Polycyclic aromatic compound and organic electroluminescent element

Abstract

To provide a material useful as a material for organic device.SOLUTION: Provided is a polycyclic aromatic compound expressed by formula (1). Rings A to C are substituted or non-substituted aryl rings or heteroaryl rings, where at least one is an aryl ring or a heteroaryl ring having a group expressed by at least formula (EABC) as a substituent, Ar is a group expressed by formula (Ar), ring P and ring Q are substituted or non-substituted aryl rings or heteroaryl rings, ring D is a substituted or non-substituted aryl ring or a heteroaryl ring, at least one G is substituted alkyl having a carbon number 1 to 24, non-substituted alkyl having a carbon number 4 to 24, or a substituted or non-substituted cycloalkyl or the like.SELECTED DRAWING: Figure 1

Description

Technical Field

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

Background Art

[0002] Conventionally, display devices using light-emitting devices that emit light by an electric field have been frequently studied because they can achieve power saving and thinning. Furthermore, organic electroluminescent devices (which may be referred to as "organic EL devices" or simply "devices" in this specification) made of organic materials have been actively studied because they can be easily made lighter and larger. In particular, regarding the development of organic materials having light-emitting characteristics such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capabilities (which may have the potential to become semiconductors or superconductors) such as holes and electrons, active research has been conducted so far regardless of whether they are high molecular compounds or low molecular compounds.

[0003] An organic EL device has a structure including a pair of electrodes composed of a positive electrode and a negative electrode, and one or more layers containing an organic compound disposed between the pair of electrodes. The layer containing an organic compound (which may be referred to as an "organic layer" in this specification) includes a light-emitting layer, 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 them, Patent Document 1 discloses that a polycyclic aromatic compound in which aromatic rings are linked by hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur is useful as a material for organic electroluminescent devices and the like. This polycyclic aromatic compound has a large HOMO-LUMO gap and a high lowest excited triplet energy level (ET), and at the same time exhibits thermally activated delayed fluorescence, and has been reported to be particularly useful as a fluorescent material for organic electroluminescent devices.

Prior Art Documents

Patent Documents

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

[0006] As described above, various materials have been developed as materials used in organic EL elements. However, in order to increase the options for materials for organic EL elements, the development of materials composed of compounds different from the conventional ones is expected. An object of the present invention is to provide a novel material useful as a material for organic devices such as organic EL elements.

[0007] Another object of the present invention is to provide an organic electroluminescent element using a new combination of materials. An object of the present invention is to provide an organic EL element having particularly high external quantum efficiency. Means for Solving the Problems

[0008] The present inventors have intensively studied to solve the above problems, and succeeded in producing a new compound as a polycyclic aromatic compound in which aromatic rings are linked by hetero elements such as boron, oxygen, nitrogen, and sulfur. Further, by arranging a layer containing this polycyclic aromatic compound between a pair of electrodes to form an organic EL element, it has been found that an excellent organic EL element can be obtained, and the present invention has been completed. That is, the present invention provides the following polycyclic aromatic compounds and materials for organic devices containing the following polycyclic aromatic compounds.

[0009] <1> A polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1): [Chemical Formula]

[0010] In formula (1), Ring A, Ring B, and Ring C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, provided that at least one selected from the group consisting of Ring A, Ring B, and Ring C is an aryl ring having a group represented by formula (E ABC ) as a substituent, or a heteroaryl ring having a group represented by formula (E ABC ) as a substituent, Each Ar is independently a group represented by formula (Ar), In formula (E ABC ), # represents the bonding position to the aryl ring or heteroaryl ring, Ring P and Ring Q are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, In formula (Ar), * represents the bonding position to nitrogen, Ring D 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, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted trialkylsilyl, a substituted or unsubstituted dialkylarylsilyl, a substituted or unsubstituted alkyldiarylsilyl, a substituted or unsubstituted triarylsilyl, a substituted or unsubstituted diarylamine, a substituted or unsubstituted arylheteroarylamine, or a substituted or unsubstituted diheteroarylamine. At least one G is a substituted alkyl having 1 to 24 carbon atoms, an unsubstituted alkyl having 4 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl. Here, when G is a substituted alkyl having 1 to 24 carbon atoms or an unsubstituted alkyl having 4 to 24 carbon atoms, the carbon atom bonded to Ring D is a quaternary carbon atom. When G is a substituted or unsubstituted cycloalkyl, the carbon atom bonded to Ring D is a tertiary carbon atom or a quaternary carbon atom. In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring can be condensed with at least one cycloalkane, the cycloalkane can be substituted with at least one substituent, and among the cycloalkanes, at least one -CH2- can be substituted with -O-. At least one hydrogen in the above structure can be replaced by deuterium, cyano or halogen, and at least one nitrogen can be replaced by nitrogen-15 ( 15 N), at least one sulfur can be replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be replaced by carbon-13 ( 13 C), at least one boron can be replaced by boron-11 ( 11 B).

[0011] <2> The polycyclic aromatic compound according to <1>, wherein the formula (Ar) is independently a group represented by the following formula (2Ar):

Chemical formula

[0012] In the formula (2Ar), G is the same as defined in claim 1, and at least one G is a substituted alkyl having 1 to 24 carbon atoms, an unsubstituted alkyl having 4 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl. When G is a substituted alkyl having 1 to 24 carbon atoms or an unsubstituted alkyl having 4 to 24 carbon atoms, the carbon bonded to the D ring is a quaternary carbon. When G is a substituted or unsubstituted cycloalkyl, the carbon bonded to the D ring is a quaternary carbon. R d is independently hydrogen, unsubstituted alkyl, unsubstituted cycloalkyl or unsubstituted aryl, R dd is hydrogen, or substituted or unsubstituted aryl.

[0013] <3> Formula (1) is a polycyclic aromatic compound as described in <1> or <2>, represented by the following formula (1X1):

Chemical Formula

[0014] In formula (1X1), Ar is the same as the definition of Ar in formula (1), R a is hydrogen or unsubstituted alkyl, R b is substituted or unsubstituted 9-carbazolyl, or substituted or unsubstituted diarylamino, Z E are each independently -C(-R ZE )= or -N=, The aforementioned R ZE are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, provided that substituents substituted on adjacent atoms can bond to each other to form a ring.

[0015] <4> Formula (1) is a polycyclic aromatic compound as described in <1>, represented by any one of the following chemical formulas:

Chemical Formula

[0016] <5> An organic electroluminescent device having a pair of electrodes consisting of a positive electrode and a negative electrode, and an organic layer disposed between the pair of electrodes, wherein the organic layer contains the polycyclic aromatic compound according to any one of <1> to <4>. <6> The organic layer is a light-emitting layer, an organic electroluminescent device. <7> The organic electroluminescent device according to <6>, wherein the light-emitting layer contains at least one selected from the group consisting of an assisting dopant and a phosphorescent material. <8> A display device or a lighting device including the organic electroluminescent device according to any one of <5> to <7>.

Advantages of the Invention

[0017] According to the present invention, a novel polycyclic aromatic compound is provided. The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a light-emitting layer material for forming a light-emitting layer of an organic electroluminescent device.

Brief Description of the Drawings

[0018]

Figure 1

Embodiments for Carrying Out the Invention

[0019] Hereinafter, the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. Also, in this specification, a numerical range indicated using "~" means a range including the numerical values described before and after "~" as a lower limit value and an upper limit value. Further, in this specification, "hydrogen" in the description of the structural formula means "hydrogen atom (H)".

[0020] In this specification, when referring to "adjacent groups", it means two groups each bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in the structural formula.

[0021] In this specification, the chemical structure and substituents may be indicated by the number of carbon atoms. However, when a substituent is substituted on a chemical structure, or when a substituent is further substituted on a substituent, the number of carbon atoms means the number of carbon atoms of each of the chemical structure and the substituent, and does not mean the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituent and the substituent. For example, "substituent B having Y carbon atoms substituted with substituent A having X carbon atoms" means that "substituent A having X carbon atoms" substitutes "substituent B having Y carbon atoms", and the number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B. Also, for example, "substituent B having Y carbon atoms substituted with substituent A" means that "(substituent A without carbon atom number limitation)" substitutes "substituent B having Y carbon atoms", and the number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B.

[0022] 1. Polycyclic aromatic compound 1-1. Polycyclic aromatic compound The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1). This polycyclic aromatic compound is useful as a compound for forming highly efficient and long-life elements. Also, compared with similar compounds having the same molecular weight, it is less likely to decompose during vapor deposition. Hereinafter, in this specification, a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) may be referred to as "the polycyclic aromatic compound represented by formula (1)".

Chemical formula

[0023] In formula (1), "A", "B", and "C" are each independently symbols representing a ring structure. In formula (1), the A ring, the B ring, and the C ring are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring. However, at least one selected from the group consisting of the A ring, the B ring, and the C ring is an aryl ring having a group represented by formula (E ABC ) as a substituent, or a heteroaryl ring having a group represented by formula (E ABC ) as a substituent.

[0024] Examples of the "aryl ring" of the A ring, B ring, and C ring in formula (1) 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.

[0025] Specific examples of the "aryl ring" include a benzene ring which is a monocyclic system, a biphenyl ring which is a bicyclic system, a naphthalene ring which is a condensed bicyclic system, an indene ring, a terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) which is a tricyclic system, an acenaphthylene ring which is a condensed tricyclic system, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a triphenylene ring which is a condensed tetracyclic system, a pyrene ring, a naphthacene ring, a chrysene ring, a perylene ring which is a condensed pentacyclic system, a pentacene ring, and the like. Further, the fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, benzofluorene ring, cyclopentane ring, etc. are spiro-bonded respectively. Further, the fluorene ring, benzofluorene ring, and indene ring in which two of the two hydrogens of methylene are each substituted with an alkyl such as methyl as the first substituent described later, such as a dimethylfluorene ring, a dimethylbenzofluorene ring, and a dimethylindene ring, are also included.

[0026] Examples of the "heteroaryl ring" of the A ring, B ring, and C ring 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, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Further, examples of the "heteroaryl ring" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0027] Examples of specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, 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, phenazasilin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, phrazan ring, thianthrene ring, indolocarbazole ring, benzindolocarbazole ring, benzobenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, dibenzazepine ring, tribenzoazepine ring, iminodibenzyl ring, etc. Further, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, it is also preferable that two of the two hydrogens of methylene are each substituted with an alkyl such as methyl as the first substituent described later, resulting in a dimethyldihydroacridine ring, dimethylxanthene ring, dimethylthioxanthene ring, etc. Also, the bipyridine ring, phenylpyridine ring, pyridylphenyl ring which are bicyclic systems, and the terpyridine ring, bispyridylphenyl ring, pyridylbiphenyl ring which are tricyclic systems are also mentioned as "heteroaryl rings". Also, the pyran ring is to be included in the "heteroaryl ring".

[0028] Among the A ring, B ring, and C ring, the aryl ring can be selected from the group consisting of a benzene ring, biphenyl ring, indene ring, naphthalene ring, fluorene ring, anthracene ring, and phenanthrene ring, and the heteroaryl ring can be selected from the group consisting of a benzofuran ring, benzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, naphthofuran ring, naphthothiophene ring, benzoindole ring, and benzoselenophene ring. As the aryl ring or heteroaryl ring among the A ring, B ring, and C ring, a benzene ring is preferred.

[0029] When at least one hydrogen in the aryl ring or heteroaryl ring is substituted with a substituent, the substituent is preferably a 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 diarylboril (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, cyano, halogen, or -L-Ak. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, cycloalkyl, cyano, halogen, or diarylamino.

[0030] In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring can be condensed with at least one cycloalkane. The cycloalkane can be substituted with at least one substituent, and among the cycloalkanes, at least one -CH2- can be substituted with -O-.

[0031] In the above structure, at least one hydrogen can be replaced with deuterium, cyano, or halogen, and at least one nitrogen can be nitrogen-15 ( 15N) can be replaced with, and at least one sulfur can be sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be carbon-13 ( 13 C), at least one boron can be boron-11 ( 11 B).

[0032] Examples of the "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, cycloalkanes having 5 carbon atoms, etc.

[0033] 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, and C1-C5 alkyl (especially methyl) substituents, halogen (especially fluorine) substituents, deuterium substituents thereof, etc.

[0034] Among these, a structure in which at least one hydrogen at the α-position carbon of the cycloalkane (in the cycloalkyl condensed to the aryl ring or heteroaryl ring, the carbon at the position adjacent to the carbon at the condensation site) is substituted is preferred, a structure in which two hydrogens at the α-position carbon are substituted is more preferred, and a structure in which a total of four hydrogens at the two α-position carbons are substituted is even more preferred. Examples of this substituent include an alkyl (especially methyl) substituent having 1 to 5 carbon atoms, a halogen (especially fluorine) substituent, and a deuterium substituent. In particular, in the aryl ring or heteroaryl ring, it is preferably a structure in which a partial structure represented by the following formula (B10) is bonded to adjacent carbon atoms.

[0035]

Chemical formula

[0036] At least one hydrogen in the “aryl ring” or “heteroaryl ring” can be substituted with a substituted or unsubstituted “aryl”, a substituted or unsubstituted “heteroaryl”, a substituted or unsubstituted “diaryl amino”, a substituted or unsubstituted “diheteroaryl amino”, a substituted or unsubstituted “aryl heteroaryl amino”, a substituted or unsubstituted “diaryl boryl (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 “aryl”, “heteroaryl”, aryl of “diaryl amino”, heteroaryl of “diheteroaryl amino”, aryl and heteroaryl of “aryl heteroaryl amino”, aryl of “diaryl boryl”, or aryl of “aryloxy” as the first substituent include the monovalent groups of the aforementioned “aryl ring” or “heteroaryl ring”.

[0037] Specifically, examples of the "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, still more preferably aryls having 6 to 16 carbon atoms, particularly preferably aryls having 6 to 12 carbon atoms, and most preferably aryls having 6 to 10 carbon atoms.

[0038] Specific examples of the aryl include, for example, phenyl which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl which is a bicyclic aryl, (1-, 2-)naphthyl, (2-, 3-, 4-, 5-, 6-, 7-)indenyl which are condensed bicyclic aryls, terphenyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) which is a tricyclic aryl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, quaterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl) which is a tetracyclic aryl, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryls, and the like.

[0039] Examples of the "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 the heteroaryl also include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0040] Specific examples of the 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, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, etc.

[0041] The "alkyl" as the first substituent may be either a straight-chain or a branched-chain, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. Alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 8 carbon atoms (branched-chain alkyl having 3 to 8 carbon atoms) is still more preferred, alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms) is particularly preferred, and alkyl having 1 to 5 carbon atoms (branched-chain alkyl having 3 to 5 carbon atoms) is most preferred.

[0042] Specific alkyl groups 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), 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.

[0043] Also, 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, 1,1-dimethylhexyl, and the like can also be mentioned.

[0044] As a substituent containing the above-mentioned "alkyl", a tertiary alkyl represented by the following formula (tR) is one of the particularly preferred substituents when at least one hydrogen in the above-mentioned aryl ring 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). Further, a substituent in which the tertiary alkyl represented by the formula (tR) is substituted with another substituent as the second substituent is also preferred. Specifically, diarylamino substituted with a tertiary alkyl represented by the formula (tR), carbazolyl substituted with a tertiary alkyl represented by the formula (tR) (preferably, N-carbazolyl), or benzocarbazolyl substituted with a tertiary alkyl represented by the formula (tR) (preferably, N-benzocarbazolyl) can be mentioned.

