Polycyclic aromatic compound

Abstract

Provided are a novel polycyclic aromatic compound and an organic EL element using the same. By means of the polycyclic aromatic compound represented by general formula (A-1), the options of materials for organic devices are increased. In addition, by using the novel material, for example, to produce an organic EL element, an excellent element is provided. (In formula (A-1), R1 represents a hydrogen atom; ra1 to Ra3, Rb1 to Rb4, and Rc1 to Rc4 are each independently a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted aryl heteroarylamino group, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group; in the formula, at least one of Ra1 to Ra3 represents a substituted aryl group or a substituted heteroaryl group, and at least one of Ra2 to Ra3 represents a substituted aryl group or a substituted heteroaryl group, and at least one of Ra3 to Ra3 represents a substituted aryl group or a substituted heteroaryl group. The substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group; the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, Y1 is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and X1 and X2 are each independently O, N-R, C (-R) 2, Si (-R) 2, S, or Se (where at least one of X1 and X2 is N-R, where R of N-R is a group represented by formula (G-1). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to polycyclic aromatic compounds and their multimers, organic devices using the same, such as organic electroluminescent devices, organic field-effect transistors, organic thin-film solar cells, and wavelength conversion filters, as well as display devices and lighting devices. It should be noted that in this specification, "polycyclic aromatic compounds" and their multimers are sometimes collectively referred to as "polycyclic aromatic compounds," and "organic electroluminescent devices" are sometimes referred to as "organic EL devices" or simply as "devices." Background Art

[0002] Display devices using electroluminescent elements have been extensively researched for their potential to achieve power savings and thinness. Furthermore, organic electroluminescent elements made of organic materials have been actively researched due to their ease of weight reduction and size reduction. In particular, research has been actively conducted on the development of organic materials that exhibit luminescence properties such as blue, one of the three primary colors of light, and organic materials that possess charge transport capabilities such as holes and electrons (possibly forming semiconductors or superconductors), regardless of whether they are high-molecular-weight or low-molecular-weight compounds.

[0003] An organic EL element has a structure consisting of a pair of electrodes, an anode and a cathode, and one or more layers containing organic compounds disposed between the electrodes. Layers containing organic compounds include light-emitting layers and charge transport / injection layers, which transport or inject charges such as holes and electrons. Various organic materials suitable for these layers have been developed.

[0004] For example, as a material used in organic EL elements and organic thin-film solar cells, a material obtained by improving a triphenylamine derivative has also been reported (International Publication No. 2012 / 118164). This material is characterized in that, with reference to the already practical N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), the aromatic rings constituting triphenylamine are connected to each other, thereby placing nitrogen at the center of the ring structure and improving its planarity. In this document, for example, the charge transport properties of an NO-linked compound (Compound 1 on page 63) are evaluated, but there is no description of the production method of materials other than the NO-linked compound. In addition, if the connected elements are different, the overall electronic state of the compound is different, so it is impossible to know the properties that can be obtained from materials other than the NO-linked compound.

[0005] The main material of an organic EL element is usually a molecule formed by connecting multiple existing aromatic rings such as benzene and carbazole through single bonds, phosphorus atoms, and silicon atoms. This is because by connecting multiple aromatic rings with smaller conjugated systems, it is possible to ensure a large HOMO-LUMO gap (band gap Eg in the film) required for the main material. Furthermore, the main material of an organic EL element using phosphorescent materials and thermally activated delayed fluorescence materials also requires a high triplet excitation energy (Eg). T ), but by connecting donor or acceptor aromatic rings or substituents to the molecule, the SOMO1 and SOMO2 of the triplet excited state (T1) are localized, reducing the exchange interaction between the two orbitals, thereby increasing the triplet excitation energy (E T However, the redox stability of aromatic rings with small conjugated systems is insufficient, and the life of devices using molecules formed by connecting existing aromatic rings as main materials is insufficient. On the other hand, polycyclic aromatic compounds with extended π conjugated systems generally have excellent redox stability, but due to the HOMO-LUMO gap (band gap Eg in thin films), triplet excitation energy (E T ) is low, so it is considered unsuitable for the main material.

[0006] Under such circumstances, in recent years, compounds formed by condensing multiple aromatic rings with boron or the like as central atoms have been reported (International Publication No. 2015 / 102118 Gazette). In this document, an organic EL element evaluation using a compound formed by condensing multiple aromatic rings as a doping material for a light-emitting layer was implemented. In addition, an example of further polymerizing such a compound (International Publication No. 2018 / 212169 Gazette) and an example of extending a conjugated system by a linking group in a molecule have been reported (Korean Patent No. 10-2020-0121228, International Publication No. 2020 / 217229 Gazette).

[0007] Prior art literature

[0008] Patent Literature

[0009] Patent Document 1: International Publication No. 2012 / 118164

[0010] Patent Document 2: International Publication No. 2015 / 102118

[0011] Patent Document 3: International Publication No. 2018 / 212169

[0012] Patent Document 4: Korean Patent Publication No. 10-2020-0121228

[0013] Patent Document 5: International Publication No. 2020 / 217229 Summary of the Invention

[0014] Problems to be solved by the invention

[0015] As reported in Patent Documents 1 to 5, various materials have been developed for use in organic EL devices. However, in order to expand the selection of materials for organic EL devices, it is desirable to develop materials composed of compounds different from those conventionally used. In particular, it would be beneficial to explore the organic EL properties obtained from materials other than NO-linked compounds having nitrogen at the center of the ring structure, and to explore methods for producing such materials.

[0016] In addition, Patent Documents 2 to 5 report polycyclic aromatic compounds containing boron and organic EL elements using the same. However, these documents disclose a large number of compounds. In order to further improve the characteristics of the element, it is beneficial to explore materials for the light-emitting layer, especially doping materials, that can improve organic EL characteristics such as luminous efficiency and element life.

[0017] In addition, as a method for forming the organic layer that constitutes the organic EL element, a wet film-forming method is currently used in addition to the vacuum evaporation method. Therefore, the development of wet film-forming ink materials for forming the hole injection layer, the hole transport layer and the light-emitting layer is particularly active, and exploring such ink materials is also beneficial.

[0018] Solutions for solving problems

[0019] The present inventors have conducted intensive research to address the above-mentioned issues and have discovered that, for example, an organic EL device can be constructed by disposing a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes. This has led to the completion of the present invention. Specifically, the present invention provides the following polycyclic aromatic compounds, and further provides organic device materials, such as organic EL device materials, containing the following polycyclic aromatic compounds.

[0020] It should be noted that in this specification, the number of carbon atoms is sometimes used to represent a chemical structure or a substituent. However, when a chemical structure is substituted with a substituent or a substituent is further substituted with a substituent, the number of carbon atoms represents the number of carbon atoms in the chemical structure or the substituent, and does not represent the total number of carbon atoms of the chemical structure and the substituents, or the total number of carbon atoms of the substituents. For example, "a substituent B having a carbon number Y substituted by a substituent A having a carbon number X" means that "a substituent A having a carbon number X" is substituted on "a substituent B having a carbon number Y", and the number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B. In addition, for example, "a substituent B having a carbon number Y substituted by a substituent A" means that "a substituent A (with an unlimited number of carbon atoms)" is substituted on "a substituent B having a carbon number Y", and the number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B.

[0021] [1] A polycyclic aromatic compound represented by the following formula (A-1), or a polymer of a polycyclic aromatic compound having at least two unit structures represented by the aforementioned formula (A-1):

[0022]

[0023] In the above formula (A-1),

[0024] R a1 ~R a3 、R b1 ~R b4 and R c1 ~R c4 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; the two aryl groups of the aforementioned diarylamino are optionally bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino are optionally bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboryl are optionally bonded to each other via a linking group.

[0025] And, R a1 ~R a3 、R b1 ~R b4 and R c1 ~R c4 Two adjacent groups are optionally bonded to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed aryl ring and heteroaryl ring is optionally substituted by 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, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group; the two aryl groups of the aforementioned diarylamino group are optionally bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino group are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino group are optionally bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboryl group are optionally bonded to each other via a linking group.

[0026] Among them, R a1 ~Ra3 At least one of is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group,

[0027] Y 1 is B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, wherein R of the aforementioned Si—R and the aforementioned Ge—R are each independently a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl;

[0028] X 1 and X 2 are independently O, NR, C(-R)2, Si(-R)2, S or Se, the R of the aforementioned NR is hydrogen, an aryl substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a group represented by formula (G-1), the R of the aforementioned C(-R)2 and Si(-R)2 are independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, the two R of the aforementioned C(-R)2 and the aforementioned Si(-R)2 are optionally bonded to each other to form a ring, and the R of the aforementioned NR and / or the R of the aforementioned C(-R)2 are optionally bonded to the a ring and / or the b ring, or to the a ring and / or the c ring by means of a connecting group. 2 Ring bonding,

[0029] Among them, X 1 and X 2 At least one of them is NR, in which case R of the aforementioned NR is a group represented by formula (G-1),

[0030]

[0031] (In the above formula (G-1),

[0032] R d1 ~R d10are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; the two aryl groups of the aforementioned diarylamino are optionally bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino are optionally bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboryl are optionally bonded to each other via a linking group.

[0033] Furthermore, two adjacent R d1 ~R d10 are optionally bonded to each other to form a cycloalkane condensed structure, wherein at least one hydrogen in the cycloalkane is optionally substituted,

[0034] Among them, R d6 ~R d10 At least one of them is an alkyl group, or two adjacent Rd 6 ~Rd 10 Bonded to each other to form a cycloalkane condensed structure,

[0035] R d1 ~R d5 Any one of them is a bond to the nitrogen atom)

[0036] The a ring, b ring, c ring in the compound or unit structure represented by the above formula (A-1) 2 At least one of the rings, aryl rings or heteroaryl rings is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, at least one -CH2- in the cycloalkane is optionally replaced with -O-,

[0037] At least one hydrogen atom in the compound or unit structure represented by the above formula (A-1) is optionally substituted by a cyano group or a halogen group, and

[0038] In the compound or unit structure represented by the above formula (A-1), at least one hydrogen is optionally replaced by deuterium, and at least one nitrogen is optionally replaced by nitrogen-15( 15 N), at least one sulfur is optionally replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36( 36 S), at least one oxygen is optionally replaced with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon is optionally replaced with a carbon-13 ( 13C), at least one boron is optionally replaced with boron-11 ( 11 B).

[0039] [2] The polycyclic aromatic compound or multimer thereof according to [1] above, wherein the formula (G-1) is a group represented by any one of formulas (G-2) to (G-21):

[0040]

[0041] (In the above formulas (G-2) to (G-21),

[0042] R 1 are independently alkyl,

[0043] R 2 are independently hydrogen or alkyl,

[0044] * is the bond to the nitrogen atom.)

[0045] [3] The polycyclic aromatic compound or multimer thereof according to [1] or [2] above, wherein the formula (A-1) is represented by any of the following formulas (A-2) to (A-12):

[0046]

[0047] (In the above formulas (A-2) to (A-12),

[0048] R a2 is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, in which case the aryl ring of the substituted aryl group or the heteroaryl ring of the substituted heteroaryl group is optionally fused with at least one cycloalkane, and at least one hydrogen in the cycloalkane is optionally substituted,

[0049] R b2 and R b3 、R c2 and R c3 are independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,

[0050] Of the two Rs, one is a group represented by formula (G-1), and the other is an aryl group substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, an aryl group condensed by a cycloalkane, a heteroaryl group condensed by a cycloalkane, or a group represented by formula (G-1),

[0051] R 2are independently hydrogen or alkyl,

[0052] R 3 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0053] X 3 O, NR 4 or C(-R 4 )2,

[0054] R 4 are independently an alkyl group, or a substituted or unsubstituted aryl group.)

[0055] [4] The polycyclic aromatic compound or multimer thereof according to [3] above, wherein in the aforementioned formulas (A-2) to (A-12),

[0056] R a2 is a diarylamino group optionally substituted by a methyl group, a tert-amyl group, or a tert-butyl group, or a substituted aryl group substituted by an alkyl group,

[0057] R b2 and R b3 Among them, one is hydrogen, and the other is methyl, tert-butyl, or tert-pentyl.

[0058] R c2 and R c3 Among them, one is hydrogen, and the other is methyl, tert-butyl, adamantyl, 3,5-dimethyl-1-adamantyl,

[0059] Of the two Rs, one is a group represented by the following formula (G-1), and the other is an aryl group substituted by an alkyl group, an aryl group condensed by a cycloalkane, or a group represented by the formula (G-1),

[0060] R 2 are each independently a methyl group,

[0061] R 3 Each independently represents the following formula (R 3 -1)~(R 3 -11) represented by any one of the groups,

[0062]

[0063] (the above formula (R 3 -1)~(R 3 -11), * represents the bond to the nitrogen atom)

[0064] X 3 is O, N-bis(4-tert-butylphenyl), C(Me)2).

[0065] [5] The polycyclic aromatic compound or its multimer according to any one of [1] to [4] above, which is represented by any one of the following formulae:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] In the formula, Me is a methyl group, tBu is a tert-butyl group, t-Am is a tert-amyl group, and D is deuterium.

[0078] [6] The polycyclic aromatic compound or its polymer according to the above [5], which is represented by any one of the aforementioned formulas (1) to (13), (15) to (16), (18), (21) to (26), (31) to (35), (40) to (41), (45) to (52), (55), (57), (59), (60), (64), or (67) to (76).

[0079] [7] A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of [1] to [6].

[0080] [8] The material for an organic device according to [7] above, which is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin-film solar cell, or a material for a wavelength conversion filter.

[0081] [9] The material for an organic device according to [8] above, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

[0082]

[10] An organic electroluminescent element comprising: a pair of electrodes including an anode and a cathode; and an organic layer disposed between the pair of electrodes, wherein the organic layer contains the polycyclic aromatic compound or a multimer thereof according to any one of [1] to [6] above.

[0083]

[11] The organic electroluminescent element according to

[10] above, wherein the organic layer is a light-emitting layer.

[0084]

[12] The organic electroluminescent element according to

[11] above, wherein the light-emitting layer comprises a dopant and a host, and the dopant is the polycyclic aromatic compound or a polymer thereof according to any one of [1] to [6] above.

[0085]

[13] The organic electroluminescent device according to

[12] above, wherein the host is an anthracene compound, a fluorene compound or a dibenzo[theta]-[io ... compound.

[0086]

[14] A display device or lighting device comprising the organic electroluminescent element described in

[10] above.

[0087]

[15] A wavelength conversion filter comprising the wavelength conversion filter material described in [8] above.

[0088] Effects of the Invention

[0089] According to a preferred embodiment of the present invention, a polycyclic aromatic compound having a novel structure that can be used as a material for organic devices such as organic EL elements can be provided. By using this polycyclic aromatic compound, an excellent organic device such as an organic EL element can be provided.

[0090] Specifically, the present inventors etc. have found that the polycyclic aromatic compounds that aromatic rings are connected using heteroelements such as boron, nitrogen, oxygen, sulphur have large HOMO-LUMO gap (band gap Eg in film). This is because the aromaticity of the 6-membered ring comprising heteroelements is low, and the reduction in the HOMO-LUMO gap accompanied by the expansion of conjugated system is suppressed. It is found in addition that the HOMO-LUMO gap can be arbitrarily changed according to the kind and connection method of heteroelements. It is believed that the reason is that, according to the spatial expansion and energy of the empty orbital of heteroelements or the lone pair of electrons, the energy of HOMO, LUMO can be moved arbitrarily.

[0091] These polycyclic aromatic compounds localize the excited SOMO1 and SOMO2 on each atom through the electronic perturbation of the heteroelement, thereby narrowing the half-value width of the fluorescence emission peak and obtaining high color purity when used as a dopant for an organic EL element. For the same reason, the singlet energy (S 1 ) and triplet energy (T1 ) energy difference (ΔS 1 T 1 ) becomes smaller and shows thermally activated delayed fluorescence, and when used as an emitting dopant in an organic EL element, high efficiency can be obtained.

[0092] Furthermore, by introducing substituents, the energies of HOMO and LUMO can be arbitrarily shifted, thereby optimizing the ionization potential and electron affinity according to the surrounding materials. However, the present invention is not particularly limited to these principles. BRIEF DESCRIPTION OF THE DRAWINGS

[0093] Figure 1 Schematic cross-sectional view showing the organic EL element of this embodiment. DETAILED DESCRIPTION

[0094] 1. Polycyclic aromatic compounds

[0095] <Description of the Overall Structure of the Compound>

[0096] The present invention is a polycyclic aromatic compound represented by the following general formula (A-1) or a multimer of polycyclic aromatic compounds having at least two unit structures represented by the aforementioned general formula (A-1).

[0097]

[0098] In the general formula (A-1), R a1 ~R a3 At least one of the substituted aryl groups is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group.

[0099] Y 1 It is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R.

[0100] X 1 and X 2 are independently O, NR, C(-R)2, Si(-R)2, S or Se. 1 and X 2 At least one of them is NR, and in this case, R of the aforementioned NR is a group represented by formula (G-1).

[0101]

[0102] It should be noted that the definitions of the symbols in the following structural formulas are the same as those defined above. Furthermore, the definitions of the symbols in all structural formulas shown in this paragraph and thereafter are also the same as those defined above. It should be noted that, unless otherwise noted, in this specification, "Me" in the structural formulas or their descriptions represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-amyl group, and "D" represents deuterium.

[0103] <Description of Substituents in Compounds>

[0104] R in the general formula (A-1) a1 ~R a3 、R b1 ~R b4 and R c1 ~R c4 Each independently represents hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio or substituted silyl. Details about them will be described later. It should be noted that the details of the rings and substituents listed here will be summarized and described later. In addition, regarding the description of "substituted or unsubstituted" in this specification, as long as there is no special description, the substituent may further have a substituent. In this case, examples of the substituent that the substituent may have include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, and preferably aryl, heteroaryl, alkyl, or cycloalkyl. At least one hydrogen atom in the aryl or heteroaryl group in the diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, aryloxy, and arylthio group may be substituted with an alkyl or cycloalkyl group. In addition, R a2 and R b2 More preferred is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group, and still more preferred is a diarylamino group substituted by an alkyl group.

[0105] The two aryl groups of the above-mentioned diarylamino group are optionally bonded to each other by means of a linking group, the two heteroaryl groups of the above-mentioned diheteroarylamino group are optionally bonded to each other by means of a linking group, the aryl and heteroaryl groups of the above-mentioned arylheteroarylamino group are optionally bonded to each other by means of a linking group, and the two aryl groups of the above-mentioned diarylboron group are optionally bonded to each other by means of a linking group. The details of the linking group and the bonded form will be summarized and described later. It should be noted that, in this specification, "linking group" refers to a single bond, an alkylene group, an alkenylene group, an alkynylene group, -N(-R)-, -O-, -S-, -Si(-R)2- or -Se-. At this time, as an alkylene group, for example, -CH2-, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -C(-R)2- can be mentioned. As an alkenylene group, for example, -CH=CH-, -CH=CR-, -CR=CR-, -CH=CH-CH2-, -CH2-CH=CH- can be mentioned. As alkynylene, for example, -C≡C-, -C≡C-CH2-, -CH2-C≡C-. In this case, the aforementioned R are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl or cycloalkyl, and at least one hydrogen in the R is optionally substituted by an alkyl or cycloalkyl group. In addition, two R bonded to the same carbon atom, two R bonded to the same silicon atom, or two R bonded to adjacent carbon atoms (for example, two R in -CHR-CHR-, -CR2-CR2-, -CR=CR-, -C(-R)2-, -Si(-R)2-) are optionally bonded to each other to form a cycloalkylene ring, an arylene ring and a heteroarylene ring. It should be noted that the details of the R listed here are described later.

[0106] For example, when two aryl groups of a diarylamino group are bonded to each other via a single bond, they can form a carbazolyl group; when two aryl groups of a diarylamino group are bonded to each other via -O-, they can form a phenoxazinyl group; and when two aryl groups of a diarylamino group are bonded to each other via -S-, they can form a phenothiazinyl group.

[0107] <R in the compound a1 ~R a3 Description>

[0108] R a1 ~R a3Each of the following is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted diarylboronyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group. In this case, the two aryl groups of the aforementioned diarylamino group may be bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino group may be bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino group may be bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboronyl group may be bonded to each other via a linking group.

[0109] Among them, R a1 ~R a3 Each of the above groups is independently preferably hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted carbazolyl group (the substituent is at least one selected from the group consisting of an alkyl group, a cycloalkyl group, and a cycloalkyl group substituted or unsubstituted by an alkyl group), more preferably hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthyl ... The substituted or unsubstituted phenyldiphenylamino group, substituted or unsubstituted phenyldibenzofuranylamino group, substituted or unsubstituted biphenyldibenzofuranylamino group, substituted or unsubstituted naphthyldibenzofuranylamino group, methyl group, tert-butyl group, tert-amyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted carbazolyl group (the substituent group is at least one selected from the group consisting of methyl group, tert-butyl group, tert-amyl group, and adamantyl group (optionally substituted with methyl group)), further preferably hydrogen, tert-butyl group, diphenylamino group, carbazolyl group, and particularly preferably hydrogen and tert-butyl group.

[0110] In one embodiment, R a1 ~R a3At least one of the amino groups is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted carbazolyl group (the substituent is at least one selected from the group consisting of an alkyl group, a cycloalkyl group, and a cycloalkyl group substituted or unsubstituted by an alkyl group), more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthyl ... The alkyl group may be a substituted or unsubstituted phenyldiphenylamino group, a substituted or unsubstituted phenyldibenzofuranylamino group, a substituted or unsubstituted biphenyldibenzofuranylamino group, a substituted or unsubstituted naphthyldibenzofuranylamino group, a methyl group, a tert-butyl group, a tert-amyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted carbazolyl group (the substituent is at least one selected from the group consisting of a methyl group, a tert-butyl group, a tert-amyl group, and an adamantyl group (optionally substituted with a methyl group)), further preferably a tert-butyl group, a diphenylamino group, a carbazolyl group, and particularly preferably a tert-butyl group.

