular substituent in this case is sometimes referred to as the "first substituent," and the further substituent is referred to as the "second substituent."

[0081] In this specification, the substituent group Zα includes the substituents of the substituent group Z and the substituents represented by formula (A30) described later.

[0082] In this specification, the substituent group Z includes:

[0083] The aryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0084] Heteroaryl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0085] The diarylamino group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the two aryl groups in the diarylamino group may be bonded to each other via a linker group.

[0086] The diheteroarylamino group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the two heteroaryl groups in the diheteroarylamino group may be bonded to each other via a linker group.

[0087] The arylheteroarylamino group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the aryl and heteroaryl groups in the arylheteroarylamino group may be bonded to each other via a linker group.

[0088] The diarylboryl group may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, wherein the two aryl groups in the diarylboryl group may be bonded by a single bond or a linker group.

[0089] Alkyl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen.

[0090] Cycloalkyl groups may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0091] The alkoxy group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen.

[0092] The aryl group may be substituted by at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen.

[0093] It can replace silyl, cyano, and halogen.

[0094] The aryl group in substituent group Z, which serves as a second substituent, may be further substituted with aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen. Similarly, the heteroaryl group, which serves as a second substituent, may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen.

[0095] In this specification, the term "substituent" does not specifically limit the type of substituent, and unless otherwise specified, it can be any group selected from the substituent group Z. For example, when "substituted or unsubstituted" is used, the group can be substituted by at least one group selected from the substituent group Z.

[0096] In this specification, "aryl" is, for example, an aryl group with 6 to 30 carbon atoms, preferably an aryl group with 6 to 20 carbon atoms, an aryl group with 6 to 16 carbon atoms, an aryl group with 6 to 12 carbon atoms, or an aryl group with 6 to 10 carbon atoms.

[0097] Specific "aryl" groups can be listed as monovalent groups formed by removing one hydrogen atom from the aforementioned "aryl ring". Examples include: a monocyclic phenyl group, a bicyclic biphenyl group (2-biphenyl, 3-biphenyl, or 4-biphenyl), a condensed bicyclic naphthyl group (1-naphthyl or 2-naphthyl), a tricyclic 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), and a condensed tricyclic acenaphthene-(1-, 3-, 4-, or 5-) group. -) group, fluorene-(1-, 2-, 3-, 4-, or 9-) group, phenaten-(1- or 2-) group, phenanthrene-(1-, 2-, 3-, 4-, or 9-) group, or anthracene-(1-, 2-, or 9-) group, are tetracyclic tetraphenyl groups (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-tetraphenyl), are condensed tetracyclic triphenyl-(1- or 2-) group, pyrene-(1-, 2-, or 4-) group, or benzotetraphenyl-(1-, 2-, or 5-) group, or condensed pentacyclic perylene-(1-, 2-, or 3-) group, or benzopentaphenyl-(1-, 2-, 5-, or 6-) group, etc. In addition, examples include monovalent bases of spirofluorene.

[0098] Furthermore, the aryl group that serves as the second substituent also includes a structure in which the aryl group is substituted with at least one group selected from the group consisting of aryl groups such as phenyl (specifically, the groups described above), alkyl groups such as methyl (specifically, the groups described later), and cycloalkyl groups such as cyclohexyl or adamantyl (specifically, the groups described later).

[0099] As an example, one could list a group at the 9-position of the fluorene group, which is a second substituent, that is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl.

[0100] "Aromaticyl" is, for example, an arylene with 6 to 30 carbon atoms, preferably an arylene with 6 to 20 carbon atoms, an arylene with 6 to 16 carbon atoms, an arylene with 6 to 12 carbon atoms, or an arylene with 6 to 10 carbon atoms.

[0101] Specific examples of "aryl" include divalent groups formed by removing one hydrogen atom from the aforementioned "aryl" (monovalent group).

[0102] "Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. In the "heteroaryl", in addition to carbon atoms, there are one or more, preferably one to five, heteroatoms selected from oxygen, sulfur, nitrogen, etc., as ring-forming atoms.

[0103] Specific examples of "heteroaryl" groups include monovalent groups formed by removing one hydrogen atom from the aforementioned "heteroaryl ring." Examples include: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isoindole, 1H-indazole, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phenanthrololinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazole, acridineyl, phenoxthiazolyl, phenoxazinyl, phenthiazolyl, phenazinyl, and phenazasilinyl. Indazinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, monovalent group of benzophosphane pentadiene oxide ring, monovalent group of dibenzophosphane pentadiene oxide ring, furazinyl, thiathanyl, indolocarbazoyl, benzoindolocarbazoyl, dibenzoindolocarbazoyl, dihydroindolocarbazoyl, benzofuranocarbazoyl, benzothiophenocarbazoyl, benzoselenophenocarbazoyl, dihydroindocarbazoyl, dihydrobenzosilicyclopentadienocarbazoyl, imidazolinyl, or oxazolinyl, etc. In addition, examples include: the monovalent group of spiro[fluorene-9,9'-xanthine], the monovalent group of spirodi[siliconium], and the monovalent group of benzo[selenene].

[0104] Furthermore, the heteroaryl group that serves as the second substituent also includes a structure in which the heteroaryl group is substituted with at least one group selected from the group consisting of aryl groups such as phenyl (specifically, the groups described above), alkyl groups such as methyl (specifically, the groups described later), and cycloalkyl groups such as cyclohexyl or adamantyl (specifically, the groups described later).

[0105] As an example, groups at the 9-position of the carbazolyl group, which is a second substituent, may be substituted with aryl groups such as phenyl, alkyl groups such as methyl, or cyclohexyl or adamantyl. Furthermore, groups in which nitrogen-containing heteroaryl groups such as pyridyl, pyrimidinyl, triazine, and carbazolyl are further substituted with phenyl or biphenyl groups are also included in heteroaryl groups that are second substituents.

[0106] "Heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms. Additionally, "heteroarylene" is, for example, a divalent group containing, in addition to carbon, one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms in a heterocycle.

[0107] Specific examples of "heteroaryl" include divalent groups formed by removing one hydrogen atom from the aforementioned "heteroaryl" (monovalent group).

[0108] "Diarylamino" is an amino group in which two aryl groups have been substituted. For details about the aryl groups, please refer to the description of "aryl".

[0109] "Diheteroarylamino" is an amino group in which two heteroaryl groups have been substituted. For details about the heteroaryl groups, please refer to the description of "heteroaryl".

[0110] "Arylheteroarylamino" refers to an amino group in which aryl and heteroaryl groups have been substituted. For details regarding the aryl and heteroaryl groups, please refer to the description of "aryl" and "heteroaryl".

[0111] In a diarylamino group where the first substituent is present, the two aryl groups can be bonded to each other via a linking group; in a diheteroarylamino group where the first substituent is present, the two heteroaryl groups can be bonded to each other via a linking group; and in an arylheteroarylamino group where the first substituent is present, the aryl and heteroaryl groups can be bonded to each other via a linking group. Here, the phrase "bonded via a linking group" is used as follows, for example, to indicate that the two phenyl groups of a diphenylamino group form a bond through a linking group. This description also applies to diheteroarylamino groups and arylheteroarylamino groups formed from aryl or heteroaryl groups.

[0112]

[0113] ( (Indicates the location of the bond).

[0114] As linking bases, specifically, examples include: >O, >NR X >C(-R X )2、-(CR X )=(CR X )-、>Si(-R X)2, >S, >CO, >CS, >SO, >SO2, and >Se. R X Each can be independently alkyl, cycloalkyl, aryl, or heteroaryl, and these can be substituted with alkyl, cycloalkyl, aryl, or heteroaryl groups. Additionally, >C(-R X )2、-(CR X )=(CR X )-、>Si(-R X )2 Each of the two R X It can be achieved via a single bond or a linker X. Y They bond together to form a loop. As X Y Examples include >O and >NR. Y >C(-R Y )2、>Si(-R Y )2, >S, >CO, >CS, >SO, >SO2, and >Se, R Y Each of these can be independently alkyl, cycloalkyl, aryl, or heteroaryl, and these can be substituted with alkyl, cycloalkyl, aryl, or heteroaryl groups. Specifically, in X... Y >C(-R) Y )2 and >Si(-R Y In the case of )2, two R Y It will not bond and further form a ring. Furthermore, as a linking group, alkenyl groups can also be cited. Any hydrogen atom of the alkenyl group can be independently bonded via R... 2X Replace, R 2X They are independently alkyl, cycloalkyl, substituted silyl, aryl, and heteroaryl groups, which can be substituted by alkyl, cycloalkyl, substituted silyl, or aryl groups. -(CR X )=(CR X The two R's in )- X They can bond with each other and together with these bonded C=C atoms to form aryl rings (such as benzene rings) or heteroaryl rings. That is, -(CR X )=(CR X - It can be an arylene (1,2-phenylene, etc.) or a heteroarylene.

[0115] Furthermore, when referred to in this specification only as "diarylamino", "diheteroarylamino", or "arylheteroarylamino", unless otherwise specified, it is assumed that the following descriptions are added respectively: "the two aryl groups of the diarylamino can be bonded to each other via a linking group", "the two heteroaryl groups of the diheteroarylamino can be bonded to each other via a linking group", and "the aryl and heteroaryl groups of the arylheteroarylamino can be bonded to each other via a linking group".

[0116] "Diarylboryl" is a boron group in which two aryl groups have been substituted. Details regarding the aryl group can be found in the description of "aryl". Furthermore, the two aryl groups can be bonded via single bonds or linking groups (e.g., -CH=CH-, -CR=CR-, -C≡C-, NR, >O, >S, >C(-R)2, >Si(-R)2, or >Se). Here, the R in -CR=CR-, >NR, >C(-R)2, and >Si(-R) are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy groups, and at least one hydrogen atom in R can be further substituted with an aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl group. Additionally, two adjacent R groups can bond together to form a ring, thus forming a cycloalkylene, arylene, or heteroarylene. For details regarding the substituents listed here, please refer to the descriptions of "aryl," "arylene," "heteroaryl," "heteroarylene," and "diarylamino" above, and the descriptions of "alkyl," "alkenyl," "alkynyl," "cycloalkyl," "cycloalkylene," "alkoxy," and "aryloxy" below. Furthermore, in this specification, when only "diarylboryl" is used, unless otherwise specified, it is assumed that "the two aryl groups of the diarylboryl group can be bonded to each other via a single bond or a linking group."

[0117] "Alkyl" can be either straight-chain or branched, for example, a straight-chain alkyl with 1 to 4 carbons or a branched alkyl with 3 to 4 carbons, preferably an alkyl with 1 to 18 carbons (branched alkyl with 3 to 18 carbons), an alkyl with 1 to 12 carbons (branched alkyl with 3 to 12 carbons), an alkyl with 1 to 6 carbons (branched alkyl with 3 to 6 carbons), an alkyl with 1 to 5 carbons (branched alkyl with 3 to 5 carbons), an alkyl with 1 to 4 carbons (branched alkyl with 3 to 4 carbons), etc.

[0118] Specific examples of "alkyl" include: methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-Ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl, etc.

[0119] "alkylene" is a divalent group obtained by removing any hydrogen atom from an "alkyl" group, such as methylene, ethylene, and propylene.

[0120] Regarding "alkenyl", please refer to the description of "alkyl". It is a group in which the C=C single bond in the structure of "alkyl" is replaced with a C=C double bond. It also includes groups in which not only one but more single bonds are replaced with double bonds (also called diene-yl or triene-yl).

[0121] "Alkenyl" is a divalent group obtained by removing any one of the hydrogen atoms from an "alkenyl" group, such as vinylidene.

[0122] Regarding "alkynyl", please refer to the description of "alkyl". It is a group in which the C C single bond in the structure of "alkyl" is replaced with a C≡C triple bond. It also includes groups in which not only one but more single bonds are replaced with triple bonds (also called diynyl or triynyl).

[0123] "Cycloalkyl" is, for example, a cycloalkyl group having 3 to 24 carbon atoms, preferably a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, or a cycloalkyl group having 5 carbon atoms, etc.

[0124] Specific examples of "cycloalkyl" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbons or 1 to 4 carbons, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, or decahydroazyl, etc.

[0125] "Cycloalkylene" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, a cycloalkylene having 3 to 14 carbon atoms, a cycloalkylene having 3 to 12 carbon atoms, a cycloalkylene having 5 to 10 carbon atoms, a cycloalkylene having 5 to 8 carbon atoms, a cycloalkylene having 5 to 6 carbon atoms, or a cycloalkylene having 5 carbon atoms, etc.

[0126] Specific examples of "cycloalkylene" can be listed, for instance, from the structure of "cycloalkyl" (monovalent group) with one hydrogen removed to make it divalent.

[0127] "Cycloalkenyl" can be listed as a group having at least one pair of single bonds between two carbons in the "cycloalkyl" group that form a double bond (e.g., a group where -CH2-CH2- is substituted to -CH=CH-), and is not equivalent to an aryl group. Specifically, 1-cyclohexenyl, 1-cyclopentenyl, etc., can be listed.

[0128] "Alkoxy" is the group represented by "Alk-O- (Alk is alkyl)", and for details about the alkyl group, please refer to the description of the "alkyl".

[0129] "Aryloxy group" is the group represented by "Ar-O- (Ar is aryl)". For details about the aryl group, please refer to the description of "aryl".

[0130] "Substituted silyl" refers to, for example, a silyl group substituted with at least one of aryl, alkyl, and cycloalkyl groups, preferably a triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0131] "Triarylsilyl" refers to a silyl group substituted with three aryl groups. For details regarding the aryl groups, please refer to the description of "aryl".

[0132] Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmonaphthylsilyl, monophenyldinaphthylsilyl, or triaphthylsilyl, etc.

[0133] "Trialkylsilyl" refers to a silyl group substituted with three alkyl groups. For details regarding the alkyl group, please refer to the description of "alkyl" above.

[0134] Specific examples of "trialkylsilyl" include: trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, ethyl dimethylsilyl, n-propyl dimethylsilyl, isopropyl dimethylsilyl, n-butyl dimethylsilyl, isobutyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, methyl diethylsilyl, n-propyl Diethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyl di-n-propylsilyl, ethyl di-n-propylsilyl, n-butyl di-n-propylsilyl, sec-butyl di-n-propylsilyl, tert-butyl di-n-propylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, n-butyl diisopropylsilyl, sec-butyl diisopropylsilyl, or tert-butyl diisopropylsilyl, etc.

[0135] "Tricycloalkylsilyl" refers to a silyl group substituted with three cycloalkyl groups. For details regarding the cycloalkyl group, please refer to the description of "cycloalkyl" above.

[0136] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl or tricyclohexylsilyl.

[0137] "Dialkylcycloalkylsilyl" refers to a silyl group substituted with two alkyl groups and one cycloalkyl group. For details regarding the alkyl and cycloalkyl groups, please refer to the description of "alkyl" and "cycloalkyl".

[0138] "alkyl-dicycloalkyl-silyl" refers to a silyl group substituted with one alkyl group and two cycloalkyl groups. For details regarding the alkyl and cycloalkyl groups, please refer to the description of "alkyl" and "cycloalkyl".

[0139] The "halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and even more preferably fluorine.

[0140] When cyano or halogen is substituted, it is preferably in the form in which all or part of the hydrogens in the aryl ring or heteroaryl ring of the structure are substituted by cyano or halogen.

[0141] The substituent represented by formula (A30) has the following structure.

[0142]

[0143] In the aforementioned formula (A30),

[0144] Ak is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted cycloalkenyl group, wherein at least one of the alkyl, cycloalkyl, and cycloalkenyl groups may be substituted with -O- or -S-.

[0145] R Ak R is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. Ak It can be bonded to Ak via a linker base or a single bond. This indicates the location of the bond.

[0146] In formula (A30), by using Ak as the substituent without conjugating it with the non-covalent electron pairs on N, the non-covalent electron pairs can be conjugated with the π electrons at the bond junction. Compared to the case where aryl groups or the like are present at the same position, a greater wavelength variation can be achieved. Furthermore, the same applies to the effect on the multiple resonance effect, resulting in a greater improvement in thermally activated delayed fluorescence (TADF).

[0147] R Ak Preferably, it is an aryl group that can be substituted with an alkyl or cycloalkyl group, a heteroaryl group that can be substituted with an alkyl or cycloalkyl group, an alkyl or cycloalkyl group, more preferably an aryl group that can be substituted with an alkyl group, a heteroaryl group that can be substituted with an alkyl group, an alkyl or cycloalkyl group, and even more preferably an aryl group that can be substituted with an alkyl group, and particularly preferably a phenyl group that can be substituted with a methyl group.

[0148] In formula (A30), Ak is preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.

[0149] R Ak It can be the same as or different from Ak, but it is preferred to be different.

[0150] R Ak It can be bonded to Ak via a linker group or a single bond. Examples of linker groups in this case include: >O, >S, or >Si(-R)2, etc. In >Si(-R)2, R is hydrogen, an aryl group with 6-12 carbon atoms, an alkyl group with 1-6 carbon atoms, or a cycloalkyl group with 3-14 carbon atoms. As R... AkExamples of structures that are linked to Ak by a linker base or a single bond include the following structures.

[0151]

[0152] In the aforementioned formulas, This indicates the location of the bond.

[0153] 1. Polycyclic aromatic compounds

[0154] 1-1. Polycyclic aromatic compounds

[0155] The polycyclic aromatic compounds of the present invention are polycyclic aromatic compounds having the structure represented by formula (1). These polycyclic aromatic compounds are useful as compounds for forming highly efficient and long-life components. Furthermore, compared to similar compounds with the same molecular weight, they are less prone to decomposition during vapor deposition.

[0156]

[0157] In equation (1), “A”, “B”, “C”, “D” and “E” are each independently a marker representing a ring structure.

[0158] In formula (1), "A", "B", "C", "D" and "E" represent rings A, B, C, D and E, which are independently substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings. At least one of rings A, B, C, D and E is represented by one of formulas (Ar-1), (Ar-2), (Ar-3) and (Ar-4).

[0159] The "aryl ring" in ring A, ring B, ring C, ring D and ring E in formula (1) can be aryl rings with 6 to 30 carbons, preferably aryl rings with 6 to 16 carbons, more preferably aryl rings with 6 to 12 carbons, and particularly preferably aryl rings with 6 to 10 carbons.

[0160] Specific examples of "aryl rings" include: monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthalene rings and indene rings, tricyclic terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl), condensed tricyclic acenaphthene rings, fluorene rings, phenanthene rings, anthracene rings, condensed tetracyclic triphenylene rings, pyrene rings, benzo[a]tetraphenyl rings, and benzo[b]benzene rings, and pentane rings, etc. Furthermore, fluorene rings, benzo[a]fluorene rings, and indene rings also contain structures with fluorene rings, benzo[a]fluorene rings, cyclopentane rings, etc., linked by spiral bonds. Furthermore, fluorene rings, benzo[a]fluorene rings, and indene rings also include rings in which two of the two hydrogens of the methylene group are replaced by alkyl groups such as methyl groups described later as first substituents, thus becoming rings such as dimethylfluorene rings, dimethylbenzo[a]fluorene rings, and dimethyl indene rings.

[0161] As for the "heteroaryl ring" in rings A, B, C, D, and E in formula (1), examples include heteroaryl rings with 2 to 30 carbon atoms, preferably heteroaryl rings with 2 to 25 carbon atoms, more preferably heteroaryl rings with 2 to 20 carbon atoms, even more preferably heteroaryl rings with 2 to 15 carbon atoms, and particularly preferably heteroaryl rings with 2 to 10 carbon atoms. In addition, examples of "heteroaryl rings" include heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon atoms.

[0162] Specific examples of "heteroaryl rings" include: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetraazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cyclophosphine ring, quinazolinoline ring, quinoxaline ring, phthalazine ring, naphthidine ring, purine ring, pteridine ring, carbazole ring, acridine ring, and phenanthridine ring. Phenoxamethonium ring, phenoxazine ring, phenthiazine ring, phenazine ring, phenazasiline ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazine ring, thiathracene ring, indole-carbazole ring, benzoindole-carbazole ring, benzobenzoindole-carbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthonium ring, thioxanthonium ring, dibenzodioxin ring, dibenzoheptanine ring, tribenzozazepine ring, iminobibenzyl ring, etc. Furthermore, in dihydroacrylidine rings, xanthones, and thioxanthones, it is preferable that two of the two hydrogens of the methylene group are replaced with alkyl groups such as methyl groups (described later as first substituents) to form dimethyldihydroacrylidine rings, dimethylxanthones, dimethylthioxanthones, etc. Additionally, bipyridine rings, phenylpyridine rings, and pyridylphenyl rings (which are bicyclic), and tricyclic rings, terpyridine rings, bispyridylphenyl rings, and pyridylbiphenyl rings (which are tricyclic) can also be listed as "heteroaryl rings." Furthermore, "heteroaryl rings" also include pyran rings.

[0163] In rings A, B, C, D, and E, the aryl ring can be selected from the group consisting of benzene ring, biphenyl ring, indene ring, naphthyl ring, fluorene ring, anthracene ring, and phenanthrene ring, and the heteroaryl ring can be selected from the group consisting of pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, phenanthridine ring, benzofuran ring, benzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, naphthioran ring, naphthiophene ring, benzoindole ring, and benzoselenophenol ring.

[0164] When at least one hydrogen atom in the aryl ring or heteroaryl ring is substituted, the substituent is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl and a heteroaryl group), a substituted or unsubstituted diarylboroyl group (the two aryl groups may be linked by a single bond or a linker group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted silyl group, a cyano group, or -L-Ak. Examples of substituents for these groups when they have substituents include: aryl, heteroaryl, alkyl or cycloalkyl, or diarylamino.

[0165] In the formula (1), at least one of the groups consisting of aryl rings and heteroaryl rings can be condensed by at least one cycloalkane, the cycloalkane can be substituted by at least one substituent, and at least one -CH2- of the cycloalkane can be substituted by -O-.

[0166] At least one hydrogen atom in formula (1) may be replaced by deuterium, halogen, or cyano, and at least one nitrogen atom may be replaced by nitrogen-15 ( 15 N) can be replaced, and at least one sulfur can be replaced by sulfur-33( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) can be replaced, at least one oxygen can be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O) can be replaced, and at least one carbon can be replaced by carbon-13 (O). 13 C) can be replaced, at least one boron can be replaced by boron-11 ( 11 B) Replacement.

[0167] Examples of "cycloalkanes" include: cycloalkanes with 3-24 carbon atoms, cycloalkanes with 3-20 carbon atoms, cycloalkanes with 3-16 carbon atoms, cycloalkanes with 3-14 carbon atoms, cycloalkanes with 5-10 carbon atoms, cycloalkanes with 5-8 carbon atoms, cycloalkanes with 5-6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0168] 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[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diadamantane, decahydronaphthalene and decahydroazine, and their alkyl (especially methyl) substituted derivatives, halogen (especially fluorine) substituted derivatives, and deuterium substituted derivatives, etc., having carbon numbers from 1 to 5.

[0169] Among these, a structure in which at least one hydrogen atom on the α-carbon of the cycloalkane (in a cycloalkane condensed with an aryl ring or heteroaryl ring, the carbon atom adjacent to the carbon at the condensation site) is substituted is preferred; a structure in which two hydrogen atoms on the α-carbon are substituted is more preferred; and a structure in which a total of four hydrogen atoms on the two α-carbons are substituted is even more preferred. Examples of substituents include alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents, and deuterium substituents. A structure in which a partial structure represented by the following formula (B10) is bonded to an adjacent carbon atom in the aryl ring or heteroaryl ring is particularly preferred.

[0170]

[0171] In formula (B10), Me represents methyl. Indicates the location of the bond.

[0172] At least one hydrogen atom in the “aryl ring” or “heteroaryl ring” may be substituted by a first substituent, a substituted or unsubstituted “aryl”, a substituted or unsubstituted “heteroaryl”, a substituted or unsubstituted “diarylamino”, a substituted or unsubstituted “diheteroarylamino”, a substituted or unsubstituted “arylheteroarylamino”, a substituted or unsubstituted “diarylboroyl (the two aryl groups may be linked by a single bond or a linker group)”, a substituted or unsubstituted “alkyl”, a substituted or unsubstituted “cycloalkyl”, a substituted or unsubstituted “alkoxy”, a substituted or unsubstituted “aryloxy”, a substituted “silylalkyl”, or -L-Ak. Regarding the "aryl" or "heteroaryl" as the first substituent, the aryl of "diarylamino", the heteroaryl of "diheteroarylamino", the aryl and heteroaryl of "arylheteroarylamino", the aryl of "diarylboryl" and the aryl of "aryloxy", the monovalent groups of the "aryl ring" or "heteroaryl ring" can be listed.

[0173] Specifically, as "aryl", examples include aryl groups with 6 to 30 carbon atoms, preferably aryl groups with 6 to 24 carbon atoms, more preferably aryl groups with 6 to 20 carbon atoms, even more preferably aryl groups with 6 to 16 carbon atoms, particularly preferably aryl groups with 6 to 12 carbon atoms, and most preferably aryl groups with 6 to 10 carbon atoms.