[0045] Regarding "diarylamino", groups described as the following "first substituent" can be mentioned. Examples of the substitution form of the group of the formula (tR) for diarylamino, carbazolyl, and benzocarbazolyl include those in which some or all of the hydrogens of the aryl ring or benzene ring in these groups are substituted with the group of the formula (tR).

Chemical formula

[0046] In the formula (tR), R a , R b , and R c are each independently an alkyl having 1 to 24 carbon atoms, and any -CH2- in the alkyl may be substituted with -O-, and * is the bonding position.

[0047] R a , R b and R cThe "alkyl group having 1 to 24 carbon atoms" may be either a straight-chain or a branched-chain, for example, a straight-chain alkyl group having 1 to 24 carbon atoms or a branched-chain alkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 18 carbon atoms (a branched-chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched-chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched-chain alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched-chain alkyl group having 3 to 4 carbon atoms) can be mentioned.

[0048] In formula (tR), the total number of carbon atoms of Ra, Rb and Rc is preferably 3 to 20 carbon atoms, particularly preferably 3 to 10 carbon atoms.

[0049] R a 、R b and R c Specific alkyl groups for R, R and R 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-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, etc.

[0050] Examples of the group represented by the 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-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, t-butyl and t-amyl are preferred.

[0051] 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, cycloalkyl having 5 carbon atoms, etc.

[0052] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituents 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, decahydroazulenyl, etc.

[0053] In addition, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0054] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

[0055] In addition, 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. For example, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl can be mentioned.

[0056] Examples of the "trialkylsilyl" include groups in which three hydrogens in the silyl group are each independently substituted with alkyl, and this alkyl can cite the groups described as "alkyl" in the aforementioned first substituent. Preferred alkyl for substitution is alkyl having 1 to 5 carbon atoms, and specifically, methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, t-amyl and the like can be mentioned.

[0057] Specific trialkylsilyls 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-amyl-dimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyl-diethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyl-dipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, t-amyl-di-i-propylsilyl, and the like.

[0058] Examples of "tricycloalkylsilyl" include groups in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl can cite the groups described as "cycloalkyl" in the aforementioned first substituent. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically, 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, decahydroazulenyl, and the like.

[0059] Specific tricycloalkylsilyls include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0060] Specific examples of a dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and an alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyls substituted with groups selected from the aforementioned specific alkyls and cycloalkyls.

[0061] Specific examples of a dialkylarylsilyl substituted with two alkyls and one aryl, an alkyldiarylsilyl substituted with one alkyl and two aryls, and a triarylsilyl substituted with three aryls include silyls substituted with groups selected from the aforementioned specific alkyls and aryls. Specific examples of the triarylsilyl include, in particular, triphenylsilyl.

[0062] In addition, as the "aryl" in the "diarylboronyl" of the first substituent, the description of the aforementioned aryl can be cited. Further, these two aryls may be bonded via a single bond or a linking group (for example, >C(−R)2, >O, >S or >N−R). Here, R in >C(−R)2 and >N−R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (the above are the first substituents), and the first substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above are the second substituents). Specific examples of these groups can cite the descriptions of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the aforementioned first substituent.

[0063] In -L-Ak of the first substituent, L is >N−R, >O or >S, and R in >N−R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. Further, R in >N−R may be bonded to Ak by a linking group or a single bond.

[0064] Ak is hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, at least one hydrogen in said alkyl and cycloalkyl may be substituted, and at least one -CH2- in said alkyl and cycloalkyl may be substituted with -O- and -S-.

[0065] L is preferably >N-R.

[0066] When L is >N-R, 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, even more preferably aryl optionally substituted with alkyl, and particularly preferably phenyl optionally substituted with methyl.

[0067] 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, even more preferably alkyl having 1 to 4 carbon atoms, and particularly preferably methyl.

[0068] When L is >N-R, R may be bonded to Ak by a linker or a single bond. Examples of the linking group at this time include >O, >S, or >Si(-R)2, etc. R of >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 the structure in which R of >N-R is bonded to Ak by a linker or a single bond include the following.

[0069]

Chemical formula

[0070] In each of the above formulas, Me is methyl, and at the position of *, it is bonded to the ring-constituting atoms of the aryl ring or heteroaryl ring in Ring A, Ring B, and Ring C.

[0071] The first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diaryl amino", a substituted or unsubstituted "diheteroaryl amino", a substituted or unsubstituted "aryl heteroaryl amino", a substituted or unsubstituted "diaryl boryl (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", or a substituted "silyl", as described as substituted or unsubstituted, at least one hydrogen in these may be substituted by a second substituent. Examples of this second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples thereof can refer to the monovalent groups of the aforementioned "aryl ring" or "heteroaryl ring", and the descriptions of "alkyl" or "cycloalkyl" as the first substituent. Also, for aryl or heteroaryl as the second substituent, structures in which at least one hydrogen in them is substituted by aryl such as phenyl (specific examples are the aforementioned groups), alkyl such as methyl or t-butyl (specific examples are the aforementioned groups), or cycloalkyl such as cyclohexyl (specific examples are the aforementioned groups) are also included in aryl or heteroaryl as the second substituent. As an example, when the second substituent is carbazolyl, carbazolyl in which at least one hydrogen at the 9-position is substituted by aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl is also included in heteroaryl as the second substituent.

[0072] The emission wavelength can be adjusted by the steric hindrance, electron-donating property, and electron-withdrawing property of the first substituent. Preferably, it is a group represented by the following structural formula, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl (especially N-carbazolyl), 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy, and even more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a larger steric hindrance is preferable for selective synthesis. 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 preferable.

[0073] In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * indicates the bonding position.

Chemical formula

[0074]

Chemical formula

[0075]

Chemical formula

[0076]

Chem.

[0077]

Chem.

[0078]

Chem.

[0079]

Chem.

[0080]

Chem.

[0081]

Chem.

[0082]

Chem.

[0083]

Chem.

[0084]

Chem.

[0085]

Chem.

[0086]

Chem.

[0087] [Chemistry]

[0088] When two or three hydrogens bonded to consecutive (adjacent) carbon atoms are substituted, the substituent may be a group represented by formula (A20). [Chemistry]

[0089] In formula (A20), L S is >N-R, >O, >Si(-R)2 or >S, where R in >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and R in >Si(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, and they may be bonded to each other to form a ring, and further, at least one of R in >N-R and R in >Si(-R)2 is bonded to at least one selected from the group consisting of ring A, ring B, ring C, ring D, ring E and R S by a linking group or a single bond, 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 may be bonded to any other R S by a linking group or a single bond, The group represented by formula (A20) is bonded to two adjacent atoms on the ring of an aryl ring, heteroaryl ring, or cycloalkane ring by two *s respectively.

[0090] When the polycyclic aromatic compound represented by formula (1) contains a group represented by formula (A20), the number thereof is preferably one or two. The group represented by formula (A20) may be a substituent in any one of the A ring, B ring, C ring, D ring, and E ring.

[0091] The group represented by formula (A20) is bonded to two * atoms, respectively, to two adjacent atoms on the ring of an aryl ring or a heteroaryl ring. The group represented by formula (A20) is preferably bonded to two adjacent atoms on the aryl ring or the heteroaryl ring with two *. At this time, it is preferable that both of the two adjacent atoms on the ring are carbon atoms. When the group represented by formula (A20) is bonded to the aryl ring or the heteroaryl ring, a condensed ring structure is formed. The compound represented by formula (1) having this condensed ring structure has a more rigid structure for the compound. When rigidified, the vibration of the molecule is suppressed, the EQE is improved, the stability of the molecule is enhanced, and the device lifetime is expected to be prolonged.

[0092] In formula (A20), L S is >N-R, >O, >Si(-R)2 or >S. By selecting the type of L S in the group represented by formula (A20), it is possible to control the HOMO and LUMO of the polycyclic aromatic compound represented by formula (1). When L S is N-R, >O or >S, the HOMO and LUMO become shallower, and when it is Si, the HOMO and LUMO become deeper. When the HOMO and LUMO become shallower, it is expected that the TTF device using this will have a long lifetime, high efficiency, and low driving voltage. On the other hand, when the HOMO and LUMO become deeper, the hole trapping property of the dopant disappears, and a significant decrease in the driving voltage is expected.

[0093] L S in formula (A20) of >N-R, R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. L S>Si(-R)2, where R is hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, and two Rs may be bonded to each other to form a ring. Further, at least one of said >N-R and said >Si(-R)2's R may be bonded to at least one selected from the group consisting of ring A, ring B, ring C, ring D, ring E and R S through a linking group or a single bond. L is preferably >N-R, >O or >S, more preferably >N-R or >O, and even more preferably >N-R.

[0094] L S When L is >N-R, 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 or cycloalkyl, or heteroaryl optionally substituted with alkyl or cycloalkyl; even more preferably aryl optionally substituted with alkyl or cycloalkyl; and particularly preferably phenyl optionally substituted with alkyl or cycloalkyl.

[0095] In formula (A20), r is an integer from 1 to 4, preferably 2 or 3, and more preferably 2.

[0096] In formula (A20), R S are each independently hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl, and any R S may be linked to any other R S through a linking group or a single bond.

[0097] R SIt is preferable that any two of them are bonded to each other by a linking group or a single bond. Examples of the linking group include >O, >S, etc. Examples of the divalent group formed by bonding to each other include alkylene. At least one hydrogen in the alkylene may be substituted with alkyl or cycloalkyl, and at least one (preferably one) -CH2- in the alkylene may be substituted with -O- and -S-. As the divalent group formed by bonding to each other, a linear alkylene having 2 to 5 carbon atoms is preferable, a linear alkylene having 3 or 4 carbon atoms is more preferable, and a linear alkylene having 4 carbon atoms (-(CH2)4-) is even more preferable. The linear alkylene having 4 carbon atoms (-(CH2)4-) is particularly preferably unsubstituted.

[0098] Two Rs respectively bonded to adjacent carbon atoms S When they are bonded to each other by a linking group or a single bond, the remaining Rs not involved in this bond S are each independently hydrogen or optionally substituted alkyl, or are preferably bonded to the R of >N-R or >Si(-R)2 which is S L.

[0099] Two Rs respectively bonded to adjacent carbon atoms S When they are bonded to each other by a linking group or a single bond, the remaining Rs not involved in this bond S As the optionally substituted alkyl as the remaining R, it 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 both are methyl.

[0100] That is, as a preferable example of the group represented by the formula (A20), a group represented by the formula (A20-a) can be mentioned.

Chemical formula

[0101] L S Among R of >N-R and >Si(-R)2, at least one of them may be bonded to at least one selected from the group consisting of A ring, B ring, C ring, D ring, E ring and R S via a linker or a single bond. L S When L is >N-R, examples thereof include a group represented by any one of the following formulas, and the group represented by formula (A20-b-1) is preferred.

Chemical formula

[0102] In each formula, Me is methyl. In each formula, *, it is bonded to two or three adjacent atoms on the ring of any one of the aryl ring, heteroaryl ring or cycloalkane ring of A ring, B ring and C ring respectively.

[0103] <Explanation of formula (1X1)>

Chemical formula

[0104] Preferable examples of the polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) include the polycyclic aromatic compound represented by formula (1X1).

[0105] In formula (1X1), Ar is the same as the definition of Ar in formula (1), and R a is hydrogen or unsubstituted alkyl, and R b is substituted or unsubstituted 9-carbazolyl, or substituted or unsubstituted diarylamino, and Z E are each independently -C(-R ZE )= or -N=, and the said R ZEis independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, provided that substituents substituted on adjacent atoms can bond to each other to form a ring.

[0106] <Formula (E ABC ) description> In the polycyclic aromatic compound structure represented by formula (1) of the present invention, at least one selected from the group consisting of ring A, ring B, and ring C is an aryl ring having at least the group represented by formula (E ABC ) as a substituent, or a heteroaryl ring having at least the group represented by formula (E ABC ) as a substituent.

Chemical formula

[0107] In formula (E ABC ), # indicates the bonding position to the aryl ring or heteroaryl ring. In formula (E ABC ), "P" and "Q" inside the circle are symbols indicating the ring structures represented by each circle. In formula (E ABC ), ring P and ring Q each form a divalent group having a bond to two adjacent elements (preferably carbon) on the aryl ring or heteroaryl ring in the structure. The two bonds are bonded to the carbon adjacent to nitrogen. In formula (E ABC ), ring P and ring Q are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring. In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring can be fused to at least one cycloalkane, the cycloalkane can be substituted with at least one substituent, and among the cycloalkanes, at least one -CH2- can be substituted with -O-.

[0108] In the above structure, at least one hydrogen can be replaced by deuterium, cyano, or halogen, at least one nitrogen can be replaced by nitrogen-15 ( 15 N), at least one sulfur can be replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be replaced by carbon-13 ( 13 C), and at least one boron can be replaced by boron-11 ( 11 B).

[0109] In the substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in the P ring and the Q ring, when it is "substituted or unsubstituted (substituted or unsubstituted)", the substituent includes at least one substituent selected from the following substituent group Z. The description of the substituent may be replaced with the common part of the descriptions in the A ring, the B ring, and the C ring. The ring having the two bonding hands as ring-constituting elements is preferably a 5-membered ring or a 6-membered ring, and more preferably a 6-membered ring. This ring can be fused with other rings. Examples of the 6-membered ring include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, etc. Examples of the 6-membered ring being condensed 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, a dibenzoselenophene ring, etc. Examples of the 5-membered ring include a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, a selenophene ring, etc. Examples of the 5-membered ring being condensed with another ring include a benzofuran ring, a benzothiophene ring, an indole ring, a benzoselenophene ring, etc.

[0110] As the P ring and the Q ring, independently of each other, 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 is preferable. It is preferable that at least one of the P ring and the Q ring is a substituted or unsubstituted benzene ring, and 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, "substitution" in the substituted benzene ring, substituted fluorene ring, substituted dibenzofuran ring, substituted dibenzothiophene ring, substituted dibenzoselenophene ring, substituted dibenzosilolane ring or substituted N-phenylcarbazole ring may be deuterium, cyano, halogen, carbazole, phenyl, biphenyl or terphenyl, but is not limited to only these examples.

[0111] Examples of the preferable group represented by formula (E ABC ) include a group represented by formula (E ABC -1), formula (E ABC -2), formula (E ABC -3), formula (E ABC -4) or formula (E ABC -5).

Chemical formula

[0112] In formula (E ABC -1) to formula (E ABC -5), Z X is -C(-R ZX )= or -N=, and preferably both are -C(-R ZX )=.

[0113] R ZX is, independently of one another, hydrogen or a substituent. When R ZX is a substituent, examples of the substituent include at least one substituent selected from the substituent group Z described below, and substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl are preferred, and unsubstituted alkyl is more preferred. R ZX is preferably hydrogen in each case. The description of the substituent may be replaced with the common part in the description of the A ring, B ring, and C ring.

