Polycyclic aromatic compound and organic electric field light-emitting element

Abstract

To provide a novel compound useful as a material for an organic device such as an organic EL element.SOLUTION: A polycyclic aromatic compound has a structure composed of at least one structural unit represented by formula (1), in which ring A is an aryl ring or heteroaryl ring having a group represented by formula (JABC) as a substituent group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polycyclic aromatic compound. The present invention also relates to a material for an organic device, an organic electroluminescent device, a display device, and a lighting device, each containing the polycyclic aromatic compound. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because of their potential for power saving and thinning, and organic electroluminescent elements (sometimes referred to herein as "organic EL elements" or simply "elements") made from organic materials have been actively studied because they can be easily made lighter and larger. In particular, the development of organic materials that have the luminescence properties of blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (potentially becoming semiconductors or superconductors), regardless of whether they are polymeric or low-molecular-weight compounds, has been actively studied.

[0003] An organic EL device has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing organic compounds disposed between the pair of electrodes. The layers containing organic compounds (sometimes referred to as "organic layers" in this specification) include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] Among these, Patent Document 1 discloses that polycyclic aromatic compounds in which aromatic rings are linked by heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur are useful as materials for organic electroluminescent devices, etc. It has been reported that these polycyclic aromatic compounds have a large HOMO-LUMO gap and a high lowest excited triplet energy level (ET), and are therefore particularly useful as fluorescent materials for organic electroluminescent devices. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0006] As described above, various materials have been developed for use in organic EL devices, but in order to increase the options for materials for organic EL devices, it is desirable to develop materials made of compounds that are different from conventional ones. An object of the present invention is to provide a novel material that is useful as a material for organic devices such as organic EL devices.

[0007] Another object of the present invention is to provide an organic electroluminescent device using a new combination of materials, and an organic EL device having particularly high external quantum efficiency. [Means for solving the problem]

[0008] The present inventors conducted extensive research to solve the above-mentioned problems and succeeded in producing a new polycyclic aromatic compound in which aromatic rings are linked by heteroatoms such as boron, oxygen, nitrogen, and sulfur. They also discovered that an excellent organic EL device can be obtained by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes, thereby completing the present invention. Specifically, the present invention provides the following polycyclic aromatic compounds, as well as materials for organic devices containing the following polycyclic aromatic compounds.

[0009] <1> A polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1): [ka]

[0010] In formula (1), ring A, ring B, ring C, ring D and ring E are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; However, the A ring is represented by the formula (J ABC an aryl ring having a group represented by the formula (J ABC ) as a substituent, X is independently O, S, or NR NX , C(-R CX )2, Si(-R IX )2 or Se, and at least one X is S; R NX , R CX and R IX are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and C(-R CX )2 of 2 R CX may be bonded to each other to form a ring, and Si(-R IX )2 of 2 R IX may be bonded to each other to form a ring, Ar are each independently a group represented by formula (Ar), Formula (J ABC ) in * indicates the point of attachment to the aryl or heteroaryl ring; ring P and ring Q each independently represent a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; In formula (Ar), # represents the position of attachment to N, Ring F is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; G is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted arylthio, a substituted or unsubstituted heteroarylthio, a substituted or unsubstituted aryloxy, a substituted or unsubstituted heteroaryloxy, a substituted or unsubstituted alkyl having 3 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl; At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen in the structure may be replaced with deuterium, a halogen, or a cyano group, and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), sulfur-34( 34 S) or sulfur-36( 36 S), and at least one oxygen may be replaced by oxygen-17( 17 O) or oxygen-18( 18 O), and at least one carbon may be replaced by carbon-13 ( 13 C), and at least one boron may be replaced by boron-11 ( 11 B) may be substituted.

[0011] <2> Formula (1) is represented by the following formula (2X): <1> The polycyclic aromatic compound according to [ka]

[0012] In formula (2X), X and Ar are defined as X and Ar in formula (1), respectively. Z a , Z b and Z d are each independently -C(-R Z )= or -N=, Z = Z are each independently C(-R Z )=C(-R Z), >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and R in the >NR, >C(-R)2, and >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 C(-R Z )=C(-R Z ), two Rs of >C(—R)2 and >Si(—R)2 may be bonded to each other to form a ring, R J is the formula (J ABC ) and R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

[0013] <3> Formula (1) is represented by the following formula (2XJ): <1> The polycyclic aromatic compound according to [ka]

[0014] In formula (2XJ), X and Ar are defined as X and Ar in formula (1), respectively. Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Zare each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

[0015] <4> Formula (1) is represented by the following formula (2XJ-1): <1> The polycyclic aromatic compound according to [ka]

[0016] In formula (2XJ-1), Ar has the same definition as Ar in formula (1), Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

[0017] <5> Formula (1) is represented by the following formula (2XJ-2): <1> The polycyclic aromatic compound according to [ka]

[0018] In formula (2XJ-2), Ar has the same definition as Ar in formula (1), Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

[0019] <6> Formula (1) is represented by the following formula (2XJ-3) or formula (2XJ-4): <1> The polycyclic aromatic compound according to [ka]

[0020] In formula (2XJ-3) and formula (2XJ-4), X and Ar are defined as X and Ar in formula (1), respectively. Y is >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and R in >NR, >C(-R)2, and >Si(-R)2 each independently represents hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two R in >C(-R)2 and >Si(-R)2 may be bonded to each other to form a ring, Z a , Z b , Z c , Zd , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

[0021] <7> Equation (1) is expressed by one of the following equations: <1> The polycyclic aromatic compound according to [ka]

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] [ka]

[0026] [ka]

[0027] [ka]

[0028]

change

[0029]

change

[0030]

change

[0031]

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[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[0038] [ka]

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] <8> Equation (1) is expressed by one of the following equations: <1> The polycyclic aromatic compound according to [ka]

[0043] [ka]

[0044] [ka]

[0045] [ka]

[0046] [ka]

[0047] <9> The device has a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes, and the organic layer <1> ~ <8> 10. An organic electroluminescent device comprising the polycyclic aromatic compound according to any one of claims 1 to 9. <10> the organic layer is an emitting layer; <9> The organic electroluminescent device according to claim 1.

[0048] <11> the light-emitting layer includes at least one selected from the group consisting of an assisting dopant and a phosphorescent material; <10> The organic electroluminescent device according to claim 1.

[0049] <12> <9> ~ <11> 2. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 1 to 11. [Effects of the Invention]

[0050] The present invention provides a novel polycyclic aromatic compound. The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for forming a light-emitting layer in an organic electroluminescent device. [Brief explanation of the drawings]

[0051] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. DETAILED DESCRIPTION OF THE INVENTION

[0052] The present invention will be described in detail below. The following explanation of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In addition, in this specification, "hydrogen" in the explanation of structural formulas means "hydrogen atom (H)."

[0053] In this specification, the term "adjacent groups" refers to two groups bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in a structural formula.

[0054] In this specification, chemical structures and substituents are sometimes represented by the number of carbon atoms. However, when a chemical structure is substituted with a substituent or when a substituent is further substituted with a substituent, the number of carbon atoms refers to the number of carbon atoms in each of the chemical structure and the substituent, and does not refer to the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X," and the carbon number Y is not the total number of carbon atoms in substituents A and B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (with no carbon number restriction)," and the carbon number Y is not the total number of carbon atoms in substituents A and B.

[0055] 1. Polycyclic aromatic compounds 1-1. Polycyclic aromatic compounds The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1). This polycyclic aromatic compound is useful as a compound for forming highly efficient and long-life elements. Furthermore, it is less likely to decompose during vapor deposition compared to similar compounds having approximately the same molecular weight. Hereinafter, in this specification, a polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1) may be referred to as a "polycyclic aromatic compound represented by formula (1)."

[0056] [ka]

[0057] <Explanation for formula (1)> In formula (1), "A", "B", "C", "D" and "E" are each independently symbols representing a ring structure. In formula (1), ring A, ring B, ring C, ring D and ring E are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. However, ring A is a ring represented by formula (J ABC an aryl ring having a group represented by the formula (J ABCThe heteroaryl ring has a group represented by the formula (J) as a substituent. ABC ) will be discussed later.

[0058] In formula (1), each X is independently O, S, or NR NX , C(-R CX )2, Si(-R IX )2 or Se, and at least one X may be S.

[0059] R NX , R CX and R IX are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and C(-R CX )2 of 2 R CX may be bonded to each other to form a ring, and Si(-R IX )2 of 2 R IX may be bonded to each other to form a ring.

[0060] In one embodiment of the present invention, each X is independently O, S, NR NX , C(-R CX )2, Si(-R IX )2 or Se, and at least one X may be S.

[0061] R NX , R CX and R IX are each independently hydrogen, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, and C(-R CX )2 of 2 R CX may be bonded to each other to form a ring, and Si(-R IX )2 of 2 R IX may be bonded to each other to form a ring.

[0062] In one embodiment of the present invention, R NX may be hydrogen, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.

[0063] R NX The aryl may be, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

[0064] In one embodiment of the present invention, R NX may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted indene group, a substituted or unsubstituted terphenyl group (m-terphenyl group, o-terphenyl group, p-terphenyl group), a substituted or unsubstituted acenaphthylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentacenyl group, etc. Furthermore, the fluorenyl group, benzofluorenyl group, and indenyl group each include a structure in which fluorene, benzofluorene, cyclopentane, etc. are spiro-bonded. For example, it may include a substituted or unsubstituted spiro-bifluorenyl group. Furthermore, the fluorenyl group, benzofluorenyl group, and indenyl group also include those in which two of the two hydrogen atoms of the methylene are each replaced by an alkyl such as methyl as the first substituent described below, resulting in a dimethylfluorenyl group, a dimethylbenzofluorenyl group, and a dimethylindenyl group. Here, the "substitution" may be selected from the group consisting of an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, a silane group, an aryl having 6 to 30 carbon atoms, and a heteroaryl having 2 to 30 carbon atoms.

[0065] R NX The heteroaryl may be, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, and particularly preferably a heteroaryl having 2 to 15 carbon atoms.

[0066] In one embodiment of the present invention, R NX may be a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted naphthofuranyl group, a substituted or unsubstituted naphthothiophenyl group, a substituted or unsubstituted benzoindolyl group, a substituted or unsubstituted benzoselenophenyl group, or the like.

[0067] In one embodiment of the present invention, R CX or R IX are each independently a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, and C(-R CX )2 of 2 R CX may be bonded to each other to form a ring, and Si(-R IX )2 of 2 R IX may be bonded to each other to form a ring.

[0068] R CX or R IX The aryl may be, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 1 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

[0069] In one embodiment of the present invention, R CX or R IXmay be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted indene group, a substituted or unsubstituted terphenyl group (m-terphenyl group, o-terphenyl group, p-terphenyl group), a substituted or unsubstituted acenaphthylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentacenyl group, etc. Furthermore, the fluorenyl group, benzofluorenyl group, and indenyl group each include a structure in which fluorene, benzofluorene, cyclopentane, etc. are spiro-bonded. For example, it may include a substituted or unsubstituted spiro-bifluorenyl group. Furthermore, the fluorenyl group, benzofluorenyl group, and indenyl group also include those in which two of the two hydrogen atoms of the methylene are each replaced by an alkyl such as methyl as the first substituent described below, resulting in a dimethylfluorenyl group, a dimethylbenzofluorenyl group, and a dimethylindenyl group. Here, the "substitution" may be selected from the group consisting of an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, a silane group, an aryl having 6 to 30 carbon atoms, and a heteroaryl having 2 to 30 carbon atoms.

[0070] R CX or R IX The heteroaryl may be, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, and particularly preferably a heteroaryl having 2 to 15 carbon atoms.

[0071] In one embodiment of the present invention, the R CX or R IXis a pyrrolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, a pyrazolyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, a 1H-indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a 1H-benzotriazolyl group, a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a naphthyridinyl group, a purinyl group, a pteridinyl group, a carbazolyl group, or an acridinyl group. , phenoxathiinyl group, phenoxazinyl group, phenothiazinyl group, phenazinyl group, phenazasilinyl group, indolizinyl group, furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, furazanyl group, thianthrenyl group, indolocarbazolyl group, benzoindolocarbazolyl group, benzobenzoindolocarbazolyl group, naphthobenzofuranyl group, dioxinyl group, dihydroacridinyl group, xanthenyl group, thioxanthenyl group, dibenzodioxinyl group, dibenzazepinyl group, tribenzazepinyl group, and iminodibenzylyl group. Furthermore, dihydroacridinyl, xanthenyl, and thioxanthenyl groups also include those in which two of the two hydrogen atoms of the methylene are replaced with alkyl groups such as methyl as the first substituent described below, resulting in dimethyldihydroacridinyl, dimethylxanthenyl, and dimethylthioxanthenyl groups. Here, examples of "heteroaryl rings" include bicyclic groups such as bipyridinyl, phenylpyridinyl, and pyridylphenylyl, and tricyclic groups such as terpyridinyl, bispyridylphenylyl, and pyridylbiphenylyl. Furthermore, "heteroaryl rings" also include pyranyl groups.

[0072] In one embodiment of the present invention, the R CX are two R CX may be bonded to each other to form a ring. This is because two substituents R bonded to the same C CXmeans that two R CX may be bonded to each other to form a substituted or unsubstituted fluorenyl group, but is not limited thereto.

[0073] In one embodiment of the present invention, the R IX are two R IX may be bonded to each other to form a ring. This is because two substituents R bonded to the same Si IX means that two R IX may be bonded to each other to form a substituted or unsubstituted 9-silafluorenyl group, but is not limited thereto.

[0074] The "aryl ring" of ring A, ring B, ring C, ring D and ring E in formula (1) includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms.

[0075] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) and a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, and an anthracene ring, fused tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, and a chrysene ring, fused pentacyclic perylene ring and a pentacene ring, etc. The fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, etc. are spiro-bonded, respectively. The fluorene ring, benzofluorene ring, and indene ring also include rings in which two of the two hydrogen atoms of the methylene are replaced by alkyl such as methyl as the first substituent described below, resulting in rings such as dimethylfluorene rings, dimethylbenzofluorene rings, and dimethylindene rings.

[0076] Examples of the "heteroaryl ring" of ring A, ring B, ring C, ring D, and ring E in formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, still more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. In addition, examples of the "heteroaryl ring" include heterocyclic rings containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0077] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, and a pteridine ring. , a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, a naphthobenzofuran ring, a dioxin ring, a dihydroacridine ring, a xanthene ring, a thioxanthene ring, a dibenzodioxin ring, a dibenzazepine ring, a tribenzazepine ring, an iminodibenzyl ring, etc. Furthermore, dihydroacridine rings, xanthene rings, and thioxanthene rings are also preferred in which two of the two hydrogen atoms of the methylene are each replaced by an alkyl such as methyl as a first substituent described below, resulting in a dimethyldihydroacridine ring, a dimethylxanthene ring, a dimethylthioxanthene ring, etc. In addition, bicyclic rings such as bipyridine ring, phenylpyridine ring, and pyridylphenyl ring, and tricyclic rings such as terpyridine ring, bispyridylphenyl ring, and pyridylbiphenyl ring are also included as "heteroaryl rings." In addition, "heteroaryl rings" also include pyran rings.

[0078] Among rings A, B, C, D and E, the aryl ring may be selected from the group consisting of a benzene ring, an indene ring, a naphthalene ring, a fluorene ring, an anthracene ring and a phenanthrene ring, and the heteroaryl ring may be selected from the group consisting of a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a naphthofuran ring, a naphthothiophene ring, a benzoindole ring and a benzoselenophene ring.

[0079] In one embodiment of the present invention, the aryl ring among rings A, B, C, D and E is preferably a benzene ring.

[0080] In one embodiment of the present invention, the heteroaryl ring among rings A, B, C, D and E is preferably a benzenefuran ring or a benzothiophene ring.

[0081] When at least one hydrogen atom in the aryl ring or heteroaryl ring is substituted with a substituent, the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted silyl, or -L-Ak. When these groups have a substituent, the substituent may be aryl, heteroaryl, alkyl or cycloalkyl, or diarylamino.

[0082] At least one selected from the group consisting of aryl rings and heteroaryl rings in the above structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0083] At least one hydrogen in the structure may be replaced with deuterium, halogen, or a cyano group, and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), sulfur-34( 34 S) or sulfur-36( 36 S), and at least one oxygen may be replaced by oxygen-17( 17 O) or oxygen-18( 18 O), and at least one carbon may be replaced by carbon-13 ( 13 C), and at least one boron may be replaced by boron-11 ( 11 B) may be substituted.

[0084] Halogen refers to fluorine, chlorine, bromine, or iodine, and the halogen is preferably fluorine. The same applies hereinafter. Examples of "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0085] Specific examples of the cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl)-substituted, halogen (particularly fluorine)-substituted, and deuterium-substituted derivatives of these compounds having 1 to 5 carbon atoms.