[0111] Composition R a1 ~R a3 The aryl or heteroaryl group of the substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted diarylamino group, substituted or unsubstituted diheteroarylamino group, substituted or unsubstituted arylheteroarylamino group, substituted or unsubstituted diarylboryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted arylthio group is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally replaced by -O-.

[0112] In one embodiment, R a1 ~R a3 At least one of the groups is preferably an aryl group condensed with a cycloalkane, and more preferably 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl or 1,1,3,3-tetramethyl-2,3-dihydro-1H-inden-5-yl.

[0113] Among them, R a1 ~R a3 At least one of the substituted aryl groups is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group.

[0114] The aryl group of the substituted aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, or a triphenyl group; more preferably a phenyl group, a biphenyl group, or a terphenyl group; and still more preferably a phenyl group.

[0115] The heteroaryl group of the substituted heteroaryl group is preferably a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group, and more preferably a dibenzofuranyl group.

[0116] The substituent of the substituted aryl group and the substituted heteroaryl group is preferably an unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group, and more preferably an unsubstituted alkyl group.

[0117] In this case, the alkyl group is preferably a methyl group, a tert-butyl group, or a tert-amyl group, and more preferably a tert-butyl group.

[0118] The substituted or unsubstituted cycloalkyl group is preferably an adamantyl group or a 3,5-dimethyl-1-adamantyl group, and more preferably a 3,5-dimethyl-1-adamantyl group.

[0119] In one embodiment, preferably R a1 ~R a3 At least one of the substituted aryl groups is more preferably 4-methylphenyl, 4-tert-butylphenyl, 3,5-di-tert-butylphenyl, 1,5-dimethyl-4-tert-butylphenyl, p-(3,5-dimethyl-1-adamantyl)phenyl, 4-diphenylaminophenyl, 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl, or 1,1,3,3-tetramethyl-2,3-dihydro-1H-inden-5-yl.

[0120] In addition, R a1 ~R a3 Among them, R is preferred a2 is the aforementioned substituted aryl or the aforementioned substituted heteroaryl, and R a1 and R a3 For hydrogen.

[0121] <R in the compound b1 ~R b4 Description>

[0122] R b1 ~R b4 Each of the following is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted diarylboronyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group. In this case, the two aryl groups of the aforementioned diarylamino group may be bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino group may be bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino group may be bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboronyl group may be bonded to each other via a linking group.

[0123] Among them, R b1 ~R b4 Preferably, it is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted carbazolyl group (the substituent is at least one selected from the group consisting of an alkyl group, a cycloalkyl group, and a cycloalkyl group substituted or unsubstituted by an alkyl group), more preferably hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthyl ... substituted phenylbiphenylamino, substituted or unsubstituted phenyldibenzofuranylamino, substituted or unsubstituted biphenyldibenzofuranylamino, substituted or unsubstituted naphthyldibenzofuranylamino, methyl, tert-butyl, tert-amyl, substituted or unsubstituted adamantyl, substituted or unsubstituted carbazolyl (the substituent is at least one selected from the group consisting of methyl, tert-butyl, tert-amyl, and adamantyl (optionally substituted with a methyl group)), further preferably hydrogen, tert-butyl, diphenylamino, carbazolyl, and particularly preferably hydrogen and tert-butyl.

[0124] In one embodiment, preferably R b1 ~R b4 At least one of the amino groups is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted carbazolyl group (the substituent is at least one selected from the group consisting of an alkyl group, a cycloalkyl group, and a cycloalkyl group substituted or unsubstituted by an alkyl group), more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, a substituted Or unsubstituted phenylbiphenylamino, substituted or unsubstituted phenyldibenzofuranylamino, substituted or unsubstituted biphenyldibenzofuranylamino, substituted or unsubstituted naphthyldibenzofuranylamino, methyl, tert-butyl, tert-amyl, substituted or unsubstituted adamantyl, substituted or unsubstituted carbazolyl (the substituent is at least one selected from the group consisting of methyl, tert-butyl, tert-amyl, and adamantyl (optionally substituted with methyl)), further preferably tert-butyl, diphenylamino, carbazolyl, and particularly preferably tert-butyl.

[0125] Additionally, in one embodiment, R b1 ~R b4 At least one of is preferably a substituted or unsubstituted diarylamino group, an unsubstituted alkyl group (the substituent is an alkyl group), more preferably a tert-butyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, or a substituted or unsubstituted phenylbiphenylamino group (the substituent is a tert-butyl group).

[0126] The b ring is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally replaced with -O-. b1 ~R b4 They are optionally bonded to each other to form a cycloalkane condensed structure, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally replaced by -O-.

[0127] In one embodiment, preferably R b1 and R b2 、R b2 and R b3 , or R b3 and R b4 bonded to each other to form a cycloalkane condensed structure, more preferably R b2 and R b3 bonded to each other to form a cycloalkane condensed structure, and more preferably R b2 and R b3 They are bonded to each other to form a cyclopentane condensed structure or a cyclohexane condensed structure.

[0128] When the b ring is condensed with a cycloalkane, it is preferably represented by the following formula.

[0129]

[0130] <R in the compound c1 ~R c4 Description>

[0131] R c1 ~R c4 Each of the following is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted diarylboronyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group. In this case, the two aryl groups of the aforementioned diarylamino group may be bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino group may be bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino group may be bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboronyl group may be bonded to each other via a linking group.

[0132] Among them, R c1 ~R c4It is preferably hydrogen, a substituted or unsubstituted aryl group (the substituent is an alkyl group), more preferably hydrogen, a substituted or unsubstituted phenyl group (the substituent is at least one selected from a methyl group, a tert-butyl group, a tert-amyl group, and an adamantyl group (optionally substituted with a methyl group)), and still more preferably hydrogen or a phenyl group.

[0133] In one embodiment, R c1 ~R c4 At least one of is preferably a substituted or unsubstituted aryl group (the substituent is an alkyl group), more preferably a substituted or unsubstituted phenyl group (the substituent is at least one selected from a methyl group, a tert-butyl group, a tert-amyl group, and an adamantyl group (optionally substituted with a methyl group)), and further preferably a phenyl group.

[0134] c 2 The ring is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally replaced with -O-. c1 ~R c4 They are optionally bonded to each other to form a cycloalkane condensed structure, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally replaced by -O-.

[0135] In one embodiment, preferably R c1 and R c2 、R c2 and R c3 , or R c3 and R c4 bonded to each other to form a cycloalkane condensed structure, more preferably R c2 and R c3 bonded to each other to form a cycloalkane condensed structure, and more preferably R c2 and R c3 They are bonded to each other to form a cyclopentane condensed structure or a cyclohexane condensed structure.

[0136] When the C ring is condensed with a cycloalkane, it is preferably represented by the following formula.

[0137]

[0138] <Description of Changes in Ring Structure Due to Bonding of Substituents>

[0139] In the general formula (A-1), R a1 ~R a3 、R b1 ~R b4 and R c1 ~R c4Two adjacent groups are optionally bonded to each other to form an aryl ring or a heteroaryl ring. At least one hydrogen atom of the formed aryl ring or heteroaryl ring is optionally substituted by 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, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group.

[0140] In this case, the two aryl groups of the above-mentioned diarylamino group may be bonded via a linking group, the two heteroaryl groups of the above-mentioned diheteroarylamino group may be bonded via a linking group, the aryl group and the heteroaryl group of the above-mentioned arylheteroarylamino group may be bonded via a linking group, and the two aryl groups of the above-mentioned diarylboron group may be bonded via a linking group, but a form in which they are not bonded via a linking group is preferred.

[0141] In the general formula (A-1), as the ring b and / or c 2 When the rings form an aryl ring or a heteroaryl ring together, the structure includes, for example, formula (A-1-1) to formula (A-1-4).

[0142]

[0143] For example, in formula (A-1-1), adjacent R c1 and R c2 with c 2 In formula (A-1-2), the adjacent R c2 and R c3 with c 2 The rings together form a pyridyl ring. b2 and R b3 Together with the b ring, a benzene ring is formed. b1 and R b2 Together with the b ring, it forms a pyridyl ring. The adjacent R b3 and R b4 Together with the b ring, it forms a benzene ring.

[0144] Thus, R a1 ~R a3 、R b1 ~R b4 、R c1 ~R c4 The two adjacent groups can be bonded to each other and to the a ring, b ring, c ring 2 The rings together form an aryl ring or a heteroaryl ring to form a 2-ring condensed ring, and Ra1 ~R a3 、R b1 ~R b4 、R c1 ~R c4 The two adjacent groups are bonded to each other and to the a ring, b ring, c ring 2 The rings together form two aryl rings or heteroaryl rings to form a 3-ring fused ring.

[0145] It should be noted that, for any substituent on the formed aryl ring or heteroaryl ring, except R a1 ~R a3 、R b1 ~R b4 、R c1 ~R c4 Other than using n R x Indicates that the upper limit of n is the maximum number that can be replaced. In this case, R x and each independently represents 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, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group.

[0146] In this case, the two aryl groups of the above-mentioned diarylamino group may be bonded via a linking group, the two heteroaryl groups of the above-mentioned diheteroarylamino group may be bonded via a linking group, the aryl group and the heteroaryl group of the above-mentioned arylheteroarylamino group may be bonded via a linking group, and the two aryl groups of the above-mentioned diarylboron group may be bonded via a linking group, but a form in which they are not bonded via a linking group is preferred.

[0147] <Central element Y in the compound 1 Description>

[0148] Y in formula (A-1) 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R. The R of the aforementioned "Si-R" and the R of "Ge-R" are each independently 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, and the substituent is preferably an alkyl group or a cycloalkyl group. In the case of P=O, P=S, Si-R or Ge-R, the ring a, ring b and ring c are 1 The ring-bonded atom is P, C, Si or Ge. 1Preferred are B, P, P═O, P═S or Si—R, more preferred are B, P, P═O or P═S, and particularly preferred are B. It is to be noted that the details of the substituents listed here will be collectively described later.

[0149] <X in the compound 1 and X 2 Description>

[0150] In formula (A-1), X 1 and X 2 are independently O, NR, C(-R)2, Si(-R)2, S or Se.

[0151] The R of the aforementioned "NR" is hydrogen, an aryl group substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a group represented by formula (G-1). In this case, at least one of the aryl group substituted by an alkyl group and the substituted or unsubstituted heteroaryl group constituting R of the NR is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally replaced with -O-.

[0152] R in the aforementioned "NR" is preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0153] The aryl group of the substituted or unsubstituted aryl group is more preferably a phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenyl group, further preferably a phenyl group, a biphenyl group, or a terphenyl group, particularly preferably a phenyl group or a biphenyl group, and most preferably a phenyl group.

[0154] The heteroaryl group of the substituted or unsubstituted heteroaryl group is preferably a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group, and more preferably a dibenzofuranyl group.

[0155] Examples of the embodiment in which the aryl group substituted with an alkyl group, the substituted or unsubstituted heteroaryl group, and the group represented by formula (G-1) in R of the aforementioned "NR" are condensed with a cycloalkane include the following structures.

[0156]

[0157] In one embodiment, at least one R of "NR" is preferably an aryl group condensed with a cycloalkane, more preferably 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl or 1,1,3,3-tetramethyl-2,3-dihydro-1H-inden-5-yl.

[0158] In addition, R of "C(-R)2" and R in "Si(-R)2" are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two Rs of the aforementioned C(-R)2 and the aforementioned Si(-R)2 are optionally bonded to each other to form a ring. In this case, at least one of the substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl constituting R of the aforementioned "C(-R)2" and R in "Si(-R)2" is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally replaced with -O-.

[0159] In addition, the R of the aforementioned NR and / or the R of the aforementioned C(-R)2 can also be connected to the a ring and / or b ring, or to the a ring and / or c ring through a linking group. 2 Ring bonding.

[0160] Among them, X 1 and X 2 At least one of them is NR, in which case R of the NR is a group represented by formula (G-1), preferably X 1 and X 2 One of them is NR (the aforementioned R is a group represented by formula (G-1)), and the other is NR (the aforementioned R of NR is an aryl group substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, an aryl group condensed by a cycloalkane, a heteroaryl group condensed by a cycloalkane, or a group represented by formula (G-1)), and more preferably X 1 and X 2 One of them is NR (the aforementioned R is a group represented by formula (G-1)), and the other is NR (the aforementioned R of NR is an aryl group substituted by an alkyl group, an aryl group condensed by a cycloalkane, or a group represented by formula (G-1)), and further preferably X 1 and X 2 One of them is NR (the aforementioned R is a group represented by formula (G-1)), and the other is NR (the aforementioned R of NR is an aryl group substituted by an alkyl group or an aryl group condensed by a cycloalkane).

[0161]

[0162] In the above formula (G-1), R d1 ~R d10and each independently represents hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl.

[0163] Furthermore, two adjacent R d1 ~R d10 They are optionally bonded to each other to form a cycloalkane condensed structure, and at least one hydrogen in the cycloalkane is optionally substituted.

[0164] In one embodiment, R d1 ~R d10 Each of them is independently preferably hydrogen, alkyl, or substituted or unsubstituted aryl, more preferably substituted or unsubstituted phenyl or alkyl, further preferably alkyl, particularly preferably methyl, tert-butyl, or tert-pentyl, and most preferably tert-butyl.

[0165] The two aryl groups of the aforementioned diarylamino group are optionally bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino group are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino group are optionally bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboron group are optionally bonded to each other via a linking group.

[0166] Among them, R d6 ~R d10 At least one of them is an alkyl group, or two adjacent R d6 ~R d10 bonded to each other to form a cycloalkane condensed structure, preferably R d7 ~R d9 At least one of them is an alkyl group, or two adjacent R d7 ~R d9 bonded to each other to form a cycloalkane condensed structure, more preferably R d7 ~R d9 At least one of R is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-amyl, or tert-butyl, or two adjacent R d7 ~R d9 Forming a cyclopentane condensed structure or a cyclohexane condensed structure, further preferably R d7 ~R d9 At least one of them is a methyl group or a tert-butyl group, or two adjacent R d7 ~R d9 A cyclohexane-fused structure is formed.

[0167] Between two adjacent R d7 ~Rd9 When a cyclopentane-condensed structure or a cyclohexane-condensed structure is formed, Formula G-1 is represented by the following formula.

[0168]

[0169] R d1 ~R d5 Any one of them is a bond to the nitrogen atom, preferably R d2 or R d3 is a bond to the nitrogen atom, more preferably R d2 is the bond to the nitrogen atom.

[0170] In one embodiment, the formula (G-1) is preferably a group represented by any of the formulas (G-2) to (G-21).

[0171]

[0172] In the above formulas (G-2) to (G-21), R 1 are each independently an alkyl group.

[0173] The alkyl group is preferably an alkyl group having 1 to 24 carbon atoms. The "alkyl group having 1 to 24 carbon atoms" may be either linear or branched, and examples thereof include linear alkyl groups having 1 to 24 carbon atoms, 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). Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, tert-amyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0174] As R 1, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, tert-pentyl, more preferably methyl, isopropyl, tert-butyl, tert-pentyl, further preferably methyl, tert-butyl, particularly preferably tert-butyl.

[0175] R 2 are each independently hydrogen or alkyl.

[0176] Examples of the alkyl group include 1 Same alkyl group.

[0177] As R 2 , preferably hydrogen, methyl, ethyl, propyl, isopropyl, more preferably hydrogen, methyl, ethyl, further preferably hydrogen, methyl, particularly preferably methyl.

[0178] Formula (G-1) is more preferably formula (G-2) to (G-7), formula (G-9) to (G-14), or formula (G-15) to (G-21), more preferably formula (G-4) to (G-7), formula (G-10), formula (G-13), or formula (G-15) to (G-19), and even more preferably formula (G-4) to (G-7), or formula (G-15) to (G-19). In this case, R 1 and R 2 As mentioned above, R 1 Preferred are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, di-tert-butylphenyl, tri-tert-butylphenyl, more preferably methyl, isopropyl, tert-butyl, tert-amyl, phenyl, further preferably methyl, tert-butyl, and particularly preferably tert-butyl. 2 Preferred are hydrogen, methyl, ethyl, propyl, and isopropyl, more preferred are hydrogen, methyl, and ethyl, further preferred are hydrogen and methyl, and particularly preferred is methyl.

[0179] <Specific Description of Ring and Substituent>

[0180] Next, details of the rings and substituents (including, in addition to the first substituent, a second substituent that further replaces the first substituent) listed in the descriptions thus far will be summarized and described.

[0181] The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or an aryl ring having 6 to 10 carbon atoms.

[0182] Specific examples of the "aryl ring" include a benzene ring as a monocyclic ring system, a naphthalene ring or an indene ring as a fused bicyclic ring system, an acenaphthene ring, a fluorene ring, a phenanthren ring, an anthracene ring or a 9,10-dihydroanthracene ring as a fused tricyclic ring system, a triphenylene ring, a pyrene ring or a tetracene ring as a fused tetracyclic ring system, or a perylene ring or a pentacene ring as a fused pentacyclic ring system.

[0183] It should be noted that at least one hydrogen atom of the “aryl ring” may be optionally substituted with 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, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group, as described below.

[0184] For example, examples of the aryl ring in which at least one hydrogen is replaced include dimethylfluorene ring, dimethylbenzofluorene ring and dimethylindene ring in which two hydrogen atoms of the methylene groups in the fluorene ring, benzofluorene ring and indene ring are replaced by methyl groups; and 9,9,10,10-tetramethyl-9,10-dihydroanthracene ring in which four hydrogen atoms of the two methylene groups in the 9,10-dihydroanthracene ring are replaced by methyl groups.

[0185] The “heteroaryl ring” includes, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, or a heteroaryl ring having 2 to 10 carbon atoms. Furthermore, the “heteroaryl ring” includes, for example, a heterocyclic ring containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring atoms.

[0186] Specific “heteroaryl rings” include, for example, pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, oxadiazole, thiadiazole, triazole, tetrazole, pyrazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, isoindole, 1H-indazole, benzimidazole, benzoxazole, benzothiazole, 1H-benzotriazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, phenanthroline, phthalazine, naphthyridine, purine, pteridine, carbazole, acridine, phenoxathiazole, phenoxazine, phenothiazine, phenazine, silaacridine (ph)

[0065] The present invention also includes an oxazolidinone) ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a naphthobenzofuran ring, a xanthene ring, a thiophene ring, a benzothiophene ring, an isobenzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a thioxanthene ring, a benzophosphole ring, a dibenzophosphole ring, a benzophosphole oxide ring, a dibenzophosphole oxide ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzindolocarbazole ring, a benzobenzindolocarbazole ring, an imidazoline ring, or an oxazoline ring.

[0187] It should be noted that at least one hydrogen atom of the “heteroaryl ring” may be optionally substituted by 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, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group, as described below.

[0188] For example, as the heteroaryl ring in which at least one hydrogen is substituted, there can be mentioned a 9-(phenyl, methyl, cyclohexyl, adamantyl, 3,5-dimethyl-1-adamantyl)carbazole ring in which the hydrogen at the 9-position of the carbazole ring is substituted by a phenyl, methyl, cyclohexyl, adamantyl, or 3,5-dimethyl-1-adamantyl group; and a dimethyldihydroacridine ring, a dimethylxanthene ring, or a dimethylthioxanthene ring in which two hydrogen atoms of the methylene groups in the acridine ring, the xanthene ring, or the thioxanthene ring are substituted by methyl groups.

[0189] The "aryl group" is, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 16 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

[0190] Specific examples of "aryl" include phenyl as a monocyclic ring system, biphenyl (2-biphenyl, 3-biphenyl, or 4-biphenyl) as a bicyclic ring system, naphthyl (1-naphthyl or 2-naphthyl) as a fused bicyclic ring system, or indenyl (2-indenyl, 3-indenyl, 4-indenyl, 5-indenyl, 6-indenyl, or 7-indenyl), terphenyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl) as a tricyclic ring system, 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), acenaphthene-( 1-, 3-, 4-, or 5-) yl, fluoren-(1-, 2-, 3-, 4-, or 9-) yl), phenanthren-(1-, 2-, 3-, 4-, or 9-) yl, or 9,10-dihydroanthracen-(1-, 2-, 3-, 4-, 5-, 6-, 7-, or 8-) yl, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl) as a tetracyclic ring system '-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), as a fused tetracyclic ring system, a triphenylene-(1- or 2-) group, a pyrene-(1-, 2-, or 4-) group, or a naphthoxy-(1-, 2-, or 5-) group, or as a fused pentacyclic ring system, a perylene-(1-, 2-, or 3-) group, or a pentacene-(1-, 2-, 5-, or 6-) group, etc.

[0191] Furthermore, a "substituted aryl group" is a structure in which at least one hydrogen atom in the aryl group is replaced by a substituent described below. For example, a "substituted aryl group" includes a structure in which the above-mentioned aryl group is substituted by an aryl group such as a phenyl group (specific examples include the above groups), an alkyl group such as a methyl group (specific examples include the groups described below), or a cycloalkyl group such as a cyclohexyl group or an adamantyl group (specific examples include the groups described below). It should be noted that a substituted aryl group substituted by an alkyl group is sometimes specifically referred to as an "alkyl-substituted aryl group."

[0192] Specific examples of "substituted aryl" include dimethylfluorenyl, dimethylbenzofluorenyl and dimethylindenyl, in which two hydrogen atoms of the methylene groups in fluorenyl, benzofluorenyl and indenyl are substituted with methyl groups; and 9,9,10,10-tetramethyl-9,10-dihydroanthracene, in which four hydrogen atoms of two methylene groups in 9,10-dihydroanthracenyl are substituted with methyl groups.

[0193] The "arylene group (ring)" is, for example, an arylene group having 6 to 30 carbon atoms, preferably an arylene group having 6 to 20 carbon atoms, an arylene group having 6 to 16 carbon atoms, an arylene group having 6 to 12 carbon atoms, or an arylene group having 6 to 10 carbon atoms.

[0194] Specific examples of the "arylene group" include a structure in which one hydrogen atom is removed from the above-mentioned "aryl group" (monovalent group) to form a divalent group.