[0174] Specific examples of aryl groups include: phenyl groups that are monocyclic aryl groups; (2-, 3-, 4-)biphenyl groups that are dicyclic aryl groups; (1-, 2-)naphthyl and (2-, 3-, 4-, 5-, 6-, 7-)indenyl groups that are condensed dicyclic aryl groups; terphenyl groups that are tricyclic aryl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); and condensed tricyclic aryl groups. Aryl acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrene, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl), triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, tetraphenyl-(1-, 2-, 5-)yl, perylene-(1-, 2-, 3-)yl, pentaphenyl-(1-, 2-, 5-)yl, etc., preferably phenyl, biphenyl, or terphenyl.

[0175] Furthermore, as a "heteroaryl group," examples include heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Additionally, examples of heteroaryl groups include heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, excluding carbon atoms.

[0176] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazonyl, thiadiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thiophene, dibenzothiophene, indole, isoindole, 1H-inzolyl, benzimidazolyl, benzoxazolyl, benzothiazole The following groups are preferred: 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purinyl, pteridinyl, carbazoleyl, dihydroindolocarbazoleyl, benzofuranocarbazoleyl, benzothiophenocarbazoleyl, benzoselenophenocarbazoleyl, dihydroindobenzocarbazoleyl, dihydrobenzosilicyclopentadienocarbazoleyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxthiazinyl, thiaxanthrayl, indazinyl, etc., preferably pyridinyl, pyrimidinyl, triazinyl, and carbazoleyl.

[0177] Furthermore, the "alkyl" group used as the first substituent can be either straight-chain or branched, for example, straight-chain alkyl groups having 1 to 24 carbon atoms or branched alkyl groups having 3 to 24 carbon atoms. Preferably, it is an alkyl group having 1 to 18 carbon atoms (branched alkyl groups having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (branched alkyl groups having 3 to 12 carbon atoms), even more preferably an alkyl group having 1 to 8 carbon atoms (branched alkyl groups having 3 to 8 carbon atoms), particularly preferably an alkyl group having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms), and most preferably an alkyl group having 1 to 5 carbon atoms (branched alkyl groups having 3 to 5 carbon atoms).

[0178] Specific alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc., preferably tert-butyl.

[0179] Other examples include: 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc.

[0180] As a substituent when at least one hydrogen atom in the aryl ring or heteroaryl ring is substituted by a substituent, one particularly preferred substituent is a tertiary alkyl group represented by the following formula (tR) that is a substituent containing the "alkyl" group. This is because the intermolecular distance increases with such a bulky substituent, thus increasing the photoluminescence quantum yield (PLQY). Furthermore, it is also preferred to use a tertiary alkyl group represented by formula (tR) as a second substituent to substitute for other substituents. Specifically, examples include: a diarylamino group substituted with a tertiary alkyl group represented by (tR), a carbazolyl group substituted with a tertiary alkyl group represented by (tR) (preferably N-carbazolyl), or a benzo[a]carbazolyl group substituted with a tertiary alkyl group represented by (tR) (preferably N-benzo[a]carbazolyl).

[0181] Regarding "diarylamino", examples of groups described above as "first substituents" can be listed, with diphenylamino being the preferred one.

[0182] As for the substitution forms of the group of formula (tR) for diarylamino, carbazolyl and benzocarbazolyl, examples can be given of the substitution of some or all of the hydrogens of the aryl ring or benzene ring in these groups by the group of formula (tR).

[0183]

[0184] In equation (tR), R a R b and R c Each is independently an alkyl group having 1 to 24 carbon atoms, wherein any -CH2- group in the alkyl group may be substituted with -O-. It is the location of the bond.

[0185] As R a R b and R cThe term "alkyl group having 1 to 24 carbon atoms" can be either straight-chain or branched. Examples include: straight-chain alkyl groups having 1 to 24 carbon atoms or branched alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched alkyl groups having 3 to 4 carbon atoms).

[0186] R in equation (tR) a R b and R c The total number of carbons is preferably 3 to 20, and more preferably 3 to 10.

[0187] As R a R b and R c Specific alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0188] Examples of groups represented by formula (tR) include: tert-butyl, tert-pentyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-Ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, tert-butyl and tert-pentyl are preferred.

[0189] Examples of "cycloalkyl" groups as the first substituent include: cycloalkyl groups with 3 to 24 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 16 carbon atoms, cycloalkyl groups with 3 to 14 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, cycloalkyl groups with 5 to 8 carbon atoms, cycloalkyl groups with 5 to 6 carbon atoms, and cycloalkyl groups with 5 carbon atoms.

[0190] Specific examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) derivatives having 1 to 5 carbon atoms, or norbornyl (bicyclo[2.2.1]heptyl), 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[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazyl, etc.

[0191] Furthermore, regarding the "alkoxy group" as the first substituent, examples include straight-chain alkoxy groups with 1 to 24 carbon atoms or branched alkoxy groups with 3 to 24 carbon atoms. Preferably, it is an alkoxy group with 1 to 18 carbon atoms (branched alkoxy groups with 3 to 18 carbon atoms), more preferably an alkoxy group with 1 to 12 carbon atoms (branched alkoxy groups with 3 to 12 carbon atoms), and even more preferably an alkoxy group with 1 to 6 carbon atoms (branched alkoxy groups with 3 to 6 carbon atoms), and particularly preferably an alkoxy group with 1 to 5 carbon atoms (branched alkoxy groups with 3 to 5 carbon atoms).

[0192] Specific alkoxy groups include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, tert-pentoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0193] Furthermore, regarding "substituted silyl" as the first substituent, examples include silyl groups substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl groups. Examples include: trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0194] As "trialkylsilyl", a group in which the three hydrogens of a silyl group are each independently substituted by an alkyl group can be listed, and the alkyl group can refer to the group described as "alkyl" in the first substituent. For substitution, the preferred alkyl group is an alkyl group having 1 to 5 carbon atoms, specifically, examples include: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert-amyl, etc.

[0195] Specific examples of trialkylsilyl groups include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, tritert-pentylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, tert-pentyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl dimethylsilyl, methyl diethylsilyl, propyl diethyl ... Ethyl silane, butyl diethyl silane, sec-butyl diethyl silane, tert-butyl diethyl silane, tert-pentyl diethyl silane, methyl dipropyl silane, ethyl dipropyl silane, butyl dipropyl silane, sec-butyl dipropyl silane, tert-butyl dipropyl silane, tert-pentyl dipropyl silane, methyl diisopropyl silane, ethyl diisopropyl silane, butyl diisopropyl silane, sec-butyl diisopropyl silane, tert-butyl diisopropyl silane, tert-pentyl diisopropyl silane, etc.

[0196] As "tricycloalkylsilyl", a group in which the three hydrogens of the silyl group are each independently substituted by a cycloalkyl group can be listed, and the cycloalkyl group can refer to the group described as "cycloalkyl" in the first substituent. Preferred cycloalkyl groups for substitution are cycloalkyl groups with 5 to 10 carbon atoms, specifically including: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazyl, etc.

[0197] Specific examples of tricycloalkylsilyl groups include tricyclopentylsilyl and tricyclohexylsilyl.

[0198] As specific examples of substituted dialkylcycloalkylsilyl groups having two alkyl groups and one cycloalkyl group, and substituted alkyldicycloalkylsilyl groups having one alkyl group and two cycloalkyl groups, examples include silyl groups substituted with groups selected from the specific alkyl and cycloalkyl groups.

[0199] Specific examples of dialkylarylsilyl substituted with two alkyl groups and one aryl group, alkyldiarylsilyl substituted with one alkyl group and two aryl groups, and triarylsilyl substituted with three aryl groups include silyl substituted with groups selected from the specific alkyl and aryl groups. Specifically, triphenylsilyl substituted is a specific example of a triarylsilyl substituted alkyl group.

[0200] Additionally, the "aryl" in "diarylboryl" as the first substituent can be referenced from the description of the aryl group. Furthermore, the two aryl groups can be bonded via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above are the first substituents), which may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above are the second substituents). Specific examples of these groups can be referenced from the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent.

[0201] In the -L-Ak of ​​the first substituent, L is >NR, >O, or >S, and the R of >NR is a substituted aryl, a substituted heteroaryl, a substituted alkyl, or a substituted cycloalkyl. Additionally, the R of >NR can be bonded to Ak via a linking group or a single bond.

[0202] Ak is hydrogen, a substituted alkyl group, or a substituted cycloalkyl group, wherein at least one hydrogen atom in the alkyl or cycloalkyl group is substituted, and at least one -CH2- atom in the alkyl or cycloalkyl group is substituted with -O- and -S-.

[0203] L is preferably greater than NR.

[0204] When L is greater than NR, R is preferably an aryl group that can be substituted with alkyl or cycloalkyl, a heteroaryl group that can be substituted with alkyl or cycloalkyl, an alkyl or cycloalkyl group, more preferably an aryl group that can be substituted with alkyl, a heteroaryl group that can be substituted with alkyl, an alkyl or cycloalkyl group, and even more preferably an aryl group that can be substituted with alkyl, and particularly preferably a phenyl group that can be substituted with methyl.

[0205] Ak is preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and is more preferably an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.

[0206] When L is >NR, R can be bonded to Ak via a linker group or a single bond. Examples of linker groups in this case include >O, >S, or >Si(-R)2. In >Si(-R)2, R is hydrogen, an aryl group with 6-12 carbon atoms, an alkyl group with 1-6 carbon atoms, or a cycloalkyl group with 3-14 carbon atoms. Examples of structures where R in >NR is bonded to Ak via a linker group or a single bond include the following structures.

[0207]

[0208] In the aforementioned formulas, Me is a methyl group, in Its position forms an atomic bond with the aryl or heteroaryl rings in rings A, B, C, D, or E.

[0209] As a first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (the two aryl groups may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silylalkyl", as described as substituted or unsubstituted, at least one hydrogen atom of which may be substituted by a second substituent. Examples of the second substituent include, for example, aryl, heteroaryl, alkyl, or cycloalkyl, with specific examples referring to the description of the monovalent group of the "aryl ring" or "heteroaryl ring" and the "alkyl" or "cycloalkyl" as the first substituent. Furthermore, in the aryl or heteroaryl groups that are the second substituents, structures in which at least one hydrogen atom is replaced by an aryl group such as phenyl (specifically, the groups described above), an alkyl group such as methyl, tert-butyl (specifically, the groups described above), or a cycloalkyl group such as cyclohexyl (specifically, the groups described above) are also included in the aryl or heteroaryl groups that are the second substituents. As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at the 9-position is replaced by an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included in the heteroaryl group that is the second substituent.

[0210] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the first substituent. Preferably, the radicals are those represented by the following structural formulas, more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole (especially N-carbazole), 3,6-dimethylcarbazole, 3,6-di-tert-butylcarbazole, and phenoxy, and even more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole. From the viewpoint of ease of synthesis, sterically hindered groups are preferred for selective synthesis. Specifically, tert-butyl, tert-pentyl, tert-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole are preferred.

[0211] In the following structural formulas, "Me" represents methyl, "tBu" represents tert-butyl, "tAm" represents tert-pentyl, and "tOct" represents tert-octyl. Indicates the location of the bond.

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227] As a substituent when two or three hydrogen atoms bonded to a continuous (adjacent) carbon atom are substituted, it can be a group represented by formula (A20).

[0228]

[0229] In formula (A20), L S The terms are >NR, >O, >Si(-R)2, or >S, wherein the R in >NR is a substituted aryl, substituted heteroaryl, substituted alkyl, or substituted cycloalkyl, and the R in >Si(-R)2 is hydrogen, a substituted aryl, a substituted alkyl, or a substituted cycloalkyl, and they can be bonded to each other to form a ring. Furthermore, at least one of the Rs in >NR and >Si(-R)2 can be bonded to a ring selected from ring A, ring B, ring C, ring D, ring E, or ring R via a linking group or a single bond. S At least one node in the group formed,

[0230] r is an integer from 1 to 4.

[0231] R S Each is independently hydrogen, a substituted alkyl group, or a substituted cycloalkyl group, and any R S It can be linked to another arbitrary R through a base or a single bond. S They are linked together.

[0232] The basis represented by equation (A20) lies in two The two atoms adjacent to each other on the ring of an aryl ring, a heteroaryl ring, or a cycloalkane ring are bonded together.

[0233] In the case where the polycyclic aromatic compound represented by formula (1) contains a group represented by formula (A20), the number of said group is preferably one or two. The group represented by formula (A20) may be a substituent in any one of the rings A, B, C, D, and E.

[0234] The basis represented by equation (A20) lies in two The group is formed by two atoms adjacent to the aryl ring or heteroaryl ring, respectively. The group represented by formula (A20) is preferably formed by two atoms... The two atoms adjacent to the aryl or heteroaryl ring are bonded at the respective sites. Preferably, both adjacent atoms on the ring are carbon atoms. A condensed ring structure is formed by bonding the group represented by formula (A20) to the aryl or heteroaryl ring. For compounds represented by formula (1) having the aforementioned condensed ring structure, the compound becomes a more rigid structure. If it becomes rigid, it is expected to suppress molecular vibrations, increase the external quantum efficiency (EQE), increase molecular stability, and extend the element lifetime.

[0235] In formula (A20), L S For >NR, >O, >Si(-R)2, or >S. The L in the base represented by the selection formula (A20) S The types of compounds can control the HOMO and LUMO of the compounds of this invention. In L S When the HOMO and LUMO values ​​are NR, >O, or >S, they become lighter, while in L... S When Si is used, the HOMO and LUMO become deeper. If the HOMO and LUMO become shallower, it is expected that triplet-triplet fusion (TTF) devices using the aforementioned compound will have long lifetime, high efficiency, and low drive voltage. On the other hand, if the HOMO and LUMO become deeper, it is expected that the hole trapping property of the dopant will disappear, and the drive voltage will be significantly reduced.

[0236] As L in formula (A20) S The R in >NR is a substituted aryl, substituted heteroaryl, substituted alkyl, or substituted cycloalkyl group. As L in formula (A20) S In the >Si(-R)2, R is hydrogen, a substituted aryl group, a substituted alkyl group, or a substituted cycloalkyl group, and the two Rs can be bonded to each other to form a ring. Additionally, at least one of the >NR and the R of the >Si(-R)2 can be bonded to a ring selected from ring A, ring B, ring C, ring D, ring E, or ring R via a linking group or a single bond. S At least one bond in the group formed. L is preferably >NR, >O or >S, more preferably >NR or >O, and even more preferably >NR.

[0237] L S When R is >NR, it is preferably an aryl group that can be substituted with alkyl or cycloalkyl, a heteroaryl group that can be substituted with alkyl or cycloalkyl, an alkyl or cycloalkyl group, more preferably an aryl group that can be substituted with alkyl or cycloalkyl, or a heteroaryl group that can be substituted with alkyl or cycloalkyl, and even more preferably an aryl group that can be substituted with alkyl or cycloalkyl, and particularly preferably a phenyl group that can be substituted with alkyl or cycloalkyl.

[0238] In formula (A20), r is an integer from 1 to 4, preferably 2 or 3, and more preferably 2.

[0239] In equation (A20), R S Each is independently hydrogen, a substituted alkyl group, or a substituted cycloalkyl group, and any R S It can be linked to another arbitrary R through a base or a single bond. S They are interconnected.

[0240] R S Preferably, any two atoms are bonded to each other via a linker group or a single bond. Examples of linker groups include >O, >S, etc. Examples of divalent groups formed by bonding are alkylene groups. At least one hydrogen atom in the alkylene group may be substituted with an alkyl or cycloalkyl group, and at least one (preferably one) -CH2- in the alkylene group may be substituted with -O- and -S-. The divalent group formed by bonding is preferably a straight-chain alkylene group having 2 to 5 carbon atoms, more preferably a straight-chain alkylene group having 3 or 4 carbon atoms, and even more preferably a straight-chain alkylene group having 4 carbon atoms (-(CH2)4-). The straight-chain alkylene group having 4 carbon atoms (-(CH2)4-) is particularly preferred to be unsubstituted.

[0241] When two R atoms are bonded to adjacent carbon atoms respectively S When linked together by linking bases or single bonds, the remaining R that does not participate in the bond... S Each is preferably hydrogen or a substituted alkyl group, or with L. S The R-bond of >NR or >Si(-R)2.

[0242] When two R atoms are bonded to adjacent carbon atoms respectively S When bonds are formed to each other through linking bases or single bonds, the remaining R, which does not participate in the bond formation, is considered... S The substituted alkyl group is more preferably a substituted alkyl group having 1 to 6 carbon atoms, and even more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, with the most preferred being methyl.

[0243] That is, as a preferred example of the basis represented by formula (A20), the basis represented by formula (A20-a) can be listed.

[0244]

[0245] In the formula, Me is a methyl group.

[0246] As L S At least one of the R in >NR and >Si(-R)2 can be linked by a linker or a single bond to rings selected from A, B, C, D, E, and R. S At least one node in the group formed. As L SExamples of the case where >NR can be listed by any of the following formulas, preferably the formula (A20-b-1).

[0247]

[0248] In each formula, Me represents a methyl group. In each formula, in... The position is formed by two or three consecutive (adjacent) atomic bonds on the aryl ring, heteroaryl ring, or cycloalkane ring of any of the rings A, B, C, D, and E.

[0249] In equations (Ar-1), (Ar-2), (Ar-3), and (Ar-4), any two or three consecutive Z's are contraction positions, and all other Z's are independently -C(-R). Z = or -N=. The "contraction position" is one of equations (Ar-1), (Ar-2), (Ar-3), and (Ar-4) that includes (B and X). 1 (B and X) 2 (B and X) 3 ) or (B and X) 4 At least one condensation site in a 6-membered ring of a carbon atom is defined as the condensation site.

[0250] When rings A, B, C, D, and E are all represented by equation (Ar-1), preferably at least one of Z in equation (Ar-1) is -N=, more preferably one or both Z are -N=. Furthermore, it is more preferable that one or both Z in equation (Ar-1) are -N=.

[0251] When at least one of the rings A, B, C, D, and E is represented by formula (Ar-2) or formula (Ar-3), preferably, Z in formula (Ar-2) or formula (Ar-3) is -C(-R). Z () = or at least one Z is -N =, and in the case where at least one Z is -N =, preferably one Z is -N =.

[0252] Z=Z can be independently set to >0 and >NR. NX >C(-R CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2 or >Se. In this case, one of the formulas (Ar-1), (Ar-2), (Ar-3) and (Ar-4) containing Z=Z can be a heteroaryl ring.

[0253] In cases where two or more of the rings A, B, C, D, and E are represented by equation (Ar-2) or (Ar-3), at least one of Z=Z in equation (Ar-2) or (Ar-3) is >O or >S; otherwise, Z can be -C(-R). Z =, one Z = Z is >O or >S, otherwise Z can be -C(-R) Z =, Z in equation (Ar-2) or equation (Ar-3) can both be -C(-R) Z = ).

[0254] The R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted. The substituents can be selected from the substituent group Z.

[0255] In equation (1), X 1 X 2 X 3 and X 4 Each can be independently N-Ar, O, S, or Se. Preferably, X... 1 and X 2 At least one of them is O or S, more preferably X 1 and X 2 All are O or all are S. Preferably, X... 3 and X 4 Each independently is N-Ar, more preferably, in X 3 and X 4 In the case of N-Ar, the Ar is the same.

[0256] The Ar in the N-Ar can be hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and can be at least one substituent selected from substituent group Z.

[0257] In X 3 In the case of N-Ar, Ar can bond to at least one of the A and B rings via a single bond or a linker group, in the X ring. 4 In the case of N-Ar, Ar can bond to at least one of the A and C rings via a single bond or a linker group, in the X ring. 1 In the case of N-Ar, Ar can bond to at least one of the B and D rings via a single bond or a linker group, in the X ring. 2In the case of N-Ar, Ar can be bonded to at least one of the C and E rings via a single bond or a linker group.

[0258] The Ar is preferably a substituted phenyl group, wherein the "substituted phenyl group" may be substituted with tert-butyl, cyclohexyl, or a substituted or unsubstituted phenyl group, and the "substituted or unsubstituted phenyl group" may be condensed with a cycloalkane.

[0259] <Explanation of equations (Ar-1-1) to (Ar-1-3), (Ar-2-1) to (Ar-2-9), (Ar-3-1) to (Ar-3-6), and (Ar-4-1) to (Ar-4-4)>

[0260] As a preferred example of a case where at least one of the B ring, D ring, and E ring is represented by one of the formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-4), the following formulas (Ar-1-1) to (Ar-1-3), (Ar-2-1) to (Ar-2-9), (Ar-3-1) to (Ar-3-6), and (Ar-4-1) to (Ar-4-4) can be listed.

[0261]

[0262] In equations (Ar-1-1) to (Ar-1-3), equations (Ar-2-1) to (Ar-2-9), equations (Ar-3-1) to (Ar-3-6), and equations (Ar-4-1) to (Ar-4-4), And # represents B and X 1 X 2 or X 3 The bonding position. B is preferably located at... .

[0263] <Explanation of Equations (Ar-5-1) to (Ar-5-3)>

[0264] As a preferred example of the case where ring A is represented by one of the formulas (Ar-1), (Ar-2) and (Ar-3), examples can be listed that are selected from the formulas (Ar-5-1) to (Ar-5-3) below.

[0265]

[0266] In equations (Ar-5-1) to (Ar-5-4), # indicates the bond position to B, and # indicates the bond position to X. 3 or X 4 The bond position.

[0267] Ring A is preferably represented by formula (Ar-5-1). When rings B to E are all benzene rings, ring A is preferably represented by formulas (Ar-5-2) to (Ar-5-4).

[0268] <Explanation of Equations (1-1) to (1-74)>

[0269] As a preferred example of the above formula (1), formulas (1-1) to (1-74) can be listed below.

[0270]

[0271]

[0272]

[0273]

[0274] In equations (1-1) to (1-74),

[0275] X 1 X 2 X 3 and X 4 Independently with X in equation (1) 1 X 2 X 3 and X 4 The definitions are the same.

[0276] Za, Zb, Zc, Zd, and Ze are each independently -C(-R) Z )= or -N=, the R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted.

[0277] Za=Za, Zb=Zb, Zc=Zc, Zd=Zd, and Ze=Ze can be independently set to >O, >NR, respectively. NX >C(-R CX )2、>Si(-R SiX )2、>S、>CO、>SO、>SO2 or>Se, where at least one of Za, Zb, Zc, Zd and Ze in equation (1-1) is -N=.

[0278] <Explanation of Equations (2-1) to (2-74)>

[0279] As a preferred example of the above formula (1), formulas (2-1) to (2-74) can be listed below.

[0280]

[0281]

[0282]

[0283]

[0284]

[0285] In equations (2-1) to (2-74),

[0286] X 1 and X 2 Independently with X in equation (1) 1 and X 2 The definitions are the same.

[0287] N-Ar 1 Ar 1 and N-Ar 2 Ar 2 Each is independently identical to the definition of Ar in N-Ar of equation (1).

[0288] Za, Zb, Zc, Zd, and Ze are each independently -C(-R) Z )= or -N=, the R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted.

[0289] Za=Za, Zb=Zb, Zc=Zc, Zd=Zd, and Ze=Ze can be independently set to >O, >NR, respectively. NX >C(-R CX )2、>Si(-R SiX )2、>S、>CO、>SO、>SO2 or>Se, where at least one of Za, Zb, Zc, Zd and Ze in equation (2-1) is -N=.

[0290] <Explanation of formula (o-Ar)>

[0291] Ar in equations (2-1) to (2-74) 1 and Ar 2 At least one of them is preferably represented by the following formula (o-Ar).

[0292]

[0293] In formula (o-Ar), This indicates the position of the nitrogen bond.

[0294] In the formula (o-Ar), the "F" inside the circle is a marker indicating a ring structure represented by a circle.

[0295] In formula (o-Ar), the F ring can be a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0296] In formula (o-Ar), G can be a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. Preferably, G is a substituted or unsubstituted phenyl or tert-butyl group.

[0297] In formula (o-Ar), the "aryl ring" in the F ring can be an aryl ring with 6 to 30 carbons, preferably an aryl ring with 6 to 16 carbons, more preferably an aryl ring with 6 to 12 carbons, and particularly preferably an aryl ring with 6 to 10 carbons.

[0298] In formula (o-Ar), the "heteroaryl ring" in the F ring can be, for example, a heteroaryl ring with 2 to 30 carbon atoms, preferably a heteroaryl ring with 2 to 25 carbon atoms, more preferably a heteroaryl ring with 2 to 20 carbon atoms, and even more preferably a heteroaryl ring with 2 to 15 carbon atoms, particularly preferably a heteroaryl ring with 2 to 10 carbon atoms. Furthermore, the "heteroaryl ring" can be, for example, a heterocycle containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon atoms.