[0086] Among the above examples, a structure in which at least one hydrogen atom is substituted on the α-carbon atom of the cycloalkane (in a cycloalkane fused to an aryl ring or heteroaryl ring, the carbon atom adjacent to the fused carbon atom) is preferred, a structure in which two hydrogen atoms are substituted on the α-carbon atom is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two α-carbon atoms is even more preferred. Examples of such a substituent include alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, halogen (particularly fluorine) substituents, and deuterium substituents. In particular, a structure in which a partial structure represented by the following formula (B10) is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring is preferred.

[0087] [ka]

[0088] In formula (B10), Me represents methyl, and * represents the bonding position.

[0089] At least one hydrogen atom in the "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, such as a substituted or unsubstituted "aryl," a substituted or unsubstituted "heteroaryl," a substituted or unsubstituted "diarylamino," a substituted or unsubstituted "diheteroarylamino," a substituted or unsubstituted "arylheteroarylamino," a substituted or unsubstituted "diarylboryl (the two aryls may be bonded via a single bond or a linking group)," a substituted or unsubstituted "alkyl," a substituted or unsubstituted "cycloalkyl," a substituted or unsubstituted "alkoxy," a substituted or unsubstituted "aryloxy," a substituted "silyl," or -L-Ak. Examples of the first substituent, the aryl of the "aryl" or "heteroaryl" or "diarylamino," the heteroaryl of the "diheteroarylamino," the aryl and heteroaryl of the "arylheteroarylamino," the aryl of the "diarylboryl," and the aryl of the "aryloxy," include the monovalent groups of the "aryl ring" or "heteroaryl ring" described above.

[0090] Specifically, examples of "aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, still more preferably aryl having 6 to 16 carbon atoms, particularly preferably aryl having 6 to 12 carbon atoms, and most preferably aryl having 6 to 10 carbon atoms.

[0091] Specific examples of the aryl include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl and (2-, 3-, 4-, 5-, 6-, 7-)indenyl, which are fused bicyclic aryls; and terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl). fused tricyclic aryls, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl; tetracyclic aryls, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl); aryls such as fused tetracyclic aryls triphenylen-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0092] Furthermore, examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, still more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Furthermore, examples of heteroaryls include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0093] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thienyl, dibenzothienyl, and indyl. hydroxyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, and the like.

[0094] Furthermore, the "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is even more preferred, alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0095] Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), and the like. ), 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.

[0096] Further, for example, 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.

[0097] As a substituent containing the alkyl group, a tertiary alkyl group represented by the following formula (tR) is particularly preferred as a substituent when at least one hydrogen atom in the aryl or heteroaryl ring is substituted with a substituent. This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Substituents in which the tertiary alkyl group represented by formula (tR) is substituted with another substituent as a second substituent are also preferred. Specific examples include diarylamino substituted with a tertiary alkyl group represented by formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a tertiary alkyl group represented by formula (tR), and benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a tertiary alkyl group represented by formula (tR).

[0098] Examples of "diarylamino" include groups explained below as "first substituents." Examples of substitution of the group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0099] [ka]

[0100] In the formula (tR), R a , R b , and R c are each independently alkyl having 1 to 24 carbon atoms, any —CH2— in the alkyl may be replaced with —O—, and * represents the bonding position.

[0101] R a , R b , and R cThe "alkyl having 1 to 24 carbon atoms" in the formula (I) may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

[0102] R in formula (tR) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0103] R a , R b , and R c Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 1-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.

[0104] Examples of the group represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Of these, t-butyl and t-amyl are preferred.

[0105] Examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0106] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituted derivatives of these having 1 to 5 carbon atoms, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0107] Furthermore, examples of the "alkoxy" as the first substituent include straight-chain alkoxy having 1 to 24 carbon atoms and branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 5 carbon atoms (branched-chain alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0108] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0109] Furthermore, examples of the "substituted silyl" as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl, such as trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0110] Examples of "trialkylsilyl" include groups in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and examples of the alkyl include the groups described above as the "alkyl" in the first substituent. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0111] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butylsilyl. butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0112] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are each independently substituted with a cycloalkyl, and examples of the cycloalkyl include the groups described above as the "cycloalkyl" in the first substituent. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specific examples include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0113] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0114] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0115] Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the above-mentioned specific alkyls and aryls. Specific examples of triarylsilyl include triphenylsilyl.

[0116] Furthermore, the "aryl" in the "diarylboryl" of the first substituent can be referenced from the above description of the aryl. Furthermore, the two aryls may be bonded via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (all of which are first substituents), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (all of which are second substituents). Specific examples of these groups can be referenced from the above description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent.

[0117] In the first substituent -L-Ak, L is >NR, >O, or >S, and R of >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. R of >NR may be bonded to Ak via a linking group or a single bond.

[0118] Ak is hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and at least one hydrogen in the alkyl and cycloalkyl may be substituted, and at least one -CH2- in the alkyl and cycloalkyl may be substituted with -O- and -S-.

[0119] Preferably, L is >NR.

[0120] When L is >NR, R is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, more preferably aryl optionally substituted with alkyl, heteroaryl optionally substituted with alkyl, alkyl or cycloalkyl, still more preferably aryl optionally substituted with alkyl, and particularly preferably phenyl optionally substituted with methyl.

[0121] Ak is preferably alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, more preferably alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, more preferably alkyl having 1 to 4 carbon atoms, and even more preferably methyl.

[0122] When L is >NR, R may be bonded to Ak via a linking group or a single bond. Examples of the linking group in this case include >O, >S, and >Si(-R)2. R in >Si(-R)2 is hydrogen, aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. Examples of a structure in which R in >NR is bonded to Ak via a linking group or a single bond include the following:

[0123] [ka]

[0124] In each of the above formulas, Me is methyl and is bonded to a ring-constituting atom of an aryl ring or heteroaryl ring in rings A, B and C at the position marked *.

[0125] As described above for the first substituent, substituted or unsubstituted "aryl," substituted or unsubstituted "heteroaryl," substituted or unsubstituted "diarylamino," substituted or unsubstituted "diheteroarylamino," substituted or unsubstituted "arylheteroarylamino," substituted or unsubstituted "diarylboryl (the two aryls may be bonded via a single bond or a linking group)," substituted or unsubstituted "alkyl," substituted or unsubstituted "cycloalkyl," substituted or unsubstituted "alkoxy," substituted or unsubstituted "aryloxy," or substituted "silyl" may have at least one hydrogen atom substituted with a second substituent. Examples of this second substituent include aryl, heteroaryl, alkyl, or cycloalkyl. For specific examples of these, see the above-described monovalent groups of "aryl ring" or "heteroaryl ring," and the description of "alkyl" or "cycloalkyl" as the first substituent. Furthermore, the aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in these aryl and heteroaryl groups is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl or t-butyl (specific examples are the groups described above), or a cycloalkyl such as cyclohexyl (specific examples are the groups described above). As an example, when the second substituent is carbazolyl, a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also included in the heteroaryl as the second substituent.

[0126] The emission wavelength can be adjusted by the structural steric hindrance, electron donating property and electron withdrawing property of the first substituent. Preferred are groups represented by the following structural formulas, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino), carbazolyl (particularly N-carbazolyl), 3,6-dimethylcarbazolyl, and the like. Preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

[0127] In the structural formula below, "Me" is methyl, "tBu" is t-butyl, "tAm" is t-amyl, "tOct" is t-octyl, and * indicates the bond position. [ka]

[0128] [ka]

[0129] [ka]

[0130]

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[0131]

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[0132]

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[0133]

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[0134]

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[0135]

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[0136]

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[0137]

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[0138]

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[0139]

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[0140]

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[0141] [ka]

[0142] When two or three hydrogens bonded to consecutive (adjacent) carbon atoms are replaced, the substituent may be a group represented by formula (A20). [ka]

[0143] In formula (A20), L S is >NR, >O, >Si(-R)2 or >S, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >Si(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and may be bonded to each other to form a ring, and at least one of the R of the >NR and the >Si(-R)2 is connected to ring A, ring B, ring C, ring D, ring E and ring R by a linking group or a single bond. S and optionally linked to at least one selected from the group consisting of: r is an integer from 1 to 4; R S are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R S is any other R S and may be bonded to each other by a linking group or a single bond, The group represented by formula (A20) is bonded to two adjacent atoms on the aryl ring, heteroaryl ring, or cycloalkane ring at the two * marks.

[0144] When the polycyclic aromatic compound represented by formula (1) contains a group represented by formula (A20), the number thereof is preferably 1 or 2. The group represented by formula (A20) may be a substituent in any one of rings A, B, C, D, and E.

[0145] The group represented by formula (A20) is bonded to two adjacent atoms on an aryl or heteroaryl ring via two * symbols. The group represented by formula (A20) is preferably bonded to two adjacent atoms on an aryl or heteroaryl ring via two * symbols. In this case, both adjacent atoms on the ring are preferably carbon atoms. A fused ring structure is formed by bonding the group represented by formula (A20) to an aryl or heteroaryl ring. A compound represented by formula (1) having this fused ring structure has a more rigid structure. This rigidity suppresses molecular vibration, improves EQE, increases molecular stability, and is expected to extend device life.

[0146] In formula (A20), L S is >NR, >O, >Si(—R)2 or >S. L in the group represented by formula (A20) S By selecting the type of L, it is possible to control the HOMO and LUMO of the polycyclic aromatic compound represented by formula (1). S When is NR, >O, or >S, the HOMO and LUMO become shallower, and when is Si, the HOMO and LUMO become deeper. If the HOMO and LUMO become shallower, TTF devices using these materials are expected to have longer lifetimes, higher efficiency, and lower drive voltages. On the other hand, if the HOMO and LUMO become deeper, the hole-trapping properties of the dopant are lost, and the drive voltage is expected to decrease significantly.

[0147] L in formula (A20) S R in >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. SR in >Si(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, and two R may be bonded to each other to form a ring. At least one of the >NR and the R in >Si(-R)2 is connected to ring A, ring B, ring C, ring D, ring E and ring R by a linking group or a single bond. S L is preferably >NR, >O or >S, more preferably >NR or >O, and even more preferably >NR.

[0148] L S When R is >NR, R is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, or alkyl or cycloalkyl, more preferably aryl optionally substituted with alkyl or cycloalkyl, or heteroaryl optionally substituted with alkyl or cycloalkyl, still more preferably aryl optionally substituted with alkyl or cycloalkyl, and particularly preferably phenyl optionally substituted with alkyl or cycloalkyl.

[0149] In formula (A20), r is an integer of 1 to 4, preferably 2 or 3, and more preferably 2.

[0150] In formula (A20), R S are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R S is any other R S and may be linked to each other via a linking group or a single bond.

[0151] R Sare preferably bonded to each other by a linking group or a single bond. Examples of the linking group include >O and >S. Examples of the divalent group formed by bonding to each other include alkylene. At least one hydrogen atom in the alkylene may be substituted with an alkyl or cycloalkyl, and at least one (preferably one) -CH2- group in the alkylene may be substituted with -O- and -S-. The divalent group formed by bonding to each other is preferably a linear alkylene having 2 to 5 carbon atoms, more preferably a linear alkylene having 3 or 4 carbon atoms, and even more preferably a linear alkylene having 4 carbon atoms (-(CH2)4-). It is particularly preferred that the linear alkylene having 4 carbon atoms (-(CH2)4-) is unsubstituted.

[0152] Two Rs bonded to adjacent carbon atoms S are bonded to each other by a linking group or a single bond, the remaining R S are each independently hydrogen or optionally substituted alkyl, or L S It is preferred that the aryl group is bonded to R in >NR or >Si(—R)2.

[0153] Two Rs bonded to adjacent carbon atoms S are bonded to each other by a linking group or a single bond, the remaining R S The optionally substituted alkyl as represented by is more preferably an optionally substituted alkyl having 1 to 6 carbon atoms, even more preferably an unsubstituted alkyl having 1 to 6 carbon atoms, and most preferably all methyl.

[0154] That is, a preferred example of the group represented by formula (A20) is a group represented by formula (A20-a). [ka]

[0155] In the formula, Me is methyl.

[0156] L S At least one of R in >NR and >Si(-R)2 is connected to ring A, ring B, ring C, ring D, ring E and ring R by a linking group or a single bond. S and L S When is >NR, examples thereof include groups represented by any of the following formulae, and a group represented by formula (A20-b-1) is preferred.

[0157] [ka]

[0158] In each formula, Me is methyl. In each formula, * binds to two or three consecutive (adjacent) atoms on the ring of any one of the aryl ring, heteroaryl ring, or cycloalkane ring of ring A, ring B, and ring C.

[0159] <expression(J ABC ) explanation> The polycyclic aromatic compound structure represented by formula (1) of the present invention has an A ring represented by formula (J ABC an aryl ring having a group represented by the formula (J ABC The heteroaryl ring may have a group represented by the formula (I) as a substituent.

[0160] [ka]

[0161] Formula (J ABC ), * indicates the point of attachment to the aryl or heteroaryl ring.

[0162] Formula (J ABC ), the "P" and "Q" in the circles are symbols indicating the ring structures shown in each circle.

[0163] Formula (J ABCIn the above formula, the P and Q rings each form a divalent group having bonds to two adjacent elements (preferably carbons) on an aryl or heteroaryl ring within the structure. The two bonds bond to the carbon adjacent to the nitrogen.

[0164] Formula (J ABC In the formula (1), the ring P and the ring Q are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. For details of the "aryl ring" and "heteroaryl ring", the explanation of the "aryl ring" and "heteroaryl ring" of the ring A, ring B, ring C, ring D and ring E in the formula (1) can be cited.

[0165] In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0166] In the above structure, at least one hydrogen may be replaced with deuterium, halogen, or a cyano group, and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), sulfur-34( 34 S) or sulfur-36( 36 S), at least one oxygen is oxygen-17( 17 O) or oxygen-18( 18 O), at least one carbon is carbon-13 ( 13 C), at least one boron is boron-11( 11 B) may be substituted.

[0167] In the substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in rings P and Q, the substituent when "substituted or unsubstituted" includes at least one substituent selected from the substituent group Z. The ring having the element having two bonds as a ring constituent element is preferably a 5- or 6-membered ring, more preferably a 6-membered ring. This ring may be further fused with another ring. Examples of 6-membered rings include a benzene ring, a pyridine ring, a pyrazine ring, and a pyrimidine ring. Examples of 6-membered rings further fused with another ring include a naphthalene ring, a quinoline ring, a benzofuran ring, a benzothiophene ring, an indole ring, a benzoselenophene ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, and a dibenzoselenophene ring. Examples of 5-membered rings include a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, and a selenophene ring. Examples of five-membered rings fused with other rings include benzofuran rings, benzothiophene rings, indole rings, and benzoselenophene rings.

[0168] The P ring and the Q ring are each independently preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzoselenophene ring, a substituted or unsubstituted dibenzosilolane ring, or a substituted or unsubstituted N-phenylcarbazole ring. Either one of the P ring and the Q ring is preferably a substituted or unsubstituted benzene ring, more preferably an unsubstituted benzene ring. When either one of the P ring and the Q ring is an unsubstituted benzene ring, the other may be a substituted or unsubstituted benzene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzoselenophene ring, or a substituted or unsubstituted N-phenylcarbazole ring. Here, the "substitution" in the substituted benzene ring, substituted fluorene ring, substituted dibenzofuran ring, substituted dibenzothiophene ring, substituted dibenzoselenophene ring, substituted dibenzosilorane ring, or substituted N-carbazole ring may be deuterium, carbazole, phenyl, biphenyl, or terphenyl, but is not limited to these examples.

[0169] Formula (J ABC Preferred examples of the group represented by the formula (J ABC -1), formula (J ABC -2), formula (J ABC -3), formula (J ABC -4) or formula (J ABC -5). [ka]

[0170] Formula (J ABC -1)~Formula(J ABC -5), Z X is -C(-R ZX )= or -N=, both of which are -C(-R ZX )= is preferred.

[0171] R ZX are each independently hydrogen or a substituent. ZX When R is a substituent, the substituent may be at least one substituent selected from the substituent group Z, and is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and more preferably an unsubstituted alkyl. ZX are preferably all hydrogen.

[0172] Y 1 is >NR NY ,>C(-R CY )2, >O, >Si(-R IY )2, >PR PY ,>P(=O)R POY , >S, >SO, >SO2 or >Se, and R NY , R CY , R IY , R PY and R POY are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; CY may be bonded to each other to form a ring, and two R IY may be bonded to each other to form a ring. NY R is preferably a substituted or unsubstituted aryl having 6 to 18 carbon atoms, and more preferably an unsubstituted phenyl. CY and R IY are each independently preferably an aryl having 6 to 18 carbon atoms or an alkyl having 1 to 18 carbon atoms, and more preferably unsubstituted phenyl or methyl.

[0173] Y 1 As for the NY , >O or >S are preferred.

[0174] Z d are each independently -C(-R Zd )= or -N= and RZd are each independently hydrogen or a substituent. Zd When R is a substituent, the substituent may be at least one substituent selected from the substituent group Z, and is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and more preferably an unsubstituted alkyl. Zd are preferably all hydrogen.