[0195] The "heteroaryl group" includes, for example, a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms. Furthermore, the "heteroaryl group" includes, for example, a monovalent group such as a heterocyclic ring containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0196] Specific examples of the "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, silaacridinyl, indolizinyl, and furyl. , benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, xanthene, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, thioxanthene, benzophosphocyclopentadienyl, dibenzophosphocyclopentadienyl, a monovalent group of a benzophosphocyclopentadienyl oxide ring, a monovalent group of a dibenzophosphocyclopentadienyl oxide ring, furazanyl, thianthrenyl, indolecarbazolyl, benzindolecarbazolyl, benzobenzindolecarbazolyl, imidazolinyl, oxazolinyl or dibenzosilacyclopentadienyl (Dibenzosilacyclopentadienyl), etc.

[0197] Furthermore, a "substituted heteroaryl group" is a structure in which at least one hydrogen atom in the heteroaryl group is replaced by a substituent described below. For example, a "substituted heteroaryl group" includes a structure in which the above-mentioned heteroaryl group is substituted by an aryl group such as a phenyl group (specific examples include the above-mentioned groups), an alkyl group such as a methyl group (specific examples include the groups described below), or a cycloalkyl group such as a cyclohexyl group or an adamantyl group (specific examples include the groups described below).

[0198] Specific examples of "substituted heteroaryl" include: 9-(phenyl, methyl, cyclohexyl or adamantyl)carbazolyl, in which the hydrogen at the 9-position of the carbazolyl is substituted by a phenyl, methyl, cyclohexyl or adamantyl group; and dimethyldihydroacridinyl, dimethylxanthenyl, and dimethylthioxanthenyl, in which two hydrogen atoms of the methylene group in the acridinyl, xanthenyl or thioxanthenyl group are substituted by methyl groups.

[0199] The "heteroarylene group (ring)" is, for example, a heteroarylene group having 2 to 30 carbon atoms, preferably a heteroarylene group having 2 to 25 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, a heteroarylene group having 2 to 15 carbon atoms, or a heteroarylene group having 2 to 10 carbon atoms. Furthermore, the "heteroarylene group" is, for example, a divalent group such as a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring atoms.

[0200] Specific examples of the "heteroarylene group" include a structure in which one hydrogen atom is removed from the above-mentioned "heteroaryl group" (monovalent group) to form a divalent group.

[0201] "Diarylamino" and "substituted diarylamino" are amino groups substituted with two aryl groups. For details of the aryl groups, the description of the above-mentioned "aryl group" and "substituted aryl group" can be cited.

[0202] "Diheteroarylamino" and "substituted diheteroarylamino" are amino groups substituted with two heteroaryl groups. For details of the heteroaryl group, the description of the above-mentioned "heteroaryl" and "substituted heteroaryl" can be cited.

[0203] "Arylheteroarylamino" and "substituted aryldiheteroarylamino" are amino groups substituted with aryl and heteroaryl groups, and the descriptions of the above-mentioned "aryl", "heteroaryl", "substituted aryl" and "substituted heteroaryl" can be cited for details of the aryl and heteroaryl groups.

[0204] The two aryl groups of "diarylamino" are optionally bonded via a linking group, the two heteroaryl groups of "diheteroarylamino" are optionally bonded via a linking group, and the aryl and heteroaryl groups of "arylheteroarylamino" are optionally bonded via a linking group. Examples of the linking group include a single bond, an alkylene group, an alkenylene group, an alkynylene group, -N(-R)-, -O-, -S-, -Si(-R)2-, or -Se-. In one embodiment, the linking group is preferably a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. It should be noted that the R of the aforementioned "-CHR-CHR-", the R of "-CR2-CR2-", the R of "-CR=CR-", the R of "-N(-R)-", the R of "-C(-R)2-", and the R of "-Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is optionally substituted by an alkyl or cycloalkyl. In addition, two adjacent Rs in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-C(-R)2-" and "-Si(-R)2-" are optionally bonded to each other to form a cycloalkylene ring, an arylene ring and a heteroarylene ring. For details of the substituents listed here, the above-mentioned descriptions of "aryl", "substituted aryl", "arylene", "heteroaryl", "substituted heteroaryl" and "heteroarylene", as well as the descriptions of "alkyl", "alkylene", "alkenyl", "alkenylene", "alkynyl", "alkynylene", "cycloalkyl" and "cycloalkylene" described later can be cited.

[0205] The "diarylboryl group" and the "substituted diarylboryl group" are boryl groups substituted with two aryl groups. For details of the aryl groups, the description of the above-mentioned "aryl group" and "substituted aryl group" can be cited.

[0206] The two aryl groups of the "diarylboryl" group are optionally bonded via a linking group. Examples of the linking group include a single bond, an alkylene group, an alkenylene group, an alkynylene group, -N(-R)-, -O-, -S-, -Si(-R)2-, or -Se-. In one embodiment, the linking group is preferably a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. It should be noted that the R of the aforementioned “-CHR-CHR-”, the R of “-CR2-CR2-”, the R of “-CR=CR-”, the R of “-N(-R)-”, the R of “-C(-R)2-”, and the R of “-Si(-R)2-” are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is optionally substituted by an alkyl or cycloalkyl. In addition, two adjacent Rs in “-CHR-CHR-”, “-CR2-CR2-”, “-CR=CR-”, “-C(-R)2-” and “-Si(-R)2-” can be bonded to each other to form a cycloalkylene ring, an arylene ring and a heteroarylene ring. For details of the substituents listed here, the above-mentioned descriptions of "aryl", "substituted aryl", "arylene", "heteroaryl", "substituted heteroaryl" and "heteroarylene", as well as the descriptions of "alkyl", "alkylene", "alkenyl", "alkenylene", "alkynyl", "alkynylene", "cycloalkyl" and "cycloalkylene" described later can be cited.

[0207] The "alkyl group" may be any of a straight chain and a branched chain, for example, a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms), etc.

[0208] Specific examples of “alkyl” include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-amyl, 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl or n-eicosyl, etc.

[0209] Furthermore, a "substituted alkyl group" is a structure in which at least one hydrogen atom in the alkyl group is replaced by a substituent described below.

[0210] The "alkylene group" may be any of a straight chain and a branched chain, for example, a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms), etc.

[0211] Specific examples of the "alkylene group" include a structure in which one hydrogen atom is removed from the above-mentioned "alkyl group" (monovalent group) to form a divalent group.

[0212] Regarding "alkenyl" and "substituted alkenyl", reference can be made to the above description of "alkyl" and "substituted alkyl". These are groups in which the C-C single bond in the structure of "alkyl" and "substituted alkyl" is replaced by a C=C double bond, and include not only one but also two or more groups in which single bonds are replaced by double bonds (also called diene-group, triene-group).

[0213] Regarding the "alkenylene group", the description of the "alkylene group" mentioned above can be referred to, and examples thereof include a structure in which one hydrogen atom is removed from an "alkenyl group" (monovalent group) to form a divalent group.

[0214] Regarding "alkynyl" and "substituted alkynyl", reference can be made to the description of "alkyl" and "substituted alkyl" above. These are groups in which the C-C single bond in the structure of "alkyl" and "substituted alkyl" is replaced by a C≡C triple bond, and include not only one but also two or more single bonds replaced by triple bonds (also called dialkynyl, trialkynyl).

[0215] Regarding the "alkynylene group", the description of the above-mentioned "alkylene group" can be referred to, and examples thereof include a structure in which one hydrogen atom is removed from the above-mentioned "alkynyl group" (monovalent group) to form a divalent group.

[0216] The “cycloalkyl group” is, for example, a cycloalkyl group having 3 to 24 carbon atoms, preferably a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, or a cycloalkyl group having 5 carbon atoms.

[0217] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, 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, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, or decahydroazulyl, or alkyl (particularly methyl)-substituted groups thereof having 1 to 5 carbon atoms or 1 to 4 carbon atoms.

[0218] Furthermore, a "substituted cycloalkyl group" is a structure in which at least one hydrogen atom in the cycloalkyl group is replaced by a substituent described below.

[0219] “Cycloalkylene (ring)” is, for example, a cycloalkylene group having 3 to 24 carbon atoms, preferably a cycloalkylene group having 3 to 20 carbon atoms, a cycloalkylene group having 3 to 16 carbon atoms, a cycloalkylene group having 3 to 14 carbon atoms, a cycloalkylene group having 3 to 12 carbon atoms, a cycloalkylene group having 5 to 10 carbon atoms, a cycloalkylene group having 5 to 8 carbon atoms, a cycloalkylene group having 5 to 6 carbon atoms, or a cycloalkylene group having 5 carbon atoms.

[0220] Specific examples of the "cycloalkylene group" include a structure in which one hydrogen atom is removed from the above-mentioned "cycloalkyl group" (monovalent group) to form a divalent group.

[0221] The "alkoxy group" may be any of a straight chain and a branched chain, for example, a straight chain alkoxy group having 1 to 24 carbon atoms or a branched chain alkoxy group having 3 to 24 carbon atoms, preferably an alkoxy group having 1 to 18 carbon atoms (a branched chain alkoxy group having 3 to 18 carbon atoms), an alkoxy group having 1 to 12 carbon atoms (a branched chain alkoxy group having 3 to 12 carbon atoms), an alkoxy group having 1 to 6 carbon atoms (a branched chain alkoxy group having 3 to 6 carbon atoms), an alkoxy group having 1 to 5 carbon atoms (a branched chain alkoxy group having 3 to 5 carbon atoms), an alkoxy group having 1 to 4 carbon atoms (a branched chain alkoxy group having 3 to 4 carbon atoms), etc.

[0222] Specific examples of "alkoxy" include methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2-trimethylpropoxy, 1,1,2,2-tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1-diethylbutoxy, 1-ethyl-1-methylbutoxy, 1-propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n-pentoxy, isopentoxy, neopentoxy, t-amyloxy, 1-methylpentoxy, 2-propylpentoxy, 1,1-dimethylpentoxy, 1-ethyl-1-methylpentoxy, 1 -propyl-1-methylpentyloxy, 1-butyl-1-methylpentyloxy, 1,1,4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1,1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1,5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, n-octyloxy, tert-octyloxy (1,1,3,3-tetramethylbutyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy, etc.

[0223] Furthermore, a "substituted alkoxy group" is a structure in which at least one hydrogen atom in the alkoxy group is substituted with a substituent group described below.

[0224] "Aryloxy" and "substituted aryloxy" are groups represented by "Ar-O-(Ar is an aryl group)", and the description of the above-mentioned "aryl" and "substituted aryl group" can be cited for details of the aryl group.

[0225] "Arylthio" and "substituted arylthio" are groups represented by "Ar-S-(Ar is an aryl group)". For details of the aryl group, the description of the above-mentioned "aryl" and "substituted aryl group" can be cited.

[0226] The "substituted silyl group" is, for example, a silyl group substituted with at least one of an aryl group, an alkyl group, and a cycloalkyl group, and is preferably a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, or an alkyldicycloalkylsilyl group.

[0227] The "triarylsilyl group" is a silyl group substituted with three aryl groups. For details of the aryl group, the description of the above-mentioned "aryl group" and "substituted aryl group" can be cited.

[0228] Specific examples of the “triarylsilyl group” include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

[0229] The "trialkylsilyl group" is a silyl group substituted with three alkyl groups. For details of the alkyl group, the description of the above-mentioned "alkyl group" and "substituted alkyl group" can be referred to.

[0230] Specific examples of the “trialkylsilyl group” include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, methyldiethylsilyl, n- Propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, sec-butyldi-n-propylsilyl, tert-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, sec-butyldiisopropylsilyl, or tert-butyldiisopropylsilyl, etc.

[0231] The "tricycloalkylsilyl group" is a silyl group substituted with three cycloalkyl groups. For details of the cycloalkyl group, the description of the above-mentioned "cycloalkyl group" and "substituted cycloalkyl group" can be cited.

[0232] Specific examples of the "tricycloalkylsilyl group" include tricyclopentylsilyl and tricyclohexylsilyl groups.

[0233] The "dialkylcycloalkylsilyl group" is a silyl group substituted with two alkyl groups and one cycloalkyl group. For details of the alkyl group and the cycloalkyl group, the above descriptions of the "alkyl group", "substituted alkyl group", "cycloalkyl group" and "substituted cycloalkyl group" can be cited.

[0234] The "alkyldicycloalkylsilyl group" is a silyl group substituted with one alkyl group and two cycloalkyl groups. For details of the alkyl group and the cycloalkyl group, the above descriptions of the "alkyl group", "substituted alkyl group", "cycloalkyl group" and "substituted cycloalkyl group" can be cited.

[0235] The substituents (including the first substituent and the second substituent) affect the emission wavelength of the polycyclic aromatic compound due to the steric hindrance, electron donating property and electron attracting property of the structure, so the emission wavelength can be adjusted by the selection of the substituents. Preferably, the group shown in the following structural formula is methyl, tert-butyl, bicyclooctyl, cyclohexyl, adamantyl, dimethyladamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, diphenylboryl, di-mesitylboryl, dibenzo[b,e][1,4]oxaborininyl, benzene Preferably, the present invention comprises a phenyldibenzo[b,e][1,4]diborinyl, a carbazolyl, a 3,6-dimethylcarbazolyl, a 3,6-di-tert-butylcarbazolyl and a phenoxy group, and more preferably a methyl group, a tert-butyl group, a phenyl group, an o-tolyl group, a 2,6-xyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl, a 3,6-dimethylcarbazolyl, a 3,6-di-tert-butylcarbazolyl and a tribenzoazetidinyl group. From the viewpoint of ease of synthesis, when steric hindrance is large, it is preferred for selective synthesis. Specifically, tert-butyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-tert-butylcarbazolyl are preferred.

[0236] In the following structural formulae, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-amyl group, "tOct" represents a tert-octyl group, and * represents a bonding position.

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248] <Description of Polycyclic Aromatic Compound Multimers>

[0249] In addition, the present invention is a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (A-1). The multimer is preferably a 2-6-mer, more preferably a 2-3-mer, and particularly preferably a 2-mer. The multimer can be any form having a plurality of the above-mentioned unit structures in one compound. For example, in addition to a form in which the above-mentioned unit structures are bonded to multiple units by a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, or the like (a bonded multimer), any ring (a ring, b ring, c ring) contained in the above-mentioned unit structure can also be shared by multiple unit structures. 1 Ring, or c 2 In addition, any ring (a ring, b ring, c ring) contained in the above unit structure may be bonded in a form (ring-sharing multimer). 1 Ring, or c 2 The form in which the two rings are bonded to each other in a fused manner (ring-fused multimer) is preferably a ring-sharing multimer and a ring-fused multimer, and more preferably a ring-sharing multimer.

[0250] As such a multimer, for example, a multimer compound represented by the following formula (M2-A-1-b1) to (M2-A-1-b3) or formula (M3-A-1-b1) can be mentioned. The multimer compound represented by the following formula (M2-A-1-b1) to (M2-A-1-b3) is a multimer compound having two unit structures represented by formula (A-1) in a manner that shares a benzene ring as the b-ring in one compound structure of formula (A-1) (ring-sharing multimer). In addition, the multimer compound represented by the following formula (M3-A-1-b1) is a multimer compound having three unit structures represented by formula (A-1) in a manner that shares a benzene ring as the b-ring in one compound structure of formula (A-1) (ring-sharing multimer).

[0251]

[0252] The multimeric compound can be a multimer formed by combining the multimerization form represented by any one of formulas (M2-A-1-b1) to (M2-A-1-b3) or formula (M3-A-1-b1) with other multimerization forms, or a multimerization form represented by any one of formulas (M2-A-1-b1) to (M2-A-1-b3) with the multimerization form represented by formula (M3-A-1-b1), or a multimerization form represented by any one of formulas (M2-A-1-b1) to (M2-A-1-b3) with the multimerization form represented by formula (M3-A-1-b1) and other multimerization forms.

[0253] <Explanation of Cycloalkane Condensation>

[0254] In addition, at least one of the aromatic ring and the heteroaromatic ring in the chemical structure of the polycyclic aromatic compound of the present invention may be condensed with at least one cycloalkane.

[0255] For example, ring a, ring b, ring c 2 rings, aryl groups (substituted or unsubstituted aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or the aryl portion of a substituted or unsubstituted triarylsilyl group) and heteroaryl groups (substituted or unsubstituted heteroaryl, substituted or unsubstituted diheteroarylamino, or the heteroaryl portion of a substituted or unsubstituted arylheteroarylamino) as the first and second substituents on these rings, and Y as 1 R of "Si-R" and R of "Ge-R" are substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, as X 1 or X 2At least one of the R of "NR" (including formula (G-1)), the R of "Si-R", and the R of "Ge-R" which is an alkyl-substituted aryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group is optionally fused with at least one cycloalkane.

[0256] Preferably, ring b, c 2 Ring, these rings or as in a ring, b ring, c 2 The aryl group (substituted or unsubstituted aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted aryloxy, or the aryl portion of a substituted or unsubstituted arylthio group) and heteroaryl group (substituted or unsubstituted heteroaryl, or the heteroaryl portion of a substituted or unsubstituted heteroarylamino group) of the first substituent on the ring, the b ring and the c ring 2 A substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring formed by bonding adjacent substituents in the ring, as X 1 or X 2 At least one of the R of "NR" (including formula (G-1)) is an alkyl-substituted aryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, which may be fused with at least one cycloalkane. In addition, R in the above formulas (A-1) to (A-36), formulas (M2-A-1-b1) to (M2-A-1-b3), and formula (M3-A-1-b1) a1 ~R a3 At least one of the aryl groups is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, or a heteroaryl group is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, but the aryl group or the heteroaryl group may also be condensed with at least one cycloalkane.

[0257] More preferably, ring b, ring c 2 Ring, these rings or as in a ring, b ring, c 2 The aryl group (substituted or unsubstituted aryl group or aryl moiety in substituted or unsubstituted diarylamino group) and heteroaryl group (heteroaryl moiety in substituted or unsubstituted heteroaryl group) of the first substituent on the ring, the substituted or unsubstituted aryl ring formed by bonding adjacent substituents in the b ring and the c ring, as X 1 or X 2At least one of the alkyl-substituted aryl groups, substituted or unsubstituted aryl groups of R (including formula (G-1)) of "NR" may be condensed with at least one cycloalkane. In addition, R in the above formulas (A-1) to (A-12), formulas (M2-A-1-b1) to (M2-A-1-b3), formula (M3-A-1-b1), the following formulas (A-1-b1) to (A-1-b22), and the following formulas (A-1-c1) to (A-1-c9) a1 ~R a3 At least one of the aryl groups is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, or a heteroaryl group is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, but the aryl or heteroaryl group may also be condensed with at least one cycloalkane.

[0258] In one embodiment, preferably as R a1 ~R a3 substituted aryl and substituted heteroaryl, more preferably as R a2 substituted aryl and substituted heteroaryl, and preferably as R a2 The substituted aryl group is optionally fused with at least one cycloalkane, and at least one hydrogen in the cycloalkane is optionally substituted.

[0259] In one embodiment, preferably, an aryl group substituted with an alkyl group, a substituted or unsubstituted heteroaryl group, more preferably an aryl group substituted with an alkyl group as R of NR is optionally fused with at least one cycloalkane, and at least one hydrogen in the cycloalkane is optionally substituted.

[0260] Examples of the “cycloalkanes” include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0261] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, 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 decahydroazulene, as well as alkyl (particularly methyl)-substituted, halogen (particularly fluorine)-substituted and deuterium-substituted products thereof having 1 to 5 carbon atoms.

[0262] Among these, preferred are structures represented by the following structural formulas (Cy-A) to (Cy-D), wherein at least one hydrogen atom at the α-position of a cycloalkane (in a cycloalkyl group fused to an aromatic ring or heteroaromatic ring, the carbon atom adjacent to the carbon atom at the fusion site) is substituted. More preferred are structures wherein two hydrogen atoms at the α-position are substituted, and even more preferred are structures wherein a total of four hydrogen atoms at the two α-positions are substituted. Examples of such substituents include alkyl groups (particularly methyl groups) having 1 to 5 carbon atoms, halogen groups (particularly fluorine groups), and deuterium groups.

[0263] In addition, in formula (Cy-A), formula (Cy-B), formula (Cy-C), and formula (Cy-D), the embodiment in which the benzene ring is condensed with the cycloalkane is exemplified, but the same applies to an aryl ring or a heteroaryl ring other than the benzene ring.

[0264]

[0265] The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are fused to one benzene ring (phenyl). In each structural formula, * refers to a benzene ring contained in the skeletal structure of the compound in the case of a benzene ring, and refers to a connecting bond substituted in the skeletal structure of the compound in the case of a phenyl group. Cycloalkanes fused as in formula (Cy-1-4) and formula (Cy-2-4) may also be fused to each other. This is also true even when the ring (group) to be fused is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), and the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0266]

[0267] At least one -CH2- in the cycloalkane can be replaced by -O-. Among them, when multiple -CH2- are replaced by -O-, the adjacent -CH2- will not be replaced by -O-. For example, the following shows an example in which one or more -CH2- in a cycloalkane fused to one benzene ring (phenyl) is replaced by -O-. In each structural formula, * refers to the benzene ring contained in the skeletal structure of the compound in the case of a benzene ring, and refers to the connecting bond substituted in the skeletal structure of the compound in the case of a phenyl group. Even in the case where the fused ring (group) is an aromatic ring or heteroaromatic ring other than the benzene ring (phenyl), the same applies when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0268]

[0269] At least one hydrogen in the cycloalkane is optionally substituted. Examples of the substituent include 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, a substituted or unsubstituted diarylboronyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted silyl group, a cyano group, or a halogen group. The two aryl groups in the diarylamino group may be bonded via a linking group, the two heteroaryl groups in the diheteroarylamino group may be bonded via a linking group, the aryl group and the heteroaryl group in the arylheteroarylamino group may be bonded via a linking group, and the two aryl groups in the diarylboronyl group may be bonded via a linking group. For details of these substituents, reference can be made to the description of the first substituent described above. Among these substituents, an alkyl group (for example, an alkyl group having 1 to 6 carbon atoms), a cycloalkyl group (for example, a cycloalkyl group having 3 to 14 carbon atoms), a halogen group (for example, a fluorine group), and the like are preferred.