[0299] In ring F, the aryl ring can be selected from the group consisting of benzene ring, biphenyl ring, terphenyl ring, indene ring, naphthyl ring, fluorene ring, anthracene ring, and phenanthrene ring, and the heteroaryl ring can be selected from the group consisting of benzofuran ring, benzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, naphthiophene ring, benzoindole ring, and benzoselenophenol ring. Ring F is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted terphenyl ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted benzofuran ring, more preferably a substituted or unsubstituted benzene ring.

[0300] When at least one hydrogen atom in the aryl or heteroaryl ring is substituted, the substituent is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl and a heteroaryl group), a substituted or unsubstituted diarylboroyl group (the two aryl groups may be linked by a single bond or a linker group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or -L-Ak, more preferably a substituted or unsubstituted phenyl or tert-butyl group. Examples of substituents for these groups include aryl, heteroaryl, alkyl or cycloalkyl, or diarylamino groups. The substituted or unsubstituted phenyl group may be condensed via a cycloalkane.

[0301] <Replacement by a heavy stable isotope>

[0302] In polycyclic aromatic compounds containing the structural unit represented by formula (1), all or part of the elements may be re-stable isotopes. More specifically, at least one hydrogen may be replaced by deuterium, and at least one nitrogen may be replaced by nitrogen-15( 15 N) can be replaced, and at least one sulfur can be replaced by sulfur-33( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) can be replaced, at least one oxygen can be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O) can be replaced, and at least one carbon can be replaced by carbon-13 (O). 13 C) can be replaced, at least one boron can be replaced by boron-11 ( 11 B) Replacement.

[0303] <Substitution of Deuterium>

[0304] The hydrogen in a polycyclic aromatic compound containing the structural unit represented by formula (1) can be all or part of deuterium.

[0305] For example, the hydrogen atoms of the aryl or heteroaryl rings of rings A, B, C, D, or E, and their substituents, can be replaced by deuterium. Examples of aryl or heteroaryl rings in which all or part of the hydrogen atoms are replaced by deuterium can be listed. All or part of the hydrogen atoms of the aryl and heteroaryl rings of formula (Ar) can be replaced by deuterium. Furthermore, from a durability point of view, the hydrogen atoms in polycyclic aromatic compounds containing the structural units represented by formula (1) are preferably all or part of them deuterated.

[0306] <Specific examples of polycyclic aromatic compounds>

[0307] Examples of polycyclic aromatic compounds containing the structural unit represented by formula (1) include compounds represented by any of the following structural formulas. Additionally, "D" in the following structural formulas represents deuterium.

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340] 1-2. Reactive compounds, polymers, polymer crosslinkers, suspended polymers, suspended... polymer crosslinkers

[0341] The polycyclic aromatic compound represented by formula (1) can also be used as a polymer (the monomer used to obtain the polymer has a polymeric substituent) or a polymer crosslinker (the polymer used to obtain the polymer crosslinker has a crosslinking substituent), or a suspended polymer (the reactive compound used to obtain the suspended polymer has a reactive substituent) or a suspended polymer crosslinker (the suspended polymer used to obtain the suspended polymer crosslinker has a crosslinking substituent) for use in organic device materials, such as materials for organic electroluminescent elements, materials for organic field-effective transistors, or materials for organic thin-film solar cells. Here, the polymer is obtained by polymerizing a reactive compound in which reactive substituents are substituted in each of the polycyclic aromatic compounds as a monomer. The polymer crosslinker is obtained by further crosslinking the polymer. The suspended polymer is obtained by reacting a main-chain polymer with the reactive compound. The suspended polymer crosslinker is obtained by further crosslinking the suspended polymer.

[0342] In addition, in this specification, "polymer compound" refers to a compound with a molecular weight distribution in which the number average molecular weight of polystyrene cycloaliphatic acid is 1 × 10⁻⁶. 3 ~1×10 8Polymers with molecular weights (1×10^3~1×10^8). The number-average molecular weight (Mn) of polystyrene cycloaliphatic acid in the polymer compound was determined using tetrahydrofuran in the mobile phase and by size exclusion chromatography (SEC). Specifically, the polymer compound to be determined was dissolved in tetrahydrofuran at a concentration of approximately 0.05% by mass, and 10 μL was injected into the SEC. The flow rate of the mobile phase was 1.0 mL / min, and the PLgelMIXED_B (manufactured by Polymer Laboratories) was used as the chromatography column. The UV_VIS detector (manufactured by Tosoh Corporation, trade name: UV-8320GPC) could be used as the detector.

[0343] The number-average molecular weight of the polymer compound of the present invention is preferably 2000~1×10⁻⁶. 8 More preferably 5000~1×10 8 .

[0344] As the reactive substituent (including the polymerizable substituent, the crosslinking substituent, and the reactive substituent for obtaining a suspended polymer, hereinafter also simply referred to as "reactive substituent"), there are no particular limitations as long as it is a substituent that can increase the molecular weight of the polycyclic aromatic compound, a substituent that can further crosslink the polymer obtained in this manner, or a substituent that can carry out a suspension reaction in a main-chain polymer. Examples include alkenyl, alkynyl, unsaturated forms of cycloalkyl (e.g., cyclobutenyl), at least one -CH2-substituted group of cycloalkyl (e.g., epoxy group), unsaturated forms of condensed cycloalkanes (e.g., condensed cyclobutene), etc., preferably substituents with the following structures. In each structural formula Indicates the location of the bond.

[0345]

[0346] L can be a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene group having 1 to 12 carbon atoms, alkylene group having 1 to 12 carbon atoms, or polyalkylene group having 1 to 12 carbon atoms. Among the substituents, those represented by formulas (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17) are preferred, and those represented by formulas (XLS-1), (XLS-3), or (XLS-17) are more preferred.

[0347] Details regarding the uses of such polymers, polymer crosslinkers, suspended polymers, and suspended polymer crosslinkers (hereinafter also referred to as "polymers and polymer crosslinkers") will be described later.

[0348] 2. Preparation methods of polycyclic aromatic compounds

[0349] The preparation method of polycyclic aromatic compounds containing the structure represented by formula (1) basically involves bonding the boron-linked A, B, and C rings with N-Ar groups. X After linking the B, D, and E rings, the B, D, and E rings are then linked via boron (reaction a), or the boron-linked B, D, and E rings are linked via N-Ar bonds. X After bonding with rings A, B, and C, rings A, B, and C are linked by boron (reaction b), or rings A, B, C, D, and E are bonded by N-Ar groups. X After bonding, rings A, B, and C, as well as rings B, D, and E, are simultaneously and separately linked via boron, thus preparing the final product (reaction c). In reactions a, b, and c, each ring is bonded via a bonding group (N-Ar). X When the rings are linked by boron (e.g., O, S, and Se), for example, in etherification reactions, general reactions such as nucleophilic substitution reactions and Ullmann reactions can be used; in amination reactions, general reactions such as the Buchwald-Hartwig reaction can be used. Furthermore, in reactions a, b, and c, when the rings are linked by boron, a tandem Hetero-Friedel-Crafts reaction (a continuous aromatic electrophilic substitution reaction, as follows) can be used. For these preparation methods, refer to existing literature such as International Publication No. 2015 / 102118.

[0350] 3. Organic devices

[0351] The polycyclic aromatic compounds of this invention can be used as materials for organic devices. Examples of organic devices include organic electroluminescent elements, organic field-effective transistors, and organic thin-film solar cells.

[0352] 3-1. Organic electroluminescent elements

[0353] An organic electroluminescent element has at least a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the respective pair of electrodes. Hereinafter, the organic EL element of this embodiment will be described in detail based on the accompanying drawings.

[0354] 3-1-1. Structure of Organic Electroluminescent Devices

[0355] Figure 1 This is a schematic cross-sectional view of an example of an organic EL element. Figure 1The organic EL element 100 shown includes: a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

[0356] Furthermore, the organic EL element 100 can also be fabricated in reverse order to form a structure such as the following, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

[0357] Not all of the layers are indispensable. The smallest structural unit is set to include an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are arbitrarily arranged layers. In addition, each layer may consist of a single layer or multiple layers.

[0358] In addition to the aforementioned structure of "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", the morphology of the layers constituting an organic EL device can also be "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode". The structural forms of “electron transport layer / cathode”, “substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode”, “substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode”, “substrate / anode / light-emitting layer / electron transport layer / cathode”.

[0359] 3-1-2. Substrate in organic electroluminescent devices

[0360] The substrate 101 is the support for the organic EL element 100, and can typically be made of quartz, glass, metal, plastic, etc. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose; for example, glass plates, metal plates, metal foils, plastic films, plastic sheets, etc., can be used. Here, glass plates and plates made of transparent synthetic resins such as polyester, polymethyl methacrylate, polycarbonate, and polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used. Furthermore, the thickness only needs to be sufficient to maintain mechanical strength; for example, 0.2 mm or more is sufficient. As an upper limit for the thickness, for example, 2 mm or less, preferably 1 mm or less, is preferred. Regarding the glass material, since the amount of dissolved ions from the glass should be minimal, alkali-free glass is preferred. Since soda-lime glass with a barrier coating such as SiO2 is also commercially available, such soda-lime glass can be used. In addition, to improve gas barrier properties, a fine gas barrier film such as a silicon oxide film may be provided on at least one side of the substrate 101. When a plate, film or sheet made of synthetic resin with low gas barrier properties is used as the substrate 101, it is particularly preferable to provide a gas barrier film.

[0361] 3-1-3. Anode in Organic Light-Emitting Devices

[0362] The anode 102 functions to inject holes into the light-emitting layer 105. Furthermore, if a hole injection layer 103 and / or a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[0363] Materials forming the anode 102 can include both inorganic and organic compounds. Examples of inorganic compounds include: metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (oxides of indium, oxides of tin, indium tin oxide (ITO), indium zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, or Nesa glass. Examples of organic compounds include: conductive polymers such as poly(3-methylthiophene), polypyrrole, and polyaniline. Furthermore, suitable materials that can be used as the anode of organic EL elements can be selected for use.

[0364] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light, but from the viewpoint of power consumption of the light-emitting element, low resistance is ideal. For example, if it is an ITO substrate of 300Ω / square or less, it functions as an element electrode, but nowadays it is also possible to supply substrates of around 10Ω / square. Therefore, it is particularly ideal to use a low-resistance product, such as 100Ω / square to 5Ω / square, preferably 50Ω / square to 5Ω / square. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50nm to 300nm.

[0365] 3-1-4. Hole injection layer and hole transport layer in organic electroluminescent devices

[0366] Hole injection layer 103 efficiently injects holes migrating from anode 102 into light-emitting layer 105 or hole transport layer 104. Hole transport layer 104 efficiently transports holes injected from anode 102 or holes injected from anode 102 via hole injection layer 103 to light-emitting layer 105. Hole injection layer 103 and hole transport layer 104 are formed by layering or mixing one or more hole injection / transport materials, or by a mixture of hole injection / transport materials and polymer binders. Alternatively, inorganic salts such as ferric chloride (III) can be added to the hole injection / transport materials to form the layers.

[0367] As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes under an applied electric field. Ideally, the injected holes should be injected efficiently and transported efficiently. Therefore, materials with low ionization potential, high hole mobility, excellent stability, and low likelihood of generating impurities that could become traps during preparation and use are preferred.

[0368] As the materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from those conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Specific examples of these include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) and other biscarbazole derivatives, triarylamine derivatives (polymers with aromatic tertiary amino groups on the main chain or side chain), 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthalene N,N'-diphenyl-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, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N4,N4,N4',N4'- Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1': The following compounds are preferred: triphenylamine derivatives such as 4',1"-triphenyl]-4-amine and starburst amine derivatives; stilbene derivatives; phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.); pyrazoline derivatives; hydrazone compounds; benzofuran derivatives or thiophene derivatives; oxadiazole derivatives; quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenyl-2,3,6,7,10,11-hexacarboxynitrile); heterocyclic compounds such as porphyrin derivatives; and polysilanes. Among polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole, and polysilanes having the aforementioned monomers on their side chains are preferred. However, there are no particular limitations on any compound that can inject holes from the anode and transport holes, as long as it is a thin film required for the fabrication of the light-emitting element.

[0369] Furthermore, it is well known that the conductivity of organic semiconductors is strongly affected by doping. The matrix materials of organic semiconductors contain compounds with good electron-donating or electron-accepting properties. For doping with electron-donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known (e.g., see references “M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204(1998)” and “J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731(1998)”). These generate so-called holes through electron migration processes from electron-donating base materials (hole-transporting materials). The conductivity of the base material varies considerably depending on the number and mobility of holes. Known matrix materials with hole transport properties include, for example, benzidine derivatives (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (TPD), etc.) or starburst amine derivatives (4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) (Japanese Patent Application Publication No. 2005-167175).

[0370] The hole injection layer material and the hole transport layer material may also be used in the hole layer material as the following polymeric compounds or their polymeric crosslinks, or as the following suspended polymeric compounds or their suspended polymeric crosslinks. Here, the polymeric compound is obtained by polymerizing a reactive compound that has replaced reactive substituents in the hole injection layer material and the hole transport layer material as a monomer. The suspended polymeric compound is obtained by reacting a main-chain polymer with the reactive compound. As the reactive substituent in the above case, the description of polycyclic aromatic compounds containing a portion of the structure represented by formula (1) can be cited.

[0371] Details regarding the applications of this polymer compound and its crosslinked polymers will be described later.

[0372] 3-1-5. Emitting layer in organic electroluminescent devices

[0373] The light-emitting layer 105 emits light by recombination of holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material forming the light-emitting layer 105 can be any compound that emits light upon excitation by the recombination of holes and electrons (a luminescent compound), preferably a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state. The light-emitting layer can be a single layer or multiple layers, either is acceptable, and is formed from light-emitting layer materials (a host material and a dopant material). The host material and the dopant material can each be one type or a combination of multiple types, either is acceptable. For example, as the dopant material, an emitting dopant and an auxiliary dopant can be used. The dopant material can be contained entirely in the host material or partially in the host material, either is acceptable. As the doping method, it can be formed by co-evaporation with the host material, or it can be mixed with the host material beforehand and then evaporated simultaneously. Alternatively, the light-emitting layer can also be formed using a wet film-forming method that employs a light-emitting layer forming composition prepared by dissolving the material in an organic solvent.

[0374] The polycyclic aromatic compound represented by formula (1) is preferably used as a material for forming the light-emitting layer of an organic electroluminescent element. More preferably, the polycyclic aromatic compound represented by formula (1) is used as an emission dopant or auxiliary dopant in the light-emitting layer, and even more preferably as an emission dopant.

[0375] The polycyclic aromatic compound represented by formula (1) is a "thermally activated delayed phosphor," which can be used as an emission dopant in organic EL elements exhibiting thermally activated delayed fluorescence (TADF) (hereinafter referred to as "TADF elements"). In a "thermally activated delayed phosphor," by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, reverse intersystem crossing migration from the lowest excited triplet state to the lowest excited singlet state, which usually has a low migration probability, is generated efficiently, resulting in emission from the singlet state (thermally activated delayed fluorescence, TADF). In conventional fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal inactivation path and therefore cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, enabling a highly efficient organic EL element.

[0376] The polycyclic aromatic compound represented by formula (1) can be used as an emission dopant for "TADF elements", an emission dopant for elements using two types of TADFs, an emission dopant for organic electroluminescent elements (TADF-assisted fluorescent elements, TAF elements) using an additional thermally activated delayed phosphor as an auxiliary dopant, and an emission dopant for organic electroluminescent elements (phosphor-sensitized fluorescent elements, PSF elements) using a phosphorescent material as an auxiliary dopant. From the viewpoint that it is easier to prepare when less material is used in the element, emission dopants for TADF elements and emission dopants for TADF elements using two types of TADFs are preferred, and emission dopants for TADF elements are more preferred. From the viewpoint of efficiency, emission dopants for TAF elements and emission dopants for phosphorescent auxiliary elements are preferred, and emission dopants for TAF elements are more preferred.

[0377] Generally, materials with faster delayed fluorescence are considered to have superior TADF properties. Specifically, when luminescent materials with a delayed fluorescence lifetime of less than 20 μsec are used as emission dopants in light-emitting elements, high device efficiency and long device lifetime can be obtained. Furthermore, generally ΔE S1T1 The smaller the value, the better the TADF property. Additionally, ΔE S1T1 The lowest excited singlet state energy level (E S1 ) and the lowest excited triplet energy level (E T1 The energy difference between them. Specifically, ΔE S1T1 The value is preferably 0.20 eV or less, more preferably 0.15 eV or less.

[0378] The luminescent layer may contain a host compound. Here, there may be one or more host compounds. All known host compounds may be used. Preferred examples of host compounds include high-T1 compounds, which will be described later.

[0379] The emitting layer can be a single layer or multiple layers; either is acceptable. Furthermore, the host compound, the emission dopant material, and the auxiliary dopant material can be contained within the same layer, or at least one of each can be contained within multiple layers. The host compound and dopant material (emission dopant or auxiliary dopant) contained in the emitting layer can each be one type, or a combination of multiple types; either is acceptable. The auxiliary dopant and emission dopant can be wholly contained within the host compound serving as the matrix, or they can be partially contained within the host compound serving as the matrix.

[0380] The amount of main material used varies depending on the type of main material, and can be determined in accordance with the characteristics of the main material. The preferred basis for the amount of main material used is 50% to 99.999% of the total mass of the material used in the light-emitting layer, more preferably 80% to 99.95% of the total mass, and even more preferably 90% to 99.9% of the total mass.

[0381] The amount of dopant material used varies depending on the type of dopant material, and can be determined in accordance with the characteristics of the dopant material. The preferred amount of dopant is 0.001% to 50% of the total mass of the material used in the luminescent layer, more preferably 0.05% to 20% by mass, and even more preferably 0.1% to 10% by mass. If it falls within this range, it is preferred, for example, in terms of preventing concentration quenching.

[0382] On the other hand, in organic electroluminescent devices using TADF material as a dopant, a low concentration of dopant material is preferable in terms of preventing concentration quenching, but a high concentration of dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in organic electroluminescent devices using TADF material as an auxiliary dopant, a low concentration of emitting dopant is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the auxiliary dopant.

[0383] When using auxiliary dopant materials, the base amounts of the host material, auxiliary dopant, and emission dopant are 40% to 99% by mass, 59% to 1% by mass, and 20% to 0.001% by mass of the total material used in the emitting layer, respectively; preferably, they are 60% to 95% by mass, 39% to 5% by mass, and 10% to 0.01% by mass, respectively; more preferably, they are 70% to 90% by mass, 29% to 10% by mass, and 5% to 0.05% by mass. When using auxiliary dopant materials, an exciplex can be formed with the host material or the emission dopant material.

[0384] 3-1-5-1. Doped Materials

[0385] The polycyclic aromatic compounds represented by formula (1) are preferably used as dopant materials.

[0386] There are no particular limitations on the dopant material that can be used other than the polycyclic aromatic compounds represented by formula (1). Known compounds can be used, and various materials can be selected according to the desired luminescence color. Specifically, examples include: condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetraphenyl, pentaphenyl, perylene, naphthylpyrene, dibenzopyrene, rubrene, and β, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bis(styrene)-anthracene derivatives, or... Distyrene-based derivatives such as stilbene (Japanese Patent Application Publication No. 1-245087), stilbene-based arylene derivatives (Japanese Patent Application Publication No. 2-247278), diazabenzodiindene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimethyltrimethylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobenzofuran and other isobenzofuran derivatives, dibenzofuran Coumarin derivatives, including 7-dialkylaminocoumarin derivatives, 7-piperidinylcoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, etc.; dicyanomethylenepyran derivatives; dicyanomethylenethiaran derivatives; polymethine derivatives; anthocyanin derivatives; oxobenzanthracene derivatives; and xanthones derivatives. Rhodamine derivatives, fluorescein derivatives, pyranone derivatives, quinolone derivatives, acridine derivatives, oxazine derivatives, phenyl ether derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furanopyridine derivatives, 1,2,5-thiadiazolpyrene derivatives, pyrrole methylene derivatives, violetone derivatives, pyrrolopyrrole derivatives, squaric acid lactone salt derivatives, violet anthrone derivatives, phenazine derivatives, acridineone derivatives, denitroflavin derivatives, fluorene derivatives, and benzo[a]fluorene derivatives, etc.

[0387] If we exemplify them by their color rendering, then blue-green dopant materials can be listed as follows: aromatic hydrocarbons or their derivatives such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and thionylene; furan, pyrrole, thiophene, thiophene, 9-silicafluorene, 9,9'-spirodisilicafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthrene, pyrazine, naphthidine, and quinoxaline. Aromatic heterocyclic compounds such as pyrrolopyridine and thioxanthate or their derivatives; stilbene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldehyde azide derivatives, coumarin derivatives; azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole and their metal complexes; and aromatic amine derivatives represented by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, etc.

[0388] In addition, examples of green to yellow dopant materials include: coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, violet ketone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridinone derivatives, quinacridone derivatives, and tetraphenyl derivatives such as rubrene. Furthermore, the following compounds are preferred examples: compounds formed by introducing substituents such as aryl, heteroaryl, arylvinyl, amino, and cyano groups that can be extended to longer wavelengths into the compounds exemplified as blue to blue-green dopant materials.

[0389] Furthermore, examples of orange to red dopant materials include: naphthalene dicarboxylate derivatives such as bis(diisopropylphenyl)perylenetetracarboxylate imide; violet ring ketone derivatives; rare earth complexes such as Eu complexes using acetylacetone or benzoylacetone with phenanthroline as a ligand; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran or its analogues; metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine; rhodamine compounds; desaturated flavin derivatives; coumarin derivatives; and quinacridones. Derivatives, such as phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squaric acid lacton salt derivatives, anthrone derivatives, phenazine derivatives, phenoxazinone derivatives, and thiadiazopyrene derivatives, etc., and preferably, the following compounds are also listed as examples: compounds formed by introducing aryl, heteroaryl, arylvinyl, amino, cyano, or other substituents capable of long-wavelength conversion into the compounds exemplified as blue dopant materials to blue-green dopant materials and green dopant materials to yellow dopant materials.

[0390] Furthermore, as a dopant, it can be appropriately selected from compounds described in the June 2004 issue of Chemical Industry, page 13, and the references listed therein.

[0391] The dopant material is particularly preferred to be an amine, perylene derivative, borane derivative, aromatic amine derivative, coumarin derivative, pyran derivative, or pyrene derivative having a stilbene structure.

[0392] Amines having a stilbene structure are represented, for example, by the following formula.

[0393]

[0394] In the formula, Ar 1 Ar is an m-valent group derived from aryl groups with 6 to 30 carbon atoms. 2 And Ar 3 Each is independently an aryl group having 6 to 30 carbon atoms, Ar 1 ~ Ar 3 At least one of them has a stilbene structure, Ar 1 ~Ar 3 It can be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl group trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0395] The amine having a stilbene structure is more preferably diaminostilbene as represented by the following formula.

[0396]

[0397] In the formula, Ar 2 And Ar 3 Each is independently an aryl group having 6 to 30 carbon atoms, Ar 2 And Ar 3 It can be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl groups that have been trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano.

[0398] Specific examples of aryl groups with 6 to 30 carbon atoms include: phenyl, naphthyl, acenaphthel, fluorenyl, phenatenyl, anthracene, fluoranyl, triphenylene, pyrene, phenyl, tetraphenyl, peryl, stilbene, stilbeneyl, stilbeneylphenyl, stilbeneylbiphenyl, stilbeneylfluorenyl, etc.

[0399] Specific examples of amines with a stilbene structure include: N,N,N',N'-tetra(4-biphenyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, N,N'-di(9-phenanthrene) 4,4'-bis[4'-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazolevinyl)-biphenyl, 4,4'-bis(9-phenyl-3-carbazolevinyl)-biphenyl, etc.

[0400] Alternatively, amines with a stilbene structure as described in Japanese Patent Application Publication No. 2003-347056 and Japanese Patent Application Publication No. 2001-307884 may also be used.

[0401] Examples of perylene derivatives include: 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-tert-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrene)-8,11-di(tert-butyl)perylene, 3-(9'-anthrayl)-8,11-di(tert-butyl)perylene, and 3,3'-bis(8,11-di(tert-butyl)perylene), etc.

[0402] Alternatively, perylene derivatives described in Japanese Patent Application Publication No. 11-97178, Japanese Patent Application Publication No. 2000-133457, Japanese Patent Application Publication No. 2000-26324, Japanese Patent Application Publication No. 2001-267079, Japanese Patent Application Publication No. 2001-267078, Japanese Patent Application Publication No. 2001-267076, Japanese Patent Application Publication No. 2000-34234, Japanese Patent Application Publication No. 2001-267075, and Japanese Patent Application Publication No. 2001-217077 may also be used.