[0175] -N = Z d is the formula (J ABC -1)~Formula(J ABC In each monocyclic ring in formula (J-5), it is preferable that the number is 0 to 2, more preferably 0 to 1, and even more preferably 0. ABC -1)~Formula(J ABC -5), Z d are both -C(-R Zd )= is preferred.

[0176] Formula (J ABC -1)~Formula(J ABC Examples of -5) include structures represented by any one of the following: [ka]

[0177] [ka]

[0178] [ka]

[0179] The formula (J ABC The number of groups represented by the formula (J) is preferably 1 to 3, more preferably 1 to 2. ABC When a plurality of groups represented by the formula (J ABCThe groups represented by the formula (J) may be the same or different from each other. ABC ) are preferably the same as each other.

[0180] Formula (J ABC The substitution position of the group represented by the formula (J) is not particularly limited. ABC When the aryl ring to which the group represented by the formula (J) is bonded is a benzene ring, ABC ) is preferably substituted at the para position of boron (B).

[0181] In the present specification, the substituent group Z is aryl optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen; heteroaryl optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen; diarylamino optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen (two aryls may be bonded to each other via a linking group); diheteroarylamino optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen (two heteroaryls may be bonded to each other via a linking group); arylheteroarylamino optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen (the aryl and heteroaryl may be bonded to each other via a linking group); diarylboryl optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen (two aryls may be bonded via a single bond or a linking group); an alkyl optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, cycloalkyl, cyano, and halogen; cycloalkyl optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen; alkoxy optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, cycloalkyl, cyano, and halogen; aryloxy optionally substituted with at least one group selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen; It consists of deuterium, substituted silyl, cyano, and halogen.

[0182] <Explanation of formula (Ar)> In formula (1), each Ar is independently a group represented by the following formula (Ar): [ka]

[0183] In formula (Ar), # indicates the position of attachment to N. In formula (Ar), "F" in a circle is a symbol indicating the ring structure shown by the circle. In formula (Ar), ring F may be a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. In formula (Ar), G may be a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted arylthio, a substituted or unsubstituted heteroarylthio, a substituted or unsubstituted aryloxy, a substituted or unsubstituted heteroaryloxy, a substituted or unsubstituted alkyl having 3 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl.

[0184] In formula (Ar), ring F may be a substituted or unsubstituted aryl ring. In formula (Ar), examples of the "aryl ring" of ring F include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. In formula (Ar), ring F may be a substituted or unsubstituted heteroaryl ring.

[0185] In formula (Ar), examples of the "heteroaryl ring" of ring F include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, and particularly preferably heteroaryl rings having 2 to 15 carbon atoms. In addition, examples of the "heteroaryl ring" include heterocyclic rings containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0186] The aryl ring in Ring F may be selected from the group consisting of a benzene ring, an indene ring, a naphthalene ring, a fluorene ring, an anthracene ring, and a phenanthrene ring, and the heteroaryl ring may be selected from the group consisting of a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a naphthofuran ring, a naphthothiophene ring, a benzoindole ring, and a benzoselenophene ring. Ring F is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted benzofuran ring.

[0187] When at least one hydrogen atom in the aryl ring or heteroaryl ring is substituted with a substituent, the substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted silyl, or -L-Ak. When these groups have a substituent, the substituent may be an aryl, a heteroaryl, an alkyl or cycloalkyl, or a diarylamino.

[0188] In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0189] In the above structure, at least one hydrogen may be replaced with deuterium, halogen, or a cyano group, and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), sulfur-34( 34 S) or sulfur-36( 36 S), and at least one oxygen may be replaced by oxygen-17( 17 O) or oxygen-18( 18 O), and at least one carbon may be replaced by carbon-13 ( 13 C), and at least one boron may be replaced by boron-11 ( 11 B) may be substituted.

[0190] <Explanation of formula (2X)> [ka]

[0191] An embodiment of the polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1) is a polycyclic aromatic compound represented by formula (2X).

[0192] In formula (2X), X and Ar are defined as X and Ar in formula (1), respectively. Z a , Z b , and Z d are each independently -C(-R Z )= or -N=, Z = Z are each independently C(-R Z )=C(-R Z ), >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and R in the >NR, >C(-R)2, and >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 C(-R Z )=C(-R Z ), two Rs in >C(—R)2 and >Si(—R)2 may be bonded to each other to form a ring, R J is the formula (J ABC ) and R Z are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

[0193] In one embodiment of the present invention, Z a , Z b , or Z d are each independently -C(-R Z )= is also possible.

[0194] In one embodiment of the present invention, each Z=Z is independently C(—R Z )=C(-R Z ), >O or >S.

[0195] <Explanation of formula (2XJ)> [ka]

[0196] One embodiment of the polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1) includes a polycyclic aromatic compound represented by formula (2XJ).

[0197] In formula (2XJ), X and Ar are defined as X and Ar in formula (1), respectively. Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that the substituents on adjacent atoms may be bonded to each other to form a ring.

[0198] In one embodiment of the present invention, Z a , Z b, Z c , Z d , Z e or Z j are each independently -C(-R Z )= is also possible.

[0199] <Explanation of formula (2XJ-1)> [ka]

[0200] An embodiment of the polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1) includes a polycyclic aromatic compound represented by formula (2XJ-1).

[0201] In formula (2XJ-1), Ar is the same as defined for Ar in formula (1), Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that the substituents on adjacent atoms may be bonded to each other to form a ring.

[0202] In one embodiment of the present invention, Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= is also possible.

[0203] <Explanation of formula (2XJ-2)> One embodiment of the polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1) includes a polycyclic aromatic compound represented by formula (2XJ-2). [ka]

[0204] In formula (2XJ-2), Ar is the same as defined for Ar in formula (1), Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that the substituents on adjacent atoms may be bonded to each other to form a ring.

[0205] In one embodiment of the present invention, Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= is also possible.

[0206] <Explanation of formula (2XJ-3)> An embodiment of the polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1) includes a polycyclic aromatic compound represented by formula (2XJ-3). [ka]

[0207] In formula (2XJ-3), X and Ar are defined as X and Ar in formula (1), respectively. Y is >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and R in the >NR, >C(-R)2, and >Si(-R)2 each independently represents hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two R in the >C(-R)2 and the >Si(-R)2 may be bonded to each other to form a ring, Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that the substituents on adjacent atoms may be bonded to each other to form a ring.

[0208] In one embodiment of the invention, Y may be >O or >S.

[0209] In one embodiment of the present invention, Z a , Z b , Zc , Z d , Z e or Z j are each independently -C(-R Z )= is also possible.

[0210] <Explanation of formula (2XJ-4)> An embodiment of the polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1) includes a polycyclic aromatic compound represented by formula (2XJ-4). [ka]

[0211] In formula (2XJ-4), X and Ar are defined as X and Ar in formula (1), respectively. Y is >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and R in the >NR, >C(-R)2, and >Si(-R)2 each independently represents hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two R in the >C(-R)2 and the >Si(-R)2 may be bonded to each other to form a ring, Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that the substituents on adjacent atoms may be bonded to each other to form a ring.

[0212] In one embodiment of the invention, Y may be >O or >S.

[0213] In one embodiment of the present invention, Z a , Z b , Z c , Z d , Z e or Z j are each independently -C(-R Z )= is also possible.

[0214] <Replacement with heavy stable isotopes> All or some of the elements in the polycyclic aromatic compound containing the structural unit represented by formula (1) may be heavy stable isotopes. More specifically, at least one hydrogen may be replaced with deuterium, and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), sulfur-34( 34 S) or sulfur-36( 36 S), and at least one oxygen may be replaced by oxygen-17( 17 O) or oxygen-18( 18 O), and at least one carbon may be replaced by carbon-13 ( 13 C), and at least one boron may be replaced by boron-11 ( 11 B) may be substituted.

[0215] <Replacement with deuterium> All or part of the hydrogen atoms in the polycyclic aromatic compound containing the structural unit represented by formula (1) may be deuterium atoms. This also applies to the polycyclic aromatic compounds represented by formula (2X), formula (2XJ), formula (2XJ-1), formula (2XJ-2), formula (2XJ-3), or formula (2XJ-4).

[0216] For example, hydrogen atoms in the aryl or heteroaryl rings of ring A, ring B, ring C, ring D, or ring E, or in the substituents thereof, may be replaced with deuterium atoms. Among these, embodiments in which all or part of the hydrogen atoms in the aryl or heteroaryl ring are replaced with deuterium atoms are exemplified. ABC All or a part of the hydrogen atoms in the P ring and the Q ring in formula (Ar) or in the aryl ring and the heteroaryl ring in the F ring in formula (Ar) may be replaced with deuterium atoms. From the viewpoint of durability, it is also preferable that all or a part of the hydrogen atoms in the polycyclic aromatic compound containing the structural unit represented by formula (1) are deuterated.

[0217] <Specific examples of polycyclic aromatic compounds> Examples of polycyclic aromatic compounds containing a structural unit represented by formula (1) include compounds represented by any of the following structural formulas. [ka]

[0218] [ka]

[0219] [ka]

[0220] [ka]

[0221] [ka]

[0222] [ka]

[0223] [ka]

[0224]

change

[0225]

change

[0226]

change

[0227]

change

[0228]

change

[0229]

change

[0230]

change

[0231]

change

[0232]

change

[0233]

change

[0234]

change

[0235]

change

[0236]

change

[0237]

change

[0238]

change

[0239]

change

[0240]

change

[0241]

change

[0242]

change

[0243] 1-2.Reactive compounds, polymer compounds, crosslinked polymers, pendant polymer compounds, pendant polymer crosslinked polymers The polycyclic aromatic compound represented by formula (1) can be used as a material for organic devices, such as a material for organic electroluminescent elements, a material for organic field-effect transistors, or a material for organic thin-film solar cells, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), a crosslinked polymer obtained by further crosslinking this polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant crosslinked polymer obtained by further crosslinking this pendant polymer compound (the pendant polymer compound for obtaining this crosslinked pendant polymer has a crosslinkable substituent).

[0244] On the other hand, in this specification, the term "polymer compound" refers to a polymer having a molecular weight distribution and a number average molecular weight of 1×10 3 ~1×10 8 This refers to a polymer with a molecular weight of 1×10^3 to 1×10^8. The polystyrene-equivalent number-average molecular weight (Mn) of a polymer compound can be determined by size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. Specifically, the polymer compound to be measured is dissolved in tetrahydrofuran at a concentration of approximately 0.05% by mass, and 10 μL is injected into the SEC. The mobile phase flow rate is 1.0 mL / min, and a PLgelMIXED_B (Polymer Laboratories) column is used. A UV-VIS detector (Tosoh Corporation, product name: UV-8320GPC) can be used as the detector.

[0245] The polymer compound of the present invention has a number average molecular weight of 2000 to 1×10 8 It is preferable that the ratio is 5000 to 1×10 8 It is more preferable that:

[0246] The reactive substituents (including the polymerizable substituents, crosslinkable substituents, and reactive substituents for obtaining a pendant polymer, hereinafter simply referred to as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction with a main-chain polymer. Examples include unsaturated alkenyl, alkynyl, and cycloalkyl (e.g., cyclobutenyl), groups in which at least one -CH2- in a cycloalkyl is replaced with -O- (e.g., epoxy), and unsaturated condensed cycloalkanes (e.g., condensed cyclobutene), and substituents with the following structures are preferred. In each structural formula, * indicates the bonding position.

[0247] [ka]

[0248] L's are each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, or polyoxyalkylene 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.

[0249] The uses of such polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant crosslinked polymers (hereinafter simply referred to as "polymer compounds and crosslinked polymers") will be described in detail below.

[0250] 2. Method for producing polycyclic aromatic compounds The method for producing polycyclic aromatic compounds containing the structure represented by formula (1) basically involves linking the A, B, and C rings, which are linked by a bonding group (N-Ar), with boron, and then linking the D and E rings with a bonding group (X), and then linking the B, D, and E rings with boron (reaction a); linking the B, D, and E rings, which are linked by a bonding group (X), with boron, and then linking the A and C rings with a bonding group (N-Ar), and then linking the A, B, and C rings with boron (reaction b); or linking the A, B, and C rings with a bonding group (N-Ar), and then linking the D and E rings with a bonding group (X), and then linking the A, B, and C rings with the B, D, and E rings simultaneously and each with boron (reaction c). The final product can be produced by connecting each ring to a bonding group (N-Ar, O, S, NR NX , C(-R CX )2, Si(-R IX When linking rings with Br or Se, for example, etherification reactions can be performed using common reactions such as nucleophilic substitution and the Ullmann reaction, while amination reactions can be performed using common reactions such as the Buchwald-Hartwig reaction. Furthermore, when linking each ring with boron in reactions a, b, and c, a tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, hereinafter the same) can be used. For these production methods, reference can be made to the methods described in prior art documents such as International Publication No. WO 2015 / 102118.

[0251] 3. Organic Devices The polycyclic aromatic compound of the present invention can be used as a material for organic devices, such as organic electroluminescent devices, organic field-effect transistors, and organic thin-film solar cells.

[0252] 3-1. Organic electroluminescent device The organic electroluminescent device has at least a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. The organic EL device according to this embodiment will be described in detail below with reference to the drawings.

[0253] 3-1-1. Structure of organic electroluminescent device Fig. 1 is a schematic cross-sectional view showing an example of an organic EL device. The organic EL device (100) shown in Fig. 1 has a substrate (101), an anode (102) provided on the substrate (101), a hole injection layer (103) provided on the anode (102), a hole transport layer (104) provided on the hole injection layer (103), a light-emitting layer (105) provided on the hole transport layer (104), an electron transport layer (106) provided on the light-emitting layer (105), an electron injection layer (107) provided on the electron transport layer (106), and a cathode (108) provided on the electron injection layer (107).

[0254] The organic EL element (100) may be fabricated in the reverse order, for example, to have a substrate (101), a cathode (108) provided on the substrate (101), an electron injection layer (107) provided on the cathode (108), an electron transport layer (106) provided on the electron injection layer (107), an emissive layer (105) provided on the electron transport layer (106), a hole transport layer (104) provided on the emissive layer (105), a hole injection layer (103) provided on the hole transport layer (104), and an anode (102) provided on the hole injection layer (103).

[0255] Not all of the above layers are essential, and the minimum structural unit is an anode (102), a light-emitting layer (105), and a cathode (108), with the hole injection layer (103), hole transport layer (104), electron transport layer (106), and electron injection layer (107) being optional layers. Each of the above layers may consist of a single layer or multiple layers.

[0256] The layers constituting the EL element may be configured as follows: "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" as described above, as well as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting ... transport layer / cathode," "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode," "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode," "substrate / anode / light-emitting layer / electron transport layer / cathode," or "substrate / anode / light-emitting layer / electron injection layer / cathode."

[0257] 3-1-2. Substrate in organic electroluminescent device The substrate (101) is a support for the organic EL device (100) and is typically made of quartz, glass, metal, plastic, or the like. The substrate (101) is formed into a plate, film, or sheet shape depending on the purpose, and examples thereof include glass plates, metal plates, metal foils, plastic films, and plastic sheets. Glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. For glass substrates, soda-lime glass or alkali-free glass is used, and the thickness should be sufficient to maintain mechanical strength, e.g., 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it minimizes ion elution from the glass. However, commercially available soda-lime glass coated with a barrier coating such as SiO2 can also be used. In addition, in order to improve the gas barrier properties of the substrate (101), a gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate (101). It is particularly preferable to provide a gas barrier film when a synthetic resin plate, film, or sheet with poor gas barrier properties is used as the substrate (101).

[0258] 3-1-3. Anode in organic electroluminescent device The anode (102) serves to inject holes into the light-emitting layer (105). If a hole injection layer (103) and / or a hole transport layer (104) are provided between the anode (102) and the light-emitting layer (105), holes are injected into the light-emitting layer (105) through these layers.

[0259] Materials for forming the anode (102) include inorganic and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and NESA glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline. Other materials that can be used as anodes in organic EL devices can be appropriately selected and used.

[0260] The resistance of the transparent electrode is not limited as long as it can supply sufficient current to light the light-emitting element, but low resistance is desirable from the perspective of the power consumption of the light-emitting element. For example, an ITO substrate with a resistance of 300 Ω / □ or less can function as an element electrode, but since substrates with a resistance of about 10 Ω / □ are now available, it is particularly desirable to use a low resistance product with a resistance of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be selected arbitrarily depending on the resistance value, but it is usually between 50 and 300 nm.

[0261] 3-1-4. Hole injection layer and hole transport layer in organic electroluminescent device The hole injection layer (103) serves to efficiently inject holes migrating from the anode (102) into the light-emitting layer (105) or the hole transport layer (104). The hole transport layer (104) serves to efficiently transport holes injected from the anode (102) or holes injected from the anode (102) via the hole injection layer (103) to the light-emitting layer (105). The hole injection layer (103) and the hole transport layer (104) are each formed by laminating or mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0262] A hole injection / transport material must be able to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. To achieve this, it is desirable for the material to have a low ionization potential, high hole mobility, excellent stability, and be less likely to generate impurities that act as traps during production and use.