[0270] In addition, in the case of cycloalkyl substitution, the substitution may be in the form of a spiro structure. For example, the following example shows an example of a spiro structure formed on a cycloalkane fused to a benzene ring (phenyl). In each structural formula, * refers to a benzene ring included in the skeletal structure of the compound in the case of a benzene ring, and refers to a bond that is substituted in the skeletal structure of the compound in the case of a phenyl group.

[0271]

[0272] As other forms of cycloalkane fusion, examples include polycyclic aromatic compounds represented by formula (A-1) substituted with, for example, a diarylamino group fused with a cycloalkane (fused to the aryl moiety), a carbazolyl group fused with a cycloalkane (fused to the benzene ring moiety), or a benzocarbazolyl group fused with a cycloalkane (fused to the benzene ring moiety). The "diarylamino group" includes the groups described above as the "first substituent."

[0273] As a more specific example, R in the polycyclic aromatic compound represented by formula (A-1) can be cited. b1 ~R b3 、R c2 ~R c3 (especially relative to Y 1 R b2 、R c2 ) is an example of a diarylamino group fused with a cycloalkane (fused to the aryl portion) or a carbazolyl group fused with a cycloalkane (fused to the benzene ring portion).

[0274] <Explanation of Cyano or Halogen Substitution>

[0275] At least one hydrogen in the polycyclic aromatic compound of the present invention is optionally substituted by a cyano group or a halogen. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and most preferably fluorine.

[0276] <Explanation of Isotope Replacement>

[0277] Each element in the unit structure of the polycyclic aromatic compound represented by formula (A-1) and its polymer contains multiple naturally occurring isotopes in a natural existence ratio unless otherwise specified. However, at least one atom of the element in each structural formula may also contain a heavy stable isotope in excess of the naturally occurring ratio (for example, more than 90 atom%). In this specification, it is referred to as "replaced with" a "heavy stable isotope". More specifically, at least one hydrogen can be replaced with deuterium, and at least one nitrogen can be replaced with nitrogen-15( 15 N), at least one sulfur can be replaced with sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36( 36 S), at least one oxygen can be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be replaced by carbon-13 ( 13 C), at least one boron can be replaced by boron-11 ( 11 B). The same applies to the structures represented by formulas (A-1-a1) to (A-1-a13), (A-1-b1) to (A-1-b22), (A-1-c1) to (A-1-c9), (A-1-d1) to (A-1-d2), (A-2) to (A-70), etc. The following description also applies to the unit structures of the polycyclic aromatic compounds and their polymers represented by the above formulas. By replacing at least a part of the elements with heavy stable isotopes, in particular by replacing at least one boron with boron-11 ( 11 B) It is possible to achieve enhanced performance of an organic electroluminescent device using a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (A-1) as a dopant.

[0278] In one embodiment, in the compound or unit structure represented by the aforementioned formula (A-1), at least one hydrogen is optionally replaced by deuterium, and at least one nitrogen is optionally replaced by nitrogen-15( 15 N), at least one sulfur is optionally replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36( 36 S), at least one oxygen is optionally replaced with oxygen-17 ( 17 O) or oxygen-18 ( 18O), at least one carbon is optionally replaced with a carbon-13 ( 13 C), at least one boron is optionally replaced with boron-11 ( 11 B).

[0279] The unit structure of the polycyclic aromatic compound represented by formula (A-1) or its polymer is preferably selected from deuterium, nitrogen-15( 15 N), sulfur-33( 33 S), sulfur-34 ( 34 S), sulfur-36 ( 36 S), oxygen-17 ( 17 O), oxygen-18 ( 18 O), carbon-13 ( 13 C) and boron-11( 11 B), more preferably replaced by at least one selected from the group consisting of deuterium, nitrogen-15 ( 15 N) and boron-11( 11 B) is replaced, more preferably replaced by deuterium. It should be noted that, in this specification, the replacement of hydrogen with deuterium is sometimes referred to as "substitution of hydrogen for deuterium" or "deuteration". That is, in one embodiment, at least one hydrogen in the unit structure of the polycyclic aromatic compound represented by formula (A-1) or its multimer is optionally replaced by deuterium.

[0280] In the description of the unit structure of the polycyclic aromatic compound represented by formula (A-1) or its multimer, when boron is represented by "B" or "boron", unless otherwise specified, it means that the synthesis is carried out using raw materials having an isotope ratio of the element at the naturally occurring ratio.

[0281] In contrast, in 11 When the mass number of an element is clearly stated as in "B", it refers to a compound synthesized using a raw material with an artificially increased abundance ratio of the target element as a raw material related to the element, or a compound synthesized using a raw material with an artificially increased abundance ratio of the target element in the synthesized compound, subjected to heavy stable isotope substitution. The same applies to other elements such as hydrogen, nitrogen, sulfur, oxygen, or carbon.

[0282] Furthermore, in the unit structure of the polycyclic aromatic compound or its multimer of the present invention, when the specific mass number of the element is not explicitly stated, even if the isotope ratio of at least one atom in the polycyclic aromatic compound molecule is any ratio different from the natural ratio, it is also included in the present invention.

[0283] In one embodiment, when replacing heavy stable isotopes, it is preferred that the isotope ratio is high. For example, when replacing boron-11 ( 11 In case of B), 11The isotope ratio of B is preferably 90atom% or more. In addition, when replaced with deuterium (D), the isotope ratio of D is preferably 40atom% or more, more preferably 60atom% or more, further preferably 80atom% or more, and most preferably 90atom% or more. It should be noted that, in the case of being replaced with multiple deuteriums (D) in the polycyclic aromatic compound of the present invention, the deuteration rates of the respective deuterium atoms are sometimes different due to the starting materials and the reaction process. In this case, the isotope ratio of at least one (preferably two, more preferably 3, further preferably 4, particularly preferably 5 or more, and most preferably all) D is preferably 40atom% or more, more preferably 60atom% or more, further preferably 80atom% or more, and most preferably 90atom% or more. It should be noted that, in this specification, the isotope ratio can be measured by NMR.

[0284] <Description of Preferred Polycyclic Aromatic Compounds of the Present Invention>

[0285] In a preferred embodiment, formula (A-1) is preferably represented by any of the following formulas (A-1-a1) to (A-1-a13), (A-1-b1) to (A-1-b22), (A-1-c1) to (A-1-c9), and (A-1-d1) to (A-1-d2).

[0286]

[0287]

[0288]

[0289]

[0290] In formulas (A-1-a1) to (A-1-a13), (A-1-b1) to (A-1-b22), (A-1-c1) to (A-1-c9), and (A-1-d1) to (A-1-d2),

[0291] R a1 ~R a3 、R b1 ~R b4 、R c1 ~R c4 and R e1 ~R e5are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; the two aryl groups of the aforementioned diarylamino are optionally bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino are optionally bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboryl are optionally bonded to each other via a linking group.

[0292] And, R a1 ~R a3 、R b1 ~R b4 、R c1 ~R c4 and R e1 ~R e5 Two adjacent groups are optionally bonded to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed aryl ring or heteroaryl ring is optionally substituted by 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, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group; the two aryl groups in the aforementioned diarylamino group are optionally bonded to each other via a linking group, the two heteroaryl groups in the aforementioned diheteroarylamino group are optionally bonded to each other via a linking group, the aryl and heteroaryl groups in the aforementioned arylheteroarylamino group are optionally bonded to each other via a linking group, and the two aryl groups in the aforementioned diarylboryl group are optionally bonded to each other via a linking group.

[0293] Among them, R a1 ~R a3 At least one of is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted arylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group,

[0294] R is hydrogen, an aryl group substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a group represented by formula (G-1). In addition, the R of the aforementioned NR may be connected to the a ring and / or b ring, or to the a ring and / or c ring through a linking group. 2 Ring bonding,

[0295] Here, at least one of R is a group represented by formula (G-1).

[0296]

[0297] In the above formula (G-1),

[0298] R d1 ~R d10 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; the two aryl groups of the aforementioned diarylamino are optionally bonded to each other via a linking group, the two heteroaryl groups of the aforementioned diheteroarylamino are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the aforementioned arylheteroarylamino are optionally bonded to each other via a linking group, and the two aryl groups of the aforementioned diarylboryl are optionally bonded to each other via a linking group.

[0299] In addition, two adjacent R d1 ~R d10 optionally bonded to each other to form a cycloalkane condensed structure,

[0300] Among them, R d6 ~R d10 At least one of them is an alkyl group, or two adjacent Rd 6 ~Rd 10 Bonded to each other to form a cycloalkane condensed structure,

[0301] R d1 ~R d5 Any one of them is a bond to the nitrogen atom.

[0302] In formulae (A-1-a1) to (A-1-a13), (A-1-b1) to (A-1-b22), (A-1-c1) to (A-1-c9), and (A-1-d1) to (A-1-d2), ring a, ring b, and ring c are 2At least one of the rings, aryl rings or heteroaryl rings is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, at least one -CH2- in the cycloalkane is optionally replaced with -O-, and at least one hydrogen is optionally substituted with cyano or halogen.

[0303] In a more preferred embodiment, formula (A-1) is preferably represented by any of the following formulae (A-2) to (A-36), and more preferably represented by any of the following formulae (A-2) to (A-12).

[0304]

[0305]

[0306]

[0307]

[0308] In the above formulas (A-2) to (A-36), R a2 is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. In this case, the aryl ring of the substituted aryl group or the heteroaryl ring of the substituted heteroaryl group is optionally fused with at least one cycloalkane, and at least one hydrogen in the cycloalkane is optionally substituted, preferably optionally fused with A substituted aryl group substituted by a diarylamino group substituted by a methyl group, a tert-amyl group or a tert-butyl group, or a substituted aryl group substituted by an alkyl group, more preferably a substituted phenyl group substituted by a methyl group or a tert-butyldiarylamino group, or an alkyl group, further preferably a group represented by any of the following formulas (a1) to (a14) (* represents a bond to the a ring), particularly preferably the following formulas (a1), (a2), (a4), (a6), (a7), (a8), (a13) and (a14), most preferably formulas (a2), (a6), (a13) and (a14).

[0309]

[0310] R b2 and R b3Each of them is independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, preferably hydrogen or substituted or unsubstituted alkyl, more preferably one is hydrogen and the other is substituted or unsubstituted alkyl, further preferably one is hydrogen and the other is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, tert-pentyl, adamantyl, or 3,5-dimethyl-1-adamantyl, particularly preferably one is hydrogen and the other is methyl, tert-butyl, or tert-pentyl. In one embodiment, R b2 is hydrogen, R b3 In another embodiment, R b2 is methyl, tert-butyl, R b3 In another embodiment, R b2 is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted carbazolyl group, R b3 is hydrogen, preferably R b2 is a substituted or unsubstituted diarylamino group, R b3 For hydrogen.

[0311] R c2 and R c3 Each is independently an alkyl group, a substituted or unsubstituted cycloalkyl group, preferably one is hydrogen and the other is a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group, more preferably one is hydrogen and the other is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, tert-amyl, adamantyl, or 3,5-dimethyl-1-adamantyl, and even more preferably one is hydrogen and the other is methyl, tert-butyl, adamantyl, or 3,5-dimethyl-1-adamantyl. In one embodiment, R b2 is hydrogen, R b3 is methyl, tert-butyl, adamantyl, 3,5-dimethyl-1-adamantyl, preferably methyl or tert-butyl. b2 is methyl, tert-butyl, adamantyl, 3,5-dimethyl-1-adamantyl, preferably methyl, tert-butyl, R b3 For hydrogen.

[0312] R e2 ~R e4 are independently alkyl, substituted or unsubstituted cycloalkyl, preferably alkyl, more preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, tert-pentyl, further preferably tert-butyl or tert-pentyl. In one embodiment, R e2 Preferably, R e3 Preferred are a methyl group, a tert-butyl group, an adamantyl group, and a 3,5-dimethyl-1-adamantyl group, and more preferred are a methyl group and a tert-butyl group.

[0313] Of the two Rs, one is a group represented by formula (G-1), and the other is an aryl group substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, an aryl group condensed by a cycloalkane, a heteroaryl group condensed by a cycloalkane, or a group represented by formula (G-1).

[0314] In this case, one R is preferably a group represented by any of the above formulas (G-2) to (G-7), formulas (G-11) to (G-14), or formulas (G-16) to (G-19), more preferably a group represented by any of the formulas (G-2) to (G-7), and even more preferably a group represented by any of the formulas (G-4) to (G-7). In this case, R 1 and R 2 As mentioned above, R 1 Preferred are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, tert-amyl, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, di-tert-butylphenyl, tri-tert-butylphenyl, more preferably methyl, isopropyl, tert-butyl, tert-amyl, phenyl, further preferably methyl, tert-amyl, tert-butyl, and particularly preferably tert-butyl. 2 Preferred are hydrogen, methyl, ethyl, propyl, and isopropyl, more preferred are hydrogen, methyl, and ethyl, further preferred are hydrogen and methyl, and particularly preferred is methyl.

[0315] In addition, the other R is preferably an aryl group substituted by an alkyl group, an aryl group condensed by a cycloalkane, or a group represented by formula (G-1), more preferably an alkyl-substituted phenyl group, a cycloalkane-condensed phenyl group, or a group represented by formula (G-1), further preferably a group represented by any of the following formulas (r1) to (r8) or formulas (G-2) to (G-7), formulas (G-11) to (G-14), or formulas (G-16) to (G-19) (* represents a bond to a nitrogen atom), further preferably formula (r3), formula (r4), formula (r5), formula (r6), formulas (G-2) to (G-7), particularly preferably formula (r3), formula (r4), formula (r6), formula (G-5), formula (G-6), or formula (G-7).

[0316]

[0317] R 2 Each independently represents hydrogen or an alkyl group, preferably an alkyl group, more preferably an alkyl group having 1 to 10 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group.

[0318] R 3 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, preferably a group of the following formula (R 3 -1)~(R 3-11) (* represents a bond to a nitrogen atom).

[0319]

[0320] It should be noted that the two R 3 They may be the same or different, but are preferably the same.

[0321] In one embodiment, R 3 More preferably, the formula (R 3 -1), formula (R 3 -3), formula (R 3 -8), formula (R 3 -10), more preferably the formula (R 3 -1), formula (R 3 -3). In another embodiment, preferably one R 3 Formula (R 3 -3) shown in the group, another R 3 Formula (R 3 -1), formula (R 3 -3), formula (R 3 -5), formula (R 3 -6) or formula (R 3 -10).

[0322] In one embodiment, N (R 3 )2 is preferably diphenylamino, bis(4-tert-butylphenyl)amino, phenyl(4-tert-butylphenyl)amino, (biphenyl-2-yl)phenylamino, (biphenyl-2-yl)(4-tert-butylphenyl)amino, (4-dibenzofuranyl)phenylamino, (4-dibenzofuranyl)(4-tert-butylphenyl)amino, and more preferably diphenylamino and bis(4-tert-butylphenyl)amino.

[0323] X 3 O, NR 4 or C(-R 4 )2. At this time, R 4 Each is independently an alkyl group or a substituted or unsubstituted aryl group, preferably an alkyl group or a substituted or unsubstituted phenyl group, more preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, phenyl group, or 4-tert-butylphenyl group, and further preferably a methyl group, tert-butyl group, or 4-tert-butylphenyl group.

[0324] In one embodiment, X 3 are independently O, N-bis(4-tert-butylphenyl), and C(Me)2.

[0325] In one embodiment, formulae (A-7) to (A-8) are preferably formulae (A-7-1) to (A-8-3), and preferably formulae (A-7-1) and (A-8-2).

[0326]

[0327] In a further preferred embodiment, the formula (A-1) is preferably represented by any of the following formulae (A-41) to (A-70).

[0328]

[0329]

[0330]

[0331] In the above formulas (A-41) to (A-70), R a2 and R are the same as those in formulas (A-2) to (A-8).

[0332] <Description of Specific Examples of the Polycyclic Aromatic Compound of the Present Invention>

[0333] Specific examples of polycyclic aromatic compounds include compounds represented by the following structural formulas: In the following structural formulas, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-amyl group, and "D" represents deuterium.

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345] Among the above, the polycyclic aromatic compound is preferably a compound represented by any one of formulas (1) to (13), (15), (16), (18), (21) to (26), (31) to (35), (40), (41), (45), (52), (55), (57), (59), (60), (64), and (67) to (76).

[0346] In one embodiment, from the viewpoint of high quantum efficiency, the polycyclic aromatic compound is preferably a compound represented by any one of Formulas (1) to (4), (6) to (12), (15), (16), (18), (21) to (23), (25), (26), (31) to (34), (40), (41), (46) to (47), (51), (52), (55), (59), (60), and (67) to (76), and more preferably a compound represented by any one of Formulas (4), (8), (18), (21), (26), (31), (34), (46), (60), and (67) to (76).

[0347] In one embodiment, from the viewpoint of long device life, the polycyclic aromatic compound is preferably a compound represented by any one of Formulas (4) to (12), (16), (18), (22) to (25), (31) to (35), (40), (41), (47), (51), (52), (55), (57), (59), (60), (67), (68), (70), (72) to (76), and more preferably a compound represented by any one of Formulas (5), (8), (10) to (12), (18), (23), (32), (34), (35), (40), (41), (51), (52), (55), (57), (59), (60), (75), and (76).

[0348] <Application of Polycyclic Aromatic Compounds in Polymers>

[0349] The polycyclic aromatic compounds of the present invention can also be used in the following forms for materials for organic devices, such as materials for organic electroluminescent elements, materials for organic field effect transistors, materials for organic thin-film solar cells, or wavelength conversion filters: a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the aforementioned monomer for obtaining the polymer compound has a polymerizable substituent), or a polymer crosslinked product obtained by further crosslinking the polymer compound (the aforementioned polymer compound for obtaining the polymer crosslinked product has a crosslinkable substituent), or a side chain polymer compound obtained by reacting a main chain polymer with the aforementioned reactive compound (the aforementioned reactive compound for obtaining the side chain polymer compound has a reactive substituent), or a side chain polymer crosslinked product obtained by further crosslinking the side chain polymer compound (the aforementioned side chain polymer compound for obtaining the side chain polymer crosslinked product has a crosslinkable substituent).

[0350] The reactive substituent (including the aforementioned polymerizable substituent, the aforementioned crosslinkable substituent, and a reactive substituent for obtaining a side chain polymer, hereinafter referred to as a "reactive substituent") is not particularly limited as long as it is a substituent capable of increasing the molecular weight of the polycyclic aromatic compound, further crosslinking the polymer compound obtained in this manner, or a substituent capable of undergoing a side chain reaction with a main chain polymer. Preferred substituents are those having the following structures. * in each structural formula indicates a bonding position.

[0351]

[0352] Z is each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene group having 1 to 12 carbon atoms, an oxyalkylene group having 1 to 12 carbon atoms, or a polyoxyalkylene group having 1 to 12 carbon atoms. Among the above substituents, groups represented by Formula (XLS-1), Formula (XLS-2), Formula (XLS-3), Formula (XLS-9), Formula (XLS-10), or Formula (XLS-17) are preferred, and groups represented by Formula (XLS-1), Formula (XLS-3), or Formula (XLS-17) are more preferred.

[0353] Such polymer compounds, polymer crosslinked bodies, side chain polymer compounds and side chain polymer crosslinked bodies may contain, in addition to the repeating units of the polycyclic aromatic compound of the present invention, at least one member selected from the group consisting of substituted or unsubstituted triarylamines, substituted or unsubstituted fluorenes, substituted or unsubstituted anthracenes, substituted or unsubstituted tetracene, substituted or unsubstituted triazines, substituted or unsubstituted carbazoles, substituted or unsubstituted tetraphenylsilanes, substituted or unsubstituted spirofluorenes, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophenes and substituted or unsubstituted dibenzofurans as repeating units.

[0354] Examples of substituents in these repeating units include substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups (two aryl groups may be bonded via a linking group), substituted or unsubstituted diheteroarylamino groups (two heteroaryl groups may be bonded via a linking group), substituted or unsubstituted arylheteroarylamino groups (aryl and heteroaryl groups may be bonded via a linking group), substituted or unsubstituted diarylboryl groups (two aryl groups may be bonded via a linking group), substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted silyl groups (such as triarylsilyl groups, trialkylsilyl groups, tricycloalkylsilyl groups, dialkylcycloalkylsilyl groups, or alkyldicycloalkylsilyl groups). For details on the "aryl group" of the triarylamine and these substituents, the description of the polycyclic aromatic compound of the present invention can be cited.

[0355] 2. Method for producing a polycyclic aromatic compound represented by general formula (A-1)

[0356] The polycyclic aromatic compound represented by the general formula (A-1) can be produced according to the methods described in many known documents, including International Publication No. 2015 / 102118.

[0357] Basically, first make the a ring, b ring and c 1 Ring and c 2 Ring with X 1 and X 2 Then, the a ring, b ring, and c ring are bonded to produce an intermediate (first reaction). 1 Ring and c 2 The ring contains the central element Y 1The final product can be produced by bonding to a group (second reaction). In the first reaction, a general amination reaction such as the Buchwald-Hartwig reaction, a nucleophilic substitution reaction, or a general etherification reaction such as the Ullmann reaction can be used. In addition, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same below) can be used.

[0358] Furthermore, by using a deuterated, cyanated or halogenated raw material at any point in these reaction steps, or by adding a deuterated, cyanated or halogenated step, a compound in which a desired position is deuterated, cyanated or halogenated can be produced.

[0359] As shown in the following scheme, the second reaction is to introduce ring a, ring b, and ring c 1 Ring and c 2 Central element Y of the ring bond 1 First, the X shown in the structure of the intermediate is treated with n-butyllithium, sec-butyllithium or tert-butyllithium. 1 and X 2 The hydrogen atoms between the two groups undergo ortho-metallation. Next, boron trichloride, boron tribromide, or the like are added to perform lithium-boron metal exchange. A Brønsted base such as N,N-diisopropylethylamine can then be added to perform a tandem boro-hetero-Friedel-Crafts reaction to obtain the target product. In this second reaction, a Lewis acid such as aluminum trichloride can be added to accelerate the reaction.