[0114] Y 1 is >N-R NY , >C(-R CY )2, >O, >Si(-R IY )2, >P-R PY , >P(=O)R POY , >S, >SO, >SO2 or >Se, and R NY , R CY , R IY , R PY and R POY are, independently of one another, hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and two R CY can be bonded to each other to form a ring, and two R IY can be bonded to each other to form a ring. R NY is preferably substituted or unsubstituted aryl having 6 to 18 carbon atoms, and more preferably unsubstituted phenyl. R CY and R IY are preferably, independently of one another, aryl having 6 to 18 carbon atoms or alkyl having 1 to 18 carbon atoms, and more preferably unsubstituted phenyl or methyl.

[0115] Y 1 is preferably >N-R NY , >O or >S.

[0116] Z d is independently -C(-R Zd )= or -N=, and R Zd is independently hydrogen or a substituent. When R Zd is a substituent, examples of the substituent include at least one substituent selected from the substituent group Z described below, and cyano, halogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl are preferred, and unsubstituted alkyl is more preferred. R Zd are preferably all hydrogen. The description of the above substituents may be replaced with the common part in the description of the A ring, B ring, and C ring.

[0117] Z which is -N= d is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0 in each monocyclic ring of formulas (E ABC -1) to (E ABC -5). In formulas (E ABC -1) to (E ABC -5), Z d is preferably all -C(-R Zd )=.

[0118] In formulas (E ABC -1) to (E ABC -5), formulas (E ABC -1), (E ABC -2), (E ABC -3) and (E ABC -5) are preferred, and formulas (E ABC -1), (E ABC -2) and (E ABC -5) are more preferred.

[0119] Examples of formulas (E ABC -1) to (E ABC -5) include structures represented by any one of the following.

Chemical formula

[0120] [Chemical formula]

[0121] [Chemical formula]

[0122] The number of the groups represented by the formula (E ABC ) in the formula (1) is preferably 1 to 3, more preferably 1 to 2. When a polycyclic aromatic compound containing the structural unit represented by the formula (1) contains a plurality of groups represented by the formula (JABC), the plurality of groups represented by the formula (E ABC ) may be the same as or different from each other. From the viewpoint of easy synthesis, the groups represented by the plurality of formulae (E ABC ) are preferably the same as each other.

[0123] The substitution position of the group represented by the formula (E ABC ) is not particularly limited. However, when the aryl ring to which the group represented by the formula (E ABC ) is bonded is a benzene ring, the group represented by the formula (E ABC ) is preferably substituted at the para position of boron (B).

[0124] In addition, the group represented by the formula (E ABC ) may be contained in any of the A ring, the B ring, and the C ring, but is preferably contained in at least one of the B ring and the C ring. When at least one, particularly both, of the B ring and the C ring is a benzene ring in which the group represented by the formula (E ABC ) is substituted at the para position of boron (B), the interaction with adjacent molecules can be more suppressed.

[0125] In this specification, the substituent group Z is aryl which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, Heteroaryl which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen, Diaryl amino (the two aryls can be bonded to each other via a linking group) which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen, Diheteroaryl amino (the two heteroaryls can be bonded to each other via a linking group) which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen, Aryl heteroaryl amino (the aryl and the heteroaryl can be bonded to each other via a linking group) which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen, Diaryl boryl (the two aryls can be bonded to each other via a single bond or a linking group) which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen, Alkyl which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano and halogen, Cycloalkyl which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen, Alkoxy which can be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano and halogen, Aryloxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen, Consisting of substituted silyl, cyano and halogen.

[0126] <Description of formula (Ar)> In formula (1), each Ar independently represents a group represented by the following formula (Ar).

Chemical formula

[0127] In formula (Ar), * indicates the bonding position to nitrogen. In formula (Ar), "D" within the circle is a symbol indicating a ring structure represented by the circle. In formula (Ar), the D ring may be a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring.

[0128] In formula (Ar), 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, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted trialkylsilyl, a substituted or unsubstituted dialkylarylsilyl, a substituted or unsubstituted alkyldiarylsilyl, a substituted or unsubstituted triarylsilyl, a substituted or unsubstituted diarylamine, a substituted or unsubstituted arylheteroarylamine, or a substituted or unsubstituted diheteroarylamine. At least one G is a substituted alkyl having 1 to 24 carbon atoms, an unsubstituted alkyl having 4 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl. Here, when G is a substituted alkyl having 1 to 24 carbon atoms or an unsubstituted alkyl having 4 to 24 carbon atoms, the carbon atom bonded to the D ring is a quaternary carbon atom. When G is a substituted or unsubstituted cycloalkyl, the carbon atom bonded to the D ring may be a tertiary carbon atom or a quaternary carbon atom. The description regarding G may be replaced with the common part in the descriptions of the A ring, B ring, and C ring.

[0129] In formula (Ar), the D ring may be a substituted or unsubstituted aryl ring. In formula (Ar), examples of the "aryl ring" of the D ring 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.

[0130] In formula (Ar), the D ring may be a substituted or unsubstituted heteroaryl ring. In formula (Ar), examples of the "heteroaryl ring" of the D ring 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, even more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" also include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0131] In the D ring, the aryl ring can be selected from the group consisting of a benzene ring, a biphenyl ring, a terphenyl ring, an indene ring, a naphthalene ring, a fluorene ring, an anthracene ring, and a phenanthrene ring, and the heteroaryl ring can 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. The D ring is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted terphenyl ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted benzofuran ring.

[0132] When at least one hydrogen 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 (amino having an aryl and a heteroaryl), 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, cyano, halogen, or -L-Ak. When these groups have substituents, examples of the substituents include aryl, heteroaryl, alkyl, cycloalkyl, cyano, halogen, or diarylamino. The description of the substituents may be replaced with the common part in the descriptions of the A ring, B ring, and C ring.

[0133] In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring can be condensed with at least one cycloalkane, the cycloalkane can be substituted with at least one substituent, and among the cycloalkanes, at least one -CH2- can be substituted with -O-.

[0134] In the above structure, at least one hydrogen can be replaced with deuterium, cyano, or halogen, at least one nitrogen can be replaced with nitrogen-15 ( 15 N), at least one sulfur can be replaced with sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be replaced with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be replaced with carbon-13 ( 13 C), and at least one boron can be replaced with boron-11 ( 11 B).

[0135] <Replacement with Heavy Stable Isotopes> Elements in the polycyclic aromatic compound containing the structural unit represented by formula (1) may be all or part of them heavy stable isotopes. More specifically, at least one hydrogen can be replaced with deuterium, and at least one nitrogen can be replaced with nitrogen-15 ( 15 N), at least one sulfur can be replaced with sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be replaced with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be replaced with carbon-13 ( 13 C), and at least one boron can be replaced with boron-11 ( 11 B).

[0136] <Replacement with Deuterium> Hydrogen in the polycyclic aromatic compound containing the structural unit represented by formula (1) may be all or part of them deuterium. The same applies to the polycyclic aromatic compound represented by formula (1X1).

[0137] For example, the hydrogen in the aryl ring or heteroaryl ring of ring A, ring B and ring C, and the substituents thereof can be replaced with deuterium, and examples thereof include the aspect in which all or part of the hydrogen in the aryl or heteroaryl is replaced with deuterium. All or part of the hydrogen in the P ring and Q ring of formula (E ABC ) or the aryl ring and heteroaryl ring of ring D of formula (Ar) can be replaced with deuterium. Also, from the viewpoint of durability, it is also preferable that all or part of the hydrogen in the polycyclic aromatic compound containing the structural unit represented by formula (1) is deuterated.

[0138] <Specific Examples of Polycyclic Aromatic Compounds> Examples of the polycyclic aromatic compound containing the structural unit represented by the formula (1) include compounds represented by any one of the following structural formulas. On the other hand, in the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, "Ad" represents 1-adamantyl, and "D" represents deuterium.

[0139]

Chemical formula

[0140]

Chemical formula

[0141]

Chemical formula

[0142]

Chemical formula

[0143]

Chemical formula

[0144]

Chemical formula

[0145]

Chemical formula

[0146]

Chemical formula

[0147]

Chemical formula

[0148] [Chemistry]

[0149] [Chemistry]

[0150] [Chemistry]

[0151] [Chemistry]

[0152] [Chemistry]

[0153] [Chemistry]

[0154] [Chemistry]

[0155] [Chemistry]

[0156] [Chemistry]

[0157] 1-2. Reactive compound, polymer compound, polymer crosslinked body, pendant-type polymer compound, pendant-type polymer crosslinked body The polycyclic aromatic compound represented by formula (1) can also be used as a polymer compound obtained by polymerizing a reactive compound having a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), or a polymer crosslinked body obtained by further crosslinking the polymer compound (the polymer compound for obtaining this polymer crosslinked body has a crosslinkable substituent), or a pendant polymer compound obtained by reacting a main chain type polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant polymer crosslinked body obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked body has a crosslinkable substituent), as a material for organic devices, for example, a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.

[0158] On the other hand, in this specification, the "polymer compound" has a molecular weight distribution and a number average molecular weight in terms of polystyrene of 1×10 3 ~1×10 8 (1×10^3 to 1×10^8). The number average molecular weight (Mn) of the polymer compound in terms of polystyrene 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 about 0.05% by mass, and 10 μL is injected into the SEC. The flow rate of the mobile phase is 1.0 mL / min, and PLgel MIXED_B (manufactured by Polymer Laboratories) is used as the column. A UV-VIS detector (manufactured by Tosoh Corporation, product name: UV-8320GPC) can be used as the detector.

[0159] The polymer compound of the present invention preferably has a number average molecular weight of 2000 to 1×10 8 and more preferably 5000 to 1×10 8 .

[0160] Examples of the aforementioned reactive substituents (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining pendant polymers, hereinafter simply referred to as "reactive substituents") include 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 undergoing a pendant reaction with the main-chain polymer, and are not particularly limited as long as they are such substituents. Examples thereof include alkenyl, alkynyl, unsaturated cycloalkyls (e.g., cyclobutenyl), groups in which at least one -CH2- in cycloalkyl is substituted with -O- (e.g., epoxy), unsaturated condensed cycloalkanes (e.g., condensed cyclobutene), etc., and substituents having the following structures are preferred. * in each structural formula indicates the bonding position.

[0161]

Chemical formula

[0162] L is each independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and 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.

[0163] Details of the uses of such polymer compounds, polymer crosslinked bodies, pendant polymer compounds, and pendant polymer crosslinked bodies (hereinafter also simply referred to as "polymer compounds and polymer crosslinked bodies") will be described later.

[0164] 2. Method for producing polycyclic aromatic compound The method for producing a polycyclic aromatic compound containing the structure represented by formula (1) basically involves bonding the A ring to each of the B ring and the C ring simultaneously or sequentially with a linking group (N-Ar), and then simultaneously linking the A ring, B ring, and C ring with boron for production (reaction a), or in the A ring, B ring, and C ring linked with boron, bonding the A ring and the B ring, and the A ring and the C ring simultaneously or sequentially with a linking group (N-Ar) respectively for production (reaction b), and the final product can be produced. When linking each ring with a linking group (N-Ar) in reaction a and reaction b, for example, in the case of an etherification reaction, general reactions such as a nucleophilic substitution reaction or a Ullmann reaction can be used, and in the case of an amination reaction, general reactions such as a Buchwald-Hartwig reaction can be used. Also, in reaction a and reaction b, when linking each ring with boron, a tandem hetero Friedel-Crafts reaction (a continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used. For these production methods, reference can be made to the methods described in prior art documents such as International Publication No. 2015 / 102118.

[0165] 3. Organic Device The polycyclic aromatic compound according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescent element, an organic field effect transistor, or an organic thin film solar cell.

[0166] 3-1. Organic electroluminescent device The organic electroluminescent element has at least a pair of electrodes composed of a positive electrode and a negative electrode, and a light-emitting layer disposed between the pair of electrodes. Hereinafter, the organic EL element according to the present embodiment will be described in detail with reference to the drawings.

[0167] 3-1-1. Structure of organic electroluminescent device FIG. 1 is a schematic cross-sectional view of an example of an organic EL element. The organic EL element (100) shown in FIG. 1 includes a substrate (101), an anode (102) disposed on the substrate (101), a hole injection layer (103) disposed on the anode (102), a hole transport layer (104) disposed on the hole injection layer (103), a light-emitting layer (105) disposed on the hole transport layer (104), an electron transport layer (106) disposed on the light-emitting layer (105), an electron injection layer (107) disposed on the electron transport layer (106), and a cathode (108) disposed on the electron injection layer (107).

[0168] Further, the organic EL element (100) may have a structure in which the manufacturing order is reversed. For example, it may include a substrate (101), a cathode (108) disposed on the substrate (101), an electron injection layer (107) disposed on the cathode (108), an electron transport layer (106) disposed on the electron injection layer (107), a light-emitting layer (105) disposed on the electron transport layer (106), a hole transport layer (104) disposed on the light-emitting layer (105), a hole injection layer (103) disposed on the hole transport layer (104), and an anode (102) disposed on the hole injection layer (103).

[0169] Not all of the above layers are necessary. The minimum structural unit may be composed of an anode (102), a light-emitting layer (105), and a cathode (108). The hole injection layer (103), the hole transport layer (104), the electron transport layer (106), and the electron injection layer (107) are optionally installed layers. Each of the above layers may be composed of a single layer or a plurality of layers.

[0170] As an aspect of the layers constituting the organic EL element, in addition to the above-described configuration aspect of "substrate / positive electrode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / negative electrode", "substrate / positive electrode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / negative electrode", "substrate / positive electrode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / negative electrode", "substrate / positive electrode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / negative electrode", "substrate / positive electrode / light-emitting layer / electron transport layer / electron injection layer / negative electrode", "substrate / positive electrode / hole transport layer / light-emitting layer / electron injection layer / negative electrode", "substrate / positive electrode / hole transport layer / light-emitting layer / electron transport layer / negative electrode", "substrate / positive electrode / hole injection layer / light-emitting layer / electron injection layer / negative electrode", "substrate / positive electrode / hole injection layer / light-emitting layer / electron transport layer / negative electrode", "substrate / positive electrode / light-emitting layer / electron transport layer / negative electrode", "substrate / positive electrode / light-emitting layer / electron injection layer / negative electrode" may also be the configuration aspect.

[0171] 3-1-2. Substrate in organic electroluminescent device The substrate (101) is a support for the organic EL element (100), and usually, quartz, glass, metal, plastic, etc. are used. The substrate (101) is formed in a plate shape, film shape, or sheet shape according to the purpose, and for example, a glass plate, metal plate, metal foil, plastic film, plastic sheet, etc. are used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, polysulfone are preferable. In the case of a glass substrate, soda-lime glass, alkali-free glass, etc. are used, and the thickness only needs to be sufficient to maintain mechanical strength, so for example, 0.2 mm or more is sufficient. As the upper limit value of the thickness, for example, 2 mm or less, preferably 1 mm or less. Regarding the material of the glass, since it is better that there are fewer eluted ions from the glass, alkali-free glass is preferable, but since soda-lime glass with a barrier coat such as SiO2 is also commercially available, this can be used. Further, in order to enhance the gas barrier property, a gas barrier film such as a dense silicon oxide film may be formed on at least one side of the substrate (101). In particular, when a plate, film, or sheet made of a synthetic resin with low gas barrier property is used as the substrate (101), it is preferable to form a gas barrier film.