[0263] As materials for forming the hole injection layer (103) and the hole transport layer (104), any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices.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 an aromatic tertiary amino group in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, and 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, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl) triphenylamine derivatives such as N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl(phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzo Examples of the suitable polymer include heterocyclic compounds such as furan derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), and porphyrin derivatives, as well as polysilanes. Among polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, and polysilanes are preferred, but there are no particular limitations on the suitable polymers as long as they are capable of forming a thin film necessary for fabricating a light-emitting device, injecting holes from the anode, and transporting holes.

[0264] It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Organic semiconductor matrix materials consist of compounds with good electron donating or accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron donating substances (see, for example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998) and J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes through an electron transfer process in an electron-donating base material (hole-transporting material). The conductivity of the base material varies considerably depending on the number and mobility of the holes. Known matrix materials with hole-transporting properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), as well as certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (see JP 2005-167175 A).

[0265] The hole injection layer material and the hole transport layer material described above can also be used as hole layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. Regarding the reactive substituent in this case, the same explanation as for the polycyclic aromatic compound having the structure represented by formula (1) can be cited.

[0266] The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0267] 3-1-5. Light-emitting layer in organic electroluminescent device The light-emitting layer (105) emits light by recombining holes injected from the anode (102) and electrons injected from the cathode (108) between electrodes under an applied electric field. The material for the light-emitting layer (105) may be a compound (light-emitting compound) that emits light upon excitation by the recombination of holes and electrons. A compound that can be formed into a stable thin film and exhibits strong luminescence (fluorescence) efficiency in the solid state is preferred. The light-emitting layer may be a single layer or multiple layers, each composed of light-emitting layer materials (host material, dopant material). The host material and dopant material may each be one type or a combination of multiple types. For example, an emitting dopant and an assisting dopant may be used as the dopant material. The dopant material may be contained entirely or partially in the host material. The dopant material can be formed by co-evaporation with the host material, or it may be mixed with the host material and then vapor-deposited simultaneously. The light-emitting layer can also be formed by a wet film-forming method using a composition for forming a light-emitting layer prepared by dissolving materials in an organic solvent.

[0268] The polycyclic aromatic compound represented by formula (1) can be preferably used as a material for forming the light-emitting layer of an organic electroluminescent device. The polycyclic aromatic compound represented by formula (1) is more preferably used as an emitting dopant or an assisting dopant in the light-emitting layer, and is more preferably used as an emitting dopant.

[0269] The polycyclic aromatic compound represented by formula (1) may be used as an emitting dopant in an organic light-emitting diode (EL) device (hereinafter referred to as a "TADF device") that exhibits thermally activated delayed fluorescence (TADF) as a "thermally activated delayed fluorescent material." By reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, a highly efficient reverse intersystem crossing occurs from the lowest excited triplet state, which normally has a low transition probability, to the lowest excited singlet state, resulting in emission from the singlet state (thermally activated delayed fluorescence, TADF). In conventional fluorescent emission, 75% of the triplet excitons generated by current excitation undergo a thermal decay pathway and cannot be extracted as fluorescence. In contrast, TADF allows all excitons to be utilized for fluorescent emission, enabling the realization of highly efficient organic EL devices.

[0270] The polycyclic aromatic compound represented by formula (1) can be used as an emitting dopant for a "TADF element," an emitting dopant for a TADF element using two types of hosts, an emitting dopant for an organic electroluminescent element using a separate thermally activated delayed phosphor as an assisting dopant (TADF-assisted fluorescent element, TAF element), or an emitting dopant for an organic electroluminescent element using a phosphorescent material as an assisting dopant (phosphor-sensitized fluorescent element, PSF element). From the viewpoint of ease of production, where fewer materials are used in the element, emitting dopants for TADF elements and TADF elements using two types of hosts are preferred, with emitting dopants for TADF elements being more preferred. From the viewpoint of efficiency, emitting dopants for TAF elements and emitting dopants for phosphorescence-assisted elements are preferred, with emitting dopants for TAF elements being more preferred.

[0271] Generally, the faster the delayed fluorescence, the better the TADF properties. Specifically, when a light-emitting material with a delayed fluorescence lifetime of 20 μsec or less is used as an emitting dopant in a light-emitting device, high device efficiency and long device lifetime can be obtained. In addition, generally, ΔE S1T1 The smaller the value, the better the TADF properties. S1T1 is the lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ) is the energy difference between the S1T1 The value is preferably 0.20 eV or less, and more preferably 0.15 eV or less.

[0272] The light-emitting layer may contain a host compound. Here, the host compound may be one type or two or more types. Any known host compound can be used. Preferred examples of the host compound include high T1 compounds described below.

[0273] The light-emitting layer may be composed of a single layer or multiple layers. The host compound, emitting dopant material, and assisting dopant material may be contained in the same layer, or at least one component may be contained in multiple layers. The host compound and dopant material (emitting dopant or assisting dopant) contained in the light-emitting layer may each be one type or a combination of multiple types. The assisting dopant and emitting dopant may be contained entirely or partially in the host compound as a matrix.

[0274] The amount of the host material used varies depending on the type of host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass of the total mass of the materials for the light-emitting layer.

[0275] The amount of dopant material used varies depending on the type of dopant material and may be determined according to the properties of the dopant material. The amount of dopant material used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass, of the total mass of the materials for the light-emitting layer. The above ranges are preferable in that, for example, concentration quenching can be prevented.

[0276] On the other hand, in an organic electroluminescent device using a TADF material as a dopant material, a low concentration of the dopant material is preferable in terms of preventing concentration quenching, but a high concentration of the dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism.Furthermore, in an organic electroluminescent device using a TADF material as an assisting dopant, a low concentration of the emitting dopant is preferable compared to the amount of the assisting dopant in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant.

[0277] When an assisting dopant material is used, the amounts of the host material, assisting dopant, and emitting dopant used are approximately 40 to 99% by mass, 59 to 1% by mass, and 20 to 0.001% by mass, respectively, based on the total mass of the materials for the light-emitting layer, preferably 60 to 95% by mass, 39 to 5% by mass, and 10 to 0.01% by mass, respectively, and more preferably 70 to 90% by mass, 29 to 10% by mass, and 5 to 0.05% by mass. When an assisting dopant material is used, it may form an exciplex with the host material or the emitting dopant.

[0278] 3-1-5-1.Dopant materials The polycyclic aromatic compound represented by formula (1) is preferably used as a dopant material.

[0279] Dopant materials that can be used other than the polycyclic aromatic compound represented by formula (1) are not particularly limited, and known compounds can be used, and can be selected from a variety of materials depending on the desired emission color.Specific examples include fused ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives (JP Patent Publication No. 245087 / 1999), bisstyrylarylene derivatives (JP Patent Publication No. 247278 / 1990), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran Coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzanthracene derivatives, xanthene derivatives, and rhodamine derivatives. conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

[0280] Examples of blue to blue-green dopant materials include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, and derivatives thereof; furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, and pyrrolopyridine; Examples include aromatic heterocyclic compounds such as lysine and thioxanthene and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and aromatic amine derivatives typified by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0281] Examples of the green to yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. Further, suitable examples include compounds obtained by introducing a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, into the compounds exemplified as the blue to blue-green dopant material.

[0282] Further examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone, and phenanthroline as ligands, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. Further preferred examples include compounds obtained by introducing a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, into the compounds exemplified above as blue to blue-green and green to yellow dopant materials.

[0283] In addition, the dopant can be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13 and the references cited therein.

[0284] Among the above-mentioned dopant materials, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

[0285] The amine having a stilbene structure is represented by, for example, the following formula: [ka]

[0286] In the formula, Ar 1 is an m-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 1~Ar 3 At least one of the groups has a stilbene structure, and Ar 1 ~Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and m is an integer of 1 to 4.

[0287] The amine having a stilbene structure is more preferably diaminostilbene represented by the following formula: [ka]

[0288] In the formula, Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano.

[0289] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenyl, and distyrylfluorenyl.

[0290] Specific examples of the amine having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, N,N'-di(9-phenanthryl)-N,N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl, and the like.

[0291] Furthermore, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may also be used.

[0292] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)perylenyl).

[0293] Additionally, perylene derivatives described in JP-A Nos. 11-97178, 2000-133457, 2000-26324, 2001-267079, 2001-267078, 2001-267076, 2000-34234, 2001-267075, and 2001-217077 may also be used.

[0294] Examples of borane derivatives include 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimesitylboryl)anthracene.

[0295] Furthermore, borane derivatives described in International Publication No. 2000 / 40586 may also be used.

[0296] The aromatic amine derivative is represented by, for example, the following formula: [ka]

[0297] In the formula, Ar 4 is an n-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is an integer of 1 to 4.

[0298] In particular, Ar 4is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is 2.

[0299] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, phenylenyl, and pentacenyl.

[0300] Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalen-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, and N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine.

[0301] Examples of pyrene-based compounds include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, and N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 ,N 6 -diphenyl-N 1 ,N 6 -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6-diamine.

[0302] Examples of anthracene compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, and N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10-diamine. -diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl) Examples include anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, and 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene.

[0303] Other examples include [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl.

[0304] Furthermore, aromatic amine derivatives described in JP-A-2006-156888 and the like may also be used.

[0305] Coumarin derivatives include coumarin-6 and coumarin-334.

[0306] Coumarin derivatives described in JP-A Nos. 2004-43646, 2001-76876, and 6-298758 may also be used.

[0307] Examples of pyran derivatives include DCM and DCJTB shown below. [ka]

[0308] Furthermore, pyran derivatives described in JP-A Nos. 2005-126399, 2005-097283, 2002-234892, 2001-220577, 2001-081090, and 2001-052869 may also be used.

[0309] As the dopant material, the following compounds may be used: [ka]

[0310] 3-1-5-2. High T1 compounds An organic electroluminescent device containing at least one polycyclic aromatic compound represented by formula (1) in an emitting layer preferably further contains at least one high T1 compound having a lowest excited triplet energy level (ET1) (sometimes referred to as "T1 energy") that is at least 0.01 eV higher than the lowest excited triplet energy level of the polycyclic aromatic compound represented by formula (1) in the emitting layer or in an organic layer adjacent to the emitting layer.

[0311] The high T1 compound can be used, for example, as a host compound when the polycyclic aromatic compound represented by formula (1) is used as a dopant compound in the light-emitting layer. The light-emitting layer may contain one type of high T1 compound, or two or more types. When two or more types are contained, it is preferable that they contain a hole-transporting host material and an electron-transporting host material that satisfy the following relationship:

[0312] The HOMO (Highest Occupied Molecular Orbital) of the hole-transporting host material (HH) is shallower than the HOMO of the electron-transporting host material (EH), The LUMO (Lowest Unoccupied Molecular Orbital) of the electron-transporting host material (EH) is deeper than the LUMO of the hole-transporting host material (HH).

[0313] E of high T1 compounds T1 is the E of the polycyclic aromatic compound represented by formula (1). T1 It is preferably 0.03 eV or more higher than the above, and more preferably 0.1 eV or more higher.

[0314] As a high T1 compound, a compound having at least one partial structure selected from partial structure group A, or at least two partial structures selected from partial structure group A and partial structure group B, and optionally having at least one partial structure selected from partial structure group C as a linking group or substituent, is preferred. Meanwhile, at least one * in each of the following structures is bonded to a partial structure other than hydrogen, and the other * is bonded to hydrogen. As can be seen from the structural formulas below, the carbon-carbon bond connecting the benzene rings in each partial structure and the bond connecting the partial structures are in the ortho or m position. In this case, a high T1 and high charge mobility can be obtained. From the viewpoint of high T1, bonding at the ortho position is preferred, and from the viewpoint of high charge mobility, bonding at the m position is preferred.

[0315] Substructure group A [ka]

[0316] Substructure group B [ka]

[0317] [ka]

[0318] substructure group C [ka]

[0319] The partial structure group A is preferably the partial structure group Aa, the partial structure group B is preferably the partial structure group Bb, and the partial structure group C is preferably the partial structure group Cc. [ka]

[0320] Examples of high T1 compounds include compounds represented by the following formula (H1), compounds represented by the following formula (H3), compounds containing a structure represented by the following formula (H4), compounds represented by the following formula (H5), compounds represented by the following formula (H6), and compounds represented by the following formula (H8).

[0321] [ka]

[0322] 3-1-5-2-1. Compound represented by formula (H1) [ka]

[0323] In formula (H1), L 1 represents an arylene having 6 to 24 carbon atoms or a heteroarylene having 5 to 23 carbon atoms, preferably an arylene having 6 to 16 carbon atoms or a heteroarylene having 5 to 15 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms or a heteroarylene having 5 to 11 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms or a heteroarylene having 5 to 9 carbon atoms. Specific examples include divalent or trivalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, a fluorene ring, a spirofluorene ring, a phenalene ring, a triphenylene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a biphenylpyridine ring, a biphenylpyrimidine ring, and a biphenyltriazine ring.

[0324] At least one hydrogen atom in the compound represented by formula (H1) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen, or deuterium. [ka]

[0325] 3-1-5-2-2. Compound represented by formula (H3) [ka]

[0326] In formula (H3), Each MU is independently a divalent aromatic group, each EC is independently a monovalent aromatic group, and k is an integer of 2 to 50,000.

[0327] More specifically, Each MU is independently arylene, heteroarylene, diarylylenearylamino, diarylylenearylboryl, oxaborine-diyl, or azaborine-diyl; each EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen atom in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000.

[0328] k is preferably an integer of 20 to 50,000, and more preferably an integer of 100 to 50,000.

[0329] At least one hydrogen atom in MU and EC in formula (H3) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen, or deuterium; further, any -CH2- in the alkyl may be substituted with -O- or -Si(CH3)2-; any -CH2- in the alkyl except for the -CH2- directly bonded to EC in formula (H3) may be substituted with arylene having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl may be substituted with fluorine.

[0330] Examples of MU include divalent derivatives of the following structures (for example, a divalent group represented by removing any two hydrogen atoms from any of the compounds of the following structures, a divalent group formed by combining two or more divalent groups represented by removing any two hydrogen atoms from any of the compounds of the following structures, and a divalent group in which at least one hydrogen atom in such a group has been substituted with an alkyl or the like).

[0331] [ka]

[0332] More specifically, examples include divalent groups having any of the following structures: In these, MU is bonded to another MU or EC at *. [ka]

[0333] [ka]

[0334] [ka]

[0335] [ka]

[0336] [ka]

[0337] [ka]

[0338] [ka]

[0339] Examples of EC include groups represented by the following formulae: In these, EC is bonded to MU at *. [ka]

[0340] [ka]

[0341] From the viewpoints of solubility and film-forming properties, the compound represented by formula (H3) preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 18 carbon atoms (branched-chain alkyls of 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 12 carbon atoms (branched-chain alkyls of 3 to 12 carbon atoms). On the other hand, from the viewpoints of in-plane alignment and charge transport, preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms (branched-chain alkyls of 7 to 24 carbon atoms).

[0342] 3-1-5-2-3. Compounds containing the structure represented by formula (H4) The compound containing the structure represented by formula (H4) contains a plurality of structures represented by formula (H4), preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and most preferably 1, and when containing a plurality of structures, the structures are directly bonded to each other via a single bond or via a specific linking group.

[0343] [ka]

[0344] In formula (H4), G is "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a substituent or another structure represented by formula (H4).

[0345] As the compound containing the structure represented by formula (H4), for example, the compounds described in WO 2012 / 153780 and WO 2013 / 038650 can be used, and can be produced according to the methods described in the above documents.

[0346] When H in "=C(-H)-" of G is substituted, examples of the substituent include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy.

[0347] Specific examples of the "aryl" substituent include phenyl, tolyl, xylyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, etc., and preferably include phenyl, biphenylyl, terphenylyl, and fluorenyl, etc. Examples of aryl having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl, etc. As shown in the specific examples, aryl includes both fused and non-fused aryl.

[0348] Specific examples of the substituent "heteroaryl" include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthalene. Examples thereof include phthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., and preferred examples include dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothienyl, etc. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, and azadibenzothienyl are more preferred.

[0349] The substituent "substituted silyl" is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0350] Specific examples of substituted or unsubstituted trialkylsilyl include trimethylsilyl and triethylsilyl. Specific examples of substituted or unsubstituted arylalkylsilyl include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of substituted or unsubstituted triarylsilyl include triphenylsilyl and tritolylsilyl.

[0351] The "substituted phosphine oxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0352] The substituent "substituted carboxy" includes, for example, benzoyloxy.

[0353] Examples of the linking group that bonds a plurality of structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, and divalent derivatives of the above-mentioned aryl and heteroaryl.

[0354] Specific examples of the compound containing the structure represented by formula (H4) are shown below. [ka]

[0355] [ka]

[0356] 3-1-5-2-4. Compounds represented by formula (H5) and compounds represented by formula (H6) 3-1-5-2-4-1. Compound represented by formula (H5) [ka]

[0357] In formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, and at least one hydrogen in these may be further substituted with aryl, heteroaryl, or diarylamino.

[0358] In addition, at least one (preferably 1 to 3) of any —C(Rn )= (n is 1 to 11) may be substituted with -N=.