[0360]

[0361] It should be noted that, regarding these polymers, it is possible to use a plurality of a rings, b rings and c rings. 1 Ring and c 2 In this case, the target compound can be obtained by doubling or tripling the amount of the reagent such as butyllithium used.

[0362] Specific examples of the solvent used in the above reaction include tert-butylbenzene and xylene.

[0363] Examples of the ortho-metallating agent include alkyl lithiums such as methyllithium, n-butyllithium, sec-butyllithium, and tert-butyllithium, and organic basic compounds such as lithium diisopropylamide, tetramethylpiperidyllithium, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

[0364] In addition, as a metal-Y 1 The metal exchange reagents include Y 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Triiodide, etc.1 Halides, CIPN(NEt2)2, etc. 1 Amido halide, Y 1 Alkoxylates, Y 1 of aryloxy compounds, etc.

[0365] In addition, examples of the Bronsted base include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, Ar4Si (it should be noted that Ar is an aromatic group such as a phenyl group), etc.

[0366] In addition, as Lewis acids, there can be listed AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, BI3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, CoBr3, etc.

[0367] In the above process, in order to promote the tandem hetero Friedel-Crafts reaction, a Bronsted base or a Lewis acid can be used. 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Triiodide, etc. 1 In the case of a halide, as the aromatic electrophilic substitution reaction proceeds, an acid such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, or hydrogen iodide is generated, and therefore the use of a Bronsted base for capturing the acid is effective. 1 Amido halide, Y 1 In the case of alkoxylates, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so in most cases, there is no need to use a Bronsted base. However, the ability of amino and alkoxy groups to leave is low, so the use of a Lewis acid to promote their departure is effective.

[0368] 3. Organic devices

[0369] In the chemical structural formulae shown below, "Me" represents a methyl group, and "tBu" represents a tert-butyl group.

[0370] The polycyclic aromatic compound of the present invention can be used as a material for organic devices, such as organic electroluminescent elements, organic field-effect transistors, organic thin-film solar cells, and wavelength conversion filters.

[0371] 3-1. Organic electroluminescent element

[0372] The polycyclic aromatic compound of the present invention can be used as a material for an organic electroluminescent device, for example. Hereinafter, the organic EL device of this embodiment will be described in detail with reference to the drawings. Figure 1 Schematic cross-sectional view showing the organic EL element of this embodiment.

[0373] <Structure of Organic Electroluminescent Element>

[0374] Figure 1 The organic EL element 100 shown has: a substrate 101; an anode 102 arranged on the substrate 101; a hole injection layer 103 arranged on the anode 102; a hole transport layer 104 arranged on the hole injection layer 103; a light-emitting layer 105 arranged on the hole transport layer 104; an electron transport layer 106 arranged on the light-emitting layer 105; an electron injection layer 107 arranged on the electron transport layer 106; and a cathode 108 arranged on the electron injection layer 107.

[0375] It should be noted that the organic EL element 100 can also be manufactured in the reverse order, for example, it can be constructed to have: a substrate 101; a cathode 108 arranged on the substrate 101; an electron injection layer 107 arranged on the cathode 108; an electron transport layer 106 arranged on the electron injection layer 107; a light-emitting layer 105 arranged on the electron transport layer 106; a hole transport layer 104 arranged on the light-emitting layer 105; a hole injection layer 103 arranged on the hole transport layer 104; and an anode 102 arranged on the hole injection layer 103.

[0376] Each of the above layers is not essential. The minimum structural unit is a structure including the anode 102, the light-emitting layer 105, and the cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers provided arbitrarily. In addition, each of the above layers may be composed of a single layer or a plurality of layers.

[0377] As a configuration of layers constituting an organic EL element, in addition to the aforementioned configuration of “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron 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 injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0378] <Substrate in Organic Electroluminescent Element>

[0379] The substrate 101 is a support for the organic EL element 100, and is generally made of quartz, glass, metal, plastic, etc. The substrate 101 is formed into a plate, film, or sheet depending on the purpose, and for example, a glass plate, metal plate, metal foil, plastic film, plastic sheet, etc. are used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. If it is a glass substrate, soda-lime glass, alkali-free glass, etc. are used. In addition, the thickness only needs to be thick enough to maintain mechanical strength, so for example, it can be 0.2 mm or more. As an upper limit value of the thickness, for example, it is 2 mm or less, and preferably 1 mm or less. Regarding the material of the glass, since the fewer ions dissolved from the glass, the better, alkali-free glass is preferred, but soda-lime glass with barrier coatings such as SiO2 is also commercially available, so it can be used. In addition, in order to improve the gas barrier properties, a dense gas barrier film such as a silicon oxide film can be provided on at least one side of the substrate 101. In particular, when a plate, film or sheet made of a synthetic resin with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[0380] <Anode in Organic Electroluminescent Element>

[0381] The anode 102 injects holes into the light-emitting layer 105. If at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via the hole injection layer 103 and the hole transport layer 104.

[0382] As materials forming the anode 102, inorganic compounds and organic compounds can be cited. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesser glass, etc. As organic compounds, examples include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline, etc. In addition, it can be appropriately selected from substances used as anodes of organic EL elements.

[0383] The resistance of the transparent electrode is not limited as long as it can supply sufficient current to generate light from the light-emitting element. However, from the perspective of power consumption of the light-emitting element, a low resistance is preferred. For example, an ITO substrate with a resistance of 300 Ω / □ or less can function as an element electrode, but substrates with resistances of around 10 Ω / □ are currently available. Therefore, low resistances of 100 to 5 Ω / □, preferably 50 to 5 Ω / □, are particularly preferred. The thickness of ITO can be arbitrarily selected depending on the resistance value, but is typically between 50 and 300 nm.

[0384] <Hole Injection Layer and Hole Transport Layer in Organic Electroluminescent Element>

[0385] The hole injection layer 103 plays the role of efficiently injecting holes moved from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays the role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are respectively formed by stacking or mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. In addition, an inorganic salt such as iron (III) chloride can also be added to the hole injection / transport material to form a layer.

[0386] Hole-injecting / transporting substances are required to efficiently inject / transport holes from the positive electrode between electrodes subjected to an electric field. They are expected to have high hole injection efficiency and efficient transport of injected holes. Therefore, substances with low ionization potential, high hole mobility, excellent stability, and low generation of impurities that act as traps during manufacturing and use are preferred.

[0387] As the material (hole transport material) forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from among photoconductive materials, compounds conventionally used as hole charge transport materials, and known compounds used in hole injection layers and hole transport layers of p-type semiconductors and organic EL devices. In the present invention, the polycyclic aromatic compound represented by the above formula (A-1) can be used as the hole transport material.

[0388] Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having aromatic tertiary amino groups in the main chain or side chain), 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 '-Diphenyl-N 4 ,N 4 '-Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4 ',N 4 Triphenylamine derivatives such as '-tetrakis([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. Among polymer systems, polycarbonates, styrene derivatives, polyvinylcarbazoles, and polysilanes having the above-mentioned monomers in the side chains are preferred. There are no particular limitations on the compound as long as it can form a thin film required for the production of a light-emitting element and can inject holes from the anode and further transport holes.

[0389] In addition, it is also known that the conductivity of organic semiconductors is strongly affected by this doping. Such organic semiconductor matrix materials are composed of compounds with good electron donating properties or compounds with good electron accepting properties. In order to dope electron donating materials, strong electron acceptors such as tetracyanobenzoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (F4TCNQ) are known (for example, see the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (22), 3202-3204 (1998)" and the literature "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998)"). They generate so-called holes through the electron transfer process in the electron donating base material (hole transport material). The conductivity of the matrix material varies significantly depending on the number and mobility of holes. Known matrix materials with hole-transporting properties include benzidine derivatives (e.g., TPD), starburst amine derivatives (e.g., TDATA), and specific metal phthalocyanines (particularly zinc phthalocyanine (ZnPc)) (Japanese Patent Application Publication No. 2005-167175).

[0390] The hole injection layer materials and hole transport layer materials can also be used as hole layer materials in the form of polymer compounds or crosslinked polymers obtained by polymerizing reactive compounds having reactive substituents as monomers, or side chain polymer compounds or crosslinked side chain polymers obtained by reacting a main chain polymer with the reactive compounds. The reactive substituents in this case can be those described above for the polycyclic aromatic compounds represented by formula (A-1).

[0391] <Light-emitting layer in organic electroluminescent element>

[0392] The light-emitting layer 105 is a layer that emits light by allowing holes injected from the anode 102 to recombine with 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 by being excited by the recombination of holes and electrons (luminescent compound), preferably a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in a solid state. In the present invention, as the material for the light-emitting layer, a polycyclic aromatic compound represented by the above formula (A-1) can be used.

[0393] The light-emitting layer may be either a single layer or a multilayer, and may be formed of light-emitting layer materials (host material, dopant material). The host material and the dopant material may be one kind or a combination of multiple kinds. In addition, the host material may be mixed with a hole transport layer material or an electron transport layer material, or a combination thereof. The dopant material may be contained in the entire host material or in part of the host material. As a doping method, it may be formed by a co-evaporation method with the host material, or it may be pre-mixed with the host material and then evaporated simultaneously, or it may be pre-mixed with the host material together with an organic solvent and then prepared by a wet film-forming method. Specific examples of dopants in combination with the compounds of the present invention are shown below when the dopant is set to a plurality of combinations.

[0394]

[0395] The amount of the host material used varies depending on the type of host material and can be determined based on the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight of the total weight of the light-emitting layer material.

[0396] The amount of dopant used varies depending on the type of dopant and can be determined based on the properties of the dopant. The amount of dopant used is preferably 0.001 to 50% by weight of the total weight of the light-emitting layer material, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight. This range is preferred, for example, from the perspective of preventing concentration quenching. Furthermore, from the perspective of durability, it is preferred that some or all of the hydrogen atoms in the dopant be deuterated.

[0397] On the other hand, in an organic EL element using a thermally active delayed fluorescence dopant material, the amount of the dopant material used is preferably low from the perspective of preventing concentration quenching, but the amount of the dopant material used is preferably high from the perspective of the efficiency of the thermally active delayed fluorescence mechanism. Furthermore, in an organic EL element using a thermally active delayed fluorescence auxiliary dopant material, the amount of the dopant material used is preferably low compared to the amount of the auxiliary dopant material used from the perspective of the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant material. The polycyclic aromatic compound of the present invention can be used as a dopant (also called an emission dopant) in an organic EL element using a thermally active delayed fluorescence auxiliary dopant material.

[0398] When an auxiliary dopant material is used, the usage amounts of the host material, auxiliary dopant material and dopant material are 40 to 99.999 wt%, 59 to 1 wt% and 20 to 0.001 wt% of the total weight of the light-emitting layer material, respectively, preferably 60 to 99.99 wt%, 39 to 5 wt% and 10 to 0.01 wt%, more preferably 70 to 99.95 wt%, 29 to 10 wt% and 5 to 0.05 wt%, respectively.

[0399] As the host material, anthracene, pyrene, dibenzo[deg.]ene, Or fused ring derivatives such as fluorene, distyrylanthracene derivatives, distyrylbenzene derivatives such as bistyryl derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, etc. Anthracene compounds, fluorene compounds or dibenzo[theta]- ... In addition, from the perspective of durability, it is also preferred that some or all of the hydrogen atoms of the host material be deuterated. Furthermore, it is also preferred that a host compound having some or all of its hydrogen atoms be deuterated be combined with a dopant compound having some or all of its hydrogen atoms be deuterated to form the light-emitting layer.

[0400] From the perspective of promoting rather than hindering the generation of TADF in the light-emitting layer, the triplet energy of the host material is preferably higher than the triplet energy of the dopant or auxiliary dopant with the highest triplet energy in the light-emitting layer. Specifically, the triplet energy of the host material is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. Alternatively, a TADF-active compound may be used as the host material.

[0401] As the main material, for example, there can be mentioned a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound having a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), a TADF material (for example, a compound represented by the general formula (H7) described later), a compound represented by the following general formula (H8), a fluorene-based compound, and a dibenzo[deg.]-[deg.]-[deg.]-[deg.]-[deg.]-[deg.]-[deg.]-[deg.]-[deg.]-[deg.]-[deg.]-[deg.]- The compound is preferably a compound represented by the general formula (H1).

[0402]

[0403] <Compound represented by general formula (H1)>

[0404]

[0405] In the above formula (H1), L 1It is an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms, preferably an arylene group having 6 to 24 carbon atoms, more preferably an arylene group having 6 to 16 carbon atoms, further preferably an arylene group having 6 to 12 carbon atoms, particularly preferably an arylene group having 6 to 10 carbon atoms, further preferably a heteroarylene group having 2 to 25 carbon atoms, more preferably a heteroarylene group having 2 to 20 carbon atoms, further preferably a heteroarylene group having 2 to 15 carbon atoms, particularly preferably a heteroarylene group having 2 to 10 carbon atoms. Specific examples of the arylene group include divalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthene ring, a fluorene ring, a phenanthren ring, a triphenylene ring, a pyrene ring, a tetracene ring, a perylene ring, and a pentacene ring. Specific examples of the heteroarylene group include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, and a phthalazine ring. and divalent groups such as a benzothiol ring, a benzothiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolecarbazole ring, a benzoindolecarbazole ring, a benzobenzoindolecarbazole ring, and a naphthobenzofuran ring.

[0406] At least one hydrogen group in the compound represented by formula (H1) may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen group, or a deuterium group.

[0407] <Compound represented by general formula (H2)>

[0408]

[0409] In the above formula (H2), L 2 and L 3 are each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, L 4is hydrogen, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms. The aryl group is preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 16 carbon atoms, further preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples thereof include monovalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthene ring, a fluorene ring, a phenanthren ring, a triphenylene ring, a pyrene ring, a tetracene ring, a perylene ring, and a pentacene ring. The heteroaryl group is preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, further preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Specific examples thereof include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, Monovalent groups such as a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiazole ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a silaacridine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring and a naphthobenzofuran ring.

[0410] At least one hydrogen group in the compound represented by formula (H2) may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen group, or a deuterium group.

[0411] Specific examples of anthracene compounds represented by general formula (H2) include compounds represented by formulas (3-131-Y) to (3-182-Y), compounds represented by formulas (3-183-N), (3-184-Y) to (3-284-Y), and compounds represented by formulas (3-500) to (3-557). The hydrogen atoms in these formulas may be partially or completely substituted with deuterium, and particularly preferred forms of deuterium substitution are listed separately. Y in the formula may be -O-, -S-, >NR- X1 (R X1 is an aryl group optionally substituted by an alkyl group, or an alkyl group) or>C(R X2 )2(R X2 For example, when Y is O, the formula (3-131-Y) is the formula (3-131-O), and when Y is -S- or >NR 29 In the case of , the formula numbers are respectively formula (3-131-S) or formula (3-131-N).

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426] <Compound represented by general formula (H3) (an example of a polymer host material)>

[0427]

[0428] In formula (H3),

[0429] MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, two hydrogen atoms in MU are replaced by EC or MU, and k is an integer of 2 to 50,000.

[0430] More specifically,

[0431] MU each independently represents an arylene group, a heteroarylene group, a diarylamino group, an arylboryl group, an oxaborine diyl group, or an azaborine diyl group,

[0432] EC are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy,

[0433] At least one hydrogen in MU and EC is optionally further substituted with aryl, heteroaryl, diarylamino, alkyl and cycloalkyl,

[0434] k is an integer from 2 to 50,000.

[0435] k is preferably an integer of 20 to 50,000, more preferably an integer of 100 to 50,000.

[0436] At least one hydrogen in MU and EC in formula (H3) is optionally substituted by an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen or a deuterium group, and further, any -CH2- in the aforementioned alkyl group is optionally replaced by -O- or -Si(CH3)2-, and any -CH2- in the aforementioned alkyl group other than the -CH2- directly bonded to EC in formula (H3) is optionally replaced by an arylene group having 6 to 24 carbon atoms, and any hydrogen in the aforementioned alkyl group is optionally substituted by fluorine.

[0437] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds.

[0438]

[0439] More specifically, the divalent groups represented by any of the following structures can be mentioned: In these, MU is bonded to other MU or EC at *.

[0440]

[0441]

[0442]

[0443] Examples of EC include monovalent groups represented by any of the following structures: Among these, EC is bonded to MU at *.

[0444]

[0445] From the viewpoints of solubility and coating film-forming properties, the compound represented by formula (H3) preferably has an alkyl group having 1 to 24 carbon atoms in 10 to 100% of the total number of MUs (k) in the molecule, more preferably has an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), and further preferably has an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms) in 50 to 100% of the total number of MUs (k) in the molecule. On the other hand, from the viewpoints of in-plane orientation and charge transport, preferably, 10 to 100% of the total number of MUs (k) in the molecule has an alkyl group having 7 to 24 carbon atoms, and more preferably, 30 to 100% of the total number of MUs (k) in the molecule has an alkyl group having 7 to 24 carbon atoms (branched alkyl group having 7 to 24 carbon atoms).

[0446] <Compounds containing the structure represented by general formula (H4)>

[0447] The compound is a compound containing a structure represented by the following formula (H4), and may contain multiple, preferably 1 to 5, more preferably 1 to 3, further preferably 1 to 2, and most preferably 1 such structure. When containing multiple structures, the structures are directly bonded to each other with a single bond or bonded with a specific connecting group.

[0448]

[0449] In the above general formula (H4), G is independently "=C(-H)-" or "=N-", and H in the above "=C(-H)-" may be substituted with a substituent or other structures represented by formula (H4).

[0450] The compound including the structure represented by the general formula (H4) can be produced by the methods described in, for example, International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650.

[0451] Examples of substituents when H in "=C(-H)-" of G is substituted include, for example, the following, but are not limited to these.

[0452] Specific examples of the "aryl group" as a substituent include phenyl, tolyl, xylyl, naphthyl, phenanthrenyl, pyrenyl, Benzo[c]phenanthrenyl, benzo[g] Examples of the aryl group include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, triphenylene, and fluorenyl. Examples of the aryl group having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, the aryl group includes both fused aryl groups and non-fused aryl groups.

[0453] Specific examples of the "heteroaryl" substituent include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, Quinoxalinyl, quinazolinyl, naphthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., preferably dibenzofuranyl, dibenzothienyl, carbazolyl, pyridinyl, pyrimidinyl, triazinyl, azadibenzofuranyl and azadibenzothienyl, etc. More preferably, dibenzofuranyl, dibenzothienyl, azadibenzofuranyl or azadibenzothienyl is used.

[0454] The "substituted silyl group" as a substituent is also preferably a group selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group.

[0455] Specific examples of substituted or unsubstituted trialkylsilyl groups include trimethylsilyl and triethylsilyl groups. Specific examples of substituted or unsubstituted arylalkylsilyl groups include diphenylmethylsilyl, dimethylphenylmethylsilyl and phenyldimethylsilyl groups. Specific examples of substituted or unsubstituted triarylsilyl groups include triphenylsilyl and trimethylphenylsilyl groups.

[0456] The "substituted phosphine oxide group" as a substituent is preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0457] Examples of the "substituted carboxyl group" as a substituent include a benzoyloxy group and the like.

[0458] Examples of the linking group for bonding a plurality of structures represented by the formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl groups.

[0459] Specific examples of the compound including the structure represented by General Formula (H4) are shown below.

[0460]

[0461] <Compound represented by general formula (H5)>

[0462]

[0463] In the above formula (H5),

[0464] R 1 ~R 11 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (the above are the first substituents), and the R 1 ~R 11 At least one hydrogen in is optionally substituted by an aryl group, a heteroaryl group, a diarylamino group, an alkyl group or a cycloalkyl group (the above being the second substituent),

[0465] R 1 ~R 11 Adjacent groups in the group may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be optionally substituted with an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group or a cycloalkyl group (the above being the first substituent), and at least one hydrogen in these substituents may be further substituted with an aryl group, a heteroaryl group, a diarylamino group, an alkyl group or a cycloalkyl group (the above being the second substituent),

[0466] Any "-C(-R)=" (where R is R) in the a ring, b ring and c ring 1 ~R 11 ) can be replaced by "-N=",

[0467] At least one hydrogen atom in the compound represented by formula (H5) may be independently substituted with a halogen or a deuterium atom.

[0468] It may also be any of "-C(-R)=" (where R is R) in the ring a, ring b, and ring c in formula (H5) 1 ~R 11 ) is replaced by "-N=" and changes to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl rings.

[0469] Preferably, in the above formula (H5),

[0470] R 1~R 11 are independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein R 1 ~R 11 At least one hydrogen in the group is optionally substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

[0471] R 1 ~R 11 Adjacent groups in the ring are optionally bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring is optionally substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and at least one hydrogen in these substituents is optionally substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

[0472] It is further preferred that in the above formula (H5),

[0473] R 1 ~R 11 are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, wherein R 1 ~R 11 At least one hydrogen in the group may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms,

[0474] R 1 ~R 11Adjacent groups in the group are optionally bonded to each other to form, together with the a, b or c rings, an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms, and at least one hydrogen in the formed ring is optionally substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and at least one hydrogen in these substituents is optionally substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms.

[0475] In the first substituent and the second substituent, examples of the "aryl" or "heteroaryl" in the aryl group, heteroaryl group, diarylamino group, diheteroarylamino group, and arylheteroarylamino group include the following.

[0476] Specific examples of the "aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, further preferably an aryl group having 6 to 16 carbon atoms, particularly preferably an aryl group having 6 to 12 carbon atoms, and most preferably an aryl group having 6 to 10 carbon atoms. For example, phenyl as a monocyclic aromatic group, (2-, 3-, 4-) biphenyl as a bicyclic aromatic group, (1-, 2-) naphthyl as a condensed bicyclic aromatic group, terphenyl (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) as a tricyclic aromatic group, acenaphthene ( Examples of the present invention include 1-, 3-, 4-, 5-) yl, fluorenyl, phenanthrenyl, (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthrenyl, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl) as a tetracyclic aromatic group, triphenylene (1-, 2-) yl, pyrene (1-, 2-, 4-) yl, naphthacene (1-, 2-, 5-) yl as a condensed tetracyclic aromatic group, and perylene (1-, 2-, 3-) yl and pentacene (1-, 2-, 5-, 6-) yl as a condensed pentacyclic aromatic group.