[0403] Examples of borane derivatives include: 1,8-diphenyl-10-(disimylideneboryl)anthracene, 9-phenyl-10-(disimylideneboryl)anthracene, 4-(9'-anthrayl)disimylideneborylnaphthalene, 4-(10'-phenyl-9'-anthrayl)disimylideneborylnaphthalene, 9-(disimylideneboryl)anthracene, 9-(4'-biphenyl)-10-(disimylideneboryl)anthracene, 9-(4'-(N-carbazolyl)phenyl)-10-(disimylideneboryl)anthracene, etc.

[0404] Alternatively, borane derivatives described in International Publication No. 2000 / 40586 may also be used.

[0405] Aromatic amine derivatives are represented, for example, by the following formula.

[0406]

[0407] In the formula, Ar 4 Ar is an n-valent group derived from an aryl group with 6 to 30 carbon atoms. 5 and Ar 6 Each is independently an aryl group having 6 to 30 carbon atoms, Ar 4 ~Ar 6 It may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl group that has been trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is an integer from 1 to 4.

[0408] More preferably, aromatic amine derivatives such as Ar are preferred. 4 Ar is a divalent group derived from anthracene, α, fluorene, benzo[a]fluorene, or pyrene. 5 And Ar 6 Each is independently an aryl group having 6 to 30 carbon atoms, Ar 4 ~Ar 6 It can be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl group trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is 2.

[0409] Specific examples of aryl groups with 6 to 30 carbon atoms include: phenyl, naphthyl, acenaphthel, fluorenyl, phenanthyl, anthracene, fluoranthyl, triphenylene, pyrene, chrysenyl, tetraphenyl, peryl, pentaphenyl, etc.

[0410] As aromatic amine derivatives, examples of the N,N,N',N'-tetraphenyl-6,12-diamine, N,N,N',N'-tetra(p-tolyl)-6,12-diamine, N,N,N',N'-tetra(m-tolyl)-6,12-diamine, N,N,N',N'-tetra(4-isopropylphenyl)-6,12-diamine, N,N,N',N'-tetra(naphthyl-2-yl)-6,12-diamine, N,N'-diphenyl N,N'-di(p-tolyl)-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-tert-butylphenyl)-6,12-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)-6,12-diamine, etc.

[0411] In addition, examples of pyrene derivatives include: N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetra(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, and N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene. -1,6-Diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-tert-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-bis(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 N 6 -diphenyl-N 1 N 6 -Bis-(4-trimethylsilyl-phenyl)-1H,8H-pyrene-1,6-diamine, etc.

[0412] In addition, examples of anthracene derivatives include: N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9, 10-Diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-tert-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-bis(p-tolyl)anthracene-9,10-diamine, 2,6-di-tert-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9 10-Diamine, 2,6-Di-tert-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-Di-tert-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N' 9,10-Diamine, 9,10-Bis(4-tert-butylphenyl)anthracene, 9,10-Bis(4-diphenylamino-phenyl)anthracene, 9,10-Bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-Bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene, etc.

[0413] In addition, the following can be listed: [4-(4-diphenylamino-phenyl)naphth-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphth-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphth-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphth-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphth-1-yl]-p-triphenyl, 4,4"-bis[6-diphenylaminonaphth-2-yl]-p-triphenyl, etc.

[0414] Alternatively, aromatic amine derivatives described in Japanese Patent Application Publication No. 2006-156888 may also be used.

[0415] Examples of coumarin derivatives include coumarin-6 and coumarin-334.

[0416] Alternatively, coumarin derivatives described in Japanese Patent Application Publication No. 2004-43646, Japanese Patent Application Publication No. 2001-76876, and Japanese Patent Application Publication No. Hei 6-298758 may also be used.

[0417] Examples of pyran derivatives include pyran nitrile derivatives (DCM) and (E)-4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran (DCJTB).

[0418]

[0419] Alternatively, pyran derivatives described in Japanese Patent Application Publication No. 2005-126399, Japanese Patent Application Publication No. 2005-097283, Japanese Patent Application Publication No. 2002-234892, Japanese Patent Application Publication No. 2001-220577, Japanese Patent Application Publication No. 2001-081090, and Japanese Patent Application Publication No. 2001-052869 may also be used.

[0420] The following compounds can be used as dopant materials.

[0421]

[0422] 3-1-5-2. High T1 Compounds

[0423] In an organic electroluminescent element comprising at least one polycyclic aromatic compound represented by formula (1) in the light-emitting layer, it is preferable that the light-emitting layer or the organic layer adjacent to the light-emitting layer also comprises at least one high T1 compound having a lowest excited triplet energy level (ET1) at least 0.01 eV higher than the lowest excited triplet energy level of the polycyclic aromatic compound represented by formula (1) (also referred to as "T1 energy").

[0424] High-T1 compounds, such as polycyclic aromatic compounds represented by formula (1) used as dopant compounds in the emissive layer, can be used as host compounds. The emissive layer may contain one or more high-T1 compounds. When two or more are included, it is preferable to include a hole-transporting host material and an electron-transporting host material that satisfy the following relationship.

[0425] The HOMO (Highest Occupied Molecular Orbital) of hole transport host materials (HH) is shallower than that of electron transport host materials (EH).

[0426] The LUMO (Lowest Unoccupied Molecular Orbital) of electron transport host materials (EH) is deeper than that of hole transport host materials (HH).

[0427] E of high T1 compounds T1 More preferably, it is the E of the polycyclic aromatic compound represented by formula (1). T1 Compared to 0.03 eV or more, it is more preferably 0.1 eV or more higher.

[0428] As a high-T1 compound, it is preferred to be a compound having at least one partial structure selected from partial structure group A, or having at least two partial structures selected from partial structure group A and partial structure group B, and further, having at least one partial structure selected from partial structure group C as a linking group or substituent. Additionally, in the following structures, at least one... At this location, it bonds with other structural components besides hydrogen, in other... The bonds are formed at the hydrogen sites. As can be seen from the following structural formula, the carbon-carbon bonds connecting the benzene rings and the bonds connecting the structures in each part of the structure are ortho or meta positions. At this time, high T1 and high charge mobility are obtained. From the viewpoint of high T1, it is preferable to bond at the ortho position, and from the viewpoint of high charge mobility, it is preferable to bond at the meta position.

[0429] Partial structure group A

[0430]

[0431] Partial structure group B

[0432]

[0433]

[0434] Partial structure group C

[0435]

[0436] The partial structure group A is preferably the partial structure group Aa, the partial structure group B is preferably the partial structure group Bb, and the partial structure group C is preferably the partial structure group Cc.

[0437]

[0438] Examples of high T1 compounds include: compounds represented by formula (H1), compounds represented by formula (H3), compounds containing the structure represented by formula (H4), compounds represented by formula (H5), compounds represented by formula (H6) and formula (H8).

[0439]

[0440] 3-1-5-2-1. Compounds represented by formula (H1)

[0441]

[0442] In formula (H1), L 1 It is an arylene group having 6 to 24 carbon atoms or a heteroarylene group having 5 to 23 carbon atoms, preferably an arylene group having 6 to 16 carbon atoms or a heteroarylene group having 5 to 15 carbon atoms, more preferably an arylene group having 6 to 12 carbon atoms or a heteroarylene group having 5 to 11 carbon atoms, and particularly preferably an arylene group having 6 to 10 carbon atoms or a heteroarylene group having 5 to 9 carbon atoms. Specifically, examples include divalent or trivalent groups such as benzene ring, biphenyl ring, terphenyl ring, fluorene ring, spirofluorene ring, finadene ring, triphenylene ring, pyridine ring, pyrimidine ring, triazine ring, biphenylpyridine ring, biphenylpyrimidine ring, and biphenyltriazine ring.

[0443] In the compound represented by formula (H1), at least one hydrogen may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen, or a deuterium.

[0444]

[0445] 3-1-5-2-2. Compounds represented by formula (H3)

[0446]

[0447] In equation (H3),

[0448] MU are independently divalent aromatic groups, EC are independently monovalent aromatic groups, and k is an integer from 2 to 50000.

[0449] More specifically,

[0450] MU can be independently arylene, heteroarylene, diarylenearylamino, diarylenearylboryl, oxaborane-diyl, or azaborane-diyl.

[0451] EC can be independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, respectively.

[0452] At least one hydrogen in MU and EC can be further substituted by aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl groups.

[0453] k is an integer from 2 to 50000.

[0454] k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0455] At least one hydrogen in MU and EC in formula (H3) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen, or a deuterium. Furthermore, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-. Any -CH2- in the alkyl group other than the -CH2- directly bonded to EC in formula (H3) may be substituted with an arylene group having 6 to 24 carbon atoms. Any hydrogen in the alkyl group may be substituted with fluorine.

[0456] As a MU, examples of divalent derivatives with the following structures can be listed (e.g., divalent groups represented by removing any two hydrogen atoms from any compound with the following structures, divalent groups comprising two or more combinations of divalent groups represented by removing any two hydrogen atoms from any compound with the following structures, divalent groups in which at least one hydrogen atom is substituted by an alkyl group, etc.).

[0457]

[0458] More specifically, divalent bases having any of the following structures can be listed. Among these, MU in It is bonded to other MUs or ECs.

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466] Furthermore, as EC, for example, the bases represented by the following formulas can be listed. Among these, EC is in It is bonded to MU.

[0467]

[0468]

[0469] From the viewpoint of solubility and coating film-forming properties, the compound represented by formula (H3) preferably has 10% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 1 to 24 carbons, more preferably 30% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 1 to 18 carbons (branched alkyl groups with 3 to 18 carbons), and even more preferably 50% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 1 to 12 carbons (branched alkyl groups with 3 to 12 carbons). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10% to 100% of the total number of MUs (k) in the molecule have alkyl groups with 7 to 24 carbons, more preferably 30% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 7 to 24 carbons (branched alkyl groups with 7 to 24 carbons).

[0470] 3-1-5-2-3. Compounds containing the structure represented by formula (H4)

[0471] The compound containing the structure represented by formula (H4) comprises a plurality of compounds, preferably 1 to 5, more preferably 1 to 3, further preferably 1 to 2, and most preferably 1 structure represented by formula (H4). When multiple compounds are included, the structures are directly bonded to each other by single bonds or by specific linking groups.

[0472]

[0473] In formula (H4), G is “=C(-H)-” or “=N-”, and the H in “=C(-H)-” can be substituted by a substituent or the structure represented by formula (H4).

[0474] As a compound with the structure represented by the inclusion formula (H4), for example, compounds described in International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650 may be used, and may be prepared according to the methods described in the documents.

[0475] Examples of substituents in cases where the H in the "=C(-H)-" of G is substituted include: aryl, heteroaryl, substituted silyl, substituted phosphine oxide, and substituted carboxyl groups, etc.

[0476] Specific examples of "aryl" as a substituent include: phenyl, tolyl, xylyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, biphenyl, terphenyl, tetraphenyl, etc., preferably phenyl, biphenyl, terphenyl, and fluorenyl. Examples of aryl groups having substituents include: tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, aryl groups include both condensed aryl groups and non-condensed aryl groups.

[0477] Specific examples of "heteroaryl" substituents include: pyrrole, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, triazinyl, indoleyl, isoindoleyl, imidazolyl, benzimidazolyl, indoleyl, imidazo[1,2-a]pyridinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, azadibenzothiophenyl, quinolinyl. The following are preferred compounds: isoquinolinyl, quinoxolinyl, quinazolinyl, naphridinyl, carbazoleyl, azacarbazoleyl, phenanthinyl, acridineyl, phenazinyl, phenothiazinyl, phenotoxazinyl, oxazolyl, oxadiazolyl, furazolyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc. More preferably, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, pyridinyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothiophenyl are also preferred.

[0478] The "substituted silyl" as a substituent is preferably selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0479] Specific examples of substituted or unsubstituted trialkylsilyl groups include trimethylsilyl and triethylsilyl. Specific examples of substituted or unsubstituted arylalkylsilyl groups include diphenylmethylsilyl, xylmethylsilyl, and phenyldimethylsilyl. Specific examples of substituted or unsubstituted triarylsilyl groups include triphenylsilyl and trimethylsilyl.

[0480] The "substituted phosphine oxide group" as a substituent is preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of substituted or unsubstituted diarylphosphine oxide groups include diphenylphosphine oxide and xylylphosphine oxide.

[0481] Regarding "substituted carboxyl groups" as substituents, examples include benzoyloxy groups, etc.

[0482] As a linking group that forms the structural bonds represented by multiple formulas (H4), divalent to tetravalent, divalent to trivalent, or divalent derivatives of the aryl or heteroaryl groups can be listed.

[0483] Specific examples of compounds containing the structure represented by formula (H4) are shown below.

[0484]

[0485]

[0486] 3-1-5-2-4. Compounds represented by formula (H5) and compounds represented by formula (H6)

[0487] 3-1-5-2-4-1. Compounds represented by formula (H5)

[0488]

[0489] In equation (H5), R 1 ~R 11 Each of these can be independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, wherein at least one of these hydrogens may be substituted by aryl, heteroaryl, or diarylamino.

[0490] Additionally, any at least one (preferably 1 to 3) of formula (H5) -C(R) n ) = (n is 1~11) can be replaced by -N =.

[0491] At least one hydrogen atom in the compound represented by formula (H5) may be substituted by an alkyl group having 1 to 24 carbon atoms, and any -CH2- atom in the alkyl group may be substituted by -O- or -Si(CH3)2- atom, any -CH2- atom in the alkyl group other than the -CH2- atom directly bonded to the compound represented by formula (H5) may be substituted by an arylene group having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl group may be substituted by fluorine.

[0492] In addition, at least one hydrogen atom in the compound represented by formula (H5) may be substituted with halogen or deuterium.

[0493] 3-1-5-2-4-2. Compounds represented by formula (H6)

[0494]

[0495] In equation (H6), R 1 ~R 16 Each of these can be independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, wherein at least one of these hydrogens may be substituted by aryl, heteroaryl, or diarylamino.

[0496] In addition, at least one hydrogen in the compound represented by formula (H-6) may be substituted by an alkyl group having 1 to 24 carbon atoms, and any -CH2- in the alkyl group may be substituted by -O- or -Si(CH3)2-, any -CH2- in the alkyl group other than the -CH2- directly bonded to the compound represented by formula (H6) may be substituted by an arylene group having 6 to 24 carbon atoms, and any hydrogen in the alkyl group may be substituted by fluorine.

[0497] In addition, at least one hydrogen atom in the compound represented by formula (H6) may be substituted with halogen or deuterium.

[0498] 3-1-5-2-4-3. R in equation (H5) 1 ~R 11 "and R in formula (H6)" 1 ~R 16 "

[0499] R in formula (H5) 1 ~R 11 "and R in formula (H6) 1 ~R 16 "Each of the following can be independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, preferably an aryl with 6 to 30 carbons, a heteroaryl with 2 to 30 carbons, a diarylamino (an amino group having two aryl groups with 6 to 30 carbons), a diheteroarylamino (an amino group having two heteroaryl groups with 2 to 30 carbons), an arylheteroarylamino (an amino group having an aryl group with 6 to 30 carbons and a heteroaryl group with 2 to 30 carbons), or an aryloxy with 6 to 30 carbons."

[0500] Aryl groups, including those labeled "aryl," "diarylamino," "aryl heteroarylamino," and "aryloxy," can be categorized as follows: monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthyl rings, tricyclic terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl), condensed tricyclic acenaphthene, fluorene, phenanthene, and phenanthrene rings, condensed tetracyclic triphenylene, pyrene, and tetraphenylene rings, and condensed pentacyclic perylene and pentaphenylene rings, etc. Furthermore, as will be discussed later, aryl groups substituted with heteroaryl groups as defined below are also defined as aryl groups in formulas (H5) and (H6).

[0501] Examples of heteroaryl groups that can be categorized as "heteroaryl", "diheteroarylamino", and "arylheteroarylamino" include: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetraazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H- The following are monovalent groups: benzotriazole ring, quinoline ring, isoquinoline ring, cyclophosphine ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthidine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxthia ring, phenoxazine ring, phenthiazine ring, phenazine ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazine ring, oxadiazole ring, thiathracene ring, and heteroaryl groups substituted with N-aryl groups. Furthermore, as described later, the groups among these heteroaryl groups that are substituted with the aryl groups defined above are also defined as heteroaryl groups in formulas (H5) and (H6).

[0502] Additionally, regarding R in equation (H5) 1 ~R 11 R in equation (H6) 1 ~R 16 The aryl, heteroaryl, diarylamino, diarylamino, arylhelelamino, or aryloxy groups described herein may have at least one hydrogen atom substituted with an aryl, heteroaryl, or diarylamino group. Examples of aryl, heteroaryl, or diarylamino groups that are thus substituted include R. 1 ~R 11 Or R 1 ~R 16 The same bases as those described in the column.

[0503] As R 1 ~R 11 Or R 1 ~R 16 Specific bases, for example, can be listed as those represented by equations (RG-1) to (RG-10) below. Furthermore, the bases represented by equations (RG-1) to (RG-10) below... The a-ring to d-ring bond is located in formula (H5) or formula (H6).

[0504]

[0505] If we refer to the specific groups mentioned above when describing "aryl" and "heteroaryl" as defined in formulas (H5) and (H6), then formulas (RG-1), (RG-4), and (RG-7) are aryl, formulas (RG-2), (RG-3), and (RG-6) are heteroaryl, formula (RG-9) is a heteroaryl with substitution, and formula (RG-10) is an aryl with substitution. Furthermore, formula (RG-5) is an aryl (phenyl) with substitution of diarylamino (diphenylamino), and formula (RG-8) is a diarylamino (diphenylamino).

[0506]

[0507] 3-1-5-2-4-4. Specific examples of compounds

[0508] The following shows a more specific structure of the compound represented by formula (H5) or formula (H6).

[0509] The specific structures of the compounds represented by the following formulas (H5) or (H6) may be substituted with alkyl groups having 1 to 24 carbon atoms.

[0510]

[0511]

[0512]

[0513]

[0514]

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536] 3-1-5-2-4-5. Methods for preparing compounds represented by formula (H5) or formula (H6).

[0537] The compound represented by formula (H5) first uses a bonding group (-O-) to bond the a-ring to the c-ring, thereby preparing an intermediate (first reaction). Then, using a bonding group (containing B), the a-ring is bonded to the c-ring again, thereby preparing the final product (second reaction). Alternatively, the compound represented by formula (H6) first uses a bonding group (>NH or a single bond) to bond the a-ring to the d-ring, thereby preparing an intermediate (first reaction). Then, using a bonding group (containing B), the a-ring is bonded to the d-ring again, thereby preparing the final product (second reaction). In the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or a Ullmann reaction can be used; if it is an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. In the second reaction, a tandem heterofried-Krawtz reaction (a continuous aromatic electrophilic substitution reaction, the same applies below) can be used.

[0538] <Preparation method: Example of the second reaction of the compound represented by formula (H5)>

[0539] As shown in the following process (1), the second reaction is a reaction that introduces boron (B) that bonds the a, b, and c rings. As an example, the case of the compound represented by formula (H5) is shown below. First, the hydrogen atom between the two O atoms is ortho-metallized using n-butyllithium, sec-butyllithium, or tert-butyllithium. Then, boron trichloride or boron tribromide is added for lithium-boron metal exchange, followed by the addition of a Brinzyl base such as N,N-diisopropylethylamine, thereby conducting a tandem borazorid-Krawtz reaction to obtain the target compound. In the second reaction, a Lewis acid such as aluminum trichloride can also be added to promote the reaction.

[0540] Process (1)

[0541]

[0542] In the process described above, lithium is introduced to the desired position by ortho metallization, but bromine atoms or the like can be introduced at the position where lithium is to be introduced, as in process (2) below. Lithium can also be introduced to the desired position by halogen-metal exchange.

[0543] Process (2)

[0544]

[0545] By appropriately selecting the synthetic method and the starting materials used, compounds having substituents at the desired positions and represented by formula (H5) can be synthesized.

[0546] <Preparation methods: Examples of preparation methods for compounds represented by formula (H6)>

[0547] The method for preparing the compound represented by formula (H6) can also apply the first and second reactions in the method for preparing the compound represented by formula (H5). Specifically, the second reaction involves introducing the reaction of NH with B (boron) bonded to the c and d rings. After ortho-metallization of the hydrogen atoms of NH using n-butyllithium, sec-butyllithium, or tert-butyllithium, boron trichloride or boron tribromide is added to perform a lithium-boron metal exchange. Then, a Brønsted base such as N,N-diisopropylethylamine is added, thereby conducting a tandem borofried-Krawtz reaction to obtain the target compound. Here, to promote the reaction in the second reaction, a Lewis acid such as aluminum trichloride can also be added.

[0548] 3-1-5-2-5. Compounds containing the structure represented by formula (H8)

[0549] The compound containing the structure represented by formula (H8) contains a plurality of, preferably 1 to 5, more preferably 1 to 3, further preferably 1 to 2, and most preferably 1 structure represented by (H8). When multiple structures are contained, the structures are directly bonded to each other by single bonds or by specific linker bonds.

[0550]

[0551] In formula (H8), Z is “=C(-H)-” or “=N-”, and the H in “=C(-H)-” can be substituted by the structure represented by the substituent.

[0552] Examples of substituents in cases where the H in “=C(-H)-” of Z is substituted include: aryl, heteroaryl, substituted silyl, substituted phosphine oxide, and substituted carboxyl groups, etc.

[0553] Specific examples of "aryl" as a substituent include: phenyl, tolyl, xylyl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, biphenyl, terphenyl, tetraphenyl, etc., preferably phenyl, biphenyl, terphenyl, and fluorenyl. Examples of aryl groups having substituents include: tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, aryl groups include both condensed aryl groups and non-condensed aryl groups.

[0554] Specific examples of "heteroaryl" substituents include: pyrroloyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, triazinyl, indolyl, isoindolyl, imidazoyl, benzimidazolyl, indolyl, imidazo[1,2-a]pyridinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolinyl, Isoquinolinyl, quinoxolinyl, quinazolinyl, naphridinyl, carbazoleyl, azacarbazoleyl, phenanthinyl, acridineyl, phenazinyl, phenothiazinyl, phenotoxazinyl, oxazolyl, oxadiazolyl, furazolyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., preferably dibenzofuranyl, dibenzothiophenyl, carbazoleyl, pyridinyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothiophenyl, etc. More preferably dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, or azadibenzothiophenyl.

[0555] The "substituted silyl" as a substituent is preferably selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0556] Specific examples of substituted or unsubstituted trialkylsilanes include trimethylsilane and triethylsilane. Specific examples of substituted or unsubstituted arylalkylsilanes include diphenylmethylsilane, xylmethylsilane, and phenyldimethylsilane. Specific examples of substituted or unsubstituted triarylsilanes include triphenylsilane and trimethylsilane.

[0557] The "substituted phosphine oxide group" as a substituent is preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of substituted or unsubstituted diarylphosphine oxide groups include diphenylphosphine oxide and xylylphosphine oxide.

[0558] Regarding "substituted carboxyl groups" as substituents, examples include benzoyloxy groups, etc.

[0559] As a linking group for the structural bonds represented by multiple formulas (H8), divalent to tetravalent, divalent to trivalent, or divalent derivatives of the aryl or heteroaryl groups can be listed.

[0560] Specific examples of compounds containing the structure represented by formula (H8) are shown below.

[0561]

[0562]

[0563] 3-1-5-2-6. TADF material

[0564] High-T1 compounds can also be used as TADF materials.

[0565] In this specification, TADF material refers to a material used as a "thermally activated delayed phosphor". In a thermally activated delayed phosphor, by reducing the energy difference between the excited singlet state and the excited triplet state, the reverse energy transfer from the self-excited triplet state to the excited singlet state, which typically has a low migration probability, is efficiently generated, resulting in luminescence from the singlet state (thermally activated delayed fluorescence, TADF). In conventional fluorescence luminescence, 75% of the triplet excitons generated by current excitation pass through the thermal inactivation path and cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence luminescence, enabling high-efficiency organic EL devices.

[0566] TADF materials are preferably designed to use electron-donating substituents called donors and electron-accepting substituents called acceptors to locally exist HOMO and LUMO within the molecule, so as to produce efficient reverse intersystem crossing donor-acceptor type TADF compounds (DA type TADF compounds).

[0567] In this specification, "electron-donating substituent" (donor) refers to the substituent and part of the structure that is locally present in the HOMO orbital of the TADF compound molecule, and "electron-accepting substituent" (acceptor) refers to the substituent and part of the structure that is locally present in the LUMO orbital of the TADF compound molecule.

[0568] Generally, TADF compounds using donors or acceptors exhibit high spin-orbit coupling (SOC) due to their structure, and the exchange interaction between HOMO and LUMO is weak, resulting in ΔE. ST The small size allows for very fast reverse intersystem crossing speeds. On the other hand, TADF compounds using donors or acceptors exhibit greater structural relaxation in the excited state (in a molecule, the stable structures in the ground and excited states differ; therefore, if a transition from the ground to the excited state occurs through external stimulation, the subsequent structural change is to the stable structure in the excited state), thus providing a broad emission spectrum. Consequently, when used as a luminescent material, it may reduce color purity.