[0172] 3-1-3. Anode in organic electroluminescent device The positive electrode (102) serves to inject holes into the light-emitting layer (105). When a hole injection layer (103) and / or a hole transport layer (104) is provided between the positive electrode (102) and the light-emitting layer (105), holes are injected into the light-emitting layer (105) through these layers.

[0173] Examples of materials for forming the positive electrode (102) include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (such as aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (such as indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (such as copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, etc. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from substances currently used as the positive electrode of the organic EL element.

[0174] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light emission of the light-emitting element, but it is preferably low resistance from the viewpoint of the power consumption of the light-emitting element. For example, an ITO substrate with a resistance of 300 Ω / square or less can function as an element electrode, but currently substrates with a resistance of about 10 Ω / square can also be supplied. Therefore, it is particularly preferable to use low-resistance products with a resistance of, for example, 100 to 5 Ω / square, preferably 50 to 5 Ω / square. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 to 300 nm in many cases.

[0175] 3-1-4. Hole injection layer and hole transport layer in organic electroluminescent device The positive hole injection layer (103) serves to efficiently inject the holes moving from the positive electrode (102) into the light-emitting layer (105) or the positive hole transport layer (104). The positive hole transport layer (104) serves to efficiently transport the holes injected from the positive electrode (102) or the holes injected from the positive electrode (102) through the positive hole injection layer (103) to the light-emitting layer (105). The positive hole injection layer (103) and the positive hole transport layer (104) are each formed by laminating or mixing one or more kinds of positive hole injection / transport materials, or by a mixture of a positive hole injection / transport material and a polymer binder. Also, an inorganic salt such as iron(III) chloride may be added to the positive hole injection / transport material to form a layer.

[0176] As the positive hole injection / transport material, it is necessary to efficiently inject and transport the holes from the positive electrode between the electrodes to which an electric field is applied. It is preferable that the positive hole injection efficiency is high and the injected holes are efficiently transported. For this purpose, it is preferably a substance having a small ionization potential, a large positive hole mobility, excellent stability, and few impurities that can act as traps during manufacturing and use.

[0177] As materials for forming the positive hole injection layer (103) and the positive hole transport layer (104), in the photoconductive material, any compound can be selected and used from among compounds conventionally and commonly used as positive hole charge transport materials, p-type semiconductors, and known compounds used for the positive hole injection layer and the positive hole transport layer of an organic EL element. 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 in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, 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)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, triphenylamine derivatives such as 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-based compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc.In the polymer system, polycarbonates, styrene derivatives, polyvinylcarbazole, polysilane, etc. having the monomer in the side chain are preferable, but it is not particularly limited as long as it is a compound that can form a thin film necessary for manufacturing a light-emitting element, can inject holes from the anode, and can further transport holes.

[0178] Also, it is known that the conductivity of an organic semiconductor is strongly affected by doping. The organic semiconductor matrix material is composed of a compound having good electron-donating properties or a compound having good electron-accepting properties. For doping with an electron-donating substance, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known (for example, refer to the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202 - 3204(1998)" and the literature "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729 - 731(1998)"). These generate so-called holes by the electron transfer process in an electron-donating base substance (hole transport substance). The conductivity of the base substance changes considerably depending on the number and mobility of the holes. As matrix materials having hole transport characteristics, for example, benzidine derivatives (such as TPD), starburst amine derivatives (such as TDATA), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Laid-Open No. 2005-167175).

[0179] The above-mentioned hole injection layer material and hole transport layer material can also be used as a hole layer material as a polymer compound obtained by polymerizing a reactive compound having a reactive substituent substituted thereon as a monomer, or a polymer cross-linked body thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a pendant polymer cross-linked body thereof. In this case, as the reactive substituent, the description of the polycyclic aromatic compound containing the structure represented by the formula (1) can be cited.

[0180] Details of the uses of such polymer compounds and polymer cross-linked bodies will be described later.

[0181] 3-1-5. Light-emitting layer in organic electroluminescent device The light-emitting layer (105) emits light by recombining holes injected from the positive electrode (102) and electrons injected from the negative electrode (108) between electrodes to which an electric field is applied. As a material for forming the light-emitting layer (105), any compound (light-emitting compound) that is excited by the recombination of holes and electrons to emit light may be used, as long as it can form a stable thin-film shape, and at the same time, a compound that exhibits strong light-emitting (fluorescent) efficiency in the solid state is preferable. The light-emitting layer may be a single layer or a multiple-layer structure, and each layer is formed of a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be of 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 in the entire host material or partially contained therein. As a doping method, it can be formed by co-evaporation with the host material, or it may be co-evaporated after being premixed with the host material. Also, the light-emitting layer can be formed by a wet film-forming method using a composition for forming a light-emitting layer prepared by dissolving the material in an organic solvent.

[0182] 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 even more preferably used as an emitting dopant.

[0183] The polycyclic aromatic compound represented by formula (1) may be used as an emitting dopant of an organic EL element (hereinafter sometimes referred to as a "TADF element") that exhibits thermally activated delayed fluorescence (TADF) as a "thermally activated delayed phosphor". In a "thermally activated delayed phosphor", by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, reverse intersystem crossing from the lowest excited triplet state, where the transition probability is usually low, to the lowest excited singlet state occurs with high efficiency, and light emission from the singlet state (thermally activated delayed fluorescence, TADF) is exhibited. In normal fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal deactivation path and thus cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, and a highly efficient organic EL element is realized.

[0184] The polycyclic aromatic compound represented by formula (1) can be used as an emitting dopant of a "TADF element", an emitting dopant of a TADF element that uses two types of hosts, an emitting dopant of an organic electroluminescent element (a TADF-assisted fluorescent (TAF) element) that uses a separate thermally activated delayed phosphor as an assisting dopant, and an emitting dopant of an organic electroluminescent element (a phosphor-sensitized fluorescent (PSF) element) that uses a phosphorescent material as an assisting dopant. From the viewpoint that the fewer the materials used in the element, the easier it is to manufacture, the emitting dopant of a TADF element and the emitting dopant of a TADF element that uses two types of hosts are preferable, and the emitting dopant of a TADF element is more preferable. From the viewpoint of efficiency, the emitting dopant of a TAF element and the emitting dopant of a phosphorescent assist element are preferable, and the emitting dopant of a TAF element is more preferable.

[0185] Generally, it is considered that faster delayed fluorescence indicates better TADF properties. Specifically, when a luminescent 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. Also, generally, the smaller the value of ΔE S1T1 , the better the TADF properties. On the other hand, ΔE S1T1 is the energy difference between the lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ). Specifically, the value of ΔE S1T1 is preferably 0.20 eV or less, and more preferably 0.15 eV or less.

[0186] The light-emitting layer may contain a host compound. Here, the host compound may be of one type or two or more types. As the host compound, all known ones can be used. Preferred examples of the host compound include the high T1 compounds described later.

[0187] The light-emitting layer may be a single layer or may be composed of multiple layers. Also, the host compound, the emitting dopant material, and the assisting dopant material may be contained within the same layer, or may be contained at least one component each in multiple layers. The host compound and the dopant materials (emitting dopant or assisting dopant) contained in the light-emitting layer may each be of one type or may be a combination of multiple types. The assisting dopant and the emitting dopant may be entirely or partially contained within the host compound as a matrix.

[0188] The usage amount of the host material varies depending on the type of the host material and may be determined according to the characteristics of the host material. The standard for the usage amount of the host material is preferably 50 to 99.999% by mass of the total material for the light-emitting layer, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass.

[0189] The amount of the dopant material used varies depending on the type of the dopant material and may be determined according to the characteristics of the dopant material. The criterion for the amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass of the total material for the light-emitting layer. If it is within the above range, for example, it is preferable in terms of preventing the concentration quenching phenomenon.

[0190] On the other hand, in an organic electroluminescent element using a TADF material as a dopant material, it is preferable that the amount of the dopant material used is low in terms of preventing the concentration quenching phenomenon, but it is preferable that the amount of the dopant material used is high from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism. Further, in an organic electroluminescent element using a TADF material as an assisting dopant, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the amount of the emitting dopant used is low with respect to the amount of the assisting dopant used.

[0191] When an assisting dopant material is used, the criteria for the amounts of the host material, the assisting dopant, and the emitting dopant are 40 to 99% by mass, 59 to 1% by mass, and 20 to 0.001% by mass, respectively, of the total material 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, respectively. When an assisting dopant material is used, an exciplex may be formed with the host material or the emitting dopant material.

[0192] 3-1-5-1. Dopant material The polycyclic aromatic compound represented by the formula (1) is preferably used as a dopant material. In addition to the polycyclic aromatic compound represented by formula (1), the dopant material that can be used is not particularly limited, and known compounds can be used, and it can be selected from various materials according to the desired emission color.Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene; benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives (Japanese Patent Laid-Open No. 1-245087), bisstyryl arylene derivatives (Japanese Patent Laid-Open No. 2-247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimethylphenylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, isobenzofuran derivatives such as phenylisobenzofuran; dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives and other coumarin derivatives; dicyanomethylene pyran derivatives, dicyanomethylene thiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyryl derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, ferrionone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives, etc. can be mentioned.

[0193] Illustrated by the emitted light color, examples of blue to blue-green dopant materials include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, chrysene and their derivatives, aromatic heterocyclic compounds such as furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole and their metal complexes, and aromatic amine derivatives represented by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, etc.

[0194] Also, examples of green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, ferronone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, naphthacene derivatives such as quinacridone derivatives and rubrene, etc. Compounds obtained by further introducing substituents that enable longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, cyano, etc., into the compounds exemplified as the blue to blue-green dopant materials can also be mentioned as preferred examples.

[0195] Furthermore, examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylene tetracarboxylic acid imide, ferronone derivatives, rare earth complexes such as Eu complexes with 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, deazafavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiazolopyrene derivatives. Compounds in which substituents that enable longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, are further introduced into the compounds exemplified as the blue to blue-green and green to yellow dopant materials can also be mentioned as preferred examples.

[0196] In addition, as the dopant, it can be appropriately selected and used from among the compounds described in the Chemical Industry June 2004 issue, page 13, and the references cited therein.

[0197] Among the aforementioned dopant materials, amines having a stilbene structure, phenylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

[0198] An amine having a stilbene structure is represented, for example, by the following formula.

Chemical formula

[0199] 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, but Ar1 ~Ar 3 at least one of which 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.

[0200] As the amine having a stilbene structure, diamino stilbene represented by the following formula is more preferable.

Chemical formula

[0201] In the formula, Ar 2 and Ar 3 are each independently 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.

[0202] 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, distryl biphenyl, distyrylfluorenyl and the like.

[0203] 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[4''-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl, and the like.

[0204] In addition, amines having a stilbene structure described in JP-A No. 2003-347056 and JP-A No. 2001-307884 may also be used.

[0205] Examples of the ferrylene derivative include 3,10-bis(2,6-dimethylphenyl)ferrylene, 3,10-bis(2,4,6-trimethylphenyl)ferrylene, 3,10-diphenylferrylene, 3,4-diphenylferrylene, 2,5,8,11-tetra-t-butylferrylene, 3,4,9,10-tetraphenylferrylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)ferrylene, 3-(9'-anthryl)-8,11-di(t-butyl)ferrylene, 3,3'-bis(8,11-di(t-butyl)ferrylenyl), and the like.

[0206] Alternatively, ferrene derivatives described in, for example, Japanese Patent Application Laid-Open No. 11-97178, Japanese Patent Application Laid-Open No. 2000-133457, Japanese Patent Application Laid-Open No. 2000-26324, Japanese Patent Application Laid-Open No. 2001-267079, Japanese Patent Application Laid-Open No. 2001-267078, Japanese Patent Application Laid-Open No. 2001-267076, Japanese Patent Application Laid-Open No. 2000-34234, Japanese Patent Application Laid-Open No. 2001-267075, and Japanese Patent Application Laid-Open No. 2001-217077 may be used.

[0207] Examples of the borane derivative include 1,8-diphenyl-10-(dimethylborolyl)anthracene, 9-phenyl-10-(dimethylborolyl)anthracene, 4-(9'-anthryl)dimethylborolylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimethylborolylnaphthalene, 9-(dimethylborolyl)anthracene, 9-(4'-biphenylyl)-10-(dimethylborolyl)anthracene, 9-(4'-(N-carbazolyl)phenyl)-10-(dimethylborolyl)anthracene, and the like.

[0208] Alternatively, borane derivatives described in International Publication No. 2000 / 40586 and the like may be used.

[0209] The aromatic amine derivative is represented by, for example, the following formula.

Chemical formula

[0210] In the formula, Ar 4 is an n-valent group derived from an aryl having 6 to 30 carbon atoms, Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 to 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.

[0211] 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 to 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 2, and an aromatic amine derivative is more preferable.

[0212] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, ferrenyl, pentacenyl and the like.

[0213] Examples of the aromatic amine derivative include, as the chrysene type, for example, 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, 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, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine and the like.

[0214] In addition, 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, 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-trimethylsilanilyl-phenyl)-1H,8H-pyrene-1,6-diamine, and the like.

[0215] In addition, 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, N,N’-diphenyl-N,N’-di(m-tolyl)anthracene-9,10-diamine, N,N’-diphenyl-N,N’-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N’-diphenyl-N,N’-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N’-diphenyl-N,N’-bis(4-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’-bis(4-t-butylphenyl)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, 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene, and the like.

[0216] In addition, [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, 4,4''-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl, etc. can be mentioned.

[0217] Moreover, aromatic amine derivatives described in JP-A-2006-156888 etc. may also be used.

[0218] Examples of the coumarin derivative include coumarin-6, coumarin-334, etc.

[0219] Moreover, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758, etc. may also be used.

[0220] Examples of the pyran derivative include the following DCM, DCJTB, etc.

Chemical formula

[0221] Moreover, pyran derivatives described in JP-A-2005-126399, JP-A-2005-097283, JP-A-2002-234892, JP-A-2001-220577, JP-A-2001-081090, JP-A-2001-052869, etc. may also be used.

[0222] As the dopant material, the following compounds may also be used.

Chemical formula

[0223] 3-1-5-2. High T1 compound An organic electroluminescent device containing at least one polycyclic aromatic compound represented by formula (1) in a light-emitting layer preferably further contains at least one high-T1 compound having a lowest excited triplet energy level (ET1) (which may also be referred to as "T1 energy") at least 0.01 eV higher than the lowest excited triplet energy level of the polycyclic aromatic compound represented by formula (1) in the light-emitting layer or an organic layer adjacent to the light-emitting layer.

[0224] 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 high-T1 compound may be contained in one kind or two or more kinds in the light-emitting layer. When two or more kinds are contained, it preferably contains a hole-transporting host material and an electron-transporting host material that satisfy the following relationship.

[0225] 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), and 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).

[0226] The E T1 of the high-T1 compound is more preferably at least 0.03 eV higher and even more preferably at least 0.1 eV higher than the E T1 of the polycyclic aromatic compound represented by formula (1).