[0477] Specific examples of the "heteroaryl group" include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, further preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, Phenothiazinyl, phenazinyl, silacridine, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophospholyl, dibenzophospholyl, a monovalent group of a benzophospholyl oxide ring, a monovalent group of a dibenzophospholyl oxide ring, furazanyl, thianthrenyl, indolylcarbazole, benzindolecarbazole, and benzobenzindolecarbazole, etc.

[0478] In the above-mentioned first substituent and second substituent, the "alkyl group" may be any of a straight chain and a branched chain, for example, a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), further preferably an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), particularly preferably an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms), and most preferably a methyl group. For example, the following groups may be mentioned: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, t-amyl, n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-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-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like. Further 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, and 1,1-dimethylhexyl.

[0479] In the above-mentioned first substituent and second substituent, examples of the "cycloalkyl group" include cycloalkyl groups having 3 to 24 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, cycloalkyl groups having 5 to 8 carbon atoms, cycloalkyl groups having 5 to 6 carbon atoms, and cycloalkyl groups having 5 carbon atoms. Examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl)-substituted groups having 1 to 4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, and decahydroazulyl.

[0480] When the first substituent is an aryl group, the preferred substitution position is R 1 、R 3 、R 4 、R 5 、R 10 and R 11 , for example, more preferably R 1 and R3 substitution, R 5 and R 10 Substitution of R 4 and R 11 The aryl group is preferably phenyl.

[0481] When the first substituent is a heteroaryl group, the preferred substitution position is R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 9 、R 10 and R 11 , for example, more preferably R 1 Substitution of R 2 Substitution of R 3 Substitution of R 1 and R 3 Substitution of R 4 and R 11 Substitution of R 5 and R 10 Substitution of R 6 and R 9 The heteroaryl group (for example, carbazolyl) may be substituted at the above position by a phenylene group.

[0482] Specific examples of the compound represented by formula (H5) include compounds represented by the following structural formula: In the formula, "Me" represents a methyl group.

[0483]

[0484] The compound shown in formula (H5) is first produced by bonding a to c rings with a bonding group (-O-) to form an intermediate (first reaction), and then, by bonding a to c rings with B (boron), a final product (second reaction) can be produced. In the first reaction, for example, a general etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used. In addition, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction) can be used. The details of the first and second reactions can be found in the description of International Publication No. 2015 / 102118.

[0485] <Compound represented by general formula (H6)>

[0486]

[0487] In the above formula (H6),

[0488] R 1 ~R 16 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (the above are the first substituents), and the R 1 ~R 16 At least one hydrogen in is optionally substituted by an aryl group, a heteroaryl group, a diarylamino group, an alkyl group or a cycloalkyl group (the above being the second substituent),

[0489] R 1 ~R 16 Adjacent groups in the group may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, and at least one hydrogen in the formed ring may be optionally substituted with an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group or a cycloalkyl group (the above being the first substituent), and at least one hydrogen in these substituents may be further substituted with an aryl group, a heteroaryl group, a diarylamino group, an alkyl group or a cycloalkyl group (the above being the second substituent),

[0490] At least one hydrogen atom in the compound represented by formula (H6) may be independently substituted by halogen or deuterium.

[0491] Preferably, in the above formula (H6),

[0492] R 1 ~R 16are independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein R 1 ~R 16 At least one hydrogen in the group is optionally substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

[0493] R 1 ~R 16 Adjacent groups in the ring are optionally bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, the b ring, the c ring, or the d ring, and at least one hydrogen in the formed ring is optionally substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and at least one hydrogen in these substituents is optionally substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

[0494] It is further preferred that in the above formula (H6),

[0495] R 1 ~R 16 are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, wherein R 1 ~R 16 At least one hydrogen in the group may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms,

[0496] R 1 ~R 16Adjacent groups in the group are optionally bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the a ring, the b ring, the c ring, or the d ring, and at least one hydrogen in the formed ring is optionally substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and at least one hydrogen in these substituents is optionally substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms.

[0497] In the first substituent and the second substituent, examples of the "aryl" or "heteroaryl" in the aryl group, heteroaryl group, diarylamino group, diheteroarylamino group, and arylheteroarylamino group include the following.

[0498] Specific examples of the "aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, further preferably an aryl group having 6 to 16 carbon atoms, particularly preferably an aryl group having 6 to 12 carbon atoms, and most preferably an aryl group having 6 to 10 carbon atoms. For example, phenyl as a monocyclic aromatic group, (2-, 3-, 4-) biphenyl as a bicyclic aromatic group, (1-, 2-) naphthyl as a condensed bicyclic aromatic group, terphenyl (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) as a tricyclic aromatic group, acenaphthene ( Examples of the present invention include 1-, 3-, 4-, 5-) yl, fluorenyl, phenanthrenyl, (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthrenyl, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl) as a tetracyclic aromatic group, triphenylene (1-, 2-) yl, pyrene (1-, 2-, 4-) yl, naphthacene (1-, 2-, 5-) yl as a condensed tetracyclic aromatic group, and perylene (1-, 2-, 3-) yl and pentacene (1-, 2-, 5-, 6-) yl as a condensed pentacyclic aromatic group.

[0499] Specific examples of the "heteroaryl group" include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, further preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, Phenothiazinyl, phenazinyl, silacridine, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophospholyl, dibenzophospholyl, a monovalent group of a benzophospholyl oxide ring, a monovalent group of a dibenzophospholyl oxide ring, furazanyl, thianthrenyl, indolylcarbazole, benzindolecarbazole, and benzobenzindolecarbazole, etc.

[0500] In the above-mentioned first substituent and second substituent, the "alkyl group" may be any of a straight chain and a branched chain, for example, a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), further preferably an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), particularly preferably an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms), and most preferably a methyl group. For example, the following groups may be mentioned: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, t-amyl, n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-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-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like. Further 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, and 1,1-dimethylhexyl.

[0501] Among the above-mentioned first substituent and second substituent, as the "cycloalkyl group", cycloalkyl groups having 3 to 24 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, cycloalkyl groups having 5 to 8 carbon atoms, cycloalkyl groups having 5 to 6 carbon atoms, cycloalkyl groups having 5 carbon atoms, etc. can be cited. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cycloctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituents having 1 to 4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazulenyl, etc. can be cited.

[0502] The compound represented by the formula (H6) can be produced by referring to the description described in International Publication No. 2014 / 042197.

[0503] <TADF material>

[0504] By reducing the energy difference between the excited singlet state and the excited triplet state, reverse energy transfer from the excited triplet state with low transition probability to the excited singlet state is usually generated with high efficiency, thereby exhibiting luminescence from the singlet state (thermally activated delayed fluorescence, TADF). In ordinary fluorescence luminescence, 75% of the triplet excitons generated by current excitation pass through the thermal deactivation path, and thus cannot be taken out as fluorescence. On the other hand, in TADF, all excitons can be utilized for fluorescence luminescence, and a highly efficient organic EL device can be realized.

[0505] As the TADF material that can be used for such a purpose, for example, a compound represented by the following general formula (H7) or a compound having the following general formula (H7) as a partial structure can be cited.

[0506] ED-Ln-EA (H7) <000​​​​​​​​​1 T 1 ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and further preferably 0.08 eV or less.

[0508] TADF materials are preferably donor-acceptor type TADF compounds (DA-type TADF compounds) designed in the following manner: using electron-donating substituents called donors and electron-accepting substituents called acceptors, the HOMO and LUMO in the molecule are localized to produce efficient reverse intersystem crossing.

[0509] Here, in this specification, "electron-donating substituent" (donor) refers to the substituent and partial structure that localizes the LUMO orbital in the TADF compound molecule, and "electron-accepting substituent" (acceptor) refers to the substituent and partial structure that localizes the HOMO orbital in the TADF compound molecule.

[0510] Generally, TADF compounds using donors or acceptors exhibit high spin-orbit coupling (SOC) due to their structure, low HOMO-LUMO exchange interaction, and low ΔE(ST), resulting in very fast reverse intersystem crossing (IRC). On the other hand, TADF compounds using donors or acceptors exhibit high structural relaxation in the excited state (the stable structures in the ground and excited states of a molecule are different, so when an external stimulus induces a transition from the ground state to the excited state, the structure subsequently changes to the stable structure in the excited state), resulting in a broad emission spectrum. Consequently, their use as luminescent materials may result in reduced color purity.

[0511] If the TADF color purity is reduced due to the material, a fluorescent compound can be added as an additional component to the light-emitting layer or a layer adjacent to the light-emitting layer. The TADF material acts as an auxiliary dopant, and the other component acts as an emitting dopant. The additional component can be any compound whose absorption spectrum at least partially overlaps with the emission peak of the auxiliary dopant.

[0512] As the donor and acceptor structures used in TADF materials, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. As ED, for example, sp 3More specifically, the functional group of nitrogen includes carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolecarbazole, phenylbicarbazole, bicarbazole, tert-carbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N 1 -(4-(diphenylamino)phenyl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine and diphenyl-dihydrodibenzazasiline. In addition, examples of EA include groups containing sp 2 Aromatic rings containing nitrogen, CN-substituted aromatic rings, rings having ketones and cyano groups, more specifically sulfonyl diphenyl, benzophenone, phenylene bis (phenyl ketone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, terephthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazabenfenalene, thiophene Ln may be derived from, for example, xanthone dioxide, dimethylanthrone, anthracene dione, pyridine, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, benzenetricarboxylic acid nitrile, fluorene dicarbonitrile, pyrazine dicarbonitrile, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. Examples of Ln include single bonds and arylene groups, and more specifically, phenylene, biphenylene, and naphthylene. In any structure, hydrogen may be substituted by an alkyl group, a cycloalkyl group, or an aryl group. Particularly preferred are compounds having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a partial structure.

[0513] More specifically, the compound represented by General Formula (H7) is a compound represented by any of the following General Formulas (H7-1), (H7-2), and (H7-3).

[0514]

[0515] In the above general formula (H7-1), formula (H7-2) and formula (H7-3),

[0516] M is independently a single bond, -O-, >N-Ar or >C(-Ar)2, preferably a single bond, -O- or >N-Ar from the viewpoint of the depth of the HOMO of the formed partial structure and the height of the excited singlet energy level and the excited triplet energy level,

[0517] J is a spacer structure separating the donor substructure from the acceptor substructure, and is independently an arylene group having 6 to 18 carbon atoms. From the viewpoint of the extent of conjugation between the donor substructure and the acceptor substructure, an arylene group having 6 to 12 carbon atoms is preferred, and more specifically, phenylene, methylphenylene, and dimethylphenylene are exemplified.

[0518] Q is independently ═C(—H)— or ═N—, preferably ═N— from the viewpoint of the shallowness of the LUMO of the formed partial structure and the height of the excited singlet and triplet energy levels.

[0519] Ar is each independently hydrogen, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 18 carbon atoms. From the viewpoint of the depth of the HOMO of the formed partial structure and the height of the excited singlet energy level and the excited triplet energy level, preferably hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 14 carbon atoms, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 6 to 10 carbon atoms; more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazine, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazole, or phenylbenzimidazole; further preferably hydrogen, phenyl, or carbazolyl.

[0520] m is 1 or 2,

[0521] n is an integer of 2 to (6-m), and is preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance.

[0522] Furthermore, at least one hydrogen atom in the compounds represented by the above formulae may be substituted with a halogen or deuterium.

[0523] Examples of the compound represented by formula (H7) include compounds represented by the following structures: In the structural formula, * represents a bonding position, "Me" represents a methyl group, and "tBu" represents a tert-butyl group.

[0524]

[0525]

[0526] <Compound represented by general formula (H8)>

[0527]

[0528] In the above formula (H8), L 5 , L 6 and L 7 Each independently represents an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. The aryl group is preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 16 carbon atoms, further preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples thereof include monovalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthene ring, a fluorene ring, a phenanthren ring, a triphenylene ring, a pyrene ring, a tetracene ring, a perylene ring, and a pentacene ring. The heteroaryl group is preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, further preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Specific examples thereof include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, Monovalent groups such as a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiazole ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a silaacridine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring and a naphthobenzofuran ring.

[0529] At least one hydrogen group in the compound represented by formula (H8) may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen group, or a deuterium group.

[0530] <Fluorene compounds>

[0531] The compound represented by the general formula (4) basically functions as a main body.

[0532]

[0533] In the above formula (4),

[0534] R 1 to R 10are independently hydrogen, aryl, heteroaryl (the heteroaryl is optionally bonded to the fluorene skeleton in the above formula (4) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen in which may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group,

[0535] In addition, R 1 With R 2 、R 2 With R 3 、R 3 With R 4 、R 5 With R 6 、R 6 With R 7 、R 7 With R 8 or R 9 With R 10 are optionally independently bonded to form a fused ring or a spiro ring, at least one hydrogen in the formed ring is optionally substituted by an aryl group, a heteroaryl group (the heteroaryl group is optionally bonded to the formed ring via a linker), a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group or an aryloxy group, at least one hydrogen in these groups is optionally substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, and,

[0536] At least one hydrogen in the compound represented by formula (4) may be substituted by halogen, cyano or deuterium.

[0537] The details of each group in the definition of the above formula (4) can be referred to the description of the polycyclic aromatic compound of the above formula (A-1).

[0538] As R 1 to R 10 Examples of the alkenyl group in the group include alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, further preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl.

[0539] Specific examples of heteroaryl groups include monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4) or (4-Ar5).

[0540]

[0541] In formula (4-Ar1) to formula (4-Ar5), Y 1 are independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen,

[0542] At least one hydrogen in the structures of the above formula (4-Ar1) to formula (4-Ar5) may be substituted with a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a methyl group, an ethyl group, a propyl group, or a butyl group.

[0543] These heteroaryl groups may be bonded to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton in formula (4) and the above heteroaryl groups may be bonded directly or via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, and -OCH2CH2O-.

[0544] In addition, R in formula (4) 1 With R 2 、R 2 With R 3 、R 3 With R 4 、R 5 With R 6 、R 6 With R 7 or R 7 With R 8 Optionally, they are independently bonded to form a condensed ring, R 9 With R 10 Optional bond to form a spiro ring. 1 to R 8 The fused ring formed is a ring fused with the benzene ring in formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and examples of the structure including the benzene ring in formula (4) include a naphthalene ring, a phenanthrene ring, and the like. 9 and R 10 The spiro ring formed is a ring spiro-coupled with the 5-membered ring in formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and examples thereof include a fluorene ring.

[0545] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), wherein R in the general formula (4) is 1 With R 2 The compound formed by the condensation of the benzene ring formed by the bonding, R in the general formula (4) 3 With R 4 The compound formed by the condensation of the benzene ring formed by the bonding, R in the general formula (4) 1 ~R 8Unbound compounds.

[0546]

[0547] R in formula (4-1), formula (4-2) and formula (4-3) 1 to R 10 The definition of R is the same as that in formula (4) 1 to R 10 Same, R in formula (4-1) and formula (4-2) 11 to R 14 The definition of R is also the same as that of R in formula (4) 1 to R 10 same.

[0548] The compound represented by the general formula (4) is further preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), wherein R in formula (4-1), formula (4-2) or formula (4-3) is 9 With R 10 A compound in which a spiro-fluorene ring is formed.

[0549]

[0550] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 to R 7 The definition of is the same as that of R in formula (4-1), formula (4-2) and formula (4-3) 2 to R 7 Same, R in formula (4-1A) and formula (4-2A) 11 to R 14 The definition of is also the same as R in formula (4-1) and formula (4-2) 11 to R 14 same.

[0551] Furthermore, all or part of the hydrogen atoms in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0552] Specific examples of the fluorene-based compound include compounds represented by any of the following formulae (4-4) to (4-22). In the following structural formulae, "Me" represents a methyl group.

[0553]

[0554] <Dibenzo Series compounds>

[0555] Dibenzoylmethane as the main The compound is, for example, a compound represented by the following general formula (5).

[0556]

[0557] In the above formula (5),

[0558] R 1 to R 16 are independently hydrogen, aryl, heteroaryl (the heteroaryl is optionally connected to the dibenzoylmethane in the above formula (5) by a linking group) backbone bonded), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen of which may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group,

[0559] In addition, R 1 to R 16 wherein adjacent groups are optionally bonded to each other to form a fused ring, at least one hydrogen in the formed ring is optionally substituted by an aryl group, a heteroaryl group (the heteroaryl group is optionally bonded to the formed ring via a linker), a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group or an aryloxy group, at least one hydrogen in which may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, and,

[0560] At least one hydrogen in the compound represented by formula (5) may be substituted by halogen, cyano or deuterium.

[0561] The details of each group in the definition of the above formula (5) can be referred to the description of the polycyclic aromatic compound of the above formula (A-1).

[0562] Examples of the alkenyl group in the definition of formula (5) include alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, further preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl.

[0563] Specific examples of heteroaryl groups include monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5).

[0564]

[0565] In formula (5-Ar1) to formula (5-Ar5), Y 1are independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen,

[0566] At least one hydrogen in the structures of the above formula (5-Ar1) to formula (5-Ar5) may be substituted with a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a methyl group, an ethyl group, a propyl group, or a butyl group.

[0567] These heteroaryl groups are optionally connected to the dibenzoylmethane in the above formula (5) via a linking group. Skeleton bonding. That is, not only the dibenzo The skeleton may be directly bonded to the above-mentioned heteroaryl groups or they may be bonded via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0568] The compound represented by the general formula (5) is preferably R 1 、R 4 、R 5 、R 8 、R 9 、R 12 、R 13 and R 16 In this case, R in formula (5) 2 、R 3 、R 6 、R 7 、R 10 、R 11 、R 14 and R 15 Each of the above-mentioned phenyl groups, biphenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, or monovalent groups having the structure of the above-mentioned formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (a monovalent group having such a structure is optionally connected with a dibenzofuran in the above-mentioned formula (5) by means of a phenylene group, a biphenylene group, a naphthylene group, anthracenyl group, a methylene group, an ethylene group, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-) backbone bonded), methyl, ethyl, propyl or butyl.

[0569] The compound represented by general formula (5) is more preferably 1 、R 2 、R 4 、R 5 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 、R15 and R 16 is hydrogen. In this case, R 3 、R 6 、R 11 and R 14 At least one (preferably one or two, more preferably one) of the alkyl groups is a monovalent group having a structure of the above-mentioned formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) connected via a single bond, a phenylene group, a biphenylene group, a naphthylene group, an anthracene group, a methylene group, an ethylene group, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-,

[0570] In addition to the foregoing at least one (i.e., except for the position substituted by the monovalent group having the foregoing structure) is hydrogen, phenyl, biphenyl, naphthyl, anthracenyl, methyl, ethyl, propyl or butyl, and at least one hydrogen among these is optionally substituted by phenyl, biphenyl, naphthyl, anthracenyl, methyl, ethyl, propyl or butyl.

[0571] In addition, as R in formula (5) 2 、R 3 、R 6 、R 7 、R 10 、R 11 、R 14 and R 15 In the case of selecting a monovalent group having a structure represented by the above formula (5-Ar1) to formula (5-Ar5), at least one hydrogen in the structure is optionally combined with R in formula (5) 1 to R 16 Any of them are bonded to form a single bond.

[0572] As dibenzo Specific examples of the compounds include compounds represented by any of the following formulae (5-1) to (5-39). In the following structural formulae, "tBu" represents a tert-butyl group.

[0573]

[0574]

[0575] In addition, as the doping material, known compounds can be used, and it can be selected from various materials according to the desired luminescent color. Specifically, for example, phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and Condensed ring derivatives, such as benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, distyryl derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, distyrylanthracene derivatives, distyrylbenzene derivatives, and other bistyryl derivatives (Japanese Patent Application Laid-Open No. 1-245087) , distyrylarylene derivatives (Japanese Patent Application Laid-Open No. 2-247278), diazaindene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesityleneisobenzofuran, bis(2-methylphenyl)isobenzofuran, bis(2-trifluoromethylphenyl)isobenzofuran, isobenzofuran derivatives such as phenylisobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinylcoumarin derivatives, 7-hydroxycoumarin Coumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxabenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, quinolone derivatives, acridine derivatives Pyridine derivatives, oxazine derivatives, phenyl ether derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, purple ring ketone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, anthrone violet derivatives, phenazine derivatives, acridone derivatives, denitroflavin derivatives, fluorene derivatives and benzofluorene derivatives, etc.

[0576] The aforementioned light-emitting layer materials (host materials and dopant materials) may also be used as light-emitting layer materials: polymer compounds or crosslinked polymers obtained by polymerizing reactive compounds having reactive substituents as monomers, or side chain polymer compounds or crosslinked side chain polymers obtained by reacting a main chain polymer with the aforementioned reactive compounds. The reactive substituents in this case may be those described above for the polycyclic aromatic compound represented by formula (A-1).

[0577] <Electron Injection Layer and Electron Transport Layer in Organic Electroluminescent Element>

[0578] The electron injection layer 107 efficiently injects electrons transferred 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 each formed by stacking or mixing one or more electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0579] Electron injection / transport layer refers to injecting electrons from the cathode, and then the layer that transmits electrons, preferably electron injection efficiency is high, efficiently transmits the injected electrons. Therefore, it is preferred that electron affinity is large, and electron mobility is large, and then stability is excellent, and it is not easy to produce a substance that becomes an impurity trap when manufactured and used. However, in the case of considering the transmission balance of holes and electrons, in the case of mainly playing the role of efficiently preventing the holes from the anode from flowing to the cathode side and no longer combining, even if the electron transport ability is not so high, it is equally with the material with the high electron transport ability to improve luminous efficiency. Therefore, the electron injection / transport layer in the present embodiment can also include the function of the layer that can efficiently prevent the movement of holes.