[0569] However, by simultaneously using the polycyclic aromatic compound represented by formula (1), which functions as an emission dopant and the TADF material as an auxiliary dopant, high color purity can be provided. The TADF material only needs to be a compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound represented by formula (1). The polycyclic aromatic compound represented by formula (1) and the TADF material can both be contained in the same layer or in adjacent layers.

[0570] As TADF materials that can be used for this purpose, examples include compounds represented by the following formula (H7) or compounds having the following formula (H7) as part of their structure.

[0571]

[0572] In formula (H7), ED is an electron-donating group, Ln is a linking group, and EA is an electron-accepting group. The lowest excited singlet state energy level (E) of the compound represented by formula (H7) is... S1 ) and the lowest excited triplet energy level (E T1 The energy difference (ΔE) ST ) is less than 0.2eV (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, ChihayaAdachi, Nature, 492,234-238(2012)). Energy difference (ΔE STThe preferred value is 0.15 eV or less, more preferably 0.10 eV or less, and even more preferably 0.08 eV or less.

[0573] As electron-donating groups (donor structures) and electron-accepting groups (acceptor structures) used in TADF materials, structures described in *Chemistry of Materials* (2017, 29, 1946-1963) can be used, for example. As EDs, structures containing sp... 3 More specifically, functional groups derived from nitrogen include: those derived from carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzo[a]fluorocarbazole, benzo[a]thieno[a]carbazole, phenyldihydroindol[a]carbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazoleylamine, tetraphenylcarbazoleyldiamine, phenoxazine, dihydrophenazine, phenthiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylphenyl-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indo[a]acridine, and diphenyl-dihydrodibenzo[a]azine, etc. Additionally, as EAs, those containing sp[a][b ... 2 Aromatic rings of nitrogen, CN-substituted aromatic rings, rings containing ketones, and cyano groups, more specifically, include: sulfonyl diphenylene, benzophenone, phenylene bis(phenyl ketone), benzonitrile, isoniconitrile, o-phthalonitrile, isophthalonitrile, terephthalonitrile, triazole, oxazole, thiadiazole, benzo[a]thiazole, benzo[a]bis(thiazole), benzo[a]oxazole, benzo[a]bis(oxazole), quinoline, benzimidazole, dibenzo[a]quinoxaline, heptaazafinaene, etc. Thioxanone dioxide, dimethylanthrone, anthrone, pyridine, 5H-cyclohepta[1,2-b:5,4-b']bipyridine, benzotricarbonyl, fluorenedicarbonyl, pyrazinedicarbonyl, pyridinedicarbonyl, dibenzoquinoxalolinedicarbonyl, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thiathracene tetroxide, and tri(dimethylphenyl)borane, etc. As Ln, for example, single bonds and arylene groups can be listed; more specifically, phenylene, biphenylene, naphthylene, etc. Furthermore, in any structure, hydrogen can be substituted by alkyl, cycloalkyl, and aryl groups. Particularly preferred are compounds having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanol, benzonitrile, o-phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, oxadiazole, thiadiazole and benzophenone as part of their structure.

[0574] In equation (H7), Ln, as a linker, functions as a spacer structure that separates the donor and acceptor partial structures.

[0575] More specifically, the compound represented by formula (H7) can be any compound represented by formula (H7-1), formula (H7-2) and formula (H7-3).

[0576]

[0577] In equations (H7-1), (H7-2), and (H7-3),

[0578] M can be independently a single bond, -O-, >N-Ar, or >C(-Ar)2. From the viewpoint of the depth of the HOMO of the formed partial structure and the height of the lowest excited singlet and triplet energy levels, a single bond, -O-, or >N-Ar is preferred.

[0579] J is the linker group corresponding to Ln in formula (H7), and is independently an arylene group having 6 to 18 carbon atoms. From the viewpoint of the magnitude of the conjugation between the self-donor and acceptor partial structures, an arylene group having 6 to 12 carbon atoms is preferred. More specifically, examples include: phenylene, methylphenylene, and dimethylphenylene.

[0580] Q can be independently =C(-H)- or =N-, and from the viewpoint of the shallowness of the LUMO of the formed partial structure and the height of the lowest excited singlet and triplet energy levels, =N- is preferred.

[0581] Ar can be hydrogen, aryl (6-24 carbons), heteroaryl (2-24 carbons), alkyl (1-12 carbons), or cycloalkyl (3-18 carbons), respectively. From the viewpoint of the depth of the HOMO of the formed partial structure and the height of the lowest excited singlet and triplet energy levels, it is preferred to be hydrogen, aryl (6-12 carbons), heteroaryl (2-14 carbons), alkyl (1-4 carbons), or cycloalkyl (6-10 carbons). More preferably, it is hydrogen, phenyl, tolyl, xylyl, mesitylelel, biphenyl, pyridyl, bipyridyl, triazine, carbazole, dimethylcarbazole, di-tert-butylcarbazole, benzimidazole, or phenylbenzimidazole. Even more preferably, it is hydrogen, phenyl, or carbazole.

[0582] m is 1 or 2

[0583] n is an integer from 2 to (6-m), and from the perspective of potential resistance, it is preferably an integer from 4 to (6-m).

[0584] Furthermore, at least one hydrogen atom in the compounds represented by the formulas may be substituted with halogen or deuterium.

[0585] Compounds represented by formula (H7) include, for example, compounds represented by the structures described below. Furthermore, the structural formulas in... The symbols indicate the bond position; "Me" represents methyl and "tBu" represents tert-butyl.

[0586]

[0587]

[0588]

[0589]

[0590]

[0591]

[0592]

[0593]

[0594]

[0595]

[0596] Among the specific compounds represented by formula (H7), PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, ACRD SO2, DTC-DBT, DTAO, 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 are preferred.

[0597] 3-1-5-3. Thermally activated delayed phosphor (auxiliary dopant)

[0598] The luminescent layer may also include a thermally activated delayed phosphor as an auxiliary dopant.

[0599] "Thermally activated delayed fluorescence" refers to compounds that can absorb thermal energy and undergo a reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, emitting delayed fluorescence through radiative inactivation from this lowest excited singlet state. "Thermally activated delayed fluorescence" also includes fluorescence that undergoes a higher-order triplet state during the excitation process from the lowest excited triplet state to the lowest excited singlet state. Examples include the paper by Monkman et al. from Durham University (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038 / ncomms13680), the paper by Hosokai et al. from the National Institute of Advanced Industrial Science and Technology (AIST) (Hosokai et al., Sci. Adv. 2017; 3:e1603282), and the paper by Sato et al. from Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-). This invention has been published in several journals, including: 05007-7; academic papers by Sato et al. (98th Spring Meeting of the Chemical Society of Japan, Published No.: 2I4-15, Mechanism of High-Efficiency Luminescence in Organic Electroluminescence Using DABNA as a Luminescent Molecule, Graduate School of Engineering, Kyoto University); comments by Bui et al. (DOI: 10.3762 / bjoc.14.18); comments by Duan et al. (DOI: 10.1063 / 1.5143501); comments by Ding et al. (DOI: 10.1088 / 1674-4926 / 42 / 5 / 050201); and comments by Xie et al. (DOI: 10.1002 / adom.202002204). In this invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300K, the target compound is determined to be a "thermally activated delayed phosphor" due to the observed delayed fluorescence component. Here, delayed fluorescence refers to fluorescence lifetime of 0.1 μsec or more. Fluorescence lifetime can be measured using, for example, a fluorescence lifetime measuring device (Hamamatsu Photonics, C11367-01).

[0600] The polycyclic aromatic compound represented by formula (1) can function as an emission dopant, and the "thermally activated delayed phosphor" can function as an auxiliary dopant to assist the emission of the polycyclic aromatic compound represented by formula (1).

[0601] In the following description, organic electroluminescent elements in which thermally activated delayed phosphors are used as auxiliary dopants are referred to as "TAF elements" (TADF Assisting Fluorescence elements).

[0602] In TAF elements, the “host compound” refers to a compound whose lowest excited singlet energy level, obtained from the shoulder of the short-wavelength side of the fluorescence spectrum peak, is higher than that of thermally activated delayed phosphors and emission dopants used as auxiliary dopants.

[0603] In this configuration, known host compounds can be used, such as compounds having at least one of a carbazole ring and a furan ring, wherein compounds having at least one of a furanyl group and a carbazole group bonded to at least one of an arylene group and a heteroarylene group are preferred. Specific examples include mCP or mCBP.

[0604] From the viewpoint that the lowest excited triplet energy level E(1,T,Sh) obtained from the shoulder of the short-wavelength side of the phosphorescence spectrum peak of the host compound promotes the generation of TADF within the emissive layer without hindering it, it is preferably higher than the lowest excited triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitting dopant or auxiliary dopant that has the highest lowest excited triplet energy level within the emissive layer. Specifically, the lowest excited triplet energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or higher than E(2,T,Sh) and E(3,T,Sh), more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. Furthermore, a TADF-active compound can be used in the host compound.

[0605] The thermally activated delayed fluorescent (TADF) compounds used in TAF elements are preferably designed to locally contain intramolecular HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) by using electron-donating substituents called donors and electron-accepting substituents called acceptors, in order to produce donor-acceptor type thermally activated delayed fluorescent (DA-type TADF compounds) with efficient reverse intersystem crossing.

[0606] In this specification, "electron-donating substituent" (donor) refers to the substituent and part of the structure that is locally present in the HOMO orbital of a thermally activated delayed fluorophore molecule, and "electron-accepting substituent" (acceptor) refers to the substituent and part of the structure that is locally present in the LUMO orbital of a thermally activated delayed fluorophore molecule.

[0607] Generally, thermally activated delayed fluorophores using donors or acceptors have large spin-orbit coupling (SOC) and small exchange interactions between HOMO and LUMO due to their structure, resulting in ΔE.S1T1 The small size allows for very fast reverse intersystem crossing speeds. On the other hand, thermally activated delayed phosphors using donors or acceptors exhibit greater structural relaxation in the excited state (in a molecule, the stable structures in the ground and excited states differ; therefore, if a transition from the ground to the excited state occurs through external stimulation, the subsequent structural change is to the stable structure in the excited state), thus providing a broad emission spectrum. However, this may reduce color purity when used as a luminescent material.

[0608] As a thermally activated delayed phosphor in a TAF element, a compound in which the donor and acceptor are directly or indirectly bonded can be used, for example. The electron-donating group (donor-type structure) and electron-accepting group (acceptor-type structure) used in the thermally activated delayed phosphor of the present invention can, for example, use the structures described in *Chemistry of Materials* (2017, 29, 1946-1963). Examples of donor structures include: carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothiophenecarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazole, tetraphenylcarbazole diamine, phenoxazine, dihydrophenazine, phenthiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylphenyl-1,4-diamine, dimethyltetraphenyldihydroacridine diamine, tetramethyl-dihydro-indoacridine, and diphenyl-dihydrodibenzodiazeline, etc. Examples of receptor-like structures include: sulfonyl diphenyl, benzophenone, phenyl bis(phenyl ketone), benzonitrile, isoniconitrile, o-phthalonitrile, isophthalonitrile, terephthalonitrile, benzotricarbonyl, triazole, oxazole, thiadiazole, benzothiazolium, benzobis(thiazolium), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazafinaene, thioxanone dioxide, dimethylanthrone, anthrone, 5H-cyclohepta[1,2-b:5,4-b']bipyridine, fluorenedicarbonyl, triphenyltriazine, pyrazinedicarbonyl, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonyl, dibenzoquinoxalinedicarbonyl, bis(phenylsulfonyl)benzene, dimethylthioxanone dioxide, thiathronetetraoxide, and tri(dimethylphenyl)borane. The compounds with thermally activated delayed fluorescence in TAF elements are particularly preferred to be compounds having at least one of the following as a partial structure: carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanol, benzonitrile, o-phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, oxadiazole, thiadiazole and benzophenone.

[0609] The compound used as the auxiliary dopant in the TAF element as the emitting layer is a thermally activated delayed phosphor, preferably a compound whose emission spectrum overlaps at least partially with the absorption peak of the emission dopant.

[0610] 3-1-5-4. Phosphorescent Materials (Auxiliary Dopant)

[0611] Phosphorescent materials can also be used as auxiliary dopants in the luminescent layer. Phosphorescent materials utilize intramolecular spin-orbit interactions (heavy atom effect) based on metal atoms to obtain luminescence from the triplet state. As phosphorescent materials as described above, luminescent metal complexes can be used, for example. Examples of luminescent metal complexes include compounds represented by formulas (B-1) and (B-2) below.

[0612]

[0613] In equation (B-1), M is selected from at least one of the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu, n is an integer from 1 to 3, and "XY" are independently bidentate ligands.

[0614] In formula (B-2), M is selected from at least one of the group consisting of Pt, Re and Cu, and "WXYZ" is a tetradentate ligand.

[0615] In equation (B-1), from the viewpoint of efficiency and lifespan, M is preferably Ir, and n is preferably 3.

[0616] In equation (B-2), from the viewpoint of efficiency and lifespan, M is preferably Pt.

[0617] The ligand (XY) in formula (B-1) has at least one ligand selected from the group consisting of the following. The ligand (WXYZ) in formula (B-2) has at least one ligand selected from the group consisting of the following as part thereof.

[0618]

[0619] In the formula,

[0620] It bonds with the central metal M in ---

[0621] 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 GeR e Rf ,

[0622] The aromatic carbons CH in the ring can also be independently substituted by N.

[0623] R e and R f They can also be arbitrarily condensed or bonded to form rings.

[0624] R a R b R c and R d They can also be obtained independently, either unsubstituted or with one of the largest substituted molecules.

[0625] R a R b R c R d R e and R f Each of these can be independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or a combination thereof.

[0626] Among them, in R a R b R c and R d Any two adjacent substituents can also form a ring through condensation or bonding, or form a polydentate ligand.

[0627] Examples of compounds represented by formula (B-1) include: Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), and fac-Tris(2-(3-p-xylyl)phenyl)pyridine. iridium(III), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(2-phq)3, Ir(BT)2(acac), Ir(D MP)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.

[0628] Other compounds that can be listed as represented by formula (B-1) include the following.

[0629]

[0630]

[0631]

[0632] Alternatively, iridium complexes described in Japanese Patent Publication No. 2006-089398, Japanese Patent Publication No. 2006-080419, Japanese Patent Publication No. 2005-298483, Japanese Patent Publication No. 2005-097263, Japanese Patent Publication No. 2004-111379, and U.S. Patent Application Publication No. 2019 / 0051845, or platinum complexes described in Advanced Materials, 26:7116-7121, NPG Asia Materials 13, 53(2021), Applied Physics Letters, 117, 253301 (2020), Light-Emitting Diode-An Outlook On the Empirical Features and Its Recent Technological Advancements, Chapter 5, may be used.

[0633] 3-1-5-5. Other doped materials

[0634] The polycyclic aromatic compound comprising the structural unit represented by formula (1) can be used in combination with other dopant materials. The other dopant materials, in a light-emitting layer, are preferably less than 100% by mass, more preferably less than 50% by mass, further preferably less than 30% by mass, and particularly preferably less than 10% by mass, relative to the total mass of the polycyclic aromatic compound comprising the structural unit represented by formula (1). Known compounds can be used as other dopant materials, and a variety of materials can be selected according to the desired color rendering.

[0635] Other preferred dopant materials include boron polycyclic aromatic compounds described in International Publication No. 2015 / 102118, International Publication No. 2020 / 162600, and Japanese Patent Application Publication No. 2021-077890, paragraphs 0097 to 0269.

[0636] Other dopant materials include, for example, the following compounds.

[0637]

[0638] 3-1-6. Electron injection layer and electron transport layer in organic electroluminescent devices

[0639] The electron injection layer 107 efficiently injects electrons migrating from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 efficiently transports electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or more electron transport / injection materials, or by forming a mixture of electron transport / injection materials and a polymer binder.

[0640] The electron injection / transport layer is a layer responsible for the injection and transport of electrons from the cathode. Ideally, it should have high electron injection efficiency and efficient transport of the injected electrons. Therefore, materials with high electron affinity and high electron mobility, resulting in excellent stability and minimizing the formation of impurities that could become traps during manufacturing and use, are preferred. However, considering the balance between hole and electron transport, materials that effectively prevent unrecombined holes from the anode from flowing to the cathode can achieve the same effect of improving luminous efficiency as materials with high electron transport capabilities, even if their electron transport capability is not very high. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that effectively prevents hole migration.

[0641] The material (electron transport material) used to form the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds commonly used as electron transport compounds in photoconductive materials, and known compounds used in electron injection layers and electron transport layers of organic EL elements.

[0642] The materials used in the electron transport layer or electron injection layer are preferably compounds containing at least one of the following: compounds containing an aromatic ring or heteroaromatic ring comprising one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their condensed ring derivatives; and metal complexes with electron-accepting nitrogen. Specifically, examples include: condensed ring aromatic ring derivatives such as naphthalene and anthracene; styryl aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl; violet ketone derivatives; coumarin derivatives; naphthalenedicarboximide derivatives; quinone derivatives such as anthraquinone or biphenylquinone; phosphorus oxide derivatives; aryl nitrile derivatives; and indole derivatives. Examples of metal complexes with electron-accepting nitrogen include: hydroxyazole complexes such as hydroxyphenyloxazole complexes; azomethyl base complexes; cycloheptatrienolone metal complexes; flavonol metal complexes; and benzoquinone metal complexes. These materials can be used alone or in combination with different materials.

[0643] In addition, specific examples of other electron-transfer compounds include: pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phenanthroline derivatives, violet ketone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole compounds, gallium complexes, pyrazole derivatives, and perfluorinated compounds. Phenyl derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirofluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6',2"-terpyridyl))benzene, naphthidine derivatives (bis(1-naphthyl)-4-(1,8-naphthidyl-2-yl)phenylphosphine oxide, etc.), aldehyde azo derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyrene derivatives, etc.

[0644] Alternatively, metal complexes with electron-accepting nitrogen can be used, such as hydroxyquinoline metal complexes or hydroxyphenyloxazole complexes, azomethyl base complexes, cycloheptatrienolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0645] The material can be used alone or in combination with different materials.

[0646] The preferred materials are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and hydroxyquinoline-based metal complexes.

[0647] <Boronane derivatives>

[0648] Borane derivatives, for example, are compounds represented by the following formula (ETM-1), which are disclosed in detail in Japanese Patent Application Publication No. 2007-27587.

[0649]

[0650] In formula (ETM-1), R11 and R 12 R is at least one of hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle, or cyano, respectively. 13 ~R 16 Each of these groups can be independently substituted alkyl, substituted cycloalkyl, or substituted aryl, where X is a substituted arylene, Y is a substituted aryl with 16 or fewer carbon atoms, a substituted boronyl, or a substituted carbazoleyl, and n is independently an integer from 0 to 3. Examples of substituents for "substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0651] The compounds represented by formula (ETM-1) are preferably those represented by formula (ETM-1-1) or those represented by formula (ETM-1-2).

[0652]

[0653] In formula (ETM-1-1), R 11 and R 12 R is at least one of hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle, or cyano, respectively. 13 ~R 16 R is independently a substituted alkyl group, a substituted cycloalkyl group, or a substituted aryl group. 21 and R 22 Each of the following groups is independently hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle, or cyano, X 1 For substituted aryl groups with 20 or fewer carbon atoms, n is an independent integer from 0 to 3, and m is an independent integer from 0 to 4. Examples of substituents for "substitutable" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0654]

[0655] In formula (ETM-1-2), R 11 and R 12 R is at least one of hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle, or cyano, respectively. 13 ~R 16 Each of the following is independently a substituted alkyl group, a substituted cycloalkyl group, or a substituted aryl group, X 1It is a substitutable aryl group with 20 or fewer carbon atoms, and n is an integer from 0 to 3. In addition, examples of substituents as "substitutable" or "substituted" include: aryl, heteroaryl, alkyl or cycloalkyl, etc.

[0656] As X 1 Specific examples can be listed as the divalent base represented by any of the following equations (X-1) to (X-9).

[0657]

[0658] (In each formula, R) a Each is independently an alkyl, cycloalkyl, or substituted phenyl group. (Indicates the location of the bond)

[0659] Specific examples of the borane derivatives include the following compounds.

[0660]

[0661] The borane derivatives can be prepared using known raw materials and known synthetic methods.

[0662] <Pyridine Derivatives>

[0663] The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

[0664] -(pyridine substituent)n (ETM-2)

[0665]

[0666] It is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4.

[0667] In equation (ETM-2-1), R 11 ~R 18 Each of the following can be independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbons), cycloalkyl (preferably cycloalkyl with 3 to 12 carbons) or aryl (preferably aryl with 6 to 30 carbons).

[0668] In equation (ETM-2-2), R 11 and R 12 Each of the following is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbons), cycloalkyl (preferably cycloalkyl with 3 to 12 carbons), or aryl (preferably aryl with 6 to 30 carbons), R11 and R 12 They can bond together to form a ring.

[0669] In each formula, "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15) (in the formula) (Indicating the bond position), the pyridine substituents can be independently substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, with methyl being preferred. Furthermore, the pyridine substituents can be substituted with the various substituents via a phenylene or naphthylene group. Anthracite rings or fluorene rings are bonded together.

[0670]

[0671] The pyridine substituents are any one of formulas (Py-1) to (Py-15) (in the formula...) (representing the bond position), preferably any one of the following formulas (Py-21) to (Py-44).

[0672]

[0673] At least one hydrogen atom in each pyridine derivative may be substituted with deuterium. In addition, one of the two “pyridine substituents” in formula (ETM-2-1) and formula (ETM-2-2) may be substituted with aryl group.

[0674] As R 11 ~R 18 The term "alkyl" can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferred "alkyl" is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms). More preferably, an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms). Even more preferably, an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms). Particularly preferred "alkyl" is an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms).

[0675] Specific examples of "alkyl groups" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0676] The description of the alkyl group can be cited as an example of an alkyl group having 1 to 4 carbon atoms that is substituted in a pyridine substituent.

[0677] As R 11 ~R 18 The term "cycloalkyl" can be exemplified by cycloalkyl groups having 3 to 12 carbon atoms. Preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. Even more preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms.

[0678] Specific examples of "cycloalkyl groups" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl, etc.

[0679] As R 11 ~R 18 The "aryl" in the text is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 18 carbon atoms, and even more preferably an aryl group with 6 to 14 carbon atoms, and particularly preferably an aryl group with 6 to 12 carbon atoms.

[0680] Specific examples of "aryl groups with 6 to 30 carbon atoms" include: phenyl groups (monocyclic aryl groups), (1-, 2-)naphthyl groups (condensed bicyclic aryl groups), acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthyl groups (condensed tricyclic aryl groups), triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetraphenylene-(1-, 2-, 5-)yl groups (condensed tetracyclic aryl groups), and perylene-(1-, 2-, 3-)yl and pentaphenylene-(1-, 2-, 5-, 6-)yl groups (condensed pentacyclic aryl groups).

[0681] Preferred "aryl group having 6 to 30 carbon atoms" may include phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, etc., and more preferably may include phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably may include phenyl, 1-naphthyl or 2-naphthyl.

[0682] R in formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0683] As specific examples of the pyridine derivative, for example, the following compounds may be cited.

[0684]

[0685] The pyridine derivative can be prepared using known raw materials and known synthesis methods.

[0686] <Fluoranthene derivative>

[0687] The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and specifically, it is disclosed in International Publication No. 2010 / 134352.

[0688]

[0689] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, as substituents in the case of being substituted, aryl, heteroaryl, alkyl or cycloalkyl, etc. may be cited.

[0690] As specific examples of the fluoranthene derivative, for example, the following compounds may be cited.

[0691]

[0692] <BO-based derivative>

[0693] The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

[0694]

[0695] R 1 ~R 11Each of the following is independently hydrogen, aryl, heteroaryl, diarylamino, diherylamino, arylherylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0696] Additionally, R 1 ~R 11 The adjacent groups in the ring can be bonded to each other and together with ring a, ring b or ring c to form an aryl ring or a heteroaryl ring. At least one hydrogen in the formed ring can be substituted by aryl, heteroaryl, diarylamino, diarylamino, arylheyarylamino, alkyl, cycloalkyl, alkoxy or aryloxy groups. At least one of these hydrogens can be substituted by aryl, heteroaryl, alkyl or cycloalkyl groups.

[0697] In addition, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may be substituted with halogen or deuterium.

[0698] For an explanation of the morphology of the substituents or rings in formula (ETM-4), please refer to the explanation of polycyclic aromatic compounds composed of the partial structures represented by formula (1).