[0359] At least one hydrogen atom in the compound represented by formula (H5) may be further substituted with an alkyl having 1 to 24 carbon atoms, any —CH— in the alkyl may be further substituted with —O— or —Si(CH)—, any —CH— in the alkyl except for the —CH— directly bonded to the compound represented by formula (H5) may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted with fluorine.

[0360] In addition, at least one hydrogen atom in the compound represented by formula (H5) may be substituted with a halogen atom or deuterium.

[0361] 3-1-5-2-4-2. Compound represented by formula (H6) [ka]

[0362] In formula (H6), R 1 ~R 16 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, and at least one hydrogen in these may be further substituted with aryl, heteroaryl, or diarylamino.

[0363] Furthermore, at least one hydrogen atom in the compound represented by formula (H-6) may be substituted with an alkyl having 1 to 24 carbon atoms, any -CH2- in the alkyl may be further substituted with -O- or -Si(CH3)2-, any -CH2- in the alkyl except for the -CH2- directly bonded to the compound represented by formula (H6) may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted with fluorine.

[0364] In addition, at least one hydrogen atom in the compound represented by formula (H6) may be substituted with a halogen atom or deuterium.

[0365] 3-1-5-2-4-3. R in Equation (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16 」 "R in formula (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16 " are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, and are preferably an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (amino having two aryl groups having 6 to 30 carbon atoms), diheteroarylamino (amino having two heteroaryl groups having 2 to 30 carbon atoms), arylheteroarylamino (amino having an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms) or aryloxy having 6 to 30 carbon atoms.

[0366] Examples of the aryl in "aryl," "diarylamino," the aryl in "arylheteroarylamino," and the aryl in "aryloxy" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a fused tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, and a fused pentacyclic perylene ring and a pentacene ring. As will be described later, these aryls substituted with a heteroaryl as defined below are also defined as aryls in Formula (H5) and Formula (H6).

[0367] Examples of the heteroaryl in "heteroaryl" and "diheteroarylamino" and the heteroaryl in "arylheteroarylamino" 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-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-indazole ring, a benzotriazole ring, a 1H-indazole ring, a benzoisomidazole ring, a benzoisothiazole ring, a 1H-ind ... -benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thianthrene ring, and monovalent groups such as the above-mentioned heteroaryl substituted with N-aryl. As will be described later, those heteroaryls substituted with the above-defined aryl are also defined as heteroaryls in formula (H5) and formula (H6).

[0368] Furthermore, R in formula (H5) 1 ~R 11 and R in equation (H6) 1 ~R 16 At least one hydrogen atom in the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy described above may be further substituted with an aryl, heteroaryl, or diarylamino. The substituted aryl, heteroaryl, or diarylamino includes R 1 ~R 11 or R 1 ~R 16 Examples include those explained in the section above.

[0369] R 1 ~R11 or R 1 ~R 16 Specific examples of include groups represented by the following formulae (RG-1) to (RG-10): The groups represented by the following formulae (RG-1) to (RG-10) are bonded to rings a to d in formula (H5) or (H6) at *. [ka]

[0370] The definitions of "aryl" and "heteroaryl" in formulae (H5) and (H6) are explained with reference to the specific groups mentioned above. Formulae (RG-1), (RG-4), and (RG-7) are aryl, formulae (RG-2), (RG-3), and (RG-6) are heteroaryl, formula (RG-9) is heteroaryl substituted with heteroaryl, and formula (RG-10) is aryl substituted with heteroaryl. In addition, formula (RG-5) is aryl (phenyl) substituted with diarylamino (diphenylamino), and formula (RG-8) is diarylamino (diphenylamino).

[0371] [ka]

[0372] 3-1-5-2-4-4.Specific examples of compounds A more specific structure of the compound represented by formula (H5) or formula (H6) is shown below.

[0373] The specific structure of the compound represented by the following formula (H5) or (H6) may be substituted with alkyl having 1 to 24 carbon atoms. [ka]

[0374] [ka]

[0375]

change

[0376]

change

[0377]

change

[0378]

change

[0379]

change

[0380]

change

[0381]

change

[0382]

change

[0383]

change

[0384]

change

[0385]

change

[0386]

change

[0387]

change

[0388]

change

[0389]

change

[0390]

change

[0391]

change

[0392]

change

[0393]

change

[0394]

change

[0395]

change

[0396] [ka]

[0397] [ka]

[0398] [ka]

[0399] 3-1-5-2-4-5. Method for producing a compound represented by formula (H5) or (H6) Compounds represented by formula (H5) can be prepared by first linking rings a through c with a linking group (-O-) to produce an intermediate (reaction 1), then linking rings a through c with a linking group (a group containing B) to produce the final product (reaction 2). Compounds represented by formula (H6) can be prepared by first linking rings a through d with a linking group (>NH or a single bond) to produce an intermediate (reaction 1), then linking rings a through d with a linking group (a group containing B) to produce the final product (reaction 2). For example, etherification reactions can be performed using common reactions such as nucleophilic substitution or the Ullmann reaction, while amination reactions can be performed using common reactions such as the Buchwald-Hartwig reaction. For reaction 2, a tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, hereinafter the same) can be used.

[0400] <Production method: Example of the second reaction of the compound represented by formula (H5)> The second reaction, as shown in Scheme (1) below, introduces B (boron), which connects the a, b, and c rings. An example is shown below for the compound represented by formula (H5). First, the hydrogen atom between the two zeros is orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium. Next, boron trichloride, boron tribromide, or the like is added to perform lithium-boron metal exchange. A Brønsted base, such as N,N-diisopropylethylamine, is then added to carry out a tandem boron-Friedel-Crafts reaction, yielding the desired product. A Lewis acid, such as aluminum trichloride, may be added to accelerate the second reaction.

[0401] [ka]

[0402] In the above scheme, lithium was introduced into the desired position by orthometalation. However, as shown in the following scheme (2), lithium can also be introduced into the desired position by introducing a bromine atom or the like into the desired position and then by halogen-metal exchange.

[0403] [ka]

[0404] By appropriately selecting the above-mentioned synthesis method and the raw materials to be used, a compound represented by formula (H-5) having a substituent at a desired position can be synthesized.

[0405] <Production Method: Example of Production Method for Compound Represented by Formula (H6)> The first and second reactions in the method for producing the compound represented by formula (H5) described above can also be applied to the method for producing the compound represented by formula (H6). In other words, the second reaction is a reaction to introduce B (boron) that bonds NH to the c and d rings. The hydrogen atom of NH is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, followed by the addition of boron trichloride, boron tribromide, or the like to perform lithium-boron metal exchange. A Brønsted base such as N,N-diisopropylethylamine is then added to carry out a tandem boron-Friedel-Crafts reaction to obtain the desired product. Again, a Lewis acid such as aluminum trichloride may be added in the second reaction to promote the reaction.

[0406] 3-1-5-2-5. Compounds containing the structure represented by formula (H8) The compound containing a structure represented by formula (H8) contains a plurality of structures represented by formula (H8), preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and most preferably 1, and when containing a plurality of structures, the structures are directly bonded to each other via a single bond or via a specific linking group.

[0407] [ka]

[0408] In formula (H8), Z is "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a structure represented by a substituent.

[0409] When H in "=C(-H)-" which is Z is substituted, examples of the substituent include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy.

[0410] Specific examples of the "aryl" substituent include phenyl, tolyl, xylyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, etc., and preferred are phenyl, biphenylyl, terphenylyl, and fluorenyl, etc. Examples of aryl having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl, etc. As shown in the specific examples, aryl includes both fused and non-fused aryl.

[0411] Specific examples of the substituent "heteroaryl" include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthalene. Examples thereof include phthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., and preferred examples include dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothienyl, etc. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, and azadibenzothienyl are more preferred.

[0412] The substituent "substituted silyl" is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0413] Specific examples of substituted or unsubstituted trialkylsilyl include trimethylsilyl and triethylsilyl. Specific examples of substituted or unsubstituted arylalkylsilyl include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of substituted or unsubstituted triarylsilyl groups include triphenylsilyl and tritolylsilyl.

[0414] The "substituted phosphine oxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0415] The substituent "substituted carboxy" includes, for example, benzoyloxy.

[0416] Examples of the linking group that bonds a plurality of structures represented by formula (H8) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl.

[0417] Specific examples of the compound containing the structure represented by formula (H8) are shown below. [ka]

[0418] [ka]

[0419] 3-1-5-2-6.TADF material The high T1 compound may be a TADF material.

[0420] In this specification, TADF material refers to a material that is a "thermally activated delayed fluorescent material." By reducing the energy difference between the excited singlet state and the excited triplet state, "thermally activated delayed fluorescent material" efficiently transfers energy from the excited triplet state, which normally has a low transition probability, to the excited singlet state, resulting in emission from the singlet state (thermally activated delayed fluorescent material, TADF). In conventional fluorescent light emission, 75% of the triplet excitons generated by current excitation pass through a thermal deactivation pathway and cannot be extracted as fluorescence. In contrast, TADF allows all excitons to be utilized for fluorescent light emission, enabling the realization of highly efficient organic electroluminescent devices.

[0421] TADF materials are preferably donor-acceptor type TADF compounds (DA type TADF compounds), which are designed to localize the HOMO and LUMO within the molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby allowing efficient reverse intersystem crossing to occur.

[0422] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO orbital is localized in a TADF compound molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the LUMO orbital is localized in a TADF compound molecule.

[0423] In general, TADF compounds using donors and acceptors have large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a low ΔE ST On the other hand, TADF compounds using donors or acceptors exhibit large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a transition from the ground state to the excited state, the structure subsequently changes to the stable structure in the excited state), which gives rise to a broad emission spectrum, and so there is a possibility that the color purity will decrease if used as an emitting material.

[0424] However, by simultaneously using the polycyclic aromatic compound represented by formula (1), the polycyclic aromatic compound represented by formula (1) functions as an emitting dopant and the TADF material functions as an assisting dopant, resulting in high color purity. The TADF material may be any compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound represented by formula (1). The polycyclic aromatic compound represented by formula (1) and the TADF material may be contained in the same layer or in adjacent layers.

[0425] Examples of TADF materials that can be used for this purpose include a compound represented by the following formula (H7) or a compound having the following formula (H7) as a partial structure. [ka]

[0426] In formula (H7), ED is an electron-donating group, Ln is a bonding group, and EA is an electron-accepting group. The lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ) energy difference (ΔE ST ) is less than 0.2 eV (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔE ST ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and even more preferably 0.08 eV or less.

[0427] As the electron donating group (donor structure) and the electron accepting group (acceptor structure) used in the TADF material, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. 3 Nitrogen-containing functional groups are exemplified, more specifically, groups derived from carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, diphenyl-dihydrodibenzoazasiline, etc. Examples of EA include, for example, sp 2Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings with ketones and cyano, more specifically sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthone, Examples of Ln include groups derived from thracenone, anthracenedione, pyridine, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, benzenetricarbonitrile, 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 a single bond and an arylene, more specifically, phenylene, biphenylene, naphthylene, and the like. In any of the structures, hydrogen may be substituted with an alkyl, cycloalkyl, or aryl. In particular, compounds having at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone are preferred.

[0428] In formula (H7), the linking group Ln functions as a spacer structure that separates the donor partial structure and the acceptor partial structure.

[0429] More specifically, the compound represented by formula (H7) may be a compound represented by any one of formulas (H7-1), (H7-2) and (H7-3). [ka]

[0430] In formula (H7-1), formula (H7-2) and formula (H7-3), M each independently represents a single bond, -O-, >N-Ar, or >C(-Ar)2, and is preferably a single bond, -O-, or >N-Ar from the viewpoint of the HOMO depth and the heights of the lowest excited singlet energy level and the lowest excited triplet energy level of the partial structure to be formed; J is a linking group corresponding to Ln in formula (H7), and each J is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferred, and more specific examples thereof include phenylene, methylphenylene, and dimethylphenylene. Q each independently represents ═C(—H)— or ═N—, and is preferably ═N— in terms of the shallowness of the LUMO of the partial structure to be formed and the heights of the lowest excited singlet energy level and the lowest excited triplet energy level; Ar each independently represents hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 18 carbon atoms; from the viewpoint of the HOMO depth and the lowest excited singlet energy level and the lowest excited triplet energy level of the partial structure to be formed, Ar is preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazole, or phenylbenzimidazole, and still more preferably hydrogen, phenyl, or carbazolyl; m is 1 or 2; n is an integer of 2 to (6-m), and from the viewpoint of steric hindrance, is preferably an integer of 4 to (6-m).

[0431] Furthermore, at least one hydrogen atom in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0432] Examples of compounds represented by formula (H7) include compounds represented by the following structures: In the structural formula, * indicates a bonding position, "Me" indicates methyl, and "tBu" indicates t-butyl. [ka]

[0433] [ka]

[0434] [ka]

[0435] [ka]

[0436] [ka]

[0437] [ka]

[0438] [ka]

[0439] [ka]

[0440] [ka]

[0441] [ka]

[0442] Of the specific compounds described above, preferred examples of the compound represented by formula (H7) are PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, ACRD SO2, DTC-DBT, DTAO, 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz.

[0443] 3-1-5-3. Thermally activated delayed phosphor (assisting dopant) The light-emitting layer may contain a thermally activated delayed phosphor as an assisting dopant.

[0444] "Thermally activated delayed fluorescent material" refers to a compound that absorbs thermal energy, undergoes reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and then radiatively deactivates from the lowest excited singlet state to emit delayed fluorescence. However, "thermally activated delayed fluorescent material" also includes compounds that undergo a higher triplet state during the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, see a paper by Monkman et al. of Durham University (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038 / ncomms 13680), a paper by Hosokai et al. of the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci.Adv. 2017; 3:e1603282), a paper by Sato et al. of Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-05007-7), and a paper by Sato et al. of Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-05007-7). (The 98th Annual Meeting of the Chemical Society of Japan, Presentation Number: 2I4-15, "Mechanism of Highly Efficient Emission in Organic Electroluminescence Using DABNA as an Emitting Molecule," Graduate School of Engineering, Kyoto University), a review by Bui et al. (DOI: 10.3762 / bjoc.14.18), a review by Duan et al. (DOI: 10.1063 / 1.5143501), a review by Ding et al. (DOI: 10.1088 / 1674-4926 / 42 / 5 / 050201), and a review by Xie et al. (DOI: 10.1002 / adom.202002204). In the present invention, when a sample containing the target compound is measured for its fluorescence lifetime at 300 K, if a slow fluorescent component is observed, the target compound is determined to be a "thermally activated delayed fluorescent substance." Here, the term "slow fluorescent component" refers to a component whose fluorescent lifetime is 0.1 μsec or longer. The fluorescent lifetime can be measured using, for example, a fluorescent lifetime measuring device (manufactured by Hamamatsu Photonics KK, C11367-01).

[0445] The polycyclic aromatic compound represented by formula (1) can function as an emitting dopant, and the "thermally activated delayed phosphor" can function as an assisting dopant that assists the emission of the polycyclic aromatic compound represented by formula (1).

[0446] In the following description, an organic electroluminescent device that uses a thermally activated delayed fluorescent substance as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device).

[0447] The "host compound" in a TAF element means a compound whose lowest excited singlet energy level, determined from the shoulder on the short-wavelength side of the peak of the fluorescence spectrum, is higher than that of the thermally activated delayed fluorescent substance as an assisting dopant and the emitting dopant.

[0448] In this embodiment, known host compounds can be used, such as compounds having at least one of a carbazole ring and a furan ring. Among them, it is preferable to use a compound in which at least one of a furanyl group and a carbazolyl group is bonded to at least one of an arylene group and a heteroarylene group. Specific examples include mCP and mCBP.

[0449] The lowest excited triplet energy level E(1,T,Sh), determined from the shoulder on the short-wavelength side of the peak of the phosphorescence spectrum of the host compound, is preferably higher than the lowest excited triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitting dopant or assisting dopant having the highest lowest excited triplet energy level in the emitting layer, from the viewpoint of promoting TADF generation without inhibiting it. Specifically, the lowest excited triplet energy level E(1,T,Sh) of the host compound is preferably higher than E(2,T,Sh) and E(3,T,Sh) by 0.01 eV or more, more preferably by 0.03 eV or more, and even more preferably by 0.1 eV or more. Furthermore, a TADF-active compound may be used as the host compound.

[0450] The thermally activated delayed phosphor (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally activated delayed phosphor (DA type TADF compound) designed to localize the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) within the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, thereby causing efficient reverse intersystem crossing.

[0451] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO orbital is localized in the thermally activated delayed fluorescent substance molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the LUMO orbital is localized in the thermally activated delayed fluorescent substance molecule.

[0452] In general, thermally activated delayed fluorescent materials using donors and acceptors have large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a low ΔE S1T1 On the other hand, thermally activated delayed fluorescent materials using donors or acceptors exhibit large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a transition from the ground state to the excited state, the structure subsequently changes to the stable structure in the excited state), giving a wide emission spectrum, which may reduce color purity when used as a light-emitting material.