[0580] The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in electron injection layers and electron transport layers of organic EL devices. In the present invention, the polycyclic aromatic compound represented by the above formula (A-1) can be used as the electron transport material.

[0581] As a material for an electron transport layer or an electron injection layer, it is preferably containing at least one of an aromatic ring or heteroaromatic ring compound selected from one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, a pyrrole derivative and its fused ring derivative and a metal complex with electron-accepting nitrogen. Specifically, fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl) biphenyl, purple ring ketone derivatives, coumarin derivatives, naphthalene dicarboximide derivatives, quinone derivatives such as anthraquinone or diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives can be cited. As a metal complex with electron-accepting nitrogen, hydroxyl azole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, cycloheptatrione metal complexes, flavonol metal complexes and benzoquinoline metal complexes can be cited. These materials can be used alone or in combination with different materials.

[0582] Specific examples of other electron-transferring compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of hydroxyquinoline derivatives, hydroxyquinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzoxazole compounds, gallium complexes, pyrazole derivatives, and perfluorophenylene derivatives. compounds, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6'2"-terpyridine))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazone derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc.

[0583] In addition, metal complexes having electron-accepting nitrogen can also be used, examples of which include hydroxyquinoline metal complexes, hydroxyoxazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, cycloheptatrione metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0584] The above materials can be used alone or mixed with different materials.

[0585] Among the above materials, preferred are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and hydroxyquinoline metal complexes described in JP-A-2021-14446.

[0586] The electron transport layer or the electron injection layer may further include a substance that can reduce the material forming the electron transport layer or the electron injection layer. As long as the reducing substance has a certain reducing property, various substances can be used. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be preferably used.

[0587] As preferred reducing substances, 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), alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0-2.5 eV) or Ba (work function 2.52 eV) can be cited, and substances with a work function of 2.9 eV or less are particularly preferred. Among them, more preferred reducing substances are alkali metals such as K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. The reducing ability of these alkali metals is particularly high, and by adding a relatively small amount of alkali metals to the material forming the electron transport layer or the electron injection layer, the luminous brightness in the organic EL element can be improved and the life span can be extended. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and a combination containing Cs is particularly preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs, Na, and K. The inclusion of Cs allows for effective reduction, and by adding it to the material forming the electron transport layer or the electron injection layer, it is possible to achieve improved luminance and longer life of the organic EL element.

[0588] The electron injection layer materials and electron transport layer materials can also be used as electron layer materials in the form of polymer compounds or crosslinked polymers obtained by polymerizing reactive compounds having reactive substituents as monomers, or side chain polymer compounds or crosslinked side chain polymers obtained by reacting a main chain polymer with the reactive compounds. The reactive substituents in this case can be those described above for the polycyclic aromatic compound represented by formula (A-1).

[0589] <Cathode in Organic Electroluminescent Element>

[0590] The cathode 108 plays a role in injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

[0591] As the material forming the cathode 108, there is no particular limitation 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. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.) are preferred. In order to improve the electron injection efficiency and improve the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium or alloys containing these low work function metals are effective. However, these low work function metals are usually mostly unstable in the atmosphere. In order to improve this point, for example, it is known to use a method of using an electrode with high stability by doping a trace amount of lithium, cesium, magnesium in the organic layer. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

[0592] Furthermore, preferred examples include stacking metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys thereof, as well as inorganic substances such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon-based polymer compounds, for electrode protection. There are no particular limitations on the methods for fabricating these electrodes, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating, as long as conductivity can be achieved.

[0593] <Binders that can be used in each layer>

[0594] The materials used in the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer and electron injection layer can form each layer independently, or can be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene ether, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, phenolic resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin and the like as a polymer binder and used.

[0595] <Method for producing an organic electroluminescent element>

[0596] Each layer constituting the organic EL element can be formed by making the material to constitute each layer into a thin film through a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular stacking, printing, spin coating, casting, or coating. There is no particular limitation on the film thickness of each layer formed in this way, and it can be appropriately set according to the properties of the material, usually in the range of 2nm to 5000nm. The film thickness can usually be measured using a quartz oscillation film thickness measuring device or the like. When using the vapor deposition method for thin film formation, the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, etc. The vapor deposition conditions are usually preferably at a boat heating temperature of +50 to +400°C and a vacuum degree of 10 -6 ~10 -3 Pa, the vapor deposition rate is 0.01 to 50 nm / second, the substrate temperature is -150 to +300°C, and the film thickness is appropriately set within the range of 2 nm to 5 μm.

[0597] When a DC voltage is applied to the organic EL element thus obtained, with the polarity of the anode at + and the cathode at -, a voltage of approximately 2 to 40 V can be observed from the transparent or translucent electrode side (the anode, cathode, or both). Furthermore, the organic EL element also emits light when pulsed current or alternating current is applied. It should be noted that the applied AC current can have any waveform.

[0598] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element composed of anode / hole injection layer / hole transport layer / light-emitting layer containing a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described.

[0599] <Evaporation method>

[0600] After a thin film of an anode material is formed on a suitable substrate by a vapor deposition method, a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a doping material are co-evaporated thereon to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and then a thin film consisting of a cathode material is formed as a cathode by a vapor deposition method, thereby obtaining a target organic EL element. It should be noted that in the production of the above-mentioned organic EL element, the production order can also be reversed, and a cathode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode are sequentially produced.

[0601] <Application Examples of Organic Electroluminescent Elements>

[0602] Furthermore, the present invention can also be applied to a display device including an organic EL element, a lighting device including an organic EL element, or the like.

[0603] A display device or lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element of this embodiment to a known driving device, and can be driven using a known driving method such as DC driving, pulse driving, or AC driving as appropriate.

[0604] 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 Laid-Open No. 10-335066, Japanese Patent Application Laid-Open No. 2003-321546, and Japanese Patent Application Laid-Open No. 2004-281086). Examples of display modes include matrix and segment modes. Matrix display and segment display may coexist on the same panel.

[0605] In a matrix, pixels used for display are arranged two-dimensionally in a grid or mosaic shape, and text and images are displayed by a collection of pixels. The shape and size of the pixel are determined by the purpose. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with a side of less than 300 μm are usually used. In addition, in the case of large displays such as display panels, pixels with a side of mm are used. In the case of monochrome display, pixels of the same color can be arranged, but in the case of color display, pixels of red, green, and blue are arranged to display. In this case, typical types are triangular and stripe types. 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 a simple structure, but when considering the operating characteristics, the active matrix is ​​sometimes more excellent, so it is also necessary to use them separately according to the purpose.

[0606] In the segmented method (type), a pattern is formed to display predetermined information, and the determined area is illuminated. Examples include digital clocks, thermometers showing the time and temperature, audio equipment, induction cookers, and other operating status displays, as well as automobile panel displays.

[0607] As lighting devices, for example, lighting devices such as indoor lighting, backlights of liquid crystal display devices, etc. can be cited (for example, refer to Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, Japanese Patent Publication No. 2004-119211, etc.). Backlight sources are mainly used to improve the visibility of non-self-luminous display devices, and are used for liquid crystal display devices, clocks, audio devices, car panels, display boards and logos. In particular, as a backlight source for liquid crystal display devices, especially personal computers for which thinning has become a problem, considering that the previous method is composed of fluorescent lamps and light guide plates and is difficult to be thinned, the backlight source using the light-emitting element of this embodiment is characterized by being thin and lightweight.

[0608] 3-2. Other organic devices

[0609] The polycyclic aromatic compound of the present invention can be used in the production of organic field effect transistors, organic thin film solar cells, wavelength conversion filters, and the like, in addition to the above-mentioned organic electroluminescent devices.

[0610] An organic field-effect transistor (FET) is a transistor that controls current by generating an electric field from a voltage input. In addition to source and drain electrodes, it also has a gate electrode. Applying a voltage to the gate electrode generates an electric field, allowing it to arbitrarily intercept the flow of electrons (or holes) between the source and drain electrodes, thereby controlling current. FETs are easier to miniaturize than simple transistors (bipolar transistors) and are often used as components in integrated circuits.

[0611] The structure of an organic field-effect transistor is generally characterized by providing a source electrode and a drain electrode in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and further providing a gate electrode via an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following.

[0612] (1) Substrate / gate electrode / insulator layer / source electrode / drain electrode / organic semiconductor active layer

[0613] (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode / drain electrode

[0614] (3) Substrate / Organic semiconductor active layer / Source electrode / Drain electrode / Insulator layer / Gate electrode

[0615] (4) Substrate / Source / Drain Electrode / Organic Semiconductor Active Layer / Insulator Layer / Gate Electrode

[0616] The organic field-effect transistor configured in this manner can be used as a pixel driving switching element in an active matrix driven liquid crystal display or an organic electroluminescent display.

[0617] Organic thin-film solar cells have a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compounds of the present invention can be used as materials for the hole transport layer, the p-type semiconductor layer, the n-type semiconductor layer, and the electron transport layer according to their physical properties. The polycyclic aromatic compounds of the present invention can function as hole transport materials or electron transport materials in organic thin-film solar cells. In addition to the above, organic thin-film solar cells may also appropriately have a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. Organic thin-film solar cells can appropriately select known materials used in organic thin-film solar cells and use them in combination.

[0618] Currently, active research is underway to apply color conversion-based multicolorization technology to liquid crystal displays, organic EL displays, and lighting. Color conversion refers to converting the wavelength of light emitted by a light source into longer wavelengths, such as converting ultraviolet or blue light into green or red. By thinning wavelength conversion materials with this color conversion function and combining them with, for example, a blue light source, it is possible to extract the three primary colors of blue, green, and red—that is, white light—from the blue light source. By combining a white light source that combines such a blue light source with a wavelength conversion filter with color conversion function as a light source unit, combined with a liquid crystal driver and color filters, a full-color display can be produced. Alternatively, if a liquid crystal driver is not required, the light source can be used directly as a white light source, for example, in LED lighting and other white light sources. Furthermore, by combining a blue organic EL element as a light source with a wavelength conversion filter that converts blue light into green and red, a full-color organic EL display can be produced without the use of a metal mask. Furthermore, by combining blue micro-LEDs as a light source with a wavelength conversion filter that converts blue light into green and red, a low-cost full-color micro-LED display can be produced.

[0619] The polycyclic aromatic compound of the present invention can be used as a material for the wavelength conversion filter. Using a wavelength conversion filter containing the polycyclic aromatic compound of the present invention, it is possible to convert light from a light source or a light-emitting element that generates ultraviolet light or a shorter wavelength blue light into blue light or green light with high color purity suitable for use in a display device (a display device using an organic EL element, a liquid crystal display device). The adjustment of the converted color can be carried out by appropriately selecting the substituents of the polycyclic aromatic compound of the present invention, the binder resin used in the wavelength conversion composition described later, and the like. The wavelength conversion material can be prepared as a wavelength conversion composition containing the polycyclic aromatic compound of the present invention. In addition, the wavelength conversion composition can also be used to form a wavelength conversion filter.

[0620] In addition to the polycyclic aromatic compound of the present invention, the wavelength conversion composition may further include a binder resin, other additives, and a solvent. For example, the binder resin described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283 can be used. Other additives include the compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283. For solvents, refer to the description of the solvent contained in the light-emitting layer-forming composition described above.

[0621] The wavelength conversion filter includes a wavelength conversion layer formed by curing a wavelength conversion composition. As a method for making a wavelength conversion layer from a wavelength conversion composition, reference can be made to a known thin film formation method. The wavelength conversion filter may be composed solely of a wavelength conversion layer formed by a composition comprising the polycyclic aromatic compound of the present invention, or may include other wavelength conversion layers (e.g., a wavelength conversion layer that converts blue light into green light or red light, or a wavelength conversion layer that converts blue light or green light into red light). Furthermore, the wavelength conversion filter may include a substrate layer and a barrier layer for preventing degradation of the color conversion layer caused by oxygen, moisture or heat.

[0622] Example

[0623] The present invention will be described in more detail below with reference to Examples, but the present invention is not limited thereto. First, a synthesis example of a polycyclic aromatic compound will be described below.

[0624] <Synthesis Example (1): Synthesis of Compound (1)>

[0625]

[0626] Under a nitrogen atmosphere, 5-bromo-1,2,3-trichlorobenzene (26.0 g), 4-methylphenylboronic acid (13.6 g), tetrakis(triphenylphosphine)palladium(0) (3.5 g) as a palladium catalyst, potassium carbonate (20.7 g), toluene (100 ml), and water (10 mL) were placed in a flask and heated at reflux for 5 hours. After the reaction was completed, water and ethyl acetate were added to the reaction mixture and stirred. The organic layer was then separated and washed with water. The crude product obtained by concentrating the organic layer was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain the intermediate (Int-1-1) (24.2 g).

[0627]

[0628] Under a nitrogen atmosphere, the intermediate (Int-1-1) (19.0 g), the intermediate (Int-1-2) (32.9 g), dichlorobis[di-tert-butyl(4-dimethylaminophenyl)phosphino]palladium(II) (Pd-132 (1.5 g) as a palladium catalyst, tBuONa (10.1 g) and toluene (100 ml) were placed in a flask and heated at reflux temperature for 8 hours. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Then, the crude product obtained by concentrating the organic layer was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain the intermediate (Int-1-3) (36.9 g).

[0629]

[0630] Under a nitrogen atmosphere, intermediate (Int-1-3) (35.2 g), intermediate (Int-1-4) (18.8 g), Pd-132 (1.1 g) as a palladium catalyst, tBuONa (7.2 g), and toluene (300 ml) were placed in a flask and heated at reflux for 6 hours. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. The crude product obtained by concentrating the organic layer was purified using a silica gel short column (eluent: toluene / heptane = 1 / 5 (volume ratio)) to obtain intermediate (Int-1) (32.2 g).

[0631]

[0632] To a flask containing intermediate (Int-1) (10.4 g) and tert-butylbenzene (100 ml) was added a 1.60 M tert-butyllithium pentane solution (12.5 ml) at 0°C under a nitrogen atmosphere. After the addition was complete, the temperature was raised to 70°C and stirred for 0.5 hours. Components with boiling points lower than that of tert-butylbenzene were removed by distillation under reduced pressure. The mixture was cooled to -50°C, boron tribromide (3.8 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (3.9 g) was added, and the mixture was stirred at room temperature until the exotherm subsided. The temperature was then raised to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an ice-cooled aqueous sodium acetate solution was added, followed by separation by ethyl acetate. The organic layer was concentrated and then purified using a silica gel short column (eluent: toluene / heptane = 1 / 5 (volume ratio)). The obtained crude product was recrystallized from toluene to obtain compound (1) (1.0 g).

[0633]

[0634] APCI-MS confirmed the target compound to be m / z (M+H) = 1017.68.

[0635] Synthesis Example (2): Synthesis of Compound (2)

[0636] In the same manner as in Synthesis Example (1), compound (2) was obtained from intermediate (Int-2).

[0637]

[0638] The product was confirmed to be the target compound by NMR measurement.

[0639] 1 H-NMR (500MHz, CDCl3): δ = 8.75 (d, 1H), 7.76-7.70 (m, 2H), 7.68 (d, 1H), 7.63 (dd, 1H) ), 7.55(s,1H), 7.50(dd,1H), 7.43(dd,1H), 7.40-7.28(m,6H), 6.94(t,1H), 6.89(d, 2H), 6.61-6.57(m,2H), 6.48(s,1H), 5.85(s,1H), 1.70-1.60(m,4H), 1.50(s,9H), 1 .48(s,9H), 1.45(s,9H), 1.35(s,6H), 1.32(s,9H), 1.02-0.98(m,6H), 0.88(s,18H).

[0640] Synthesis Example (3): Synthesis of Compound (3)

[0641] In the same manner as in Synthesis Example (1), compound (3) was obtained from intermediate (Int-3).

[0642]

[0643] The product was confirmed to be the target compound by NMR measurement.

[0644] 1 H-NMR (500MHz, CDCl3): δ = 8.74 (d, 1H), 7.76-7.67 (m, 3H), 7.63 (d, 1H), 7.56 (s, 1H), 7. 53(dd,1H), 7.45(dd,1H), 7.41(d,1H), 7.34(dd,1H), 7.33(t,1H), 7.21(d,2H), 6.94(t, 1H), 6.89(d,2H), 6.75(d,1H), 6.56(s,1H), 6.40(s,1H), 5.99(s,1H), 1.70-1.60(m,4H) , 1.48-1.43(m,27H), 1.37-1.34(m,6H), 1.25(s,18H), 1.01-0.98(m,6H), 0.87(s,18H).

[0645] Synthesis Example (4): Synthesis of Compound (4)

[0646] In the same manner as in Synthesis Example (1), compound (4) was obtained from intermediate (Int-4).

[0647]

[0648] APCI-MS confirmed the target compound to be m / z (M+H) = 949.62.

[0649] Synthesis Example (5): Synthesis of Compound (5)

[0650] In the same manner as in Synthesis Example (1), compound (5) was obtained from intermediate (Int-5).

[0651]

[0652] APCI-MS confirmed the target compound to be m / z (M+H) = 1223.89.

[0653] Synthesis Example (6): Synthesis of Compound (6)

[0654] In the same manner as in Synthesis Example (1), compound (6) was obtained from intermediate (Int-6).

[0655]

[0656] The product was confirmed to be the target compound by NMR measurement.

[0657] 1 H-NMR (500MHz, CDCl3): δ = 8.70 (s, 1H), 7.72 (m, 2H), 7.58 (m, 2H), 7.48 (d, 1H), 7.36(m,6H), 7.14(m,1H), 6.96(m,2H), 6.88(s,2H), 6.76(s,1H), 6.37(s,1H), 6.14 (s, 1H), 1.82 (m, 4H), 1.70 (m, 4H), 1.53 (s, 9H), 1.47 (m, 6H), 1.40 (s, 6H), 1.34(s, 12H), 1.27(d, 3H), 1.22(s, 9H), 1.07(d, 6H), 0.81(s, 9H), 0.79(s, 9H).

[0658] Synthesis Example (7): Synthesis of Compound (7)

[0659] In the same manner as in Synthesis Example (1), compound (7) was obtained from intermediate (Int-7).

[0660]

[0661] The product was confirmed to be the target compound by NMR measurement.

[0662] 1 H-NMR (500MHz, CDCl3): δ = 8.68 (s, 1H), 7.70 (m, 2H), 7.55 (m, 2H), 7.48 (d, 1H), 7.38 (m, 2H), 7.3 0(s, 1H), 7.24(m, 2H), 7.04(m, 1H), 6.91(d, 1H), 6.87(s, 1H), 6.80(s, 1H), 6.74(s, 1H), 6.45(d , 1H), 6.32(s, 1H), 6.28(d, 1H), 1.78(m, 4H), 1.70(m, 4H), 1.54(s, 3H), 1.47(s, 15H), 1.41(d, 3 H), 1.36 (m, 6H), 1.27 (s, 9H), 1.25 (s, 9H), 1.21 (s, 9H), 1.07 (d, 6H), 0.81 (s, 9H), 0.79 (s, 9H).

[0663] Synthesis Example (8): Synthesis of Compound (8)

[0664] In the same manner as in Synthesis Example (1), compound (8) was obtained from intermediate (Int-8).

[0665]

[0666] APCI-MS confirmed the target compound to be m / z (M+H) = 1111.76.

[0667] Synthesis Example (9): Synthesis of Compound (9)

[0668] In the same manner as in Synthesis Example (1), compound (9) was obtained from intermediate (Int-9).

[0669]

[0670] APCI-MS confirmed the target compound to be m / z (M+H) = 1081.71.

[0671] Synthesis Example (10): Synthesis of Compound (10)

[0672] In the same manner as in Synthesis Example (1), compound (10) was obtained from intermediate (Int-10).

[0673]

[0674] APCI-MS confirmed the target compound to be m / z (M+H) = 1135.76.

[0675] Synthesis Example (11): Synthesis of Compound (11)

[0676] In the same manner as in Synthesis Example (1), compound (11) was obtained from intermediate (Int-11).

[0677]

[0678] APCI-MS confirmed the target compound to be m / z (M+H) = 1284.88.

[0679] Synthesis Example (12): Synthesis of Compound (12)

[0680] In the same manner as in Synthesis Example (1), compound (12) was obtained from intermediate (Int-12).

[0681]

[0682] APCI-MS confirmed the target compound to be m / z (M+H) = 1190.71.

[0683] Synthesis Example (13): Synthesis of Compound (13)

[0684] In the same manner as in Synthesis Example (1), compound (13) was obtained from intermediate (Int-13).

[0685]

[0686] APCI-MS confirmed the target compound to be m / z (M+H) = 1318.83.

[0687] Synthesis Example (14): Synthesis of Compound (15)

[0688] In the same manner as in Synthesis Example (1), compound (15) was obtained from intermediate (Int-15).

[0689]

[0690] APCI-MS confirmed the target compound to be m / z (M+H) = 1163.79.

[0691] Synthesis Example (15): Synthesis of Compound (16)

[0692] In the same manner as in Synthesis Example (1), compound (16) was obtained from intermediate (Int-16).

[0693]

[0694] APCI-MS confirmed the target compound to be m / z (M+H) = 1135.76.

[0695] Synthesis Example (16): Synthesis of Compound (18)

[0696] In the same manner as in Synthesis Example (1), compound (18) was obtained from intermediate (Int-18).

[0697]

[0698] APCI-MS confirmed the target compound to be m / z (M+H) = 1114.68.

[0699] Synthesis Example (17): Synthesis of Compound (21)

[0700] In the same manner as in Synthesis Example (1), compound (21) was obtained from intermediate (Int-21).

[0701]

[0702] APCI-MS confirmed the target compound to be m / z (M+H) = 1128.69.

[0703] Synthesis Example (18): Synthesis of Compound (22)

[0704] In the same manner as in Synthesis Example (1), compound (22) was obtained from intermediate (Int-22).

[0705]

[0706] APCI-MS confirmed the target compound to be m / z (M+H) = 1217.84.

[0707] Synthesis Example (19): Synthesis of Compound (23)

[0708] In the same manner as in Synthesis Example (1), compound (23) was obtained from intermediate (Int-23).