[0699] Specific examples of the BO-based derivatives include the following compounds.

[0700]

[0701] The BO-based derivatives can be prepared using known raw materials and known synthetic methods.

[0702] Benzo[a]fluorene derivatives

[0703] Benzo[a]fluorene derivatives are, for example, compounds represented by the following formula (ETM-6).

[0704]

[0705] Ar 1 Each is an aryl group with 6 to 20 carbon atoms, and can be referenced in Ar of formula (ETM-5). 2 The same description applies to "aryl group with 6 to 20 carbon atoms". Preferably, it is an aryl group with 6 to 16 carbon atoms, more preferably an aryl group with 6 to 12 carbon atoms, and particularly preferably an aryl group with 6 to 10 carbon atoms. Specific examples include: phenyl, biphenyl, naphthyl, terphenyl, anthracene, acenaphthene, fluorenyl, phenatenyl, phenylene, pyrene, tetraphenyl, perylene, etc.

[0706] Ar 2 Each of the two Ar groups is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbons), cycloalkyl (preferably cycloalkyl with 3 to 12 carbons), or aryl (preferably aryl with 6 to 30 carbons). 2They can bond together to form a ring.

[0707] As Ar 2 The term "alkyl" can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferred "alkyl" is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms). More preferably, an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms). Further preferred "alkyl" is an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms). Particularly preferred "alkyl" is an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms). Specific examples of "alkyl" 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, etc.

[0708] As Ar 2 The term "cycloalkyl" can be exemplified by cycloalkyl groups having 3 to 12 carbon atoms. Preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. Even more preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0709] As Ar 2 The "aryl" in the text is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 18 carbon atoms, and even more preferably an aryl group with 6 to 14 carbon atoms, and particularly preferably an aryl group with 6 to 12 carbon atoms.

[0710] Specific examples of "aryl groups with 6 to 30 carbon atoms" include: phenyl, naphthyl, acenaphthel, fluorenyl, phenatenyl, phenylene, pyrene, tetraphenyl, peryl, pentaphenyl, etc.

[0711] Two Ar 2 It can bond to form rings, resulting in the formation of cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene, etc., on the 5-membered ring of the fluorene skeleton.

[0712] Specific examples of the benzo[a]fluorene derivatives include the following compounds.

[0713]

[0714] The benzo[a]fluorene derivatives can be prepared using known raw materials and known synthetic methods.

[0715] Phosphine oxide derivatives

[0716] Phosphine oxide derivatives are, for example, compounds represented by the following formula (ETM-7-1). Details are also described in International Publication Nos. 2013 / 079217 and 2013 / 079678.

[0717]

[0718] R 5 It can be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 carbon atoms.

[0719] R 6 CN, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, heteroalkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 5 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, or aryloxy groups having 6 to 20 carbon atoms.

[0720] R 7 and R 8 They are independently substituted or unsubstituted aryl groups with 6 to 20 carbon atoms or heteroaryl groups with 5 to 20 carbon atoms.

[0721] R 9 It is oxygen or sulfur.

[0722] j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.

[0723] Here, examples of substituents that are substituted include: aryl, heteroaryl, alkyl, or cycloalkyl.

[0724] Phosphine oxide derivatives may be, for example, compounds represented by the following formula (ETM-7-2).

[0725]

[0726] R 1 ~R 3 They may be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and condensed rings formed between them and adjacent substituents.

[0727] Ar 1 They can be the same or different, and can be aryl or heteroaryl. Ar 2 They can be the same or different, and can be aryl or heteroaryl. Here, Ar 1 and Ar2 At least one of them has a substituent, or forms a condensation ring with an adjacent substituent. n is an integer from 0 to 3. When n is 0, there is no unsaturated structural part; when n is 3, there is no R. 1 .

[0728] Among these substituents, the term alkyl refers to, for example, saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl. The alkyl group may be unsubstituted or substituted. There are no particular limitations on the substituents used when substituted; examples include alkyl, aryl, and heterocyclic groups, and this aspect will be consistent throughout the following description. Furthermore, there is no particular limitation on the number of carbon atoms in the alkyl group; it is generally in the range of 1 to 20, considering ease of acquisition and cost.

[0729] Furthermore, the term "cycloalkyl" refers to, for example, saturated alicyclic hydrocarbon groups such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, typically ranging from 3 to 20.

[0730] Furthermore, the term "aralkyl" refers to aromatic hydrocarbon groups such as benzyl and phenylethyl, which are separated by an aliphatic hydrocarbon. Both aliphatic and aromatic hydrocarbons can be unsubstituted or substituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, and is usually in the range of 1 to 20.

[0731] Furthermore, the term "alkenyl" refers to unsaturated aliphatic hydrocarbon groups containing double bonds, such as vinyl, allyl, and butadienyl. The alkenyl group may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is typically in the range of 2 to 20.

[0732] In addition, the term "cycloalkenyl" refers to, for example, unsaturated alicyclic hydrocarbon groups containing double bonds such as cyclopentenyl, cyclopentadienyl, and cyclohexenyl, and the cycloalkenyl group may be unsubstituted or substituted.

[0733] Furthermore, the term "alkynyl" refers to, for example, an acetylenic group or other unsaturated aliphatic hydrocarbon group containing a triple bond, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is typically in the range of 2 to 20.

[0734] In addition, the term alkoxy refers to an aliphatic hydrocarbon group, such as a methoxy group, separated by an ether bond. These aliphatic hydrocarbon groups can be unsubstituted or substituted. The number of carbon atoms in an alkoxy group is not particularly limited, typically ranging from 1 to 20.

[0735] In addition, the oxygen atom in the ether bond of the so-called alkoxy group is replaced by a sulfur atom.

[0736] In addition, the so-called cycloalkanethio group is a group in which the oxygen atom of the ether bond of the cycloalkoxy group is replaced by a sulfur atom.

[0737] In addition, the term aryl ether refers to an aromatic hydrocarbon group, such as phenoxy, separated by an ether bond. The aromatic hydrocarbon group may be unsubstituted or substituted. There is no particular limitation on the number of carbon atoms in aryl ethers, which is usually in the range of 6 to 40.

[0738] In addition, so-called aryl thioethers are aryl ethers in which the oxygen atom of the ether bond is replaced by a sulfur atom.

[0739] In addition, the term "aryl" can refer to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, and pyrene. Aryl groups can be unsubstituted or substituted. The number of carbon atoms in an aryl group is not particularly limited, typically ranging from 6 to 40.

[0740] Furthermore, the term "heterocyclic group" refers to cyclic structural groups such as furanyl, thiophene, oxazolyl, pyridyl, quinolinyl, and carbazole, which have atoms other than carbon atoms. These heterocyclic groups may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is typically in the range of 2 to 30.

[0741] The term halogen refers to fluorine, chlorine, bromine, and iodine.

[0742] The formyl, carbonyl, and amino groups may also contain groups substituted by aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic hydrocarbons, etc.

[0743] In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons can be unsubstituted or substituted.

[0744] The term silyl group refers to silicon compounds such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, typically ranging from 3 to 20. Additionally, the number of silicon atoms is typically 1 to 6.

[0745] The so-called condensation ring formed between the adjacent substituent is, for example, in Ar 1 With R 2 Ar 1 With R 3 Ar 2 With R 2 Ar 2 With R 3 R 2 With R 3 Ar 1 with Ar 2 Conjugate or non-conjugate condensation rings formed between equals. Here, when n is 1, the two R... 1 They can form conjugated or non-conjugated condensation rings. These condensation rings may contain nitrogen, oxygen, and sulfur atoms in their internal structure, and may further condense with other rings.

[0746] Specific examples of the phosphine oxide derivatives include the following compounds.

[0747]

[0748] The phosphine oxide derivatives can be prepared using known raw materials and known synthetic methods.

[0749] <Pyrimidine derivatives>

[0750] The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Further details are described in International Publication No. 2011 / 021689.

[0751]

[0752] Ar can be a substituted aryl group or a substituted heteroaryl group, respectively. n is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 2 or 3.

[0753] The "aryl" as "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and even more preferably aryl groups having 6 to 12 carbon atoms.

[0754] Specific examples of "aryl" groups include: phenyl groups that are monocyclic aryl groups; (2-, 3-, 4-)biphenyl groups that are dicyclic aryl groups; (1-, 2-)naphthyl groups that are condensed dicyclic aryl groups; terphenyl groups that are tricyclic aryl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); and terphenyl groups that are condensed tricyclic aryl groups. Acenatho-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrene, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl), triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, benzotetraphenyl-(1-, 2-, 5-)yl, perylene-(1-, 2-, 3-)yl, benzopentaphenyl-(1-, 2-, 5-)yl, etc., are tetraphenyl aryl compounds.

[0755] The term "heteroaryl" as "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon, can be cited as examples.

[0756] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazolyl, thiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thiophene, indolyl, isoindolyl, 1H-indolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, thiazothiazyl, thiazothiazyl, indazinyl, etc.

[0757] In addition, the aryl and heteroaryl groups can be substituted, for example, by the aryl or heteroaryl groups respectively.

[0758] Specific examples of the pyrimidine derivatives include the following compounds.

[0759]

[0760] The pyrimidine derivatives can be prepared using known starting materials and known synthetic methods.

[0761] <Arylnitrile derivatives>

[0762] Aryl nitrile derivatives are, for example, compounds represented by the following formula (ETM-9), or polymers formed by the bonding of multiple said compounds through single bonds or the like. Details are described in U.S. Patent Application Publication No. 2014 / 0197386.

[0763]

[0764] From the perspective of rapid electron transport, Ar ni Preferably, Ar has a higher carbon number, which is desirable from the perspective of high T1. ni Preferably, it has a low carbon number. Specifically, when used as a layer adjacent to the light-emitting layer, it is preferable to have a high T1, thereby increasing the Ar... niThe aryl group has 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms. Regarding the number of nitrile group substitutions n, from the viewpoint of high T1, a higher number is preferable, and from the viewpoint of high S1, a lower number is preferable. Specifically, the number of nitrile group substitutions n is an integer from 1 to 4, preferably an integer from 1 to 3, more preferably an integer from 1 to 2, and even more preferably 1.

[0765] Ar is independently a substituted aryl or a substituted heteroaryl. From the viewpoint of high S1 and high T1, a donor heteroaryl is preferred, and since it serves as an electron transport layer, a small number of donor heteroaryl groups is preferable. From the viewpoint of charge transport, an aryl or heteroaryl group with a large number of carbon atoms is preferred, and a large number of substituents is also preferred. Specifically, the number of substitutions m of Ar is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 1 to 2.

[0766] The "aryl" as "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and even more preferably aryl groups having 6 to 12 carbon atoms.

[0767] Specific examples of "aryl" groups include: phenyl groups that are monocyclic aryl groups; (2-, 3-, 4-)biphenyl groups that are dicyclic aryl groups; (1-, 2-)naphthyl groups that are condensed dicyclic aryl groups; terphenyl groups that are tricyclic aryl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); and terphenyl groups that are condensed tricyclic aryl groups. Acenatho-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrene, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl), triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, benzotetraphenyl-(1-, 2-, 5-)yl, perylene-(1-, 2-, 3-)yl, benzopentaphenyl-(1-, 2-, 5-)yl, etc., are tetraphenyl aryl compounds.

[0768] The term "heteroaryl" as "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon, can be cited as examples.

[0769] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazolyl, thiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thiophene, indolyl, isoindolyl, 1H-indolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, thiazothiazyl, thiazothiazyl, indazinyl, etc.

[0770] In addition, the aryl and heteroaryl groups can be substituted, for example, by the aryl or heteroaryl groups respectively.

[0771] Aryl nitrile derivatives can be polymers formed by bonding compounds represented by multiple formulas (ETM-9) through single bonds or the like. In this case, in addition to single bonds, they can also be bonded through aryl rings (preferably polyvalent benzene rings, naphthyl rings, anthracene rings, fluorene rings, benzo[a]fluorene rings, phenanthracene rings, or triphenylene rings).

[0772] Specific examples of the aryl nitrile derivatives include the following compounds.

[0773]

[0774] The aryl nitrile derivatives can be prepared using known starting materials and known synthetic methods.

[0775] <Triazine derivatives>

[0776] Triazine derivatives are, for example, compounds represented by the following formula (ETM-10), preferably compounds represented by the following formula (ETM-10-1). Details are described in U.S. Patent Application Publication No. 2011 / 0156013.

[0777]

[0778] Ar can be a substituted aryl group or a substituted heteroaryl group, respectively. n is an integer from 1 to 3, preferably 2 or 3.

[0779] The "aryl" as "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and even more preferably aryl groups having 6 to 12 carbon atoms.

[0780] Specific examples of "aryl" groups include: phenyl groups that are monocyclic aryl groups; (2-, 3-, 4-)biphenyl groups that are dicyclic aryl groups; (1-, 2-)naphthyl groups that are condensed dicyclic aryl groups; terphenyl groups that are tricyclic aryl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); and terphenyl groups that are condensed tricyclic aryl groups. Acenatho-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrene, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl), triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, benzotetraphenyl-(1-, 2-, 5-)yl, perylene-(1-, 2-, 3-)yl, benzopentaphenyl-(1-, 2-, 5-)yl, etc., are tetraphenyl aryl compounds.

[0781] The term "heteroaryl" as "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon, can be cited as examples.

[0782] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazolyl, thiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thiophene, indolyl, isoindolyl, 1H-indolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, thiazothiazyl, thiazothiazyl, indazinyl, etc.

[0783] In addition, the aryl and heteroaryl groups can be substituted, for example, by the aryl or heteroaryl groups respectively.

[0784] Specific examples of the triazine derivatives include the following compounds.

[0785]

[0786] The triazine derivatives can be prepared using known raw materials and known synthetic methods.

[0787] <benzimidazole derivatives>

[0788] Benzimidazole derivatives are, for example, compounds represented by the following formula (ETM-11).

[0789] -(benzimidazole substituent)n (ETM-11)

[0790] The aryl ring is n-valent (preferably an n-valent benzene ring, naphthyl ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4. The "benzimidazole substituent" is the pyridinium group in the "pyridine substituent" of formulas (ETM-2), (ETM-2-1), and (ETM-2-2) that is replaced with the following benzimidazole group (where, Substituents (indicating the bond position) can be formed by deuteration substitution of at least one hydrogen atom in a benzimidazole derivative.

[0791]

[0792] The R in the benzimidazole group 11 It is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R in formulas (ETM-2-1) and (ETM-2-2) can be referenced. 11 Explanation.

[0793] Preferably, it is an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to the description in formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18 The description in formula (ETM-2-1) or formula (ETM-2-2) can be referenced. Furthermore, formula (ETM-2-1) or formula (ETM-2-2) is described in the form of two pyridine substituents, but when these are substituted with benzimidazole substituents, both pyridine substituents can be substituted by a benzimidazole substituent (i.e., n=2), or any one of the pyridine substituents can be substituted by a benzimidazole substituent and then R... 11 ~R 18 The other pyridine substituent can be replaced (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) can be replaced by a benzimidazole substituent. 11 ~R 18 At least one of and by R 11 ~R 18 Replace "pyridine substituents".

[0794] Specific examples of the benzimidazole derivatives include: 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benzimidazole, 2-(4-(10-(naphthyl-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzimidazole, 2-(3-(10-(naphthyl-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzimidazole, 5-(10-(naphthyl-2-yl)anthracene-9-yl)-1,2-diphenyl-1H-benzimidazole Imidazole, 1-(4-(10-(naphth-2-yl)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazol, 2-(4-(9,10-bis(naphth-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazol, 1-(4-(9,10-bis(naphth-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazol, 5-(9,10-bis(naphth-2-yl)anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazol, etc.

[0795]

[0796] The benzimidazole derivative can be prepared using known raw materials and known synthetic methods.

[0797] <Phenanthroline derivatives>

[0798] Phenanthroline derivatives are, for example, compounds represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006 / 021982.

[0799]

[0800] It is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4.

[0801] Various R 11 ~R 18 Each of these components can be independently hydrogen, alkyl (preferably an alkyl group having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl group having 3 to 12 carbon atoms), or aryl (preferably an aryl group having 6 to 30 carbon atoms). Furthermore, in formula (ETM-12-1), R... 11 ~R 18 Either of them becomes associated with the aryl ring. The key arm.

[0802] At least one hydrogen atom in each phenanthrene derivative may be substituted with deuterium.

[0803] As R 11 ~R 18 The alkyl, cycloalkyl, and aryl groups in the formula (ETM-2) can be referenced from R. 11 ~R 18 The explanation. Additionally, regarding... In addition to the examples described above, the following structural formulas may be listed, for example. Furthermore, in the following structural formulas, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl, or terphenyl. Indicates the location of the bond.

[0804]

[0805] Specific examples of the phenanthroline derivatives include: 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-bis(1,10-phenanthroline-2-yl)anthracene, 2,6-bis(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tris(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl), 2,9-dimethyl-4,7-biphenyl-1,10-phenanthroline (bathocuproine), 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, or compounds represented by the following structural formulas.

[0806]

[0807] The phenanthroline derivatives can be prepared using known raw materials and known synthetic methods.

[0808] Hydroxyquinoline metal complexes

[0809] Hydroxyquinoline metal complexes are, for example, compounds represented by the following formula (ETM-13).

[0810]

[0811] In the formula, R 1 ~R 6 Each of the following can be independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl, where M is Li, Al, Ga, Be, or Zn, and n is an integer from 1 to 3.

[0812] Specific examples of hydroxyquinoline-based metal complexes include: lithium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, tris(4-methyl-8-hydroxyquinoline)aluminum, tris(5-methyl-8-hydroxyquinoline)aluminum, tris(3,4-dimethyl-8-hydroxyquinoline)aluminum, tris(4,5-dimethyl-8-hydroxyquinoline)aluminum, tris(4,6-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-methylphenol)aluminum, bis( 2-Methyl-8-hydroxyquinoline)(4-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,3-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,4-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum Aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-diphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-triphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-trimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,5,6-tetramethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(1-naphthol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-naphthol)aluminum, bis(2,4-dimethyl... bis(2,4-dimethyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2,4-di ...4-Dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum, bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum, bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[0813] The hydroxyquinoline-based metal complexes can be prepared using known raw materials and known synthetic methods.

[0814] <Thiazole derivatives and benzothiazole derivatives>

[0815] Thiazole derivatives are, for example, compounds represented by the following formula (ETM-14-1).

[0816] -(thiazole substituent)n (ETM-14-1)

[0817] Benzothiazole derivatives are, for example, compounds represented by the following formula (ETM-14-2).

[0818] -(benzothiazole substituent)n (ETM-14-2)

[0819] Various The aryl ring is n-valent (preferably an n-valent benzene ring, naphthyl ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4. The "thiazolium substituent" or "benzo[a]thiazolium substituent" refers to the pyridinium group in formulas (ETM-2), (ETM-2-1), and (ETM-2-2) that is substituted with a thiazolium group or a benzo[a]thiazolium group. The substituent (indicating the bond position) may be formed by deuteration substitution of at least one hydrogen atom in thiazole derivatives and benzothiazole derivatives.

[0820]

[0821] Preferably, it is an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to the description in formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18The description in ETM-2-1 or ETM-2-2 can be referenced. Furthermore, ETM-2-1 or ETM-2-2 is described in the form of two pyridine substituents, but when these are replaced with thiazole substituents (or benzothiazole substituents), both pyridine substituents (i.e., n=2) can be replaced by a thiazole substituent (or a benzothiazole substituent), or any one pyridine substituent can be replaced by a thiazole substituent (or a benzothiazole substituent) and R... 11 ~R 18 Replace another pyridine substituent (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) can be replaced by a thiazole substituent (or a benzothiazole substituent). 11 ~R 18 At least one of and by R 11 ~R 18 Replace "pyridine substituents".

[0822] These thiazole derivatives or benzothiazole derivatives can be prepared using known starting materials and known synthetic methods.

[0823] <Thiophene derivatives>

[0824] Thiol derivatives are, for example, compounds represented by the following formula (ETM-15). Details are described in Japanese Patent Application Publication No. 9-194487.

[0825]

[0826] X and Y are independently alkyl, cycloalkyl, alkenyl, alkoxy, alkenyloxy, alkynyl, aryl, and heteroaryl groups, which may be substituted. For details regarding these groups, please refer to the descriptions in formula (1) and formula (ETM-7-2). Furthermore, alkenyloxy and alkynyloxy groups are formed by replacing the alkyl portion of the alkoxy group with an alkenyl or alkynyl group, respectively. For details regarding these alkenyl and alkynyl groups, please refer to the descriptions in formula (ETM-7-2).

[0827] In addition, the X and Y atoms of both alkyl groups can bond together to form a ring.

[0828] R 1 ~R 4Each of these groups can be independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isothiocyanate, or cyano. These groups can be substituted with alkyl, cycloalkyl, aryl, or halogen groups, and can also form condensation rings with adjacent substituents.

[0829] Regarding R 1 ~R 4 For details on the halogens, alkyl groups, cycloalkyl groups, alkoxy groups, aryloxy groups, amino groups, aryl groups, heteroaryl groups, alkenyl groups, and alkynyl groups in formula (1), please refer to the description in formula (1).

[0830] Regarding R 1 ~R 4 For details on the alkyl, aryl, and alkoxy groups in alkyl carbonyl, aryl carbonyl, alkoxy carbonyl, aryl carbonyl, alkoxy carbonyl, and aryl carbonyl, please refer to the description in formula (1).

[0831] As a silyl group, examples include silyl groups and groups in which at least one of the three hydrogens of a silyl group is independently substituted with an aryl, alkyl, or cycloalkyl group, preferably trisubstituted silyl groups, such as triarylsilyl groups, trialkylsilyl groups, tricycloalkylsilyl groups, dialkylcycloalkylsilyl groups, and alkyldicycloalkylsilyl groups. For details regarding the aryl, alkyl, and cycloalkyl groups among these, please refer to the description in formula (1).

[0832] The so-called condensation ring formed between the adjacent substituent is, for example, in R 1 With R 2 R 2 With R 3 R 3 With R 4 These are conjugated or non-conjugated condensation rings formed between elements. These condensation rings may contain nitrogen, oxygen, or sulfur atoms within their internal structure, and may further condense with other rings.

[0833] Among them, the preferred one is in R 1 and R 4 In the case of phenyl, X and Y are not alkyl or phenyl. Furthermore, it is preferable that they do not simultaneously satisfy the condition in R. 1 and R 4 In the case of thiophene group, X and Y are alkyl groups and R is an alkyl group. 2 and R 3It is alkyl, aryl, alkenyl or R 2 With R 3 A cycloalkyl structure formed by bonding. Additionally, it is preferable when R... 1 and R 4 When it is silane, R 2 R 3 X and Y are each independently not hydrogen or an alkyl group having 1 to 6 carbon atoms. Furthermore, it is preferable that R... 1 and R 2 In the case of a structure with a benzene ring condensed in the middle, X and Y are not alkyl and phenyl.

[0834] These thiophene derivatives can be prepared using known starting materials and known synthetic methods.

[0835] <Zazoline derivatives>

[0836] Azoline derivatives are, for example, compounds represented by the following formula (ETM-16). Details are described in International Publication No. 2017 / 014226.

[0837]

[0838] In formula (ETM-16),

[0839] It is an m-valent group derived from aromatic hydrocarbons with 6 to 40 carbon atoms or an m-valent group derived from aromatic heterocycles with 2 to 40 carbon atoms. At least one hydrogen atom may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[0840] Y is independently -O-, -S-, or >N-Ar, where Ar is an aryl group with 6 to 12 carbon atoms or a heteroaryl group with 2 to 12 carbon atoms, and at least one hydrogen atom of Ar may be substituted by an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 12 carbon atoms, or a heteroaryl group with 2 to 12 carbon atoms. R 1 ~R 5 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein the Ar in the >N-Ar and the R are... 1 ~R 5 Any one of them is a site that forms an L-bond.

[0841] L is independently selected from the groups consisting of the divalent bases represented by equation (L-1) and the divalent bases represented by equation (L-2), respectively.

[0842]

[0843] In equation (L-1), X 1 ~X6 Each independently =CR 6 -or =N-, X 1 ~X 6 At least two of them are =CR 6 -, X 1 ~X 6 The two in =CR 6 -in R 6 To and Or the site of the zoline ring bond, other than =CR 6 -in R 6 It is hydrogen.

[0844] In equation (L-2), X 7 ~X 14 Each independently =CR 6 -or =N-, X 7 ~X 14 At least two of them are =CR 6 -, X 7 ~X 14 The two =CR 6 -in R 6 To and Or the site of the zoline ring bond, other than =CR 6 -in R 6 It is hydrogen.

[0845] At least one hydrogen atom of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0846] m is an integer from 1 to 4. When m is 2 to 4, the groups formed by the zoline ring and L can be the same or different, and...

[0847] At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0848] The specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2).