[0227] As the high-T1 compound, a compound having at least one partial structure selected from the partial structure group A, or having at least two partial structures selected from the partial structure group A and the partial structure group B, and further optionally having at least one partial structure selected from the partial structure group C as a linking group or a substituent is preferred. On the other hand, at least one of the following structures is bonded to another partial structure other than hydrogen, and the other is bonded to hydrogen. As can be seen from the following structural formula, the carbon-carbon bond connecting benzene rings in each partial structure and the bond connecting partial structures are ortho or meta positions. At this time, 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 meta position is preferred.

[0228] Partial structure group A

Chemical formula

[0229] Partial structure group B

Chemical formula

[0230]

Chemical formula

[0231] Partial structure group C

Chemical formula

[0232] 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.

Chemical formula

[0233] Examples of the high-T1 compound include a compound represented by the following formula (H1), a compound represented by the following formula (H3), a compound containing a structure represented by the following formula (H4), a compound represented by the following formula (H5), a compound represented by the following formula (H6), and a compound represented by the following formula (H8).

Chem.

[0234] 3-1-5-2-1. Compound represented by formula (H1)

Chem.

[0235] In formula (H1), L 1 is 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 and a heteroarylene having 5 to 15 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms and / or a heteroarylene having 5 to 11 carbon atoms, particularly preferably an arylene having 6 to 10 carbon atoms or a heteroarylene having 5 to 9 carbon atoms. Specifically, divalent or trivalent groups such as benzene ring, biphenyl ring, terphenyl ring, fluorene ring, spirofluorene ring, phenalene ring, triphenylene ring, pyridine ring, pyrimidine ring, triazine ring, biphenylpyridine ring, biphenylpyrimidine ring, and biphenyltriazine ring can be mentioned.

[0236] At least one hydrogen in the compound represented by formula (H1) may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, cyano, halogen, or deuterium.

Chem.

[0237] 3-1-5-2-2. Compound represented by formula (H3)

Chem.

[0238] In formula (H3), MU is each independently a divalent aromatic group, EC is each independently a monovalent aromatic group, and k is an integer from 2 to 50000.

[0239] More specifically, MU is each independently arylene, heteroarylene, diarylene arylamino, diarylene arylboryl, oxaborin-diyl, or azaborin-diyl, EC is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl, k is an integer from 2 to 50000.

[0240] k is preferably an integer from 20 to 50000, more preferably an integer from 100 to 50000.

[0241] At least one hydrogen 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. Any -CH2- in the alkyl may be further substituted with -O- or -Si(CH3)2-. Any -CH2- in the alkyl excluding the -CH2- directly connected to EC in formula (H3) may be substituted with arylene having 6 to 24 carbon atoms. Any hydrogen in the alkyl may be substituted with fluorine.

[0242] Examples of MU include divalent derivatives having the following structures (for example, divalent groups represented by removing any two hydrogen atoms from any one of the compounds having the following structures, divalent groups composed of combinations of two or more divalent groups represented by removing any two hydrogen atoms from any one of the compounds having the following structures, divalent groups in which at least one of the hydrogens in these groups is substituted with alkyl, etc.).

[0243]

Chemical Formula

[0244] More specifically, divalent groups having any one of the following structures can be mentioned. In these, MU binds to another MU or EC at *.

[0245]

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

[0246] Examples of EC include groups represented by the following formula. In these, EC binds to MU at *.

Chemical Formula

Chemical Formula

[0247] From the viewpoints of solubility and coatability to form a film, it is preferable that 10 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 1 to 24 carbon atoms for the compound represented by the formula (H3), more preferably 30 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), and still more preferably 50 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms). On the other hand, from the viewpoints of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 7 to 24 carbon atoms (branched alkyl group having 7 to 24 carbon atoms).

[0248] 3-1-5-2-3. Compound containing structure represented by formula (H4) The compound containing the structure represented by the formula (H4) contains a plurality of structures represented by the formula (H4), preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 2, and most preferably 1. When a plurality of the structures are contained, the structures are bonded to each other directly by a single bond or by a specific linking group.

Chemical formula

[0249] In the formula (H4), G is “=C(-H)-” or “=N-”, and the H in the “=C(-H)-” may be substituted with a substituent or a structure represented by another formula (H4).

[0250] As the compound containing the structure represented by the formula (H4), for example, the compounds described in International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650 can be used, and they can be produced according to the methods described in the above-mentioned documents.

[0251] Examples of substituents when the H in "=C(-H)-" which is G is substituted include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy, etc.

[0252] Specific examples of the substituent "aryl" include phenyl, tolyl, xylyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, etc., preferably phenyl, biphenylyl, terphenylyl, fluorenyl, etc. Examples of aryl having a substituent include tolyl, xylyl, 9,9-dimethylfluorenyl, etc. As shown in the specific examples, aryl includes both condensed aryl and non-condensed aryl.

[0253] 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, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., preferably dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, azadibenzothienyl, etc. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl or azadibenzothienyl is more preferred.

[0254] The "substituted silyl" which is a substituent is preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0255] Specific examples of the substituted or unsubstituted trialkylsilyl include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl include diphenylmethylsilyl, ditolylmethylsilyl, phenyldimethylsilyl and the like. Specific examples of the substituted or unsubstituted triarylsilyl include triphenylsilyl and tritolylsilyl and the like.

[0256] The "substituted phosphine oxide group" which is a substituent is preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide and the like.

[0257] Examples of the "substituted carboxy" as a substituent include benzoyloxy and the like.

[0258] Examples of the linking group that links a plurality of structures represented by the formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the aforementioned aryl and heteroaryl.

[0259] Specific examples of the compound containing the structure represented by the formula (H4) are shown below.

Chemical formula

Chemical formula

[0260] 3-1-5-2-4. Compound represented by formula (H5) and compound represented by formula (H6) 3-1-5-2-4-1. Compound represented by formula (H5)

Chemical formula

[0261] 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.

[0262] Further, any at least one (preferably 1 to 3) of -C(R n )(where n is 1 to 11) in formula (H5) may be substituted with -N=.

[0263] At least one hydrogen in the compound represented by formula (H5) may be further 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-, and any -CH2- in the alkyl excluding the -CH2- directly bonded to the compound represented by formula (H5) may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

[0264] Further, at least one hydrogen in the compound represented by formula (H5) may be substituted with a halogen or deuterium.

[0265] 3-1-5-2-4-2. Compound represented by formula (H6) [Chemical formula]

[0266] In formula (H6), R 1 ~R 16Each is 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.

[0267] In addition, at least one hydrogen 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-, and 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 in the alkyl may be substituted with fluorine.

[0268] In addition, at least one hydrogen in the compound represented by formula (H6) may be substituted with halogen or deuterium.

[0269] 3-1-5-2-4-3. "R in formula (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 aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (amino having two aryls each having 6 to 30 carbon atoms), diheteroarylamino (amino having two heteroaryls each having 2 to 30 carbon atoms), arylheteroarylamino (amino having an aryl having 6 to 30 carbon atoms and a heteroaryl having 2 to 30 carbon atoms) or aryloxy having 6 to 30 carbon atoms are preferred.

[0270] Examples of the aryl groups in "aryl", "diaryl amino", "aryl heteroaryl amino", and "aryloxy" include monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthalene rings, tricyclic terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl), condensed tricyclic acenaphthylene rings, fluorene rings, phenalene rings, phenanthrene rings, condensed tetracyclic triphenylene rings, pyrene rings, naphthacene rings, condensed pentacyclic perylene rings, pentacene rings, and the like. Also, as described later, those in which these aryl groups are substituted with heteroaryl groups defined below are also defined as aryl groups in formulas (H5) and (H6).

[0271] Examples of the heteroaryl groups in "heteroaryl", "diheteroaryl amino", and "aryl heteroaryl amino" include monovalent groups such as pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, 1H-benzotriazole rings, quinoline rings, isoquinoline rings, cinnoline rings, quinazoline rings, quinoxaline rings, phthalazine rings, naphthyridine rings, purine rings, pteridine rings, carbazole rings, acridine rings, phenoxathiin rings, phenoxazine rings, phenothiazine rings, phenazine rings, indolizine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, thiophene rings, benzothiophene rings, dibenzothiophene rings, furazan rings, oxadiazole rings, thianthrene rings, and the above-mentioned heteroaryl groups substituted with N-aryl. Also, as described later, those in which these heteroaryl groups are substituted with the aryl groups defined above are also defined as heteroaryl groups in formulas (H5) and (H6).

[0272] In addition, for R in formula (H5), 1 ~R 11 and for R in formula (H6), 1 ~R 16 The aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy described as such may have at least one hydrogen in these further substituted with aryl, heteroaryl or diarylamino. Examples of such aryl, heteroaryl or diarylamino that are substituted include R 1 ~R 11 and R 1 ~R 16 as described in the columns of.

[0273] R 1 ~R 11 and R 1 ~R 16 Specific examples of include, for example, the groups represented by the following formulas (RG-1) to (RG-10). Further, the groups represented by the following formulas (RG-1) to (RG-10) are bonded to the a-ring to d-ring in formula (H5) or formula (H6) by *.

Chemical formula

[0274] Referring to the aforementioned specific groups, the "aryl" and "heteroaryl" defined in formulas (H5) and (H6) will be described. Formulas (RG-1), (RG-4) and (RG-7) are aryl, formulas (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. Further, formula (RG-5) is aryl (phenyl) substituted with diarylamino (diphenylamino), and formula (RG-8) is diarylamino (diphenylamino).

Chemical formula

[0275] 3-1-5-2-4-4. Specific examples of compounds The more specific structures of the compounds represented by formula (H5) or formula (H6) are shown below.

[0276] The specific structures of the compounds represented by the following formula (H5) or formula (H6) may be substituted with an alkyl group having 1 to 24 carbon atoms. [Chemical formula]

[0277] [Chemical formula]

[0278] [Chemical formula]

[0279] [Chemical formula]

[0280] [Chemical formula]

[0281] [Chemical formula]

[0282] [Chemical formula]

[0283] [Chemical formula]

[0284] [Chemical formula]

[0285] [Chemical]

[0286] [Chemical]

[0287] [Chemical]

[0288] [Chemical]

[0289] [Chemical]

[0290] [Chemical]

[0291] [Chemical]

[0292] [Chemical]

[0293] [Chemical]

[0294] [Chemical]

[0295] [Chemical]

[0296]

Chem.

[0297]

Chem.

[0298]

Chem.

[0299]

Chem.

[0300]

Chem.

[0301]

Chem.

[0302] 3-1-5-2-4-5. Method for producing compound represented by formula (H5) or formula (H6) The compound represented by formula (H5) can be prepared by first producing an intermediate by bonding the a to c rings with a linking group (-O-) (the first reaction), and then producing the final product by bonding the a to c rings with a linking group (a group containing B) (the second reaction). Also, the compound represented by formula (H6) can be prepared by first producing an intermediate by bonding the a to d rings with a linking group (>NH or a single bond) (the first reaction), and then producing the final product by bonding the a to d rings with a linking group (a group containing B) (the second reaction). In the first reaction, for example, in the case of an etherification reaction, general reactions such as a nucleophilic substitution reaction or a Ullmann reaction can be used, and in the case of an amination reaction, general reactions such as a Backwald-Hartwig reaction can be used. Also, in the second reaction, a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction, the same applies hereinafter) can be used.

[0303] <Production method: Example of the second reaction of the compound represented by formula (H5)> The second reaction is a reaction for introducing B (boron) that bonds the a ring, b ring, and c ring, as shown in the following scheme (1). As an example, the case of the compound represented by formula (H5) is shown below. First, the hydrogen atom between the two Os is ortho-metalated with n-butyllithium, sec-butyllithium, t-butyllithium, etc. Next, boron trichloride, boron tribromide, etc. are added to perform a metal exchange of lithium-boron, and then a Brønsted base such as N,N-diisopropylethylamine is added to cause a tandem borofriedel-crafts reaction to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.

[0304]

Chemical formula

[0305] In the above scheme, lithium was introduced at the desired position by orthometalation. However, as in the following scheme (2), a bromine atom or the like can be introduced at the position where lithium is to be introduced, and lithium can also be introduced at the desired position by halogen-metal exchange.

[0306]

Chemical formula

[0307] By appropriately selecting the above synthetic method and also appropriately selecting the raw materials to be used, a compound having a substituent at the desired position and represented by the formula (H-5) can be synthesized.

[0308] <Manufacturing method: Example of the manufacturing method of the compound represented by the formula (H6)> Regarding the manufacturing method of the compound represented by the formula (H6), the first reaction and the second reaction in the manufacturing method of the compound represented by the above formula (H5) can also be applied. That is, the second reaction is a reaction for introducing B (boron) that binds NH to the c-ring and the d-ring. After orthometalating the hydrogen atom of NH with n-butyllithium, sec-butyllithium, t-butyllithium, etc., boron trichloride, boron tribromide, etc. are added to perform metal exchange between lithium and boron, and a Brønsted base such as N,N-diisopropylethylamine is further added to cause a tandem borofriedel-crafts reaction to obtain the target product. Here too, in the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.

[0309] 3-1-5-2-5. Compound containing structure represented by formula (H8) The compound containing the structure represented by the formula (H8) contains a plurality of, preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 2, and most preferably 1 structure represented by the formula (H8). When a plurality of structures are included, the structures are directly bonded by a single bond or bonded by a specific linking group.

[0310]

Chemical formula

[0311] In formula (H8), Z is "=C(-H)-" or "=N-", and H in the "=C(-H)-" may be substituted with a structure represented by a substituent.

[0312] Examples of the substituent when H in "=C(-H)-" which is Z is substituted include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy, etc.

[0313] Specific examples of the "aryl" which is a substituent include phenyl, tolyl, xylyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, etc., preferably phenyl, biphenylyl, terphenylyl, fluorenyl, etc. Examples of the aryl having a substituent include tolyl, xylyl, 9,9-dimethylfluorenyl, etc. As can be seen from the specific examples, aryl includes both condensed aryl and non-condensed aryl.

[0314] Specific examples of the "heteroaryl" as a substituent 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, naphthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc. Preferably, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl and azadibenzothienyl, etc. can be mentioned. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl or azadibenzothienyl is more preferable.

[0315] The "substituted silyl" as a substituent is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0316] Specific examples of the substituted or unsubstituted trialkylsilyl can include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl can include diphenylmethylsilyl, ditolylmethylsilyl, phenyldimethylsilyl, etc. Specific examples of the substituted or unsubstituted triarylsilyl can include triphenylsilyl and tritolylsilyl, etc.

[0317] The "substituted phosphine oxide group" which is a substituent is preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide, etc.

[0318] Examples of the "substituted carboxy" which is a substituent include benzoyloxy, etc.

[0319] Examples of the linking group that links a plurality of structures represented by formula (H8) include divalent, trivalent, or tetravalent derivatives of the aforementioned aryl or heteroaryl.

[0320] Specific examples of the compound containing the structure represented by formula (H8) are shown below.

Chemical formula

[0321]

Chemical formula

[0322] 3-1-5-2-6. TADF material The high T1 compound may be a TADF material.

[0323] In this specification, the TADF material means a material which is a "thermally activated delayed phosphor". In the "thermally activated delayed phosphor", by reducing the energy difference between the excited singlet state and the excited triplet state, reverse energy transfer from the excited triplet state, where the transition probability is usually low, to the excited singlet state occurs with high efficiency, thereby emitting light from the singlet state (thermally activated delayed fluorescence, TADF). In normal fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal deactivation path, so they cannot be taken out as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, and a highly efficient organic EL element is realized.