[0453] As the thermally activated delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer can be used.As the electron donating group (donor structure) and electron accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzazasiline.Acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorene dicarbonitrile, triphenyltriazine, pyrazine dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. In particular, the compound having thermally activated delayed fluorescence in the TAF element is preferably a compound having at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0454] The compound used as the assisting dopant in the light-emitting layer of the TAF element is preferably a thermally activated delayed phosphor, the emission spectrum of which at least partially overlaps with the absorption peak of the emitting dopant.

[0455] 3-1-5-4. Phosphorescent materials (assisting dopants) In the light-emitting layer, a phosphorescent material may be used as an assisting dopant. The phosphorescent material utilizes the intramolecular spin-orbit interaction (heavy atom effect) of a metal atom to obtain light emission from triplets. For example, a luminescent metal complex can be used as such a phosphorescent material. For example, the luminescent metal complex can be a compound represented by the following formula (B-1) or (B-2).

[0456] [ka]

[0457] In formula (B-1), M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu, n is an integer of 1 to 3, and each "XY" is independently a bidentate ligand. In formula (B-2), M is at least one selected from the group consisting of Pt, Re, and Cu, and "WXYZ" is a tetradentate ligand.

[0458] In the formula (B-1), M is preferably Ir and n is preferably 3 from the viewpoints of efficiency and life. In the formula (B-2), M is preferably Pt from the viewpoint of efficiency and life.

[0459] The ligand (XY) in formula (B-1) has at least one ligand selected from the group consisting of: The ligand (WXYZ) in formula (B-2) has at least one ligand selected from the group consisting of:

[0460] [ka]

[0461] During the ceremony, --- binds to the central metal M, Y is independently BR e , N.R. e , PR e, O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f , or GeR e R f and Each aromatic carbon atom CH in the ring may be independently substituted with N; R e and R f may be optionally fused or linked to form a ring, R a , R b , R c , and R d may each independently be unsubstituted or substituted with from 1 to the maximum possible number of substitutions, R a , R b , R c , R d , R e , and R f are each independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or a combination thereof; However, R a , R b , R c , and R d Any two adjacent substituents in may be fused or linked to form a ring or to form a multidentate ligand.

[0462] Examples of the compound represented by formula (B-1) include Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), and fac-Tris(2-(3-p-xylyl)phenyl)pyridine. iridium(III), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(2-phq)3, Ir(BT)2(acac), Ir(DMP)3 , Ir(Mphq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, etc.

[0463] Other examples of the compound represented by formula (B-1) include the following compounds: [ka]

[0464] [ka]

[0465] [ka]

[0466] In addition, iridium complexes described in JP 2006-089398 A, JP 2006-080419 A, JP 2005-298483 A, JP 2005-097263 A, and JP 2004-111379 A, ​​U.S. Patent Application Publication No. 2019 / 0051845, or Advanced Materials, 26: 7116-7121, NPG Asia Materials 13, 53 (2021), Applied Physics Letters, 117, 253301 (2020), Light-Emitting Diode—An Outlook On the Empirical Features and Its Recent Technological Advancements, Chapter 5 may also be used.

[0467] 3-1-6. Electron injection layer and electron transport layer in organic electroluminescent devices The electron injection layer (107) plays a role of efficiently injecting electrons moving from the cathode (108) into the light-emitting layer (105) or the electron transport layer (106). The electron transport layer (106) plays a role of efficiently transporting electrons injected from the cathode (108) or electrons injected from the cathode (108) via the electron injection layer (107) to the light-emitting layer (105). The electron transport layer (106) and the electron injection layer (107) are each formed by laminating or mixing one or more electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0468] The electron injection / transport layer is a layer responsible for injecting electrons from the cathode and transporting them. It is desirable for the layer to have high electron injection efficiency and efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and be less likely to generate trapping impurities during manufacture and use. However, considering the balance between hole and electron transport, if a material primarily serves to efficiently block holes from the anode from flowing to the cathode without recombining, it can have the same effect of improving luminous efficiency as a material with high electron transport ability, even if it does not have a particularly high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also function as a layer that can efficiently block the movement of holes.

[0469] The material (electron transport material) forming the electron transport layer (106) or the electron injection layer (107) can be arbitrarily 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.

[0470] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their fused ring derivatives; and metal complexes containing electron-accepting nitrogen. Specific examples include fused ring aromatic derivatives such as naphthalene and anthracene; styryl aromatic derivatives such as 4,4'-bis(diphenylethenyl)biphenyl; perinone derivatives; coumarin derivatives; naphthalimide derivatives; quinone derivatives such as anthraquinone and diphenoquinone; phosphine oxide derivatives; arylnitrile derivatives; and indole derivatives. Examples of metal complexes containing electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with other materials.

[0471] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (e.g., 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, and triazine derivatives. compounds, pyrazine derivatives, benzoquinoline derivatives (e.g., 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (e.g., tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (e.g., 1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene), naphthyridine derivatives (e.g., bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, and bisstyryl derivatives.

[0472] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0473] The above-mentioned materials may be used alone or in combination with other materials.

[0474] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0475] <Borane derivatives> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587.

[0476] [ka] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, an optionally substituted heterocyclic compound having a nitrogen atom, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or fewer carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0477] Among the compounds represented by formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following formula (ETM-1-2) are preferred.

[0478] [ka]

[0479] In formula (ETM-1-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, an optionally substituted heterocyclic compound having a nitrogen atom, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, an optionally substituted heterocyclic compound having a nitrogen atom, or cyano; and X 1 represents an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0480] [ka]

[0481] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, an optionally substituted heterocyclic compound having a nitrogen atom, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1is an arylene having 20 or less carbon atoms which may be substituted, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0482] X 1 Specific examples of include divalent groups represented by any of the following formulae (X-1) to (X-9). [ka]

[0483] (In each formula, R a are each independently alkyl, cycloalkyl or optionally substituted phenyl, and * indicates the bonding position.

[0484] Specific examples of the borane derivative include the following compounds: [ka]

[0485] This borane derivative can be produced using known raw materials and known synthesis methods.

[0486] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and is preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0487] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4.

[0488] In formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms).

[0489] In formula (ETM-2-2), R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms), and R 11 and R 12 may be bonded to form a ring.

[0490] In each formula, the "pyridine-based substituent" is any of the following formulae (Py-1) to (Py-15) (in the formula, * indicates the bonding position), and each pyridine-based substituent may be independently substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl, with methyl being preferred. In addition, the pyridine-based substituent may be bonded to φ, an anthracene ring, or a fluorene ring in each formula via phenylene or naphthylene.

[0491] [ka]

[0492] The pyridine-based substituent is any one of formulas (Py-1) to (Py-15) (where * indicates the bonding position), and among these, any one of formulas (Py-21) to (Py-44) below is preferred.

[0493] [ka]

[0494] At least one hydrogen atom in each pyridine derivative may be replaced with deuterium, and one of the two "pyridine-based substituents" in formulae (ETM-2-1) and (ETM-2-2) may be replaced with aryl.

[0495] R 11 ~R 18 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0496] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 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.

[0497] The above description of alkyl can be cited for the alkyl having 1 to 4 carbon atoms substituted with a pyridine-based substituent.

[0498] R 11~R 18 In the above, examples of the "cycloalkyl" include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms.

[0499] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0500] R 11 ~R 18 As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is aryl having 6 to 12 carbon atoms.

[0501] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl, which are fused tricyclic aryl; triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, which are fused tetracyclic aryl; and perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl, which are fused pentacyclic aryl.

[0502] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 2-naphthyl.

[0503] R in Equation (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0504] Specific examples of the pyridine derivative include the following compounds: [ka]

[0505] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0506] <Fluoranthene derivatives> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and is disclosed in detail in WO 2010 / 134352. [ka]

[0507] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched, or cyclic alkyl, linear, branched, or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. In the case of substitution, examples of the substituent include aryl, heteroaryl, alkyl, and cycloalkyl.

[0508] Specific examples of the fluoranthene derivative include the following compounds: [ka]

[0509] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

Chemical formula

[0510] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0511] Also, among R 1 ~R 11 adjacent groups may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring or c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0512] Also, at least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.

[0513] Regarding the description of the substituents and ring formation forms in the formula (ETM-4), the description of the polycyclic aromatic compound composed of the partial structure represented by the formula (1) can be cited.

[0514] Specific examples of this BO-based derivative include, for example, the following compounds. [ka]

[0515] This BO derivative can be produced using known raw materials and known synthesis methods.

[0516] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0517] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and Ar in formula (ETM-5) 2 The same explanation as for "aryl having 6 to 20 carbon atoms" in the above can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0518] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms), and two Ar 2 may be bonded to form a ring.

[0519] Ar 2The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0520] Ar 2 In the above, the "cycloalkyl" can be, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0521] Ar 2 As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is aryl having 6 to 12 carbon atoms.

[0522] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, phenylenyl, and pentacenyl.

[0523] Two Ar 2 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0524] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0525] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0526] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): Details are also described in WO 2013 / 079217 and WO 2013 / 079678.

[0527] [ka]

[0528] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms, R 7 and R 8 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.

[0529] Here, when substituted, the substituent includes aryl, heteroaryl, alkyl, cycloalkyl, and the like.

[0530] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0531] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0532] Ar 1 may be the same or different and are arylene or heteroarylene. 2 may be the same or different and are aryl or heteroaryl, provided that Ar1 and Ar 2 At least one of R has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural portion, and when n is 3, there is no unsaturated structural portion. 1 does not exist.

[0533] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. When substituted, the substituent is not particularly limited, and examples thereof include alkyl, aryl, and heterocyclic groups, which also apply to the following description. The number of carbon atoms in the alkyl is not particularly limited, but is usually in the range of 1 to 20 from the viewpoints of availability and cost.

[0534] The term "cycloalkyl" refers to a saturated alicyclic hydrocarbon group, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be substituted or unsubstituted. The number of carbon atoms in the alkyl moiety is not particularly limited, but is usually in the range of 3 to 20.

[0535] The term "aralkyl" refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be substituted or unsubstituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, but is usually in the range of 1 to 20.

[0536] The term "alkenyl" refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, or butadienyl, which may be substituted or unsubstituted. The number of carbon atoms in the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0537] Furthermore, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc., which may be unsubstituted or substituted.

[0538] The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be substituted or unsubstituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually in the range of 2 to 20.

[0539] The term "alkoxy" refers to an aliphatic hydrocarbon group formed by an ether bond, such as methoxy, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[0540] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is substituted with a sulfur atom.

[0541] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is substituted with a sulfur atom.

[0542] The aryl ether refers to an aromatic hydrocarbon group formed by an ether bond, such as phenoxy, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether is not particularly limited, but is usually in the range of 6 to 40.

[0543] An aryl thioether is a group in which the oxygen atom of the ether bond of an aryl ether is substituted with a sulfur atom.

[0544] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, or pyrenyl. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0545] The heterocyclic group refers to a cyclic structural group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0546] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0547] The aldehyde, carbonyl, and amino groups may include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

[0548] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be unsubstituted or substituted.

[0549] Silyl refers to a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in the silyl is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[0550] The fused ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 It is a conjugated or non-conjugated fused ring formed between two R 1 They may form conjugated or non-conjugated fused rings together, which may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused to another ring.

[0551] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0552] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0553] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689.

[0554] [ka]

[0555] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

[0556] Examples of the "aryl" in "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0557] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl; the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the fused tetracyclic aryl group is triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl; and the fused pentacyclic aryl group is perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0558] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0559] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0560] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0561] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0562] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0563] <Arylnitrile derivatives> The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded via single bonds, etc. Details are described in the specification of U.S. Application Publication No. 2014 / 0197386. [ka]

[0564] Ar niFrom the viewpoint of high-speed electron transport properties, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, in order to be used in a layer adjacent to the light-emitting layer, it is preferable that the aryl group has a high T1 and is an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 14 carbon atoms, and more preferably an aryl having 6 to 10 carbon atoms. Furthermore, the number of nitrile group substitutions, n, is preferably large from the viewpoint of a high T1, and is preferably small from the viewpoint of a high S1. Specifically, the number of nitrile group substitutions, n, is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 or 2, and even more preferably 1.

[0565] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. From the viewpoint of high S1 and high T1, donor heteroaryls are preferred, and since the layer is used as an electron transport layer, it is preferable that there are fewer donor heteroaryls. From the viewpoint of charge transportability, aryls or heteroaryls with a large number of carbon atoms are preferred, and it is preferable that they have many substituents. The number of substitutions m of Ar is specifically an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

[0566] Examples of the "aryl" in "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0567] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl; the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the fused tetracyclic aryl group is triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl; and the fused pentacyclic aryl group is perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0568] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. In addition, examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0569] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0570] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0571] The aryl nitrile derivative may be a polymer in which a plurality of compounds represented by formula (ETM-9) are bonded via single bonds, etc. In this case, they may be bonded via an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) in addition to a single bond.

[0572] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0573] The arylnitrile derivative can be produced using known raw materials and known synthesis methods.

[0574] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in the specification of U.S. Patent Application Publication No. 2011 / 0156013. [ka]

[0575] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 3, preferably 2 or 3.

[0576] Examples of the "aryl" in "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0577] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl; the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the fused tetracyclic aryl group is triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl; and the fused pentacyclic aryl group is perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0578] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. In addition, examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0579] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0580] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0581] Specific examples of the triazine derivative include the following compounds: [ka]

[0582] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0583] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0584] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), n is an integer of 1 to 4, and the "benzimidazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the following benzimidazolyl (in the formula, * indicates the bonding position), and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[0585] [ka]

[0586] R in the benzimidazolyl 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R 11 The explanation can be cited.

[0587] Φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure can be as described in formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described as being bonded together. However, when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent, and the "pyridine-based substituent" is replaced with R 11 ~R 18 may be replaced with

[0588] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

[0589] [ka]

[0590] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0591] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982.

[0592] [ka]

[0593] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4.

[0594] R in each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 One of these bonds becomes a bond to the aryl ring φ.

[0595] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0596] R 11 ~R 18 The alkyl, cycloalkyl and aryl in formula (ETM-2) include R 11 ~R 18 can be cited. In addition to the examples mentioned above, φ can also be represented by the following structural formulas. In the structural formulas below, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates the bonding position.

[0597] [ka]

[0598] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6-di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10-phenanthrolin-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthrolin-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthrolin-9-yl)benzene, and compounds represented by the following structural formula:

[0599] [ka]

[0600] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0601] <Quinolinol-based metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka]

[0602] In the formula, R 1 ~R 16 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, Ga, Be, or Zn; and n is an integer of 1 to 3.

[0603] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolate)aluminum, and bis(2-methyl-8-quinolinolato). Bis(2-methyl-8-quinolinolate)(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,3 -dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum linolinolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- Examples of suitable bis(2-methyl-4-ethyl-8-quinolinolate)aluminum include bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, and bis(10-hydroxybenzo[h]quinoline)beryllium.

[0604] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0605] <Thiazole Derivatives and Benzothiazole Derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka]

[0606] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0607] In each formula, φ represents an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4. A "thiazole-based substituent" or a "benzothiazole-based substituent" refers to a substituent in which the pyridyl in the "pyridine-based substituent" in formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is substituted with the following thiazolyl or benzothiazolyl (* indicates the bonding position), and at least one hydrogen atom in the thiazole derivative or benzothiazole derivative may be substituted with deuterium.

[0608] [ka]

[0609] φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure can be as described in formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine-based substituents are bonded, but when these are replaced with thiazole-based substituents (or benzothiazole-based substituents), both pyridine-based substituents may be replaced with thiazole-based substituents (or benzothiazole-based substituents) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be replaced with .

[0610] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0611] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15): Details are described in JP-A-9-194487. [ka]

[0612] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, the explanations in formula (1) and formula (ETM-7-2) can be further referenced. Furthermore, alkenyloxy and alkynyloxy are groups in which the alkyl moiety in alkoxy is substituted with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, the explanations in formula (ETM-7-2) can be referenced.

[0613] Furthermore, X and Y, both of which are alkyl, may be bonded to form a ring.

[0614] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a fused ring with an adjacent substituent.

[0615] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in the formula (1), reference can be made to the explanation for the formula (1).

[0616] R 1 ~R 4 Among alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, and aryloxycarbonyloxy in the above, the details of alkyl, aryl, and alkoxy can also be found from the explanation in formula (1).

[0617] Examples of silyl include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, alkyl, or cycloalkyl, and tri-substituted silyl is preferred, including triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the aryl, alkyl, and cycloalkyl in these groups, the explanation in formula (1) can be cited.

[0618] The fused ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be further fused with other rings.

[0619] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. 1 and R 4 When R is thienyl, X and Y are alkyl, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 and R are preferably cycloalkyl groups that do not simultaneously satisfy the condition that R 1 and R 4 is a silyl group, R 2 , R 3 , X and Y are not each independently hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0620] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0621] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16): Details are described in WO 2017 / 014226. [ka]

[0622] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ is optionally substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen atom of Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms, and R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and the R 1 ~R 5 is a site that binds to L, L's are each independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2):

[0623] [ka]

[0624] In formula (L-1), X 1 ~X 6are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, At least one hydrogen atom in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom of the compound represented by formula (ETM-16) may be substituted with deuterium.