[0849]

[0850] In equations (ETM-16-1) and (ETM-16-2),

[0851] It is an m-valent group derived from aromatic hydrocarbons with 6 to 40 carbon atoms or an m-valent group derived from aromatic heterocycles with 2 to 40 carbon atoms. At least one hydrogen atom may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[0852] In formula (ETM-16-1), Y is independently -O-, -S-, or >N-Ar, Ar is an aryl group with 6 to 12 carbon atoms or a heteroaryl group with 2 to 12 carbon atoms, and at least one hydrogen atom of Ar may be substituted by an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 12 carbon atoms, or a heteroaryl group with 2 to 12 carbon atoms.

[0853] In formula (ETM-16-1), R 1 ~R 4 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, and R 3 With R 4 same,

[0854] In formula (ETM-16-2), R 1 ~R 5 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, and R 3 With R 4 same,

[0855] In equations (ETM-16-1) and (ETM-16-2),

[0856] L is independently selected from the groups consisting of the divalent bases represented by equation (L-1) and the divalent bases represented by equation (L-2), respectively.

[0857]

[0858] In equation (L-1), X 1 ~X 6 Each independently =CR 6 -or =N-, X 1 ~X 6 At least two of them are =CR 6 -, X 1 ~X 6 The two =CR 6 -in R 6 To and Or the site of the zoline ring bond, other than =CR 6 -in R 6 It is hydrogen.

[0859] In equation (L-2), X 7 ~X 14 Each independently =CR 6 -or =N-, X7 ~X 14 At least two of them are =CR 6 -, X 7 ~X 14 The two =CR 6 -in R 6 To and Or the site of the zoline ring bond, other than =CR 6 -in R 6 It is hydrogen.

[0860] At least one hydrogen atom of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0861] m is an integer from 1 to 4. When m is 2 to 4, the groups formed by the zoline ring and L can be the same or different, and...

[0862] At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0863] Preferred options are: Choose from the following formulas ( 1-1)~Equation ( The monovalent base represented by 1-18), the following formula ( 2-1)~Equation ( The divalent base represented by 2-34), the following formula ( 3-1)~Equation ( The trivalent base represented by 3-3) and the following formula ( 4-1)~Equation ( In the group consisting of the tetravalent bases represented in 4-2), At least one hydrogen atom may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[0864]

[0865]

[0866]

[0867] In the formula, Z represents >CR2, >N-Ar, >NL, -O-, or -S-; R in >CR2 is independently an alkyl group with 1-4 carbon atoms, a cycloalkyl group with 5-10 carbon atoms, an aryl group with 6-12 carbon atoms, or a heteroaryl group with 2-12 carbon atoms; R can bond with each other to form a ring; Ar in >N-Ar is an aryl group with 6-12 carbon atoms or a heteroaryl group with 2-12 carbon atoms; and L in >NL is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). Indicates the location of the bond.

[0868] Preferably, L is a divalent group of a ring selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthidine, phthalazine, quinoxaline, quinazoline, cycloazolinine, cycloalpine, and pteridine, and at least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbons, a cycloalkyl group having 5 to 10 carbons, an aryl group having 6 to 10 carbons, or a heteroaryl group having 2 to 10 carbons.

[0869] Preferably, the Ar in the >N-Ar of Y or Z is selected from the group consisting of phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthidyl, phthalazinyl, quinoxolinyl, quinazolinyl, cycloazolinyl, terpineyl, and pteridinyl, and at least one hydrogen atom in the >N-Ar of Y may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

[0870] Preferred option: R 1 ~R 4 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, R 3 With R 4 Same, and R 1 ~R 4 Not all of them will become hydrogen at the same time, and m is 1 or 2. When m is 2, the group formed by the azoline ring and L is the same.

[0871] Specific examples of azoline derivatives include the following compounds. Furthermore, "Me" in the structural formula represents a methyl group.

[0872]

[0873] More preferably: Choose from the following formulas ( 2-1) Equation ( 2-31), Equation ( 2-32), Equation ( 2-33) and formula ( In the group consisting of the divalent bases represented by 2-34), At least one hydrogen atom may be substituted by an aryl group having 6 to 18 carbon atoms. Furthermore, in the following formula... Indicates the location of the bond.

[0874]

[0875] L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine. At least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 14 carbon atoms.

[0876] The Ar in the >N-Ar of Y is selected from the group consisting of phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, wherein at least one hydrogen atom of Ar may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

[0877] R 1 ~R 4 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, R 3 With R 4 Same, and R 1 ~R 4 Not all of them will become hydrogen at the same time, and,

[0878] m is 2, and the group formed by the zoline ring and L is the same.

[0879] Other specific examples of azoline derivatives include the following compounds. Furthermore, "Me" in the structural formula represents a methyl group.

[0880]

[0881] For details regarding the alkyl, cycloalkyl, aryl, or heteroaryl groups in the various formulas specifying the zoline derivatives, please refer to the description in formula (1).

[0882] The zoline derivatives can be prepared using known raw materials and known synthetic methods.

[0883] <Reducing substances>

[0884] The electron transport layer or electron injection layer may also contain a substance that can reduce the material forming the electron transport layer or electron injection layer. The reducing substance can be any substance with a certain reducing property, and for example, preferably at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

[0885] Preferred reducing agents include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV), or alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 eV~2.5 eV), or Ba (work function 2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Among these, alkali metals such as K, Rb, or Cs are more preferred, Rb or Cs are more preferred, and Cs is most preferred. These alkali metals have particularly high reducing power, and by adding a relatively small amount of these alkali metals to the material forming the electron transport layer or electron injection layer, the luminous brightness or lifetime of organic EL devices can be improved. Furthermore, combinations of two or more alkali metals are preferred as reducing agents with a work function of 2.9 eV or less, and combinations containing Cs are particularly preferred, such as Cs with Na, Cs with K, Cs with Rb, or combinations of Cs with Na and K. By including Cs, the reducing ability can be effectively utilized, and by adding it to the material forming the electron transport layer or electron injection layer, the luminous brightness or lifetime of organic EL devices can be improved.

[0886] The electron injection layer material and the electron transport layer material may also be used in the electron layer material as the following polymeric compounds or their polymeric crosslinks, or as the following suspended polymeric compounds or their suspended polymeric crosslinks. The polymeric compounds are obtained by polymerizing a reactive compound, in which reactive substituents are substituted in the electron injection layer material and the electron transport layer material, as a monomer. The suspended polymeric compounds are obtained by reacting a main-chain polymer with the reactive compound. As reactive substituents in the above cases, descriptions of polycyclic aromatic compounds containing a portion of the structure represented by formula (1) may be cited.

[0887] Details regarding the applications of this polymer compound and its crosslinked polymers will be described later.

[0888] 3-1-7. Cathode in Organic Electroluminescent Devices

[0889] The cathode 108 functions to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0890] The material forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, and the same material as the material forming the anode 102 can be used. Preferred materials include metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloys, magnesium-indium alloys, lithium fluoride / aluminum and other aluminum-lithium alloys, etc.). To improve the electron injection efficiency and thus enhance the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, generally, these low work function metals are unstable in the atmosphere in most cases. To improve this, methods such as doping the organic layer with trace amounts of lithium, cesium, or magnesium and using a highly stable electrode are known. Inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used as other dopants. However, these are not limited to these.

[0891] Furthermore, the following are preferred examples: To protect the electrodes, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys of these metals, as well as inorganic materials such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymers are layered. There are no particular restrictions on the methods used to fabricate these electrodes, as long as they are methods that achieve conductivity, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0892] 3-1-8. Adhesives that can be used in each layer

[0893] The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer can be formed individually or dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene ether, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate resins, acrylonitrile butadiene styrene (ABS) resins, and polyurethane resins, or curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins.

[0894] 3-1-9. Fabrication method of organic electroluminescent elements

[0895] The layers constituting an organic electroluminescent (EL) element can be formed by depositing thin films of the materials to be formed into each layer using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating, casting, and coating. The film thickness of each layer formed in these methods is not particularly limited and can be appropriately set according to the properties of the material, but is typically in the range of 2 nm to 5000 nm. The film thickness can usually be measured using a quartz oscillating film thickness measuring device. When using vapor deposition for thin film formation, the vapor deposition conditions vary depending on the type of material, the crystal structure of the target film, and the associative structure. Generally, the preferred vapor deposition conditions are a boat heating temperature of +50°C to +400°C and a vacuum degree of 10... -6 ~10 -3 The appropriate settings are as follows: Pa, evaporation rate (0.01 nm / s to 50 nm / s), substrate temperature (-150℃ to +300℃), and film thickness (2 nm to 5 μm).

[0896] When a DC voltage is applied to the organic EL element obtained in the manner described, it is sufficient to apply the voltage with the anode as the positive polarity and the cathode as the negative polarity. If a voltage of approximately 2V to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, the organic EL element also emits light when a pulsed current or alternating current is applied. Moreover, the waveform of the applied alternating current can be arbitrary.

[0897] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device including an anode / hole injection layer / hole transport layer / light-emitting layer containing host material and dopant material / electron transport layer / electron injection layer / cathode will be described.

[0898] <Evaporation method>

[0899] On a suitable substrate, an anode is fabricated by forming a thin film of anode material using a vapor deposition method, followed by the formation of a hole injection layer and a hole transport layer on the anode. A light-emitting layer is then formed by co-depositing a host material and a dopant material onto the light-emitting layer. An electron transport layer and an electron injection layer are formed on the light-emitting layer, and finally, a thin film containing a cathode material is formed using a vapor deposition method to serve as the cathode, thereby obtaining the target organic EL device. Alternatively, the fabrication sequence of the organic EL device can be reversed, with the order being cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0900] <Wet film formation method>

[0901] A low-molecular-weight compound capable of forming organic layers of an organic EL element is prepared as a liquid composition for forming organic layers, and used to perform a wet film-forming method. In the absence of a suitable organic solvent to dissolve the low-molecular-weight compound, a composition for forming organic layers may also be prepared from polymeric compounds, wherein the polymeric compound is polymerized together with other monomers or main-chain polymers that are reactive compounds formed by substituting reactive substituents into the low-molecular-weight compound and thus possess solubility.

[0902] Wet film-forming methods generally form a coating film through the following steps: a coating step of applying an organic layer-forming composition to a substrate, and a drying step of removing the solvent from the coated organic layer-forming composition. In cases where the polymer compound has crosslinking substituents (also referred to as a crosslinked polymer compound), further crosslinking is performed through the drying step to form a polymer crosslinked body. Depending on the coating process, methods using a spin coater are called spin coating, methods using a slot coater are called slot coating, methods using a printing plate are called gravure, offset, reverse offset, or flexographic printing, methods using an inkjet printer are called inkjet printing, and methods using a mist are called spray coating.

[0903] The drying process includes methods such as air drying, heating, and vacuum drying. The drying process can be performed only once, or multiple times using different methods or conditions. Alternatively, different methods can be combined, such as in calcination under reduced pressure.

[0904] Wet film deposition refers to film deposition methods that use solutions, such as partial printing (inkjet printing), spin coating, casting, and coating. Unlike vacuum evaporation, wet film deposition does not require expensive vacuum evaporation equipment and can be carried out under atmospheric pressure. Furthermore, wet film deposition allows for large-area or continuous production, resulting in lower manufacturing costs.

[0905] On the other hand, compared with vacuum evaporation, wet film deposition methods are sometimes difficult to laminate. When using wet film deposition methods to fabricate laminated films, it is necessary to prevent the dissolution of the lower layer caused by the composition of the upper layer, and to use compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that are insoluble in each other). However, even with these techniques, it is difficult to use wet film deposition methods for coating all types of films.

[0906] Therefore, the following method is generally used: a wet film deposition method is used to form only a few layers, and the remaining layers are formed by vacuum evaporation to produce organic EL devices.

[0907] For example, the following describes a procedure for fabricating organic EL elements using a wet film deposition method.

[0908] (Procedure 1) Film formation of the anode using vacuum evaporation method

[0909] (Program 2) Film formation using a wet film formation method for a composition containing a material for a hole injection layer.

[0910] (Procedure 3) Film formation of a composition for forming a hole transport layer containing a material for the hole transport layer using a wet film formation method.

[0911] (Procedure 4) Film formation using a wet film formation method for a composition comprising a host material and a dopant material for forming a light-emitting layer.

[0912] (Procedure 5) Electron transport layer film formation using vacuum evaporation

[0913] (Procedure 6) Electron injection layer film formation using vacuum evaporation method

[0914] (Program 7) Film formation of the cathode using vacuum evaporation method

[0915] By going through the aforementioned process, an organic EL element comprising an anode / hole injection layer / hole transport layer / light-emitting layer containing host material and dopant material / electron transport layer / electron injection layer / cathode can be obtained.

[0916] Of course, for the electron transport layer and the electron injection layer, a layer-forming composition containing materials for the electron transport layer and the electron injection layer, respectively, can be used to form the film by a wet film-forming method. In this case, it is preferable to use a method that prevents the dissolution of the underlying light-emitting layer, or a method that forms the film from the cathode side in the opposite direction to the above procedure.

[0917] <Other Film Formation Methods>

[0918] Laser-induced thermal imaging (LITI) can be used in the film formation of compositions for forming organic layers. LITI refers to a method of heating and vaporizing a compound attached to a substrate using a laser, and the compositions for forming organic layers can be used in materials coated on a substrate.

[0919] <Any process>

[0920] Appropriate treatment, cleaning, and drying processes can be added before and after each step of the film formation process. Examples of treatment processes include: exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning with appropriate solvents, and heat treatment. Furthermore, a series of processes for fabricating the embankment can also be listed.

[0921] Photolithography can be used in the fabrication of the embankment. Positive and negative resist materials can be used as embankment materials suitable for photolithography. Alternatively, printing methods capable of creating patterns, such as inkjet printing, gravure printing, reverse lithography, and screen printing, can also be used. In these cases, permanent resist materials can also be used.

[0922] Materials used for embankments include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing vinyl monomers, biopolymers, polyacrylamide compounds, polyesters, polystyrene, polyimide, polyamide-imide, polyether-imide, polysulfone, polyphenylene, polyphenyl ether, polyurethane, epoxy methacrylate, melamine methacrylate, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyvinylidene fluoride, polytetrafluoroethylene, polyhexafluoropropylene and other fluorinated polymers, fluoroolefin-hydrocarbon copolymers, and fluorocarbon polymers.

[0923] <Organic layer-forming compositions used in wet film-forming processes>

[0924] The composition for forming organic layers is obtained by dissolving low-molecular-weight compounds capable of forming organic EL elements, or high-molecular-weight compounds obtained by polymerizing said low-molecular-weight compounds, in an organic solvent. For example, the composition for forming a light-emitting layer contains at least one dopant material, namely a polycyclic aromatic compound (or its polymeric compound), as a first component, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as the dopant component of the light-emitting layer obtained from the composition, and the second component functions as the host component of the light-emitting layer. The third component functions as a solvent for dissolving the first and second components in the composition, and provides a smooth and uniform surface shape during coating by utilizing the controlled evaporation rate of the third component itself.

[0925] <Organic solvents>

[0926] The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, film-forming properties, the presence or absence of coating defects, surface roughness, and smoothness can be controlled and improved. Furthermore, when using inkjet printing for film formation, the meniscus stability at the inkjet head pinholes can be controlled, and ejection performance can be controlled / improved. Moreover, by controlling the film drying rate and the orientation of derivative molecules, the electrical properties, luminescent properties, efficiency, and lifetime of organic EL elements having an organic layer obtained from the aforementioned composition for forming an organic layer can be improved.

[0927] (1) Properties of organic solvents

[0928] The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. From the viewpoint of inkjet ejection performance, a boiling point higher than 130°C is preferred. Furthermore, from the viewpoint of coating defects, surface roughness, residual solvent, and smoothness, a boiling point lower than 300°C is preferred. From the viewpoint of good inkjet ejection performance, film formation, smoothness, and low residual solvent, the organic solvent is more preferably composed of two or more organic solvents. On the other hand, depending on the circumstances, considering factors such as transportability, the composition may also be a solid composition obtained by removing the solvent from the organic layer forming composition.

[0929] Furthermore, the organic solvent includes a good solvent (GS) and a poor solvent (PS) for at least one solute, and particularly preferably a good solvent (GS) with a boiling point (BP). GS () Below the boiling point (BP) of the unsuitable solvent (PS) PS The structure of ).

[0930] By adding a high-boiling-point undesirable solvent, while the low-boiling-point good solvent evaporates first during film formation, the concentration of the contents and the concentration of the undesirable solvent in the composition increase, promoting rapid film formation. As a result, a coating film with fewer defects, lower surface roughness, and higher smoothness can be obtained.

[0931] Difference in solubility (S) GS -S PS The content of boiling point difference (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS The temperature is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0932] After film formation, the organic solvent is removed from the coating film through drying processes such as vacuum, reduced pressure, and heating. When heating is performed, from the viewpoint of improving film formation properties, it is preferable to heat at a temperature below +30°C of the glass transition temperature (Tg) of at least one solute. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at a temperature above -30°C of the glass transition temperature (Tg) of at least one solute. Even if the heating temperature is below the boiling point of the organic solvent, the organic solvent is sufficiently removed due to the thin film. Additionally, multiple drying processes can be performed at different temperatures, and various drying methods can be used in combination.

[0933] (2) Specific examples of organic solvents

[0934] Organic solvents used in compositions for forming organic layers include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents with a diester skeleton, and fluorinated solvents. Specific examples include: pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecylol, dodecanol, tetradecylol, hexane-2-ol, heptane-2-ol, octane-2-ol, decane-2-ol, dodecane-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixtures), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and diethylene glycol dimethyl ether. Dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-dimethylpyridine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3- Fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, tert-butylbenzene, 2-methylanisole, phenethyl ether, benzodioxole, 4-methylanisole, sec-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, isopropyltoluene (cymene), 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroo-dimethoxybenzene, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene 2,5-Dimethyl anisole, 2,4-Dimethyl anisole, benzonitrile, 3,5-Dimethyl anisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethyl anisole, o-toluenenitrile, n-pentylbenzene, o-dimethoxybenzene, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-dimethylbiphenyl (2,2'-bitolyl), dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-Dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butoxymethyl)benzene, 1-methyl-4-(pentoxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptoxymethyl)benzenebenzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether, etc., but not limited to these. Furthermore, the solvent can be used alone or in mixtures.

[0935] <Any ingredient>

[0936] The composition for forming organic layers may also contain any components without impairing its properties. Examples of such components include adhesives and surfactants.

[0937] (1) Adhesive

[0938] The composition for forming an organic layer may also contain an adhesive. The adhesive forms a film during film formation and bonds the obtained film to a substrate. Additionally, the composition for forming an organic layer plays a role in dissolving and dispersing other components, as well as in bonding them together.

[0939] Examples of adhesives used in compositions for forming organic layers include: acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene (AES) copolymers, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene (ABS) copolymers, acrylonitrile-styrene (AS) copolymers, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of said resins and polymers, but are not limited thereto.

[0940] The adhesive used in compositions for forming organic layers may be a single type or a mixture of multiple types.

[0941] (2) Surfactants

[0942] For example, to control the film surface uniformity, solvent affinity, and liquid repellency of the organic layer forming composition, the organic layer forming composition may also contain a surfactant. Surfactants are classified as ionic or nonionic based on the structure of their hydrophilic groups, and further classified as alkyl, silicone, and fluorinated based on the structure of their hydrophobic groups. Additionally, based on molecular structure, they are classified as monomolecular systems with simple structures and polymeric systems with side chains or branches. Furthermore, based on composition, they are classified as single-component systems and mixed systems containing two or more surfactants and a substrate. All types of surfactants can be used as surfactants in the organic layer forming composition.

[0943] Examples of surfactants include: Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, and Disperbyk 16. 4. Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK 300, BYK 306, BYK 310, BYK 320, BYK 330, BYK 342, BYK 344, BYK 346 (trade name, BYK-Chemie Japan) (Japan) Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by NEOS Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (trade name, manufactured by Mitsubishi Materials Co., Ltd.) Material Co., Ltd. manufactures the following Megafac products: F-470, F-471, F-475, R-08, F-477, F-479, F-553, and F-554.The following are listed as compounds: fluoroalkylbenzene sulfonates, fluoroalkyl carboxylates, fluoroalkyl polyoxyethylene ethers, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonates, diglycerol tetra(fluoroalkyl polyoxyethylene ether), fluoroalkyl trimethylammonium salt, fluoroalkyl aminosulfonates, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, dehydrated sorbitol laurate, dehydrated sorbitol palmitate, dehydrated sorbitol stearate, dehydrated sorbitol oleate, dehydrated sorbitol fatty acid ester, polyoxyethylene dehydrated sorbitol laurate, polyoxyethylene dehydrated sorbitol palmitate, polyoxyethylene dehydrated sorbitol stearate, polyoxyethylene dehydrated sorbitol oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonates, and alkyl diphenyl ether disulfonates.

[0944] In addition, one surfactant may be used, or two or more surfactants may be used in combination.

[0945] Composition and properties of compositions for organic layer formation

[0946] The content of each component in the organic layer-forming composition is determined from the perspectives of good solubility, storage stability, and film-forming properties of each component, high-quality film quality of the coating obtained from the organic layer-forming composition, good ejectibility when using inkjet printing, and good electrical properties, luminescence properties, efficiency, and lifetime of the organic EL element with the organic layer formed using the composition. For example, in the case of a light-emitting layer-forming composition, it is preferable that: the first component is 0.0001% to 2.0% by mass relative to the total mass of the light-emitting layer-forming composition, the second component is 0.0999% to 8.0% by mass relative to the total mass of the light-emitting layer-forming composition, and the third component is 90.0% to 99.9% by mass relative to the total mass of the light-emitting layer-forming composition.

[0947] More preferably, the first component is 0.005% to 1.0% by mass relative to the total mass of the composition for forming the light-emitting layer, the second component is 0.095% to 4.0% by mass relative to the total mass of the composition for forming the light-emitting layer, and the third component is 95.0% to 99.9% by mass relative to the total mass of the composition for forming the light-emitting layer. Even more preferably, the first component is 0.05% to 0.5% by mass relative to the total mass of the composition for forming the light-emitting layer, the second component is 0.25% to 2.5% by mass relative to the total mass of the composition for forming the light-emitting layer, and the third component is 97.0% to 99.7% by mass relative to the total mass of the composition for forming the light-emitting layer.

[0948] The composition for forming an organic layer can be prepared by selectively stirring, mixing, heating, cooling, dissolving, dispersing, etc., using known methods. Alternatively, it can be appropriately subjected to filtration, degassing (also known as degassing), ion exchange treatment, and inert gas replacement / sealing treatment after preparation.

[0949] Regarding the viscosity of the composition for forming the organic layer, a high viscosity provides good film-forming properties and good ejection properties when using inkjet printing. On the other hand, a low viscosity makes it easier to produce thin films. Accordingly, the viscosity of the composition for forming the organic layer is preferably 0.3 mPa·s to 3 mPa·s at 25°C, more preferably 1 mPa·s to 3 mPa·s. In this invention, the viscosity is a value measured using a cone-plate type rotational viscometer.

[0950] Regarding the surface tension of the composition for forming the organic layer, a low surface tension results in good film-forming properties and a defect-free coating. Conversely, a high surface tension results in good inkjet ejection properties. Accordingly, the composition for forming the organic layer preferably has a surface tension of 20 mN / m to 40 mN / m at 25°C, more preferably 20 mN / m to 30 mN / m. In this invention, the surface tension is a value measured using the pendant drop method.

[0951] <Cross-linked polymers: compounds represented by formula (XLP-1)>

[0952] Next, the case where the polymer compound has cross-linking substituents will be described. Such cross-linking polymer compounds are, for example, compounds represented by the following formula (XLP-1).

[0953]

[0954] In formula (XLP-1),

[0955] MUx, ECx, and k are defined the same as MU, EC, and k in formula (H3), wherein the compound represented by formula (XLP-1) has at least one crosslinking substituent (XLS), preferably the content of monovalent or divalent aromatic groups with crosslinking substituents is 0.1% to 80% by mass in the molecule.

[0956] The content of monovalent or divalent aromatic groups with crosslinking substituents in the molecule is preferably 0.5% to 50% by mass, more preferably 1% to 20% by mass.

[0957] As a crosslinking substituent (XLS), there is no particular limitation as long as it is a group that can further crosslink the polymer compound, but the following substituents are preferred. In each structural formula... Indicates the location of the bond.

[0958]

[0959] L can be a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene group having 1 to 12 carbon atoms, alkylene group having 1 to 12 carbon atoms, or polyalkylene group having 1 to 12 carbon atoms. Among the substituents, those represented by formulas (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17) are preferred, and those represented by formulas (XLS-1), (XLS-3), or (XLS-17) are more preferred.

[0960] Examples of divalent aromatic compounds having crosslinking substituents include compounds having the following partial structures.