[0324] The TADF material is preferably a donor-acceptor type TADF compound (D-A type TADF compound) designed to localize the HOMO and LUMO in the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, so that efficient reverse intersystem crossing occurs.

[0325] Here, in this specification, the "electron-donating substituent" (donor) means a substituent and a partial structure in which the HOMO orbital is localized in the TADF compound molecule, and the "electron-accepting substituent" (acceptor) means a substituent and a partial structure in which the LUMO orbital is localized in the TADF compound molecule.

[0326] Generally, TADF compounds using donors or acceptors have a large spin-orbit coupling (SOC) due to their structure, a small exchange interaction between HOMO and LUMO, and a small ΔE ST Therefore, a very fast reverse intersystem crossing rate can be obtained. On the other hand, TADF compounds using donors or acceptors have a large structural relaxation in the excited state (in some molecules, since the stable structures in the ground state and the excited state are different, when the conversion from the ground state to the excited state occurs due to an external stimulus, the structure then changes to the stable structure in the excited state), and give a broad emission spectrum, so there is a possibility of reducing the color purity when used as a light-emitting material.

[0327] 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, and can exhibit 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 both be contained in the same layer or in adjacent layers.

[0328] Examples of TADF materials that can be used for such purposes include compounds represented by the following formula (H7), or compounds having the following formula (H7) as a partial structure.

[0329]

Chemical formula

[0330] In formula (H7), ED is an electron-donating group, Ln is a linking group, EA is an electron-accepting group, and the energy difference (ΔE S1 ) between the lowest excited singlet energy level (E T1 ) and the lowest excited triplet energy level (E ST ) of the compound represented by formula (H7) is 0.2 eV or less (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.

[0331] 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. As ED, for example, sp 3Examples of the nitrogen-containing functional group include, more specifically, groups derived from carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbiscarbazole, biscarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyl diamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenacridine, and diphenyl-dihydrodibenzazasiline. Examples of EA include, for example, sp 2A nitrogen-containing aromatic ring, a CN-substituted aromatic ring, a ring having a ketone, and a cyano group. More specifically, sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, terephthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxantone dioxide, dimethylanthraquinone, anthraquinone, pyridine, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, benzenetricarbonitrile, fluorenedicarbonitrile, pyrazinedicarbonitrile, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetroxide, and tris(dimethylphenyl)borane, etc. Groups derived from the like can be mentioned. As Ln, for example, a single bond and an arylene can be mentioned, and more specifically, phenylene, biphenylene, naphthylene, etc. can be mentioned. Also, in any structure, hydrogen may be substituted with alkyl, cycloalkyl, and aryl. In particular, as a partial structure, it is preferably a compound having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0332] In formula (H7), the linking group Ln functions as a spacer structure that separates the donor-type partial structure and the acceptor-type partial structure.

[0333] The compound represented by formula (H7) may be, more specifically, a compound represented by any one of formula (H7-1), formula (H7-2), and formula (H7-3). [Chemical formula]

[0334] In formula (H7-1), formula (H7-2) and formula (H7-3), M is independently a single bond, -O-, >N-Ar or >C(-Ar)2 respectively, and from the viewpoints of the depth of the HOMO of the partial structure to be formed, the lowest excited singlet energy level and the height of the lowest excited triplet energy level, preferably, it is a single bond, -O- or >N-Ar, J is a linking group corresponding to Ln in formula (H7), and is independently an arylene having 6 to 18 carbon atoms respectively. From the viewpoint of the magnitude of the conjugation oozing from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferable, and more specifically, phenylene, methylphenylene and dimethylphenylene can be mentioned, Q is independently =C(-H)- or =N- respectively, and from the viewpoints of the shallowness of the LUMO of the partial structure to be formed, the lowest excited singlet energy level and the height of the lowest excited triplet energy level, preferably, it is =N-, Ar is independently hydrogen, aryl having 6 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 18 carbon atoms respectively. From the viewpoints of the depth of the HOMO of the partial structure to be formed, the lowest excited singlet energy level and the height of the lowest excited triplet energy level, preferably, it is hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms or cycloalkyl having 6 to 10 carbon atoms, more preferably, it is hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazolyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazole or phenylbenzimidazole, and even more preferably, it is hydrogen, phenyl or carbazolyl, m is 1 or 2, n is an integer from 2 to (6 - m), and from the viewpoint of steric hindrance, preferably, it is an integer from 4 to (6 - m).

[0335] Also, at least one hydrogen in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0336] Examples of the compound represented by formula (H7) include, for example, the compounds represented by the following structures. In the structural formula, * indicates the bonding position, "Me" represents methyl, and "tBu" represents t-butyl.

[0337]

Chemical formula

[0338]

Chemical formula

[0339]

Chemical formula

[0340]

Chemical formula

[0341]

Chemical formula

[0342]

Chemical formula

[0343]

Chemical formula

[0344]

Chemical formula

[0345] [Chemistry]

[0346] [Chemistry]

[0347] As the compound represented by formula (H7), among the above specific compounds, PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, ACRD SO2, DTC-DBT, DTAO, 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz are preferable.

[0348] 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.

[0349] "Thermally activated delayed phosphor" means a compound that can absorb thermal energy, cause reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, undergo radiative deactivation from the lowest excited singlet state, and emit delayed fluorescence. However, "thermally activated delayed fluorescence" also includes passing through higher-order triplets during the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, papers by Monkman et al. of Durham University (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038 / ncomms 13680), papers by Hosokai et al. of the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci.Adv. 2017; 3:e1603282), papers by Sato et al. of Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-05007-7), as well as conference presentations by Sato et al. of Kyoto University (The 98th Spring Meeting of the Chemical Society of Japan, Presentation Number: 2I4-15, Mechanism of High-Efficiency Luminescence in Organic Electroluminescence Using DABNA as a Luminescent Molecule, Graduate School of Engineering, Kyoto University), reviews by Bui et al. (DOI:10.3762 / bjoc.14.18), reviews by Duan et al. (DOI:10.1063 / 1.5143501), reviews by Ding et al. (DOI:10.1088 / 1674-4926 / 42 / 5 / 050201), and reviews by Xie et al. (DOI:10.1002 / adom.202002204), etc. can be cited. In the present invention, for a sample containing the target compound, when the fluorescence lifetime is measured at 300K and a slow fluorescence component is observed, the target compound shall be determined to be a "thermally activated delayed phosphor". Here, the slow fluorescence component refers to a component with a fluorescence lifetime of 0.1 μsec or more. The measurement of the fluorescence lifetime can be carried out, for example, using a fluorescence lifetime measurement device (manufactured by Hamamatsu Photonics, C11367-01).

[0350] 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).

[0351] In the following description, an organic electroluminescent device using a thermally activated delayed phosphor as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device).

[0352] The "host compound" in a TAF device means a compound in which the 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 phosphor as the assisting dopant and the emitting dopant.

[0353] In this embodiment, known compounds can be used as the host compound. For example, compounds having at least one of a carbazole ring and a furan ring can be mentioned. Among them, it is preferable to use a compound in which at least one of furanyl and carbazolyl is bonded to at least one of arylene and heteroarylene. Specific examples include mCP, mCBP, and the like.

[0354] 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 the assisting dopant having the highest lowest excited triplet energy level in the light-emitting layer from the viewpoint of promoting the generation of TADF in the light-emitting layer without inhibiting it. Specifically, the lowest excited triplet energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or more higher than E(2,T,Sh) and E(3,T,Sh), more preferably 0.03 eV or more higher, and even more preferably 0.1 eV or more higher. Also, a compound having TADF activity may be used as the host compound.

[0355] The thermally activated delayed phosphor (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally activated delayed phosphor (D-A type TADF compound) designed to localize the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) within the molecule by using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, so that efficient reverse intersystem crossing occurs.

[0356] Here, in this specification, the "electron-donating substituent" (donor) means a substituent and partial structure in which the HOMO orbital is localized in the thermally activated delayed phosphor molecule, and the "electron-accepting substituent" (acceptor) means a substituent and partial structure in which the LUMO orbital is localized in the thermally activated delayed phosphor molecule.

[0357] Generally, a thermally activated delayed phosphor using a donor or acceptor has a large spin-orbit coupling (SOC: Spin Orbit Coupling) due to its structure. At the same time, the exchange interaction between the HOMO and LUMO is small, and ΔE S1T1 is small, so a very fast reverse intersystem crossing rate can be obtained. On the other hand, a thermally activated delayed phosphor using a donor or acceptor has a large structural relaxation in the excited state (in some molecules, since the stable structures are different in the ground state and the excited state, when the conversion from the ground state to the excited state occurs due to an external stimulus, the structure then changes to the stable structure in the excited state), and provides a broad emission spectrum, so there is a possibility of reducing the color purity when used as a luminescent material.

[0358] 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 the electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of the donor structure include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarba zole, bicarba zole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyl diamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydroindenacridine, and diphenyldihydrodibenzazasiline, etc.Examples of acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethane), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, terephthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxantonedioxide, dimethylanthraquinone, anthraquinone, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorenedicarbonitrile, triphenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxantenedioxide, thianthrene tetraoxide and tris(dimethylphenyl)borane. In particular, a compound having thermally activated delayed fluorescence in a TAF element preferably has at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone as a partial structure.

[0359] The compound used as an assisting dopant in the light-emitting layer of a TAF element is preferably a thermally activated delayed phosphor, and its emission spectrum preferably overlaps at least partially with the absorption peak of the emitting dopant.

[0360] 3-1-5-4. Phosphorescent material (assisting dopant) In the light-emitting layer, a phosphorescent material may be used as an assisting dopant. The phosphorescent material obtains light emission from the triplet state by using the intramolecular spin-orbit interaction (heavy atom effect) by metal atoms. As such a phosphorescent material, for example, a luminescent metal complex can be used. Examples of the luminescent metal complex include compounds represented by the following formula (B-1) and the following formula (B-2).

[0361] [Chemical Formula]

[0362] 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 from 1 to 3, and "X-Y" are each independently a bidentate ligand. In formula (B-2), M is at least one selected from the group consisting of Pt, Re, and Cu, and "W-X-Y-Z" is a tetradentate ligand. In formula (B-1), from the viewpoints of efficiency and lifetime, M is preferably Ir and n is preferably 3. In formula (B-2), from the viewpoints of efficiency and lifetime, M is preferably Pt.

[0363] The ligand (X-Y) in formula (B-1) has at least one ligand selected from the group consisting of the following. The ligand (W-X-Y-Z) in formula (B-2) has at least one ligand selected from the group consisting of the following as a part.

[0364] [Chemical Formula]

[0365] In the formula --- binds to the central metal M Y are each independently BR e , NR e , PR e, O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f , or GeR e R f and each aromatic carbon C-H in the ring may independently be substituted with N, R e and R f may optionally condense or bond to form a ring, R a R b R c , and R d may each independently be unsubstituted or substituted up to the maximum number of substituents possible, 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, provided that any two adjacent substituents in R a R b R c , and R d may condense or bond to form a ring or form a polydentate ligand.

[0366] Examples of the compound represented by the formula (B-1) include, for example, 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), 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.

[0367] Other examples of the compound represented by the formula (B-1) include, for example, the following compounds.

Chemical formula

[0368]

Chemical formula

[0369]

Chemical formula

[0370] Alternatively, iridium complexes described in JP-A Nos. 2006-089398, 2006-080419, 2005-298483, 2005-097263, and 2004-111379, U.S. Patent Application Publication No. 2019 / 0051845, etc., or platinum complexes described in Advanced Materials, 26:7116-7121, NPG Asia Materials 13, 53(2021), Applied Physics Letters, 117, 253301 (2020), Light-Emitting Diode - An Outlook On the Empirical Features and Its Recent Technological Advancements, Chapter 5 may be used.

[0371] 3-1-6. Electron injection layer and electron transport layer in organic electroluminescent device The electron injection layer (107) serves to efficiently inject electrons moving from the negative electrode (108) into the light-emitting layer (105) or the electron transport layer (106). The electron transport layer (106) serves to efficiently transport electrons injected from the negative electrode (108) or electrons injected from the negative electrode (108) through 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 kinds of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0372] The electron injection / transport layer is a layer responsible for injecting electrons into the negative electrode and transporting electrons. It preferably has a high electron injection efficiency and can efficiently transport the injected electrons. For this purpose, it is preferably a substance with a large electron affinity, a large electron mobility, excellent stability, and is less likely to generate trap impurities during manufacturing and use. However, when considering the transport balance of holes and electrons, if it mainly plays a role in efficiently preventing holes from recombining at the positive electrode and flowing to the negative electrode side, even if the electron transport ability is not so high, the effect of improving the light emission efficiency is equivalent to that of a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

[0373] As the material (electron transport material) for forming the electron transport layer (106) or the electron injection layer (107), it can be arbitrarily selected and used from compounds that have been conventionally used as electron transfer compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0374] As a material used for an electron transport layer or an electron injection layer, it preferably contains at least one selected from compounds composed of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylethenyl)biphenyl, ferinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, aryl nitrile derivatives, and indole derivatives can be mentioned. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with other materials.

[0375] In addition, as specific examples of other electron transfer compounds, pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, ferinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, ferrylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirofluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6',2''-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc. can be mentioned.

[0376] Moreover, metal complexes having electron-accepting nitrogen can also be used, for example, quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes, etc. can be mentioned.

[0377] The above-mentioned materials can be used alone or in combination with other materials. Among the aforementioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0378] <Borane derivative> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and specifically, it is disclosed in JP-A-2007-27587.

Chemical formula

[0379] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, a heterocyclic compound having a nitrogen atom which may be substituted, or cyano, and R 13 ~R 16 are each independently alkyl which may be substituted, cycloalkyl which may be substituted, or aryl which may be substituted, X is arylene which may be substituted, Y is aryl having 16 or less carbon atoms which may be substituted, boryl which is substituted, or carbazolyl which may be substituted, and n is each independently an integer of 0 to 3. Further, examples of the substituent in the case of "which may be substituted" or "which is substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0380] Among the compounds represented by formula (ETM-1), the compounds represented by the following formula (ETM-1-1) and the compounds represented by the following formula (ETM-1-2) are preferred.

Chemical formula

[0381] In formula (ETM-1-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, a heterocyclic compound having a nitrogen atom which may be substituted, or cyano, and R 13 ~R 16 are each independently alkyl which may be substituted, cycloalkyl which may be substituted, or aryl which may be substituted, and R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, a heterocyclic compound having a nitrogen atom which may be substituted, or cyano, X 1 is an arylene having 20 or less carbon atoms which may be substituted, n is an integer of 0 to 3 respectively independently, and m is an integer of 0 to 4 respectively independently. Further, examples of the substituent in the case of "which may be substituted" or "which is substituted" include aryl, heteroaryl, alkyl or cycloalkyl, etc.

[0382]

Chemical formula

[0383] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, a heterocyclic compound having a nitrogen atom which may be substituted, or cyano, and R 13 ~R 16 are each independently alkyl which may be substituted, cycloalkyl which may be substituted, or aryl which may be substituted, and X 1is an arylene having 20 or fewer carbon atoms which may be substituted, and n is an integer of 0 to 3, each independently. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl, and the like.