[0625] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or (ETM-16-2). [ka]

[0626] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ is optionally substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen atom of Ar is optionally substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical,

[0627] In formula (ETM-16-1) and formula (ETM-16-2), L's are each independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2): [ka]

[0628] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X1 ~X 6 At least two of the =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, At least one hydrogen atom in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom of the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0629] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formulas (φ1-1) to (φ1-18), divalent groups represented by the following formulas (φ2-1) to (φ2-34), trivalent groups represented by the following formulas (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen atom of φ may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms.

[0630] [ka]

[0631] [ka]

[0632] [ka]

[0633] In the formula, Z is >CR2, >N-Ar, >NL, -O-, or -S-, and each R in >CR2 is independently alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms, and the Rs may be bonded to each other to form a ring, Ar in >N-Ar is aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and L in >NL is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). * in the formula indicates the bonding position.

[0634] Preferably, L is a divalent ring group selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine, and at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms.

[0635] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen atom of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0636] Preferably, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen atoms at the same time, and m is 1 or 2. When m is 2, the group formed by the azoline ring and L is the same.

[0637] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0638] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulae (φ2-1), (φ2-31), (φ2-32), (φ2-33), and (φ2-34), and at least one hydrogen atom of φ may be substituted with an aryl having 6 to 18 carbon atoms. In the following formulae, * indicates a bonding position. [ka]

[0639] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen atom of L is optionally substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of Ar may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the group formed by the azoline ring and L is the same.

[0640] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0641] For details of the alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanation for formula (1) can be cited.

[0642] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0643] <Reducing substances> The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. Various substances can be used as this reducing substance as long as they have a certain level of reducing ability. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0644] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), and Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), and Ba (2.52 eV), with substances with a work function of 2.9 eV or less being particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb, and Cs, with Rb or Cs being even more preferred, and Cs being the most preferred. These alkali metals have particularly high reducing ability, and adding a relatively small amount of these to the material forming the electron transport layer or electron injection layer can improve the luminance and extend the life of the organic EL device. 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 in particular, a combination containing Cs is preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs, Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding Cs to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL device can be improved and the lifetime can be extended.

[0645] The electron injection layer material and the electron transport layer material described above can also be used as electron layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. Regarding the reactive substituent in this case, the same explanation as for the polycyclic aromatic compound having the partial structure represented by formula (1) can be cited.

[0646] The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0647] 3-1-7. Cathode in organic electroluminescent devices The cathode (108) serves to inject electrons into the light-emitting layer (105) through the electron injection layer (107) and the electron transport layer (106).

[0648] The material for the cathode (108) is not particularly limited as long as it can efficiently inject electrons into the organic layer, but it can be similar to the material for the anode (102). Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (e.g., magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum alloy), are preferred. To increase electron injection efficiency and improve device performance, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low-work-function metals are effective. However, these low-work-function metals are generally unstable in air. To address this issue, a method has been proposed in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to create a highly stable electrode. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, these are not limited to these.

[0649] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method for producing these electrodes is not particularly limited as long as electrical conduction can be achieved, and may be resistance heating, electron beam evaporation, sputtering, ion plating, coating, or the like.

[0650] 3-1-8. Binders that may be used in each layer The materials used for the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can be used alone to form each layer, but they can also be dispersed as a polymer binder in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, and polyurethane resin, or curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin.

[0651] 3-1-9. Method for producing organic electroluminescent device Each layer constituting an organic EL device can be formed by forming the material to be formed into a thin film using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, and coating. There are no particular limitations on the film thickness of each layer formed in this way, and it can be set appropriately depending on the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a quartz oscillator film thickness measuring device or the like. When forming a thin film using vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10 -6~10 -3 It is preferable to appropriately set the pressure, the deposition rate, the substrate temperature, and the film thickness in the range of 0.01 to 50 nm / sec, -150 to +300° C., and 2 nm to 5 μm.

[0652] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the applied AC current can be any waveform.

[0653] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element comprising an anode, a hole injection layer, a hole transport layer, an emitting layer composed of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

[0654] <Vapor deposition method> An anode is prepared by forming a thin film of an anode material on a suitable substrate by vapor deposition or the like, and then forming thin films of a hole injection layer and a hole transport layer on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film to serve as an emissive layer. An electron transport layer and an electron injection layer are then formed on the emissive layer, and a thin film of a cathode material is then formed by vapor deposition or the like to serve as a cathode, thereby obtaining the desired organic EL device. It should be noted that the above-described organic EL device can also be fabricated in the reverse order, with the layers fabricated in the order of cathode, electron injection layer, electron transport layer, emissive layer, hole transport layer, hole injection layer, and anode.

[0655] <Wet film formation method> The wet film formation method is carried out by preparing a liquid organic layer-forming composition from a low molecular weight compound capable of forming each organic layer of an organic EL device, and using this. If there is no suitable organic solvent that can dissolve this low molecular weight compound, the organic layer-forming composition may be prepared from a reactive compound obtained by substituting a reactive substituent on the low molecular weight compound, such as another monomer having a solubility function as a reactive compound, or a polymer compound polymerized together with a main-chain polymer.

[0656] In wet film formation methods, a coating film is generally formed through a coating step in which an organic layer-forming composition is applied to a substrate and a drying step in which the solvent is removed from the applied organic layer-forming composition. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), this drying step causes further crosslinking to form a crosslinked polymer. Depending on the coating step, a method using a spin coater is called a spin coating method; a method using a slit coater is called a slit coating method; a method using a plate is called a gravure, offset, reverse offset, or flexographic printing method; a method using an inkjet printer is called an inkjet method; and a method spraying in a mist is called a spray method.

[0657] The drying process can be carried out by air drying, heating, drying under reduced pressure, etc. The drying process can be carried out once or multiple times using different methods and conditions. Also, different methods can be used in combination, such as calcination under reduced pressure.

[0658] Wet film formation methods are film formation methods that use solutions, such as some printing methods (inkjet methods), spin coating or casting methods, and coating methods. Unlike vacuum deposition methods, wet film formation methods do not require expensive vacuum deposition equipment and can form films under atmospheric pressure. In addition, wet film formation methods allow for large-area and continuous production, which leads to reduced manufacturing costs.

[0659] On the other hand, compared to vacuum deposition, wet deposition can be difficult to layer. When using wet deposition to create layered films, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and methods such as controlled solubility compositions, crosslinking of the lower layer, and orthogonal solvents (solvents that are not soluble in each other) are used. However, even with these techniques, it can be difficult to use wet deposition for all film application.

[0660] Therefore, a common method for producing organic EL elements is to use a wet film-forming method for only some layers and a vacuum deposition method for the remaining layers.

[0661] For example, the procedure for producing an organic EL element by partially applying a wet film formation method is shown below.

[0662] (Step 1) Forming the anode film by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Forming a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum evaporation Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, a light-emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained.

[0663] Of course, the electron transport layer and the electron injection layer may also be formed by a wet film formation method using layer-forming compositions containing the electron transport layer material and the electron injection layer material, respectively. In this case, it is preferable to use a means for preventing dissolution of the underlying light-emitting layer or a means for forming the layer from the cathode side, which is the opposite of the above procedure.

[0664] <Other film formation methods> The organic layer-forming composition can be formed into a film by laser thermal imaging (LITI), a method in which a compound attached to a substrate is heated and vapor-deposited with a laser, and the organic layer-forming composition can be used as the material applied to the substrate.

[0665] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be added as appropriate. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

[0666] Photolithography can be used to fabricate the banks. Positive and negative resist materials can be used as bank materials for photolithography. Patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In these cases, permanent resist materials can also be used.

[0667] Materials that can be used for banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubbers, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

[0668] <Composition for forming organic layer used in wet film formation method> The organic layer-forming composition is obtained by dissolving a low-molecular-weight compound capable of forming each organic layer of an organic EL device, or a polymer compound obtained by polymerizing such a low-molecular-weight compound, in an organic solvent. For example, the light-emitting layer-forming composition contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a dopant material as a first component, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component for the light-emitting layer obtained from the composition, and the second component functions as a host component for the light-emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and upon application, the controlled evaporation rate of the third component itself provides a smooth and uniform surface profile.

[0669] <Organic solvents> The organic layer-forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve film-forming properties, the presence or absence of defects in the coating film, surface roughness, and smoothness. Furthermore, when forming a film using an inkjet method, it is possible to control meniscus stability at the pinhole of the inkjet head and control and improve ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, luminescence properties, efficiency, and lifespan of an organic EL device having an organic layer obtained from the organic layer-forming composition.

[0670] (1) Physical properties of organic solvents The boiling point of the at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. A boiling point higher than 130°C is preferred from the viewpoint of inkjet dischargeability. A boiling point lower than 300°C is preferred from the viewpoints of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoints of good inkjet dischargeability, film-forming properties, smoothness, and low residual solvent, it is more preferred that the organic solvent contains two or more organic solvents. Meanwhile, in some cases, taking into consideration transportability, etc., the composition may be a solid composition obtained by removing the solvent from the organic layer-forming composition.

[0671] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP) of the poor solvent (PS) PS ) is particularly preferred.

[0672] By adding a high-boiling poor solvent, the low-boiling good solvent volatilizes first during film formation, increasing the concentrations of the ingredients in the composition and the poor solvent, facilitating rapid film formation, resulting in a coating with fewer defects, less surface roughness, and high smoothness.

[0673] Difference in solubility (S GS -S PS The difference in boiling point (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS ) is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0674] After film formation, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving coating film-forming properties, it is preferable to perform the heating at a temperature not higher than +30°C of the glass transition temperature (Tg) of at least one of the solutes. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at a temperature not lower than -30°C of the glass transition temperature (Tg) of at least one of the solutes. Even if the heating temperature is lower than the boiling point of the organic solvent, the film is thin, so the organic solvent can be sufficiently removed. Furthermore, drying may be performed multiple times at different temperatures, or multiple drying methods may be used in combination.

[0675] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming an organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol ethyl ... glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-Trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene, veratrol, 1,2,3,4-tetramethylanisole Examples of the solvent include, but are not limited to, tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvents may be used alone or in combination.

[0676] <Optional ingredients> The composition for forming the organic layer may contain optional components, such as a binder and a surfactant, as long as the optional components do not impair the properties of the composition.

[0677] (1) Binder The organic layer-forming composition may contain a binder. The binder forms a film during film formation and simultaneously bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the organic layer-forming composition.

[0678] Examples of binders used in the organic layer-forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diaryl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0679] The binder used in the organic layer-forming composition may be one type only, or a mixture of two or more types may be used.

[0680] (2) Surfactants The organic layer-forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity, and liquid repellency of the organic layer-forming composition. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic group, and further classified into alkyl, silicon, and fluorine-based based on the structure of their hydrophobic group. Furthermore, based on their molecular structure, they are classified into monomolecular systems with relatively small and simple molecular weights and polymer systems with large molecular weights and side chains or branches. Based on their composition, they are classified into single systems and mixed systems containing two or more surfactants and base materials. Any type of surfactant can be used in the organic layer-forming composition.

[0681] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, and Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), DisperBake (DisperBYK) 161, DisperBake 162, DisperBake 163, DisperBake 164, DisperBake 166, DisperBake 170, DisperBake 180, DisperBake 181, DisperBake 182, BYK300, and BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade names, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade names, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade names, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (trade name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (trade name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethylene ethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerin tetrakis(fluoroalkylpolyoxyethylene ether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonates and alkyl diphenyl ether disulfonates.

[0682] The surfactant may be used alone or in combination of two or more.

[0683] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined taking into consideration the good solubility, storage stability, and film-forming properties of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good dischargeability when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency, and lifespan of an organic EL device having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component be 0.0001% to 2.0% by mass, the second component be 0.0999% to 8.0% by mass, and the third component be 90.0% to 99.9% by mass, relative to the total mass of the composition for forming an emitting layer.

[0684] More preferably, the first component is 0.005% by mass to 1.0% by mass, the second component is 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9% by mass, based on the total mass of the composition for forming the light-emitting layer. More preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, based on the total mass of the composition for forming the light-emitting layer.

[0685] The composition for forming an organic layer can be produced by appropriately selecting and performing known methods such as stirring, mixing, heating, cooling, dissolving, dispersing, etc. After preparation, the composition may be appropriately subjected to filtration, degassing (also called degassing), ion exchange treatment, and inert gas substitution / filling treatment, etc.

[0686] The higher the viscosity of the composition for forming an organic layer, the better the film-forming properties and the better the ejection properties when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. In this respect, the viscosity of the composition for forming an organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

[0687] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the defect-free coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. In this respect, the composition for forming an organic layer preferably has a surface tension at 25°C of 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0688] <Crosslinkable polymer compound: Compound represented by formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1). [ka]

[0689] In formula (XLP-1), MUx, ECx, and k have the same definitions as MU, EC, and k in formula (H3), except that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic group having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

[0690] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5 to 50 mass %, more preferably 1 to 20 mass %, in the molecule.

[0691] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the polymer compound described above, but substituents having the following structures are preferred: * in each structural formula indicates the bonding position.

[0692] [ka]

[0693] L's are each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, or polyoxyalkylene 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.

[0694] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structure: [ka]

[0695] [ka]

[0696] [ka]

[0697] [ka]

[0698] <Methods of producing polymer compounds and crosslinkable polymer compounds> The methods for producing the polymer compound and the crosslinkable polymer compound will be described below using the compound represented by formula (H3) and the compound represented by formula (XLP-1) as examples. These compounds can be synthesized by appropriately combining known production methods.

[0699] Solvents used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, and ether solvents, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

[0700] The reaction may also be carried out in a two-phase system, in which case a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[0701] The compounds of formula (H3) and formula (XLP-1) may be produced in a single step or multiple steps. Furthermore, they may be produced by batch polymerization, in which all raw materials are placed in a reaction vessel and the reaction is initiated; by dropwise polymerization, in which raw materials are added dropwise to a reaction vessel; or by precipitation polymerization, in which the product precipitates as the reaction proceeds. These methods can be combined as appropriate. For example, when synthesizing a compound represented by formula (H3) in a single step, the target product is obtained by adding a monomer having a polymerizable group bonded to a monomer unit (MU) and a monomer having a polymerizable group bonded to an end-capping unit (EC) to a reaction vessel and then reacting them. Furthermore, when synthesizing a compound represented by formula (H3) in multiple steps, the target product is obtained by polymerizing a monomer having a polymerizable group bonded to a monomer unit (MU) to the desired molecular weight, followed by adding a monomer having a polymerizable group bonded to an end-capping unit (EC) and reacting them. By adding monomers with polymerizable groups bonded to different types of monomer units (MU) in multiple stages, it is possible to prepare polymers with a concentration gradient according to the monomer unit structure. Also, after preparing a precursor polymer, the target polymer can be obtained by post-reaction.

[0702] Furthermore, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize a polymer with a random primary structure (Synthetic Scheme 1) or a polymer with a regular primary structure (Synthetic Schemes 2 and 3), and these can be used in appropriate combinations depending on the target product. Furthermore, if a monomer with three or more polymerizable groups is used, it is possible to synthesize a hyperbranched polymer or dendrimer.

[0703] [ka]

[0704] Monomers that can be used in the present invention include those described in JP 2010-189630 A, WO 2012 / 086671, WO 2013 / 191088, WO 2002 / 045184, WO 2011 / 049241, WO 2013 / 146806, WO 2005 / 049546, WO 2015 / 145871, JP 2010-215886 A, JP 2008-106241 A, WO 2016 / 031639, and JP 2011-174062 A.

[0705] Further, for the specific polymer synthesis order, JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / 031639 A, WO 2016 / 125560 A, WO 2011 / 049241 A It can be synthesized in accordance with the method described in.

[0706] 3-1-10.Application examples of organic electroluminescent devices The present invention can also be applied to a display device equipped with an organic EL element or a lighting device equipped with an organic EL element.

[0707] A display device or lighting device including an organic EL element can be manufactured by a known method, for example, by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0708] 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, JP-A-10-335066, JP-A-2003-321546, and JP-A-2004-281086). Examples of display methods include matrix and / or segment methods. Note that matrix display and segment display may coexist in the same panel.

[0709] In a matrix display, pixels are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, images and text displayed on computers, monitors, and televisions typically use square pixels with sides of 300 μm or less. Large displays such as display panels use pixels on the order of millimeters. For monochrome displays, pixels of the same color are simply arranged, while for color displays, red, green, and blue pixels are displayed side by side. These types are typically known as delta and stripe types. The matrix can be driven by either line-sequential or active matrix methods. While line-sequential driving has the advantage of being simpler, active matrix methods can sometimes be superior in terms of operating characteristics, so the choice must be made based on the application.

[0710] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include the time and temperature displays on digital clocks and thermometers, the operating status displays on audio equipment and induction cookers, and panel displays on automobiles.