[0961]

[0962]

[0963]

[0964]

[0965] <Preparation Methods of Polymers and Cross-linked Polymers>

[0966] The preparation methods of polymeric compounds and cross-linked polymeric compounds will be described using compounds represented by formula (H3) and formula (XLP-1) as examples. These compounds can be synthesized by appropriately combining known preparation methods.

[0967] Solvents used in the reaction can include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc. For example, dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, etc.

[0968] Alternatively, the reaction can also be carried out in a two-phase system. In the case of a two-phase system reaction, a phase transfer catalyst such as a quaternary ammonium salt can be added as needed.

[0969] When preparing compounds of formula (H3) and (XLP-1), preparation can be carried out in a single stage or in multiple stages. Alternatively, synthesis can be performed via general polymerization, where all starting materials are placed in the reaction vessel and the reaction begins; via dropwise polymerization, where starting materials are added dropwise to the reaction vessel; or via precipitation polymerization, where the product precipitates as the reaction proceeds. These methods can be appropriately combined for synthesis. For example, when synthesizing the compound represented by formula (H3) in a single stage, the reaction is carried out with monomers having polymerizable groups bonded in monomer units (MU) and monomers having polymerizable groups bonded in end-capping units (EC) added to the reaction vessel, thereby obtaining the target compound. Conversely, when synthesizing the compound represented by formula (H3) in multiple stages, the monomers having polymerizable groups bonded in monomer units (MU) are polymerized to the target molecular weight, and then monomers having polymerizable groups bonded in end-capping units (EC) are added and reacted, thereby obtaining the target compound. By reacting monomers with polymerizable groups bonded to different types of monomer units (MUs) in multiple stages, polymers with concentration gradients relative to the structure of the monomer units can be produced. Furthermore, after preparing the precursor polymer, the target polymer can be obtained through subsequent reactions.

[0970] Furthermore, by selecting the polymerizable groups of the monomers, the primary structure of the polymer can be controlled. For example, as shown in synthesis procedures 1 to 3, polymers with random primary structures (synthesis procedure 1) and polymers with regular primary structures (synthesis procedures 2 and 3) can be synthesized, and can be used in appropriate combinations according to the target material. Moreover, if monomers with three or more polymerizable groups are used, hyperbranched polymers or dendrimers can be synthesized.

[0971]

[0972] As a monomer that can be used in this invention, it can be synthesized according to the methods described in Japanese Patent Application Publication No. 2010-189630, International Publication No. 2012 / 086671, International Publication No. 2013 / 191088, International Publication No. 2002 / 045184, International Publication No. 2011 / 049241, International Publication No. 2013 / 146806, International Publication No. 2005 / 049546, International Publication No. 2015 / 145871, Japanese Patent Application Publication No. 2010-215886, Japanese Patent Application Publication No. 2008-106241, International Publication No. 2016 / 031639, and Japanese Patent Application Publication No. 2011-174062.

[0973] Furthermore, the specific polymer synthesis sequence can be synthesized according to the methods described in Japanese Patent Application Publication No. 2012-036388, International Publication No. 2015 / 008851, Japanese Patent Application Publication No. 2012-36381, Japanese Patent Application Publication No. 2012-144722, International Publication No. 2015 / 194448, International Publication No. 2013 / 146806, International Publication No. 2015 / 145871, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, and International Publication No. 2011 / 049241.

[0974] 3-1-10. Examples of applications of organic electroluminescent elements

[0975] In addition, the present invention can also be applied to display devices including organic EL elements or lighting devices including organic EL elements.

[0976] Display devices or lighting devices including organic EL elements can be manufactured by known methods such as connecting the organic EL element of this embodiment to a known driving device, and can be driven by known driving methods such as DC driving, pulse driving, AC driving, etc.

[0977] Examples of display devices include panel displays such as color flat panel displays and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Application Publication No. 10-335066, Japanese Patent Application Publication No. 2003-321546, and Japanese Patent Application Publication No. 2004-281086). Furthermore, examples of display methods include matrix displays and / or segmented displays. Moreover, matrix displays and segmented displays can coexist on the same panel.

[0978] In a matrix, pixels for display are arranged two-dimensionally in a grid or mosaic pattern, so that text or images are displayed by the collection of pixels. The shape or size of the pixels is determined by the application. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with one side less than 300μm are usually used. In the case of large displays such as screens, pixels with one side in the millimeter range are used. In the case of monochrome display, pixels of the same color are simply arranged. In the case of color display, red, green, and blue pixels are displayed side by side. In these cases, triangular and striped patterns are typical. Moreover, the driving method of the matrix can be either a line-sequential driving method or an active matrix. Line-sequential driving has the advantage of simple structure, but when considering operating characteristics, sometimes an active matrix is ​​superior. Therefore, the driving method also needs to be selected according to the application.

[0979] In the segmented method (type), a pattern is formed to display pre-determined information, and the determined area is illuminated. Examples include: time or temperature displays in digital clocks or thermometers, operating status displays in audio equipment or induction cookers, and panel displays in automobiles.

[0980] Examples of lighting devices include indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Application Publication Nos. 2003-257621, 2003-277741, and 2004-119211). Backlights are primarily used to improve the visibility of display devices that do not emit light themselves, and are used in liquid crystal displays, clocks, audio devices, automotive panels, display boards, and signs. In particular, for backlights used in personal computers where thinning is becoming a challenge in liquid crystal displays, considering that existing methods are difficult to make thinner due to the inclusion of fluorescent lamps or light guide plates, the backlight using the light-emitting element of this embodiment is characterized by its thinness and light weight.

[0981] 3-2. Other organic devices

[0982] In addition to being used in the aforementioned organic electroluminescent elements, the polycyclic aromatic compounds of the present invention can also be used to fabricate organic electro-effective transistors or organic thin-film solar cells, etc.

[0983] An organic field-effect transistor (FET) is a transistor that controls current by using an electric field generated by a voltage input. In addition to source and drain electrodes, it also has a gate electrode. An organic field-effect transistor works as follows: when a voltage is applied to the gate electrode, an electric field is generated, which can arbitrarily block the flow of electrons (or holes) between the source and drain electrodes to control the current. Compared to a single transistor (bipolar transistor), FETs are easier to miniaturize and are commonly used as components in integrated circuits.

[0984] Regarding the structure of an organic field-effective transistor, generally, the source electrode and drain electrode are simply provided in contact with the organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and the gate electrode is provided sandwiched between an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following.

[0985] (1) Substrate / Gate electrode / Insulator layer / Source electrode and drain electrode / Organic semiconductor active layer

[0986] (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode and drain electrode

[0987] (3) Substrate / Organic semiconductor active layer / Source electrode and drain electrode / Insulator layer / Gate electrode

[0988] (4) Substrate / Source and Drain Electrodes / Organic Semiconductor Active Layer / Insulator Layer / Gate Electrode

[0989] The organic field-active transistor constructed in the manner described above can be used as a pixel driving switching element in an active matrix driven liquid crystal display or an organic electroluminescent display, etc.

[0990] Organic thin-film solar cells have a structure in which an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, such as ITO, are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compounds of the present invention, depending on their physical properties, can be used as materials for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer. In organic thin-film solar cells, the polycyclic aromatic compounds of the present invention can function as hole transport materials or electron transport materials. In addition to the above-described components, organic thin-film solar cells may suitably include hole blocking layers, electron blocking layers, electron injection layers, hole injection layers, smoothing layers, etc. Known materials used in organic thin-film solar cells can be suitably selected and combined in combination in organic thin-film solar cells.

[0991] 4. Wavelength conversion materials

[0992] The polycyclic aromatic compounds of this invention can be used as wavelength conversion materials.

[0993] Currently, research is actively underway to apply multicolor technology based on color conversion to liquid crystal displays (LCDs), organic EL displays, and lighting. Color conversion refers to converting light emitted from a light source into light with longer wavelengths, such as converting ultraviolet or blue light into green or red light. By film-coating a wavelength conversion material with this color conversion function, for example, and combining it with a blue light source, it is possible to extract the three primary colors—blue, green, and red—from the blue light source, i.e., extract white light. Using this white light source, which combines a blue light source with a wavelength conversion film with color conversion function, as a light source unit, and combining it with a liquid crystal driving section and color filters, a full-color display can be fabricated. Alternatively, without a liquid crystal driving section, it can be used directly as a white light source, for example, as a white light source for light-emitting diode (LED) lighting. Furthermore, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green and red light, a full-color organic EL display without a metal mask can be fabricated. Furthermore, by using blue microLEDs as a light source and combining them with wavelength conversion films that convert blue light into green and red light, it is possible to produce low-cost full-color microLED displays.

[0994] The polycyclic aromatic compounds of the present invention can be used as the wavelength conversion material. Wavelength conversion materials containing the polycyclic aromatic compounds of the present invention can be used to convert ultraviolet light or light from light sources or light-emitting elements that generate shorter wavelength blue light into blue or green light with high color purity suitable for use in display devices (display devices utilizing organic EL elements or liquid crystal display devices). The converted color can be adjusted by appropriately selecting the substituents of the polycyclic aromatic compounds of the present invention, the adhesive resin used in the wavelength conversion composition described later, etc. The wavelength conversion material can be prepared as a wavelength conversion composition containing the polycyclic aromatic compounds of the present invention. Alternatively, the wavelength conversion composition can also be used to form a wavelength conversion film.

[0995] In addition to the polycyclic aromatic compounds of the present invention, the wavelength conversion composition may also contain a binder resin, other additives, and a solvent. As a binder resin, for example, the resin described in paragraphs 0173-0176 of International Publication No. 2016 / 190283 may be used. As other additives, compounds described in paragraphs 0177-0181 of International Publication No. 2016 / 190283 may be used. As a solvent, refer to the description of the solvents contained in the composition for forming the light-emitting layer.

[0996] The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. As a method for producing the wavelength conversion layer from the wavelength conversion composition, known film formation methods can be referenced. The wavelength conversion film may contain only a wavelength conversion layer formed from a composition comprising the polycyclic aromatic compounds of the present invention, or it may contain other wavelength conversion layers (e.g., a wavelength conversion layer that converts blue light to green or red light, or a wavelength conversion layer that converts blue or green light to red light). Furthermore, the wavelength conversion film may also include a substrate layer, or a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[0997] [Example]

[0998] The present invention will now be described in more detail with reference to embodiments, but the present invention is not limited thereto.

[0999] <<Synthesis example>>

[1000] Synthesis Example (1): Synthesis of compound (s-1)

[1001]

[1002] Under a nitrogen atmosphere and at -30°C, a 1.6M solution of tert-butyllithium pentane (1.5 mL) was added to a flask containing compound (s-1-p) (1.6 g) and tert-butylbenzene (7.0 mL). After the addition was complete, the temperature was raised to 60°C and stirred for 2 hours. Components with boiling points lower than tert-butylbenzene were removed by vacuum distillation. The mixture was cooled to -30°C and boron tribromide (0.65 g) was added. The temperature was raised to room temperature and stirred for 0.5 hours. Then, after cooling to 0°C again, N,N-diisopropylethylamine (0.40 mL) was added. The mixture was stirred at room temperature until heating ceased, then the temperature was raised to 20°C and stirred for 3 hours. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath was added. Heptane was then added for separation. Next, after purification using a silica gel short-path column (eluent: toluene), the solid obtained by removing the solvent by vacuum distillation was dissolved in toluene, and heptane was added for reprecipitation, thereby obtaining compound (s-1) (0.4 g).

[1003] Synthesis Example (14): Synthesis of compound (s-14)

[1004] Except for changing compound (s-1-p) to compound (s-14-p), compound (s-14) was obtained by following the same steps as in synthesis example (1).

[1005]

[1006] Synthesis Example (19): Synthesis of compound (s-19)

[1007] Except for changing compound (s-1-p) to compound (s-19-p), compound (s-19) was obtained by following the same steps as in synthesis example (1).

[1008]

[1009] Compounds (s-2) to (s-24) were synthesized using the same method as in Synthesis Example (1). Compounds (Ref-1) to (Ref-8) are compounds described in International Publication No. 2022 / 185896, and compound (Ref-9) is a compound described in International Publication No. 2022 / 034916, which were synthesized according to the method described in the patent.

[1010]

[1011] The formation of the target analyte was confirmed by MALDI-TOF-MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry).

[1012] Table 1

[1013]

[1014] <<Preparation and Evaluation of Vapor Deposition Organic Electron Components>>

[1015] <TAF Composition>

[1016] Blue: Examples T-s-1 to T-s-15 and Comparative Examples T-1 to T-5

[1017] ITO(50nm) / HAT-CN(10nm) / HT-1(60nm) / SiCzCz(5nm) / SiCzCz:SiTrzCz2:TADF-1: Each compound described in Table 1(60:26:13:1)(35nm) / mSiTrz(5nm) / mSiTrz: Liq(1:1)(30nm) / LiF(1nm) / Al(100nm)

[1018] Green: Examples T-s-16 to T-s-24 and Comparative Examples T-6 to T-9

[1019] ITO(50nm) / HAT-CN(10nm) / HT-1(60nm) / SiCzCz(5nm) / SiCzCz:SiTrzCz2:TADF-2: Each compound described in Table 1(60:26:13:1)(35nm) / mSiTrz(5nm) / mSiTrz: Liq(1:1)(30nm) / LiF(1nm) / Al(100nm)

[1020] A 26mm×28mm×0.7mm glass substrate (manufactured by Opto Science Co., Ltd.) with ITO film formed by sputtering to a thickness of 200nm and polished to 50nm was used as the transparent support substrate. The transparent support substrate was fixed to the substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and molybdenum evaporation boats containing HAT-CN, HT-1, SiCzCz, SiTrzCz2, (TADF-1 or TADF-2), each compound described in Table 1, mSiTrz, and Liq, and tungsten evaporation boats containing LiF and aluminum were installed.

[1021] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was evacuated to 5×10 - 4Pa, first, heat HAT-CN and perform evaporation to form a hole injection layer with a film thickness of 10 nm. Then, heat HT-1 and perform evaporation to form a hole transport layer 1 with a film thickness of 60 nm, and heat SiCzCz and perform evaporation to form a hole transport layer 2 with a film thickness of 5 nm. Next, heat SiCzCz, SiTrzCz2, (TADF-1 or TADF-2), and each compound described in Table 1 simultaneously and perform evaporation to form a light-emitting layer with a film thickness of 35 nm. Adjust the evaporation rate so that the mass ratio of SiCzCz, SiTrzCz2, (TADF-1 or TADF-2), and each compound described in Table 1 is approximately 60:26:13:1. Then, heat mSiTrz and perform evaporation to form an electron transport layer 1 with a film thickness of 5 nm, and heat mSiTrz and Liq and perform evaporation to form an electron transport layer 2 with a film thickness of 30 nm. Adjust the evaporation rate so that the mass ratio of SiTrz and Liq is approximately 1:1. The evaporation rate of each layer is 0.01 - 1 nm / sec. Subsequently, heat LiF and perform evaporation at an evaporation rate of 0.01 - 0.1 nm / sec with a film thickness of 1 nm, and then heat aluminum and perform evaporation to form a cathode with a film thickness of 100 nm, thereby obtaining an organic EL device. At this time, the aluminum evaporation rate is adjusted to 1 - 10 nm / sec. In addition, SiCzCz in the light-emitting layer corresponds to a hole-transporting host material, and SiTrzCz2 corresponds to an electron-transporting host material.

[1022] <PSF Configuration>

[1023] Blue: Examples P-s-1 to Examples P-s-15 and Comparative Examples P-1 to Comparative Examples P-5

[1024] ITO(50 nm) / HAT-CN(10 nm) / HT-1(60 nm) / SiCzCz(5 nm) / SiCzCz:SiTrzCz2:PtON-TBBI: Each compound described in Table 1 (60:26:13:1)(35 nm) / mSiTrz(5 nm) / mSiTrz: Liq(1:1)(30 nm) / LiF(1 nm) / Al(100 nm)

[1025] Green: Examples P-s-16 to Examples P-s-24 and Comparative Examples P-6 to Comparative Examples P-9

[1026] ITO (50nm) / HAT-CN (10nm) / HT-1 (60nm) / SiCzCz (5nm) / SiCzCz:SiTrzCz2:Ir(PPy)3:The compounds listed in Table 1 (60:26:13:1) (35nm) / mSiTrz (5nm) / mSiTrz: Liq (1:1) (30nm) / LiF (1nm) / Al (100nm)

[1027] The TAF-formed (TADF-1 or TADF-2) was replaced with (PtON-TBBI or Ir(PPy)3) respectively, and the components were fabricated in the same manner.

[1028] The chemical structures of the compounds used in the preparation of each element are shown below.

[1029]

[1030] [evaluate]

[1031] Evaluation parameters include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength of the emission spectrum (nm), and half-width (nm). These evaluation parameters can be used, for example, with a 1000 cd / m² emission intensity. 2 The value when it emits light.

[1032] There are two types of quantum efficiency for light-emitting elements: internal quantum efficiency and external quantum efficiency. Internal quantum efficiency represents the ratio of energy injected into the light-emitting layer of the light-emitting element as electrons (or holes) to that energy being purely converted into photons. On the other hand, external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element. Photons generated in the light-emitting layer are absorbed inside the light-emitting element or continue to be reflected without being released to the outside of the light-emitting element. Therefore, external quantum efficiency is lower than internal quantum efficiency.

[1033] The methods for measuring spectroradiance (emission spectrum) and external quantum efficiency are as follows. Using an Advantest voltage / current generator R6144, the applied element's luminance reaches 1000 cd / m². 2The element emits light due to the voltage applied. Using a Topcon SR-3AR spectroradiometer, the spectroradiance in the visible light region was measured from a direction perpendicular to the emitting surface. Assuming the emitting surface is a perfectly diffused surface, the number of photons at each wavelength was obtained by dividing the measured spectroradiance value of each wavelength component by the wavelength energy and multiplying by ð. The number of photons was then accumulated over the observed entire wavelength region and set as the total number of photons emitted from the element. The number of carriers injected into the element was determined by dividing the applied current value by the elementary charge, and the external quantum efficiency was obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element. Furthermore, the half-width of the emission spectrum was obtained by the width between wavelengths above and below the maximum emission wavelength where its intensity reaches 50%.

[1034] A DC voltage was applied using an ITO electrode as the anode and a LiF / aluminum electrode as the cathode, and the voltage was measured at 1000 cd / m². 2 Characteristics during light emission. In addition, for devices constructed with TAF, the time (lifetime) for maintaining more than 50% of the initial brightness was measured, and for devices constructed with PSF, the time (lifetime) for maintaining more than 90% of the initial brightness was measured.

[1035] In addition, regarding the emission peak of the device, blue is in the range of 450~470nm, and green is in the range of 510~540nm.

[1036] The results are shown in Tables 2 through 5 below.

[1037] Table 2

[1038] <Blue> <blue>)

[1039]

[1040] Table 3

[1041] <Blue> <blue>)

[1042]

[1043] Table 4

[1044] <Green>

[1045]

[1046] Table 5

[1047] <Green>

[1048]

[1049] The results show that, compared with the components of the comparative examples that utilize compounds having a skeleton corresponding to the compounds of the examples, the components of the examples achieve high efficiency or long lifespan.< / blue> < / blue>

Claims

1. A polycyclic aromatic compound, represented by the following formula (1): In equation (1), Rings A, B, C, D, and E are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring, wherein... At least one of rings A, B, C, D, and E is represented by one of equations (Ar-1), (Ar-2), (Ar-3), and (Ar-4). X 1 X 2 X 3 and X 4 They are independently N-Ar, O, S, or Se. In N-Ar, Ar can be hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. In X 3 In the case of N-Ar, Ar can be bonded to at least one of the A and B rings via a single bond or a linker group, in the X 4 In the case of N-Ar, Ar can be bonded to at least one of the A and C rings via a single bond or a linker group, in the X 1 In the case of N-Ar, Ar can be bonded to at least one of the B and D rings via a single bond or a linker group, in the X 2 In the case of N-Ar, Ar can be bonded to at least one of the C and E rings via a single bond or a linker group. In formula (1), at least one of the groups selected from aryl rings and heteroaryl rings can be condensed by at least one cycloalkane, the cycloalkane can be substituted by at least one substituent, and at least one -CH2- in the cycloalkane can be substituted by -O-. In equations (Ar-1), (Ar-2), (Ar-3), and (Ar-4), Any two or three consecutive Z's are contraction positions, and all other Z's are independently -C(-R). Z = or -N=, Z=Z are independently >O and >NR respectively. NX >C(-R CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2 or >Se, The R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted. When rings A, B, C, D, and E are all represented by equation (Ar-1), at least one of Z in equation (Ar-1) is -N=. In the formula (1), at least one hydrogen may be replaced by deuterium, halogen or cyano, at least one nitrogen may be replaced by nitrogen-15, and at least one boron may be replaced by boron-11.

2. The polycyclic aromatic compound according to claim 1, wherein, At least one of rings B, D, and E is represented by one of equations (Ar-1), (Ar-2), (Ar-3), and (Ar-4). The formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-4) are selected from at least one of the following formulas: (Ar-1-1) to (Ar-1-3), (Ar-2-1) to (Ar-2-9), (Ar-3-1) to (Ar-3-6), and (Ar-4-1) to (Ar-4-4). In equations (Ar-1-1) to (Ar-1-3), equations (Ar-2-1) to (Ar-2-9), equations (Ar-3-1) to (Ar-3-6), and equations (Ar-4-1) to (Ar-4-4), And # represents B and X 1 X 2 or X 3 The bond position.

3. The polycyclic aromatic compound according to claim 1, wherein, Ring A is represented by one of the formulas (Ar-1), (Ar-2), and (Ar-3). The formulas (Ar-1), (Ar-2), and (Ar-3) are selected from the following formulas (Ar-5-1) to (Ar-5-4): In equations (Ar-5-1) to (Ar-5-4), # indicates the bond position to B, and # indicates the bond position to X. 3 or X 4 The bond position.

4. The polycyclic aromatic compound according to claim 1, wherein, Equation (1) is represented by the following equations (1-1) to (1-74): In equations (1-1) to (1-74), X 1 X 2 X 3 and X 4 Independently with X in equation (1) 1 X 2 X 3 and X 4 The definitions are the same. Za, Zb, Zc, Zd, and Ze are each independently -C(-R) Z )= or -N=, the R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted. Za=Za, Zb=Zb, Zc=Zc, Zd=Zd, and Ze=Ze are independently >O, >NR, respectively. NX >C(-R CX )2、>Si(-R SiX )2、>S、>CO、>SO、>SO2 or>Se, where at least one of Za, Zb, Zc, Zd and Ze in equation (1-1) is -N=.

5. The polycyclic aromatic compound according to claim 1, wherein, X 3 and X 4 They are N-Ar, respectively.

6. The polycyclic aromatic compound according to claim 1, wherein, Equation (1) is represented by the following equations (2-1) to (2-74): In equations (2-1) to (2-74), X 1 and X 2 Independently with X in equation (1) 1 and X 2 The definitions are the same. N-Ar 1 Ar 1 and N-Ar 2 Ar 2 Each is independently identical to the definition of Ar in N-Ar of equation (1). Za, Zb, Zc, Zd, and Ze are each independently -C(-R) Z )= or -N=, the R Z For hydrogen or substituents, two adjacent -C(-R) Z R = ) Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted. Za=Za, Zb=Zb, Zc=Zc, Zd=Zd, and Ze=Ze are independently >O, >NR, respectively. NX >C(-R CX )2、>Si(-R SiX )2、>S、>CO、>SO、>SO2 or>Se, where at least one of Za, Zb, Zc, Zd and Ze in equation (2-1) is -N=.

7. The polycyclic aromatic compound according to claim 1, wherein, X 1 and X 2 At least one of them is O or S.

8. The polycyclic aromatic compound according to claim 6, wherein, Ar 1 and Ar 2 At least one of them is represented by the following formula (o-Ar): In formula (o-Ar), Indicates the bonding position with nitrogen. The F ring is a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring. G is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group.

9. The polycyclic aromatic compound according to any one of claims 1 to 5 and 7, wherein, In X 3 and X 4 In the case of N-Ar, the Ar is the same.

10. The polycyclic aromatic compound according to claim 6 or 8, wherein, The Ar 1 and the Ar 2 same.

11. The polycyclic aromatic compound according to claim 1, wherein, The polycyclic aromatic compound is represented by any of the following formulas: 。 12. An organic electroluminescent element, in, include: A pair of electrodes, consisting of an anode and a cathode; and An organic layer is disposed between the pair of electrodes. The organic layer contains a polycyclic aromatic compound according to any one of claims 1 to 11.

13. The organic electroluminescent element according to claim 12, wherein, The organic layer is a light-emitting layer.

14. The organic electroluminescent element according to claim 13, wherein, The light-emitting layer comprises at least one selected from the group consisting of auxiliary dopants and phosphorescent materials.

15. A display device or lighting device, wherein, It has an organic electroluminescent element according to claim 12.

Images