[0384] X 1 Specific examples of X include a divalent group represented by any one of the following formulas (X-1) to (X-9).

[0385]

Chemical formula

[0386] (In each formula, R a is independently alkyl, cycloalkyl, or phenyl which may be substituted, and * indicates the bonding position.) Specific examples of this borane derivative include, for example, the following compounds.

Chemical formula

[0387] This borane derivative can be produced using known raw materials and known synthesis methods.

[0388] <Pyridine derivative> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

Chemical formula

[0389] 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.

[0390] 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).

[0391] 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.

[0392] In each formula, the "pyridine-based substituent" is any one of the following formulas (Py-1) to (Py-15) (the * in the formula indicates the bonding position), and the pyridine-based substituents may each independently be 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, or t-butyl, etc., and methyl is preferred. Further, the pyridine-based substituent may be bonded to φ, anthracene ring, or fluorene ring in each formula via phenylene or naphthylene.

[0393]

Chemical formula

[0394] The pyridine-based substituent is any one of the formulas (Py-1) to (Py-15) (the * in the formula indicates the bonding position), and among these, it is preferably any one of the following formulas (Py-21) to (Py-44).

[0395]

Chemical formula

[0396] At least one hydrogen in each pyridine derivative may be substituted with deuterium, and one of the two "pyridine-based substituents" in Formula (ETM-2-1) and Formula (ETM-2-2) may be substituted with aryl.

[0397] R 11 ~R 18 The "alkyl" in can be either straight-chain or branched-chain, for example, straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms can be mentioned. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms). Even more preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms).

[0398] 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-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, etc.

[0399] For the alkyl having 1 to 4 carbon atoms substituted with a pyridine-based substituent, the description of the above alkyl can be cited.

[0400] R 11 ~R 18 Examples of the "cycloalkyl" in R~R include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms.

[0401] Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, and the like.

[0402] R 11 ~R 18 Examples of the "aryl" in R~R include preferred aryls having 6 to 30 carbon atoms, more preferred aryls having 6 to 18 carbon atoms, even more preferred aryls having 6 to 14 carbon atoms, and particularly preferred aryls having 6 to 12 carbon atoms.

[0403] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl which is a monocyclic aryl, (1-,2-)naphthyl which is a condensed bicyclic aryl, acenaphthylen-(1-,3-,4-,5-)yl which is a condensed tricyclic aryl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, triphenylene-(1-,2-)yl which is a condensed tetracyclic aryl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, perylene-(1-,2-,3-)yl which is a condensed pentacyclic aryl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0404] Preferred "aryl having 6 to 30 carbon atoms" includes phenyl, naphthyl, phenanthryl, chrysenyl, triphenylenyl, etc., more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

[0405] R in formula (ETM-2-2) 11 and R 12 may be combined to form a ring. As a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0406] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0407] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0408] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and specifically, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0409] In formula (ETM-3), X12 to X21 represent hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl, cycloalkyl, etc.

[0410] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0411] <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]

[0412] 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.

[0413] 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.

[0414] Also, at least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.

[0415] Regarding the description of the substituents and the form of ring formation in formula (ETM-4), the description of the polycyclic aromatic compound consisting of the partial structure represented by formula (1) can be cited.

[0416] Specific examples of this BO-based derivative include, for example, the following compounds.

Chemical formula

[0417] This BO-based derivative can be produced using known raw materials and known synthesis methods.

[0418] <Benzofluorene derivative> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Chemical formula

[0419] Ar 1 is each independently an aryl having 6 to 20 carbon atoms, and the description such as "aryl having 6 to 20 carbon atoms" in Ar of formula (ETM-5) 2 can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, ferrenyl, etc.

[0420] Ar 2 is 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.

[0421] Ar 2 As the "alkyl" in Ar, it 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. Preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (a branched-chain alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (a branched-chain alkyl having 3 to 12 carbon atoms). Even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (a branched-chain alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (a branched-chain 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.

[0422] Ar 2 As the "cycloalkyl" in Ar, examples thereof include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, and the like.

[0423] Ar 2 As the "aryl" in Ar, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, even more preferably aryl having 6 to 14 carbon atoms, and particularly preferably aryl having 6 to 12 carbon atoms.

[0424] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl, and the like.

[0425] Two Ars 2 may be bonded to form a ring. As a result, a cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0426] Specific examples of this benzofluorene derivative include, for example, the following compounds.

Chemical formula

[0427] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0428] <Phosphine oxide derivative> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013 / 079217 and International Publication No. 2013 / 079678.

Chemical formula

[0429] 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, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms or an 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 from 0 to 4, and q is an integer from 1 to 3.

[0430] Here, examples of the substituent in the case of being substituted include aryl, heteroaryl, alkyl, cycloalkyl, etc.

[0431] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [Chemical formula]

[0432] 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), arylthioether (arylthioether group), aryl, heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a condensed ring formed between adjacent substituents.

[0433] Ar 1 may be the same or different and is arylene or heteroarylene. Ar 2 may be the same or different and is aryl or heteroaryl. However, Ar 1and Ar 2 At least one of them has a substituent or forms a condensed ring with an adjacent substituent. n is an integer from 0 to 3. When n is 0, there is no unsaturated structure portion. When n is 3, R 1 does not exist.

[0434] Among these substituents, alkyl refers to, for example, saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, etc. This may be unsubstituted or substituted. There are no particular restrictions on the substituents when it is substituted. For example, alkyl, aryl, heterocyclic groups, etc. can be mentioned. Such points are also common in the following descriptions. Also, the number of carbon atoms in the alkyl is not particularly limited, but usually ranges from 1 to 20 from the viewpoints of availability and cost.

[0435] Also, cycloalkyl refers to, for example, saturated alicyclic hydrocarbon groups such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc. This may be unsubstituted or substituted. The number of carbon atoms in the alkyl portion is not particularly limited, but usually ranges from 3 to 20.

[0436] Also, aralkyl refers to, for example, aromatic hydrocarbon groups via aliphatic hydrocarbons such as benzyl, phenylethyl, etc. Both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but usually ranges from 1 to 20.

[0437] Also, alkenyl refers to, for example, unsaturated aliphatic hydrocarbon groups containing a double bond such as vinyl, allyl, butadienyl, etc. This may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but usually ranges from 2 to 20.

[0438] Also, cycloalkenyl refers to, for example, unsaturated alicyclic hydrocarbon groups containing a double bond such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc. This may be unsubstituted or substituted.

[0439] Also, alkynyl refers to, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as ethynyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually in the range of 2 to 20.

[0440] Also, alkoxy refers to, for example, 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.

[0441] Also, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is substituted by a sulfur atom. Also, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is substituted by a sulfur atom. Also, aryl ether refers to, for example, 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. Also, arylthioether is a group in which the oxygen atom of the ether bond of aryl ether is substituted by a sulfur atom.

[0442] Also, aryl refers to, for example, aromatic hydrocarbon groups such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, pyrenyl, etc. The aryl may be unsubstituted or substituted. The number of carbon atoms in the aryl is not particularly limited, but is usually in the range of 6 to 40.

[0443] Also, heterocyclic group refers to, for example, a cyclic structural group having an atom 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. Halogen refers to fluorine, chlorine, bromine, and iodine.

[0444] The aldehyde, carbonyl, and amino groups can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, etc. In addition, the aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, and heterocycle may be unsubstituted or substituted. Silyl refers to, for example, a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in silyl is not particularly limited, but is usually in the range of 3 to 20. Also, the number of silicon atoms is usually 1 to 6.

[0445] The condensed 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 etc. is a conjugated or non-conjugated condensed ring formed therebetween. Here, when n is 1, two R 1 may form a conjugated or non-conjugated condensed ring with each other. These condensed rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure and may be further condensed with other rings.

[0446] Specific examples of this phosphine oxide derivative include, for example, the following compounds.

Chemical formula

[0447] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0448] <Pyrimidine derivative> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011 / 021689.

Chemical formula

[0449] Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 2 or 3.

[0450] Examples of the "aryl" in the "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 still more preferably aryl having 6 to 12 carbon atoms.

[0451] 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), acenaphthylen-(1-, 3-, 4-, 5-) yl, fluorene-(1-, 2-, 3-, 4-, 9-) yl, phenalen-(1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl which are fused tricyclic aryls, quarterphenyl which is a tetracyclic aryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quarterphenyl), triphenylene-(1-, 2-) yl, pyrene-(1-, 2-, 4-) yl, naphthacene-(1-, 2-, 5-) yl which are fused tetracyclic aryls, perylene-(1-, 2-, 3-) yl, pentacene-(1-, 2-, 5-, 6-) yl which are fused pentacyclic aryls, and the like.

[0452] Examples of "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. Further, examples of heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

[0453] Specific heteroaryl groups include, for example, 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, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, and the like.

[0454] Also, the aryl and heteroaryl groups may be substituted, for example, each may be substituted with the aryl or heteroaryl group.

[0455] Specific examples of this pyrimidine derivative include, for example, the following compounds.

Chemical formula

[0456] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0457] <Aryl nitrile derivative> The aryl nitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of them are bonded by a single bond or the like. Details are described in U.S. Patent Application Publication No. 2014 / 0197386.

Chemical formula

[0458] Ar niFrom the perspective of fast electron transport property, it is preferably a high-carbon number, and from the perspective of high T1, it is preferably a low-carbon number. Ar ni Specifically, for use in the layer adjacent to the light-emitting layer, it is preferably a high T1, an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 14 carbon atoms, more preferably an aryl having 6 to 10 carbon atoms. Also, from the perspective of high T1, the substitution number n of the nitrile group is preferably large, and from the perspective of high S1, it is preferably small. Specifically, the substitution number n of the nitrile group is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

[0459] Ar is each independently an optionally substituted aryl or an optionally substituted heteroaryl. From the perspectives of high S1 and high T1, it is preferably a donor heteroaryl. Since it is used as an electron transport layer, it is preferably a donor heteroaryl with a small number. From the perspective of charge transport property, an aryl or heteroaryl with a large carbon number is preferred, and it is preferred to have many substituents. Specifically, the substitution number m of Ar is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 1 to 2.

[0460] Examples of the "aryl" in the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0461] Specific "aryl" includes phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, terphenyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) which is a tricyclic aryl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, quaterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl) which is a tetracyclic aryl, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryls, etc. can be mentioned.

[0462] 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, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Also, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0463] Specific heteroaryls include, for example, 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, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, etc.

[0464] Also, the aryl and heteroaryl may be substituted, and each may be substituted with, for example, the aryl or heteroaryl.

[0465] The aryl nitrile derivative may be a multimer in which the compound represented by formula (ETM-9) is bonded by a plurality of single bonds or the like. In this case, in addition to the single bond, it may be bonded by an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring).

[0466] Specific examples of this aryl nitrile derivative include, for example, the following compounds.

Chemical formula

[0467] This aryl nitrile derivative can be produced using known raw materials and known synthetic methods.

[0468] <Triazine derivative> 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 US Patent Application Publication No. 2011 / 0156013. [Chemical formula]

[0469] Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer from 1 to 3, preferably 2 or 3.

[0470] Examples of the "aryl" in the "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.

[0471] Specific "aryl" includes phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, terphenyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) which is a tricyclic aryl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, quarterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quarterphenyl) which is a tetracyclic aryl, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl etc. which are condensed pentacyclic aryls.

[0472] 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. Further, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

[0473] Specific heteroaryls include, for example, 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, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, etc.

[0474] In addition, the aryl and heteroaryl may be substituted, for example, each may be substituted with the aryl or heteroaryl.

[0475] Specific examples of this triazine derivative include, for example, the following compounds.

Chemical formula

[0476] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0477] <Benzimidazole derivative>< The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

Chemical formula

[0478] 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 from 1 to 4, and the "benzimidazole-based substituent" is such that the pyridyl in the "pyridine-based substituent" in Formula (ETM-2), Formula (ETM-2-1) and Formula (ETM-2-2) is replaced by the following benzimidazolyl (where * indicates the bonding position), and at least one hydrogen in the benzimidazole derivative may be replaced by deuterium.

[0479]

Chemical formula

[0480] R in the said 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 the description of R 11 in Formula (ETM-2-1) and Formula (ETM-2-2) can be cited.

[0481] φ is preferably also an anthracene ring or a fluorene ring, and in this case the structure can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2), and R 11 ~R 18 in each formula can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2). Also, in Formula (ETM-2-1) or Formula (ETM-2-2), although the two pyridine-based substituents are described in a bonded form, when substituting these with benzimidazole-based substituents, both pyridine-based substituents may be replaced by benzimidazole-based substituents (i.e., n = 2), or either one of the pyridine-based substituents may be replaced by a benzimidazole-based substituent and the other pyridine-based substituent may be replaced by R 11 ~R 18 (i.e., n = 1). Also, for example, R 11 ~R 18At least one of which is substituted with a benzimidazole-based substituent, and the "pyridine-based substituent" is replaced with R 11 ~R 18 may be replaced.

[0482] Specific examples of this benzimidazole derivative include, for example, 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, 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.

[0483]

Chemical formula

[0484] This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0485] <Phenanthroline derivative> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006 / 021982.

Chemical formula

[0486] 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 from 1 to 4.

[0487] 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). Also, in formula (ETM-12-1), one of R 11 ~R 18 is a bond to φ which is an aryl ring.

[0488] At least one hydrogen in each phenanthroline derivative may be substituted with deuterium.

[0489] R 11 ~R 18 For the alkyl, cycloalkyl and aryl in R 11 ~R 18 in formula (ETM-2), the description can be cited. Also, in addition to the above examples, φ can be, for example, the following structural formulas. Also, R in the following structural formulas are each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl, and * indicates the bonding position.

[0490]

Chemical formula

[0491] Specific examples of this phenanthroline derivative include, for example, 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), bathocuproin, 1,3-bis(2-phenyl-1,10-phenanthrolin-9-yl)benzene, and compounds represented by the following structural formula, etc.

[0492]

Chem.

[0493] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0494] <Quinolinol-based metal complex> The quinolinol-based metal complex is, for example, a compound represented by the following formula (ETM-13).

Chem.

[0495] In the formula, R 1 ~R 6 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 from 1 to 3.

[0496] Specific examples of the quinolinol-based metal complex include lithium 8-quinolinolate, 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)(phenolato)aluminum, bis(2-methyl-8-quinolinolato)(2-methylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3-methylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(4-methylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,3-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,4-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-di-t-butylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6-diphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-trimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,5,6-tetramethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinolato)(2-naphtholato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(2-phenylphenolato)aluminum, bis(2,Aluminum (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)-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, Aluminum bis(2,4-dimethyl-8-quinolinolate)-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, Aluminum bis(2-methyl-4-ethyl-8-quinolinolate)-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, Aluminum bis(2-methyl-4-methoxy-8-quinolinolate)-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, Aluminum bis(2-methyl-5-cyano-8-quinolinolate)-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, Aluminum bis(2-methyl-5-trifluoromethyl-8-quinolinolate)-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, Beryllium bis(10-hydroxybenzo[h]quinoline), etc. can be mentioned.,

[0497] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.,

[0498] <Thiazole Derivatives and Benzothiazole Derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

Chemical Formula

[0499] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).