[0711] Examples of lighting devices include lighting devices for indoor lighting and backlights for liquid crystal display devices (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are primarily used to improve the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for backlights of liquid crystal display devices, particularly those used for personal computers, where thinning is an issue, conventional backlights are difficult to achieve because they use fluorescent lamps and light guide plates. Therefore, a backlight using the light-emitting element according to this embodiment is characterized by its thinness and light weight.

[0712] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used to produce not only the organic electroluminescent device described above, but also an organic field effect transistor or an organic thin film solar cell.

[0713] An organic field-effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the transistor can control the current by arbitrarily blocking the flow of electrons (or holes) flowing between the source and drain electrodes. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements that make up integrated circuits.

[0714] The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the device structure include the following structures.

[0715] (1) Substrate / gate electrode / insulator layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source and drain electrodes (3) Substrate / organic semiconductor active layer / source and drain electrodes / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor configured in this manner can be used as a pixel driving switching element for an active matrix driving liquid crystal display or an organic electroluminescence display.

[0716] An organic thin-film solar cell has 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 laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, or electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may also include a hole blocking layer, electron blocking layer, electron injection layer, hole injection layer, smoothing layer, etc. as appropriate. Known materials used in organic thin-film solar cells can be appropriately selected and combined for use in the organic thin-film solar cell.

[0717] 4. Wavelength conversion materials The polycyclic aromatic compound of the present invention can be used as a wavelength converting material.

[0718] Currently, the application of color conversion technology to multicolor displays, organic light-emitting diode (OLED) displays, and lighting is being actively investigated. Color conversion refers to the wavelength conversion of light emitted from a light emitter to light of longer wavelengths, such as converting ultraviolet or blue light to green or red light. By fabricating a film of wavelength conversion materials with color conversion functionality and combining them with a blue light source, for example, it is possible to extract the three primary colors of blue, green, and red from the blue light source, i.e., white light. A white light source combining such a blue light source with a wavelength conversion film with color conversion functionality can be used as a light source unit, and combined with a liquid crystal driver and color filters, it is possible to create a full-color display. Furthermore, if the liquid crystal driver is not required, the white light source can be used as is, for example, in LED lighting. Furthermore, by combining a blue organic light-emitting diode (OLED) element as a light source with a wavelength conversion film that converts blue light to green and red, it is possible to fabricate a full-color OLED display without using a metal mask. Furthermore, by using blue microLEDs as a light source in combination with wavelength conversion films that convert blue light into green and red light, it becomes possible to create low-cost full-color microLED displays.

[0719] The polycyclic aromatic compound of the present invention can be used as this wavelength converting material. Using a wavelength converting material containing the polycyclic aromatic compound of the present invention, light from a light source or light-emitting element that generates ultraviolet light or shorter-wavelength blue light can be converted into blue light or green light with high color purity suitable for use in display devices (display devices using organic EL elements and liquid crystal display devices). The converted color can be adjusted by appropriately selecting the substituents of the polycyclic aromatic compound of the present invention, the binder resin used in the wavelength converting composition described below, and the like. The wavelength converting material can be prepared as a wavelength converting composition containing the polycyclic aromatic compound of the present invention. Furthermore, this wavelength converting composition may be used to form a wavelength conversion film.

[0720] The wavelength-converting composition may contain, in addition to the polycyclic aromatic compound of the present invention, a binder resin, other additives, and a solvent. Examples of binder resins that can be used include those described in paragraphs

[0173] to

[0176] of WO 2016 / 190283. Examples of other additives that can be used include compounds described in paragraphs

[0177] to

[0181] of WO 2016 / 190283. For the solvent, the description of the solvent contained in the composition for forming an emitting layer can be referenced.

[0721] The wavelength conversion film includes a wavelength converting layer formed by curing a wavelength converting composition. Known film formation methods can be referred to as a method for producing a wavelength converting layer from a wavelength converting composition. The wavelength conversion film may consist solely of a wavelength converting layer formed from a composition containing the polycyclic aromatic compound of the present invention, or may also include other wavelength converting layers (e.g., a wavelength converting layer that converts blue light to green light or red light, or a wavelength converting layer that converts blue light or green light to red light). The wavelength conversion film may further include a substrate layer and a barrier layer to prevent deterioration of the color converting layer due to oxygen, moisture, or heat. [Example]

[0722] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0723] <Synthesis example> Synthesis Example (1): Synthesis of Compound (1-1) [ka]

[0724] A 1.6 M tert-butyllithium pentane solution (4.8 ml) was added to a flask containing compound (S-1) (1.5 g) and tert-butylbenzene (13 ml) under a nitrogen atmosphere at -30°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 2 hours, after which components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -30°C, boron tribromide (1.9 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (1.3 ml) was added, and the mixture was stirred at room temperature until the heat generation subsided, after which the mixture was heated to 120°C and stirred for 3 hours. The reaction mixture was cooled to room temperature, and aqueous sodium acetate solution cooled in an ice bath was added, followed by heptane, and the mixture was separated. The residue was then purified using a silica gel short-path column (eluent: toluene), and the solvent was distilled off under reduced pressure to obtain a solid. The solid was then dissolved in toluene and reprecipitated by adding heptane to obtain compound (1-1) (0.1 g).

[0725] Compounds (1-3) to (2-38) shown in Table 1 below were synthesized according to the method of Synthesis Example (1).

[0726] Compounds (Ref-1) to (Ref-4) were synthesized according to the compounds described in U.S. Patent Application Publication No. 2023 / 0120766 or WO 2018 / 212169 or the aforementioned synthesis method. [ka]

[0727] The formation of the target substance was confirmed by APCI-MS (atmospheric pressure chemical ionization mass spectrometry).

[0728] [Table 1]

[0729] <Production and evaluation of vapor-deposited organic EL devices> Using the synthesized compounds of the present invention and the comparative compounds, TADF, TAF, and PSF organic EL devices were manufactured.

[0730] <TADF structure> ITO (50 nm) / HAT-CN (10 nm) / HT-1 (60 nm) / SiCzCz (5 nm) / SiCzCz:SiTrzCz2: each compound described in Table 2 (60:39:1) (35 nm) / mSiTrz (5 nm) / mSiTrz:Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) A glass substrate (manufactured by Opto Science Co., Ltd.) with dimensions of 26 mm × 28 mm × 0.7 mm, on which ITO film with a thickness of 200 nm formed by sputtering was polished to 50 nm, was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boats containing HAT-CN, HT-1, SiCzCz, SiTrzCz2, each compound described in Table 2, mSiTrz and Liq, and tungsten vapor deposition boats containing LiF and aluminum were installed respectively.

[0731] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5×10 -4The pressure was reduced to Pa, and first, HAT-CN was heated and vapor-deposited to a thickness of 10 nm to form a hole injection layer. Next, HT-1 was heated and vapor-deposited to a thickness of 60 nm to form a hole transport layer (1), and further, SiCzCz was heated and vapor-deposited to a thickness of 5 nm to form a hole transport layer (2). Next, SiCzCz, SiTrzCz2, and each compound described in Table 2 were heated simultaneously and vapor-deposited to a thickness of 35 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of SiCzCz, SiTrzCz2, and each compound described in Table 2 was approximately 60:39:1. Next, mSiTrz was heated and vapor-deposited to a thickness of 5 nm to form an electron transport layer (1), and further, mSiTrz and Liq were heated and vapor-deposited to a thickness of 30 nm to form an electron transport layer (2). The deposition rate was adjusted so that the mass ratio of SiTrz and Liq was approximately 1:1. The deposition rate of each layer was 0.01 - 1 nm / second. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 - 0.1 nm / second to a thickness of 1 nm, and then, aluminum was heated and vapor-deposited to a thickness of 100 nm to form a cathode. Thereafter, an organic EL device was obtained. At this time, the deposition rate of aluminum was adjusted to be 1 - 10 nm / second. SiCzCz in the light-emitting layer corresponds to a hole-transporting host material, and SiTrzCz2 corresponds to an electron-transporting host material.

[0732] <TAF Structure> ITO(50 nm) / HAT-CN(10 nm) / HT-1(60 nm) / SiCzCz(5 nm) / SiCzCz:SiTrzCz2:TADF-1:Each compound described in Table 3(60:26:13:1)(35 nm) / mSiTrz(5 nm) / mSiTrz:Liq(1:1)(30 nm) / LiF(1 nm) / Al(100 nm) Except for the light-emitting layer, it was fabricated in the same manner as the TADF structure. In the light-emitting layer, SiCzCz, SiTrzCz2, (TADF-1), and each compound described in Table 3 were heated simultaneously and vapor-deposited to a thickness of 35 nm. The deposition rate was adjusted so that the mass ratio of SiCzCz, SiTrzCz2, (TADF-1), and each compound described in Table 3 was approximately 60:26:13:1.

[0733] <PSF structure> ITO (50 nm) / HAT-CN (10 nm) / HT-1 (60 nm) / SiCzCz (5 nm) / SiCzCz:SiTrzCz2:PtON-TBBI: each compound described in Table 4 (60:26:13:1) (35 nm) / mSiTrz (5 nm) / mSiTrz:Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) The (TADF-1) of the TAF structure was replaced with PtON-TBBI, and the device was fabricated in the same manner.

[0734] The chemical formula structures of the compounds used in the manufacture of each device are shown below. [Chemical formula]

[0735] [Evaluation] The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum, etc. These evaluation items can use the values at the time of emission, for example, at 1000 cd / m 2

[0736] The quantum efficiency of the light-emitting device includes internal quantum efficiency and external quantum efficiency. The internal quantum efficiency indicates the ratio at which the external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting device is purely converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting device. Since some of the photons generated in the light-emitting layer are absorbed or continuously reflected inside the light-emitting device and are not emitted to the outside of the light-emitting device, the external quantum efficiency is lower than the internal quantum efficiency.

[0737] The measurement methods of spectral radiance (emission spectrum) and external quantum efficiency are as follows. Using a voltage / current generator R6144 manufactured by Advantest Corporation, when the luminance of the device is 1000 cd / m 2 ​The device emits light by applying a voltage equal to the wavelength of the light emitted. Using a TOPCON SR-3AR spectroradiometer, the spectral radiance in the visible light region is measured perpendicular to the light-emitting surface. Assuming the light-emitting surface is a perfectly diffusing surface, the measured spectral radiance value for each wavelength component is divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. The number of photons is then integrated over the entire wavelength range observed to obtain the total number of photons emitted from the device. The applied current value divided by the elementary charge is the number of carriers injected into the device, and the total number of photons emitted from the device divided by the number of carriers injected into the device is the external quantum efficiency. The half-width of the emission spectrum is calculated as the width between the wavelengths above and below the maximum emission wavelength at which the intensity is 50%.

[0738] A DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the LiF / aluminum electrode as the cathode. 2 The characteristics of light emission were measured. Furthermore, the time (lifetime) during which 95% or more of the initial luminance was maintained was measured for the TTF-configured element, and the time (lifetime) during which 50% or more of the initial luminance was maintained was measured for the TADF-configured, TAF-configured, and PSF-configured elements. The emission peaks of all elements were in the range of 450 to 470 nm. The results are shown in Tables 2 to 4 below.

[0739] [Table 2]

[0740] [Table 3]

[0741] [Table 4]

[0742] The results obtained show that the devices of the examples have higher efficiency or longer life than the devices of the comparative examples that use compounds having skeletons corresponding to the compounds of the examples. [Explanation of symbols]

[0743] 100: Organic electroluminescent device 101: Circuit board 102: Anode 103: Hole injection layer 104: Hole transport layer 105: Light-emitting layer 106:Electron transport layer 107: Electron injection layer 108: Cathode

Claims

1. A polycyclic aromatic compound having a structure consisting of at least one structural unit represented by formula (1): 【Chemical 1】 In formula (1), ring A, ring B, ring C, ring D and ring E each independently represent a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; wherein ring A is a group represented by the formula (J ＡＢＣ an aryl ring having a group represented by the formula (J) as a substituent; ＡＢＣ ) as a substituent, X's each independently represent O, S, or N-R ＮＸ , C(-R ＣＸ ) ２ , Si(-R ＩＸ ) ２ or Se, and at least one X is S; R ＮＸ , R ＣＸ and R ＩＸ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and C(—R ＣＸ ) ２ The two R's ＣＸ may be bonded to each other to form a ring, and Si(-R ＩＸ ) ２ The two R's ＩＸ may be bonded to each other to form a ring, Ar are each independently a group represented by formula (Ar), Formula (J ＡＢＣ ) in * indicates the point of attachment to the aryl or heteroaryl ring; ring P and ring Q each independently represent a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; In formula (Ar), # represents the position of attachment to N, Ring F is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; G is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted arylthio, a substituted or unsubstituted heteroarylthio, a substituted or unsubstituted aryloxy, a substituted or unsubstituted heteroaryloxy, a substituted or unsubstituted alkyl having 3 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl; At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one —CH ２ - may be replaced by -O-, At least one hydrogen in the structure may be replaced with deuterium, a halogen, or a cyano group, and at least one nitrogen may be replaced with nitrogen-15 ( １５ N), and at least one sulfur may be replaced by sulfur-33 ( ３３ S), sulfur-34 ( ３４ S) or sulfur-36 ( ３６ S), and at least one oxygen may be replaced by oxygen-17 ( １７ O) or oxygen-18 ( １８ O), and at least one carbon may be replaced by carbon-13 ( １３ C), and at least one boron may be replaced by boron-11 ( １１ B) may be substituted.

2. The polycyclic aromatic compound according to claim 1, characterized in that formula (1) is represented by the following formula (2X): 【Chemistry 2】 In formula (2X), X and Ar are defined as X and Ar in formula (1), respectively. Z ａ , Z ｂ and Z ｄ are each independently -C(-R Ｚ )= or -N=, Z = Z are each independently C(-R Ｚ ) = C(-R Ｚ ), >O, >NR, >C(-R) ２ , >Si(-R) ２ , >S, or >Se, and the >N-R, >C(-R) ２ and Si(-R) ２ R is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and Ｚ ) = C(-R Ｚ ), > C(-R) ２ and Si(-R) ２ two R's may be bonded to each other to form a ring, R Ｊ is the formula (J ＡＢＣ ) and R Ｚ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, provided that substituents on adjacent atoms may be bonded to each other to form a ring.

3. The polycyclic aromatic compound according to claim 1, characterized in that formula (1) is represented by the following formula (2XJ): 【Chemistry 3】 In formula (2XJ), X and Ar are defined as X and Ar in formula (1), respectively. Z ａ , Z ｂ , Z ｃ , Z ｄ , Z ｅ and Z ｊ are each independently -C(-R Ｚ )= or -N=, R Ｚ are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that substituents on adjacent atoms may be bonded to each other to form a ring.

4. The polycyclic aromatic compound according to claim 1, characterized in that formula (1) is represented by the following formula (2XJ-1): 【Chemistry 4】 In formula (2XJ-1), Ar is the same as defined for Ar in formula (1), Z ａ , Z ｂ , Z ｃ , Z ｄ , Z ｅ and Z ｊ are each independently -C(-R Ｚ )= or -N=, R Ｚ are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that substituents on adjacent atoms may be bonded to each other to form a ring.

5. The polycyclic aromatic compound according to claim 1, characterized in that formula (1) is represented by the following formula (2XJ-2): 【Chemistry 5】 In formula (2XJ-2), Ar is the same as defined for Ar in formula (1), Z ａ , Z ｂ , Z ｃ , Z ｄ , Z ｅ and Z ｊ are each independently -C(-R Ｚ )= or -N=, R Ｚ are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that substituents on adjacent atoms may be bonded to each other to form a ring.

6. The polycyclic aromatic compound according to claim 1, wherein the formula (1) is represented by the following formula (2XJ-3) or formula (2XJ-4): 【Chemistry 6】 In formula (2XJ-3) and formula (2XJ-4), X and Ar are defined as X and Ar in formula (1), respectively. Y is >O, >NR, >C(-R) ２ , >Si(-R) ２ , >S, or >Se, and the >NR, >C(-R) ２ and Si(-R) ２ R is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the >C(-R) ２ and the above >Si(—R) ２ two R's may be bonded to each other to form a ring, Z ａ , Z ｂ , Z ｃ , Z ｄ , Z ｅ and Z ｊ are each independently -C(-R Ｚ )= or -N=, R Ｚ are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, provided that substituents on adjacent atoms may be bonded to each other to form a ring.

7. The polycyclic aromatic compound according to claim 1, wherein formula (1) is represented by any one of the following formulas: 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】 【Chemical 26】 【Chemical 27】

8. The polycyclic aromatic compound according to claim 1, wherein formula (1) is represented by any one of the following formulas: 【Chemical Formula 28】 【Chemical 29】 【Chemistry 30】 【Chemical 31】 【Chemical 32】

9. An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes, wherein the organic layer contains the polycyclic aromatic compound according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, wherein the organic material layer is a light-emitting layer.

11. The organic electroluminescent device according to claim 10, wherein the light-emitting layer includes at least one selected from the group consisting of an assisting dopant and a phosphorescent material.

12. A display device or a lighting device comprising the organic electroluminescent device according to claim 9.

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