[0709]

[0710] APCI-MS confirmed the target compound to be m / z (M+H) = 1231.82.

[0711] Synthesis Example (20): Synthesis of Compound (24)

[0712] In the same manner as in Synthesis Example (1), compound (24) was obtained from intermediate (Int-24).

[0713]

[0714] APCI-MS confirmed the target compound to be m / z (M+H) = 1175.79.

[0715] Synthesis Example (21): Synthesis of Compound (25)

[0716] In the same manner as in Synthesis Example (1), compound (25) was obtained from intermediate (Int-25).

[0717]

[0718] APCI-MS confirmed the target compound to be m / z (M+H) = 1175.76.

[0719] Synthesis Example (22): Synthesis of Compound (26)

[0720] In the same manner as in Synthesis Example (1), compound (26) was obtained from intermediate (Int-26).

[0721]

[0722] APCI-MS confirmed the target compound to be m / z (M+H) = 1191.79.

[0723] Synthesis Example (23): Synthesis of Compound (31)

[0724] In the same manner as in Synthesis Example (1), compound (31) was obtained from intermediate (Int-31).

[0725]

[0726] APCI-MS confirmed the target compound to be m / z (M+H) = 1091.70.

[0727] Synthesis Example (24): Synthesis of Compound (32)

[0728] In the same manner as in Synthesis Example (1), compound (32) was obtained from intermediate (Int-32).

[0729]

[0730] APCI-MS confirmed the target compound to be m / z (M+H) = 1321.90.

[0731] Synthesis Example (25): Synthesis of Compound (33)

[0732] In the same manner as in Synthesis Example (1), compound (33) was obtained from intermediate (Int-33).

[0733]

[0734] APCI-MS confirmed the target compound to be m / z (M+H) = 1149.78.

[0735] Synthesis Example (26): Synthesis of Compound (34)

[0736] In the same manner as in Synthesis Example (1), compound (34) was obtained from intermediate (Int-34).

[0737]

[0738] APCI-MS confirmed the target compound to be m / z (M+H) = 1069.71.

[0739] Synthesis Example (27): Synthesis of Compound (35)

[0740] In the same manner as in Synthesis Example (1), compound (35) was obtained from intermediate (Int-35).

[0741]

[0742] APCI-MS confirmed the target compound to be m / z (M+H) = 1187.79.

[0743] Synthesis Example (28): Synthesis of Compound (40)

[0744] In the same manner as in Synthesis Example (1), compound (40) was obtained from intermediate (Int-40).

[0745]

[0746] APCI-MS confirmed the target compound to be m / z (M+H) = 1135.92.

[0747] Synthesis Example (29): Synthesis of Compound (41)

[0748] In the same manner as in Synthesis Example (1), compound (41) was obtained from intermediate (Int-41).

[0749]

[0750] APCI-MS confirmed the target compound to be m / z (M+H) = 1075.76.

[0751] Synthesis Example (30): Synthesis of Compound (45)

[0752] In the same manner as in Synthesis Example (1), compound (45) was obtained from intermediate (Int-45).

[0753]

[0754] APCI-MS confirmed the target compound to be m / z (M+H) = 1094.72.

[0755] Synthesis Example (31): Synthesis of Compound (46)

[0756] In the same manner as in Synthesis Example (1), compound (46) was obtained from intermediate (Int-46).

[0757]

[0758] APCI-MS confirmed the target compound to be m / z (M+H) = 1025.65.

[0759] Synthesis Example (32): Synthesis of Compound (47)

[0760] In the same manner as in Synthesis Example (1), compound (47) was obtained from intermediate (Int-47).

[0761]

[0762] APCI-MS confirmed the target compound to be m / z (M+H) = 1081.71.

[0763] Synthesis Example (33): Synthesis of Compound (48)

[0764] In the same manner as in Synthesis Example (1), compound (48) was obtained from intermediate (Int-48).

[0765]

[0766] APCI-MS confirmed the target compound to be m / z (M+H) = 1113.78.

[0767] Synthesis Example (34): Synthesis of Compound (49)

[0768] In the same manner as in Synthesis Example (1), compound (49) was obtained from intermediate (Int-49).

[0769]

[0770] APCI-MS confirmed the target compound to be m / z (M+H) = 1009.62.

[0771] Synthesis Example (35): Synthesis of Compound (50)

[0772] In the same manner as in Synthesis Example (1), compound (50) was obtained from intermediate (Int-50).

[0773]

[0774] APCI-MS confirmed the target compound to be m / z (M+H) = 1169.75.

[0775] Synthesis Example (36): Synthesis of Compound (51)

[0776] In addition to changing BBr3 to 10 Compound (51) was obtained from intermediate (Int-51) in the same manner as in Synthesis Example (1) except for BBr 3 .

[0777]

[0778] APCI-MS confirmed the target compound to be m / z (M+H) = 948.62.

[0779] Synthesis Example (37): Synthesis of Compound (52)

[0780] In addition to changing BBr3 to 11 Compound (52) was obtained from intermediate (Int-52) in the same manner as in Synthesis Example (1) except for BBr 3 .

[0781]

[0782] APCI-MS confirmed the target compound to be m / z (M+H) = 949.62.

[0783] Synthesis Example (38): Synthesis of Compound (55)

[0784] In the same manner as in Synthesis Example (1), compound (55) was obtained from intermediate (Int-55).

[0785]

[0786] APCI-MS confirmed the target compound to be m / z (M+H) = 1170.85.

[0787] Synthesis Example (39): Synthesis of Compound (57)

[0788] In the same manner as in Synthesis Example (1), compound (57) was obtained from intermediate (Int-57).

[0789]

[0790] APCI-MS confirmed the target compound to be m / z (M+H) = 1116.80.

[0791] Synthesis Example (40): Synthesis of Compound (59)

[0792] In the same manner as in Synthesis Example (1), compound (59) was obtained from intermediate (Int-59).

[0793]

[0794] APCI-MS confirmed the target compound to be m / z (M+H) = 1168.79.

[0795] Synthesis Example (41): Synthesis of Compound (60)

[0796] In the same manner as in Synthesis Example (1), compound (60) was obtained from intermediate (Int-60).

[0797]

[0798] APCI-MS confirmed the target compound to be m / z (M+H) = 1170.85.

[0799] Synthesis Example (42): Synthesis of Compound (64)

[0800] In the same manner as in Synthesis Example (1), compound (64) was obtained from intermediate (Int-64).

[0801]

[0802] APCI-MS confirmed the target compound to be m / z (M+H) = 1292.93.

[0803] Synthesis Example (43): Synthesis of Compound (67)

[0804] In the same manner as in Synthesis Example (1), compound (67) was obtained from intermediate (Int-67).

[0805]

[0806] APCI-MS confirmed the target compound to be m / z (M+H) = 1061.75.

[0807] Synthesis Example (44): Synthesis of Compound (68)

[0808] In the same manner as in Synthesis Example (1), compound (68) was obtained from intermediate (Int-68).

[0809]

[0810] APCI-MS confirmed the target compound to be m / z (M+H) = 1167.82.

[0811] Synthesis Example (45): Synthesis of Compound (69)

[0812] In the same manner as in Synthesis Example (1), compound (69) was obtained from intermediate (Int-69).

[0813]

[0814] APCI-MS confirmed the target compound to be m / z (M+H) = 1069.71.

[0815] Synthesis Example (46): Synthesis of Compound (70)

[0816] In the same manner as in Synthesis Example (1), compound (70) was obtained from intermediate (Int-70).

[0817]

[0818] APCI-MS confirmed the target compound to be m / z (M+H) = 1192.73.

[0819] Synthesis Example (47): Synthesis of Compound (71)

[0820] In the same manner as in Synthesis Example (1), compound (71) was obtained from intermediate (Int-71).

[0821]

[0822] APCI-MS confirmed the target compound to be m / z (M+H) = 1284.88.

[0823] Synthesis Example (48): Synthesis of Compound (72)

[0824] In the same manner as in Synthesis Example (1), compound (72) was obtained from intermediate (Int-72).

[0825]

[0826] APCI-MS confirmed the target compound to be m / z (M+H) = 1192.73.

[0827] Synthesis Example (49): Synthesis of Compound (73)

[0828] In the same manner as in Synthesis Example (1), compound (73) was obtained from intermediate (Int-73).

[0829]

[0830] APCI-MS confirmed the target compound to be m / z (M+H) = 1031.70.

[0831] Synthesis Example (50): Synthesis of Compound (74)

[0832] Similar to Synthesis Example (1), Compound (74) was obtained from Intermediate (Int-74).

[0833]

[0834] The target compound was confirmed by APCI-MS to have m / z (M+H) = 997.65.

[0835] Synthesis Example (51): Synthesis of Compound (75)

[0836] Similar to Synthesis Example (1), Compound (75) was obtained from Intermediate (Int-75).

[0837]

[0838] The target compound was confirmed by APCI-MS to have m / z (M+H) = 1008.70.

[0839] Synthesis Example (52): Synthesis of Compound (76)

[0840] Similar to Synthesis Example (1), Compound (76) was obtained from Intermediate (Int-76).

[0841]

[0842] The target compound was confirmed by APCI-MS to have m / z (M+H) = 956.66.

[0843] <Possibility in Application to Organic EL Devices>

[0844] The compounds of the present invention are expected to have appropriate energy gaps (Eg), high triplet excitation energies (E T ), and small ΔEST as characteristics, and thus can be expected to be applied to, for example, light-emitting layers and charge transport layers, and particularly to light-emitting layers.

[0845] <B. Evaluation of Vacuum Deposition-Type Organic EL Devices>

[0846] Next, the fabrication and evaluation of organic EL devices using the polycyclic aromatic compounds of the present invention will be described.

[0847] <Structure of Organic EL Devices>

[0848] The material compositions of the respective layers in the organic EL devices of Examples B1 to B52 and Comparative Examples B1 to B5 are shown in Tables B-1 to B-4 below.

[0849] [Table B-1]

[0850]

[0851] [Table B-2]

[0852]

[0853] [Table B-3]

[0854]

[0855] [Table B-4]

[0856]

[0857] The chemical structures of "HI", "HAT-CN", "HT-1", "HT-2", "BH", "ET-1", "ET-2", "Liq" in Tables B-1 to B-4, "Comparative Compound (1)" described in the specification of Korean Patent Application Publication No. 2022 / 010243, "Comparative Compound (2)" described in International Publication No. 2021 / 107699, "Comparative Compound (3)" described in International Publication No. 2021 / 107743, "Comparative Compound (4)" described in International Publication No. 2021 / 107743, and "Comparative Compound (5)" described in International Publication No. 2022 / 196612 are shown below.

[0858]

[0859] <Elements of Example B1>

[0860] An ITO film formed by sputtering to a thickness of 180 nm was polished to 150 nm, and a 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science) was used as a transparent supporting substrate. This transparent supporting substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing HI, HAT-CN, HT-1, HT-2, BH, compound (1), ET-1, and ET-2, and an aluminum nitride vapor deposition boat containing Liq, LiF, and aluminum, respectively, were installed.

[0861] The following layers were formed in sequence on the ITO film of the transparent supporting substrate. The vacuum chamber was decompressed to 5×10 -4Pa, first, HI was heated and vapor-deposited to a film thickness of 40 nm, then HAT-CN was heated and vapor-deposited to a film thickness of 5 nm, then HT-1 was heated and vapor-deposited to a film thickness of 45 nm, then HT-2 was heated and vapor-deposited to a film thickness of 10 nm, thereby forming a hole layer consisting of four layers. Next, BH and compound (1) were heated simultaneously and vapor-deposited to a film thickness of 25 nm to form a light-emitting layer. The vapor deposition rate was adjusted so that the mass ratio of BH to compound (1) was approximately 97:3. Furthermore, ET-1 was heated and vapor-deposited to a film thickness of 5 nm, then ET-2 and Liq were heated simultaneously and vapor-deposited to a film thickness of 25 nm to form an electron layer consisting of two layers. The vapor deposition rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The vapor deposition rate of each layer was 0.01 to 1 nm / second. Then, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1 nm / s to a film thickness of 1 nm. Subsequently, aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0862] <Elements of Examples B2 to B52 and Comparative Example B1>

[0863] Organic EL devices of Examples B2 to B52 and Comparative Examples B1 to B5 were obtained in the same manner as in Example B1 except that the dopant materials listed in Tables B-1 to B-4 were used instead of Compound (1).

[0864] <Evaluation of Organic EL Characteristics>

[0865] For the organic EL devices of Examples B1 to B52 and Comparative Examples B1 to B5, a DC voltage was applied with an ITO electrode as an anode and a LiF / aluminum electrode as a cathode, and the luminance at 1000 cd / m 2 The driving voltage, external quantum efficiency and device life during luminescence. In addition, the device life is based on 1000cd / m 2 The voltage during light emission was continuously driven, and the time for which the luminance was maintained at 95% or more of the initial luminance was shown in Tables B-5 to B-7.

[0866] The quantum efficiency of a light-emitting element can be divided into internal quantum efficiency and external quantum efficiency. The internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the light-emitting element in the form of electrons (or holes) that is purely converted into photons. Meanwhile, the external quantum efficiency is calculated based on the amount of these photons emitted outside the light-emitting element. Because some photons generated in the light-emitting layer are absorbed or continuously reflected within the light-emitting element and are not emitted outside, the external quantum efficiency is lower than the internal quantum efficiency.

[0867] The external quantum efficiency was measured as follows: Using a voltage / current generator R6144 manufactured by Advantest, a voltage was applied so that the device luminance became 1000 cd / m 2 A voltage of 100° is applied to cause the device to emit light. Using a TOPCON SR-3AR spectroradiometer, the spectral radiance in the visible light region is measured perpendicular to the light-emitting surface. Assuming a perfectly diffuse light-emitting surface, the measured spectral radiance for each wavelength component is divided by the wavelength energy and then multiplied by π to obtain the number of photons at each wavelength. The number of photons emitted by the device is then accumulated over the entire observed wavelength range to determine the total number of photons emitted. The number obtained by dividing the applied current by the elementary charge is the number of carriers injected into the device, and the external quantum efficiency is the total number of photons emitted by the device divided by the number of carriers injected into the device.

[0868] [Table B-5]

[0869]

[0870] [Table B-6]

[0871]

[0872] [Table B-7]

[0873]

[0874] As described above, some of the compounds of the present invention were evaluated as materials for organic EL devices and were shown to be excellent materials. However, other compounds that were not evaluated also have the same basic skeleton and a similar overall structure. Those skilled in the art will understand that they are also excellent materials for organic EL devices.

[0875] Industrial applicability

[0876] The polycyclic aromatic compounds of the present invention are useful as materials for organic devices, particularly as materials for light-emitting layers used to form light-emitting layers in organic electroluminescent devices. By using the polycyclic aromatic compounds of the present invention as dopants for the light-emitting layers, organic electroluminescent devices with long lifespans, low driving voltages, and high-efficiency light emission can be obtained, particularly those with long lifespans and high-efficiency light emission.

[0877] Description of Reference Numerals

[0878] 100 organic electroluminescent elements

[0879] 101 substrate

[0880] 102 Anode

[0881] 103 hole injection layer

[0882] 104 hole transport layer

[0883] 105 Luminescent Layer

[0884] 106 Electron Transport Layer

[0885] 107 Electron Injection Layer

[0886] 108 cathode

Claims

1. A polycyclic aromatic compound represented by the following formula (A-1), or a multimer of a polycyclic aromatic compound having at least two unit structures represented by the formula (A-1), In the formula (A-1), R a1 ~R a3 、R b1 ~R b4 and R c1 ~R c4 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; the two aryl groups of the diarylamino group are optionally bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group are optionally bonded to each other via a linking group, and the two aryl groups of the diarylboryl group are optionally bonded to each other via a linking group. And, R a1 ~R a3 、R b1 ~R b4 and R c1 ~R c4 Two adjacent groups are optionally bonded to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed aryl ring and heteroaryl ring is optionally substituted by 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, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group; the two aryl groups of the diarylamino group are optionally bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group are optionally bonded to each other via a linking group, and the two aryl groups of the diarylboryl group are optionally bonded to each other via a linking group. in, R a1 ~R a3 At least one of is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, Y 1 is B, P, P═O, P═S, Al, Ga, As, Si-R or Ge-R, wherein R of the Si-R and the Ge-R are each independently a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X 1 and X 2 are independently O, NR, C(-R)2, Si(-R)2, S or Se, the R of the NR is hydrogen, an aryl substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a group represented by formula (G-1), the R of the C(-R)2 and the Si(-R)2 are independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, the two R of the C(-R)2 and the Si(-R)2 are optionally bonded to each other to form a ring, and the R of the NR and / or the R of the C(-R)2 are optionally bonded to the a ring and / or the b ring, or to the a ring and / or the c ring by means of a connecting group. 2 Ring bonding, Among them, X 1 and X 2 At least one of them is NR, in which case R of the NR is a group represented by formula (G-1), In the formula (G-1), R d1 ~R d10 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; the two aryl groups of the diarylamino group are optionally bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group are optionally bonded to each other via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group are optionally bonded to each other via a linking group, and the two aryl groups of the diarylboryl group are optionally bonded to each other via a linking group. Furthermore, two adjacent R d1 ~R d10 are optionally bonded to each other to form a cycloalkane condensed structure, at least one hydrogen in the cycloalkane is optionally substituted, Among them, R d6 ~R d10 At least one of them is an alkyl group, or two adjacent Rd 6 ~Rd 10 Bonded to each other to form a cycloalkane condensed structure, R d1 ~R d5 Any one of is a bond to a nitrogen atom; The compound represented by the formula (A-1) or the unit structure of the ring a, ring b, ring c 2 At least one of the rings, aryl rings or heteroaryl rings is optionally fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, at least one -CH2- in the cycloalkane is optionally replaced with -O-, At least one hydrogen in the compound or unit structure represented by formula (A-1) is optionally substituted by a cyano group or a halogen group, and In the compound or unit structure represented by formula (A-1), at least one hydrogen is optionally replaced by deuterium, and at least one nitrogen is optionally replaced by nitrogen-15( 15 N), at least one sulfur is optionally replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36( 36 S), at least one oxygen is optionally replaced with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon is optionally replaced with a carbon-13 ( 13 C), at least one boron is optionally replaced with boron-11 ( 11 B).

2. The polycyclic aromatic compound or its polymer according to claim 1, wherein The above-mentioned formula (G-1) is a group represented by any of formulas (G-2) to (G-21): In the formulas (G-2) to (G-21), R 1 are independently alkyl, R 2 are independently hydrogen or alkyl, * is the bond to the nitrogen atom.

3. The polycyclic aromatic compound or its polymer according to claim 1, wherein The formula (A-1) is represented by any of the following formulas (A-2) to (A-12): In the formulas (A-2) to (A-12), R a2 is a substituted aryl group or a substituted heteroaryl group, wherein the substituted aryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the substituted heteroaryl group is substituted by a substituted or unsubstituted diarylamino group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, in which case the aryl ring of the substituted aryl group or the heteroaryl ring of the substituted heteroaryl group is optionally fused with at least one cycloalkane, and at least one hydrogen in the cycloalkane is optionally substituted, R b2 and R b3 、R c2 and R c3 are independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, Of the two Rs, one is a group represented by formula (G-1), and the other is an aryl group substituted by an alkyl group, a substituted or unsubstituted heteroaryl group, an aryl group condensed by a cycloalkane, a heteroaryl group condensed by a cycloalkane, or a group represented by formula (G-1), R 2 are independently hydrogen or alkyl, R 3 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, X 3 O, NR 4 or C(-R 4 )2, R 4 are each independently an alkyl group, or a substituted or unsubstituted aryl group.

4. The polycyclic aromatic compound or its polymer according to claim 3, wherein In the formulas (A-2) to (A-12), R a2 is a diarylamino group optionally substituted by a methyl group, a tert-amyl group, or a tert-butyl group, or a substituted aryl group substituted by an alkyl group, R b2 and R b3 Among them, one is hydrogen, and the other is methyl, tert-butyl, or tert-pentyl. R c2 and R c3 Among them, one is hydrogen, and the other is methyl, tert-butyl, adamantyl, 3,5-dimethyl-1-adamantyl, Of the two Rs, one is a group represented by the following formula (G-1), and the other is an aryl group substituted by an alkyl group, an aryl group condensed by a cycloalkane, or a group represented by the formula (G-1), R 2 are each independently a methyl group, R 3 Each independently represents the following formula (R 3 -1)~(R 3 -11) represented by any one of the groups, The formula (R 3 -1)~(R 3 -11), * represents the bond to the nitrogen atom; X 3 It is O, N-bis(4-tert-butylphenyl), C(Me)2.

5. The polycyclic aromatic compound or multimer thereof according to claim 1, which is represented by any one of the following formulae: In the formula, Me is a methyl group, tBu is a tert-butyl group, t-Am is a tert-amyl group, and D is deuterium.

6. The polycyclic aromatic compound or its multimer according to claim 5, which is represented by any one of the formulas (1) to (13), (15) to (16), (18), (21) to (26), (31) to (35), (40) to (41), (45) to (52), (55), (57), (59), (60), (64), or (67) to (76). 7 . A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to claim 1 . 8 . The organic device material according to claim 7 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin-film solar cell, or a material for a wavelength conversion filter.

9. The material for an organic device according to claim 8, wherein The material for the organic electroluminescent element is a material for a light-emitting layer.

10. An organic electroluminescent element comprising: a pair of electrodes consisting of an anode and a cathode; and An organic layer is disposed between the pair of electrodes and contains the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 6. The organic electroluminescent element according to claim 10 , wherein: The organic layer is a light-emitting layer.

12. The organic electroluminescent element according to claim 11, wherein The light-emitting layer includes a dopant and a host, and the dopant is the polycyclic aromatic compound or a polymer thereof according to any one of claims 1 to 6.

13. The organic electroluminescent element according to claim 12, wherein The main body is an anthracene compound, a fluorene compound or a dibenzo compound. 14 . A display device or a lighting device comprising the organic electroluminescent element according to claim 10 . 15 . A wavelength conversion filter comprising the wavelength conversion filter material according to claim 8 .

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