Chemistry

[0500] Each 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 from 1 to 4, and the "thiazole-based substituent" and "benzothiazole-based substituent" are such that the pyridyl in the "pyridine-based substituent" in Formula (ETM-2), Formula (ETM-2-1) and Formula (ETM-2-2) is substituted by the following thiazolyl or benzothiazolyl (* indicates the bonding position), and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be substituted by deuterium.

[0501]

Chemistry

[0502] φ is preferably also an anthracene ring or a fluorene ring. In this case, the structure can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2), and R 11 ~R 18 in each formula can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2). Also, in Formula (ETM-2-1) or Formula (ETM-2-2), although the two pyridine-based substituents are described in a bonded form, when substituting these with thiazole-based substituents (or benzothiazole-based substituents), both pyridine-based substituents may be substituted with thiazole-based substituents (or benzothiazole-based substituents) (i.e., n = 2), or either one of the pyridine-based substituents may be substituted with a thiazole-based substituent (or benzothiazole-based substituent), and the other pyridine-based substituent may be substituted with R 11 ~R 18 (i.e., n = 1). Also, for example, R 11 ~R 18At least one of them is substituted with a thiazole-based substituent (or a benzothiazole-based substituent), and the "pyridine-based substituent" is R 11 ~R 18 may be substituted.

[0503] These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0504] <Sylol derivative> The sylol derivative is, for example, a compound represented by the following formula (ETM-15). Details are described in JP-A-9-194487.

Chemical formula

[0505] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, and these may be substituted. For details of these groups, the descriptions in formula (1) and formula (ETM-7-2) can be further cited. Also, alkenyloxy and alkynyloxy are groups in which the alkyl part in alkoxy is substituted with alkenyl or alkynyl, and for details of these alkenyl and alkynyl, the description in formula (ETM-7-2) can be cited.

[0506] Also, X and Y, both of which are alkyl, may combine to form a ring.

[0507] R 1 ~R 4is, independently of each other, 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 condensed ring with an adjacent substituent.

[0508] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the description in formula (1) can be cited.

[0509] R 1 ~R 4 For details of alkyl, aryl and alkoxy in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in, the description in formula (1) can also be cited.

[0510] Examples of silyl include a silyl group and a group in which at least one of the three hydrogens of the silyl group is independently substituted with aryl, alkyl or cycloalkyl, and trisubstituted silyl is preferred, and examples thereof include triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl and alkyldicycloalkylsilyl. For details of aryl, alkyl and cycloalkyl in these, the description in formula (1) can be cited.

[0511] The condensed ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 and the like, which are conjugated or non-conjugated condensed rings. These condensed rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure and may further condense with other rings.

[0512] However, preferably, when R 1 and R 4 are phenyl, X and Y are not alkyl or phenyl. Also, preferably, when R 1 and R 4 are thienyl, X and Y are not alkyl. R 2 and R 3 are not simultaneously alkyl, aryl, alkenyl, or cycloalkyl in which R 2 and R 3 are bonded to form a ring. Also, preferably, when R 1 and R 4 are silyl groups, R 2 , R 3 , X, and Y are each independently not hydrogen or alkyl having 1 to 6 carbon atoms. Also, preferably, when R 1 and R 2 have a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0513] These silole derivatives can be produced using known raw materials and known synthetic methods.

[0514] <Azoline derivative> The azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in International Publication No. 2017 / 014226.

Chemical formula

[0515] 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 heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen in φ may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms or a heteroaryl having 2 to 18 carbon atoms. Y is 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 in 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, R 1 ~R 5 are each independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and R 1 ~R 5 any one of which is a site that binds to L. L is 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).

[0516]

Chemical formula

[0517] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N-, and at least two of X 1 ~X 6 are =CR 6 -, and R in two of =CR 1 ~X 6 in the two =CR 6 - is a site that binds to φ or an azoline ring, and R in the other =CR 6 - is hydrogen, 6 and R in the other =CR 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N-, and among X 7 ~X 14 at least two are =CR 6 -, and among X 7 ~X 14 the two =CR 6 - at R 6 is a site bonding to a phenyl or an azoline ring, and R 6 at the other =CR 6 is hydrogen, at least one hydrogen in L 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 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms, m is an integer of 1 to 4. 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 in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0518] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2).

Chemical formula

[0519] 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 heterocyclic ring having 2 to 40 carbon atoms. At least one hydrogen in φ may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms or a heteroaryl having 2 to 18 carbon atoms, In formula (ETM-16-1), Y is independently -O-, -S- or >N-Ar, Ar is aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in Ar may be substituted with 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. 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 the same, and R 3 and R 4 are the same. 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 the same, and R 3 and R 4 are the same. In formula (ETM-16-1) and formula (ETM-16-2), L is 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).

[0520]

Chemical formula

[0521] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N-, and at least two of X 1 ~X 6 are =CR 6 -, and among two =CR 1 ~X 6 -, the R 6 in 6is a site that binds to a φ or 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 6 are =CR 7 ~X 14 Among two =CR 6 R in 6 is a site that binds to a φ or azoline ring, and the other =CR 6 R in 6 is hydrogen, At least one hydrogen in L 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 10 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. m is an integer from 1 to 4. When m is from 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0522] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formula (φ1-1) to formula (φ1-18), divalent groups represented by the following formula (φ2-1) to formula (φ2-34), trivalent groups represented by the following formula (φ3-1) to formula (φ3-3), and tetravalent groups represented by the following formula (φ4-1) to formula (φ4-2). At least one hydrogen in φ may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms.

[0523]

Chemical formula

[0524] [Chemistry]

[0525] [Chemistry]

[0526] In the formula, Z is >CR2, >N-Ar, >N-L, -O- or -S-, and R in >CR 2 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 respectively, and R 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 >N-L is L in formula (ETM-16), formula (ETM-16-1) or formula (ETM-16-2). * in the formula indicates the bonding position.

[0527] Preferably, L is a divalent group of a ring 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 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.

[0528] 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 in 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.

[0529] Preferably, R1 ~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 the same, R 3 and R 4 are the same, and also, all of R 1 ~R 4 are not simultaneously hydrogen, and m is 1 or 2. When m is 2, the group formed by the azoline ring and L is the same.

[0530] Specific examples of the azoline derivative include, for example, the following compounds. Also, "Me" in the structural formula indicates methyl.

[0531]

Chemical formula

[0532] More preferably, φ is selected from the group consisting of divalent groups represented by the following formula (φ2-1), formula (φ2-31), formula (φ2-32), formula (φ2-33), and formula (φ2-34), and at least one hydrogen in φ may be substituted with aryl having 6 to 18 carbon atoms. Also, in the following formula, * indicates the bonding position.

[0533]

Chemical formula

[0534] L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen 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 14 carbon atoms, In >N-Ar as Y, Ar is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of said Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, or an aryl having 6 to 10 carbon atoms. R 1 ~R 4 are each independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are the same, R 3 and R 4 are the same, and also, R 1 ~R 4 do not all simultaneously become hydrogen, and m is 2, and the group formed by the azoline ring and L is the same.

[0535] As other specific examples of the azoline derivative, for example, the following compounds can be mentioned. Also, "Me" in the structural formula indicates methyl.

[0536]

Chemical formula

[0537] Regarding the details of the alkyl, cycloalkyl, aryl, or heteroaryl in the above formulas that define this azoline derivative, the description in formula (1) can be cited. This azoline derivative can be produced using known raw materials and known synthesis methods.

[0538] <Reducing substance> 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. As long as the reducing substance has a certain reducibility, various substances can be used. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be preferably used.

[0539] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 - 2.5 eV), or Ba (2.52 eV). Substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb, or Cs, even more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, an improvement in the emission luminance and an extension of the lifespan of the organic EL element are expected. Also, as reducing substances with a work function of 2.9 eV or less, combinations of two or more of these alkali metals are also preferred, particularly combinations containing Cs, such as combinations of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K. By containing Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or the electron injection layer, an improvement in the emission luminance and an extension of the lifespan of the organic EL element are expected.

[0540] The aforementioned materials for the electron injection layer and the electron transport layer can also be used as materials for the electron layer in the form of a polymer compound obtained by polymerizing a reactive compound having a reactive substituent substituted thereon as a monomer, or a polymer crosslinked body thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a pendant polymer crosslinked body thereof. As the reactive substituent in this case, the description in the polycyclic aromatic compound containing the partial structure represented by the formula (1) can be cited.

[0541] Details of the uses of such polymer compounds and polymer crosslinked bodies will be described later.

[0542] 3-1-7. Cathode in organic electroluminescent device The negative electrode (108) serves to inject electrons into the light-emitting layer (105) via the electron injection layer (107) and the electron transport layer (106).

[0543] The material for forming the negative electrode (108) is not particularly limited as long as it is a substance capable of efficiently injecting electrons into the organic layer, and the same material as that for forming the positive electrode (102) can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (such as magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.) are preferable. In order to improve the electron injection efficiency and device characteristics, an alloy containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals is effective. However, these low work function metals are generally unstable in the air in many cases. In order to improve such a point, for example, a method of doping a trace amount of lithium, cesium, or magnesium into the organic layer and using a highly stable electrode is known. Other dopants can also be inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, it is not limited thereto.

[0544] Also, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, etc. can be laminated as preferable examples. The manufacturing methods of these electrodes are not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0545] 3-1-8. Binder that may be used in each layer The materials used for the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can form each layer independently. However, as a polymer binder, solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, etc., or curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. can also be dispersed and used.

[0546] 3-1-9. Method for manufacturing organic electroluminescent device Each layer constituting the organic EL element can be formed by making a thin film of the material to constitute each layer by methods such as evaporation method, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination method, printing method, spin coating method, casting method, coating method, etc. There is no particular limitation on the film thickness of each layer thus formed, and it can be appropriately set according to 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 crystal oscillator type film thickness measuring device, etc. When thinning by using the evaporation method, the evaporation conditions vary depending on the type of material, the intended crystal structure and associative structure of the film, etc. The evaporation conditions are generally boat heating temperature +50 to +400 °C, vacuum degree 10 -6 ~10 -3Pa, it is preferably appropriately set within the range of a vapor deposition rate of 0.01 to 50 nm / second, a substrate temperature of -150 to +300 °C, and a film thickness of 2 nm to 5 μm.

[0547] When applying a DC voltage to the organic EL element thus obtained, it may be applied with the anode as + and the cathode as - polarities. When applying a voltage of about 2 to 40 V, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, and both sides). Also, this organic EL element emits light when applying a pulsed current or an alternating current. Also, the waveform of the applied alternating current may be arbitrary.

[0548] Next, as an example of a method for manufacturing an organic EL element, a method for manufacturing an organic EL element composed of an anode / hole injection layer / hole transport layer / light-emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described.

[0549] <Vapor deposition method> After forming a thin film of the anode material on a suitable substrate by vapor deposition or the like to fabricate the anode, thin films of the hole injection layer and the hole transport layer are formed on this anode. On this, a host material and a dopant material are co-evaporated to form a thin film as the light-emitting layer, an electron transport layer and an electron injection layer are formed on this light-emitting layer, and a thin film made of a cathode material is formed by vapor deposition or the like to serve as the cathode, whereby a desired organic EL element is obtained. Also, in the fabrication of the above-described organic EL element, it is also possible to reverse the fabrication order and fabricate in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0550] <Wet film formation method> The wet film formation method is carried out by preparing a low molecular compound capable of forming each organic layer of the organic EL element as a liquid composition for forming an organic layer and using this. When there is no suitable organic solvent for dissolving this low molecular compound, an organic layer forming composition may be prepared from a reactive compound in which a reactive substituent is substituted for the low molecular compound, together with other monomers or main chain type polymers having a solubility function, such as a polymer compound polymerized therewith.

[0551] The wet film-forming method generally forms a coating film through a coating step of applying a composition for forming an organic layer on a substrate and a drying step of removing a solvent from the applied composition for forming an organic layer. When the polymer compound has a crosslinkable substituent (this is also referred to as a crosslinkable polymer compound), further crosslinking occurs during this drying step to form a polymer crosslinked body. Depending on the difference in the coating step, the method using a spin coater is called the spin coating method, the method using a slit coater is called the slit coating method, the method using a plate is called gravure, offset, reverse offset, flexographic printing method, the method using an inkjet printer is called the inkjet method, and the method of spraying in a mist is called the spray method.

[0552] For the drying step, there are methods such as air drying, heating, and vacuum drying. The drying step may be performed only once, or it may be performed multiple times using other methods and conditions. Also, for example, other methods may be used in combination, such as firing under reduced pressure.

[0553] The wet film-forming method is a film-forming method using a solution, such as some printing methods (inkjet method), spin coating method, casting method, coating method, etc. Different from the vacuum evaporation method, the wet film-forming method does not require the use of an expensive vacuum evaporation apparatus and can form a film under atmospheric pressure. Furthermore, since the wet film-forming method enables large-area formation and continuous production, it leads to a reduction in manufacturing costs.

[0554] On the other hand, when compared with the vacuum evaporation method, the wet film-forming method may be difficult to laminate. When producing a laminated film using the wet film-forming method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that do not dissolve in each other) are used extensively. However, even when using these techniques, it may be difficult to use the wet film-forming method for coating all films.

[0555] Therefore, generally, a method is adopted in which the wet film-forming method is used for only some layers, and the remaining layers are formed by the vacuum evaporation method to fabricate an organic EL element.

[0556] For example, the procedure for manufacturing an organic EL element by partially applying a wet film-forming method is shown below.

[0557] (Step 1) Film formation by vacuum evaporation method for the positive electrode (Step 2) Film formation by wet film-forming method of a composition for forming a hole injection layer containing a hole injection layer material (Step 3) Film formation by wet film-forming method of a composition for forming a hole transport layer containing a hole transport layer material (Step 4) Film formation by wet film-forming method of a composition for forming a light-emitting layer containing a host material and a dopant material (Step 5) Film formation by vacuum evaporation method for the electron transport layer (Step 6) Film formation by vacuum evaporation method for the electron injection layer (Step 7) Film formation by vacuum evaporation method for the negative electrode By going through this procedure, an organic EL element composed of a positive electrode / hole injection layer / hole transport layer / light-emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / negative electrode can be obtained.

[0558] Of course, for the electron transport layer and the electron injection layer as well, a layer-forming composition containing an electron transport layer material and an electron injection layer material respectively may be used for film formation by the wet film-forming method. In that case, it is preferable to use means for preventing dissolution of the lower light-emitting layer, or means for film formation from the negative electrode side in reverse to the above procedure.

[0559] <Other film-forming methods> For film formation of the organic layer-forming composition, laser-induced thermal imaging (LITI) can be used. LITI is a method of heating and evaporating a compound adhered to a substrate with a laser, and an organic layer-forming composition can be used as the material applied to the substrate.

[0560] <Any process> Before and after each step of film formation, appropriate treatment steps, washing steps, and drying steps may be appropriately inserted. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, washing treatment using an appropriate solvent, and heat treatment, etc. Also, a series of steps for manufacturing a bank can be included.

[0561] For the production of the bank, photolithography technology can be used. As bank materials that can be used for photolithography, positive resist materials and negative resist materials can be used. Also, patternable printing methods such as inkjet method, gravure offset printing, reverse offset printing, screen printing, etc. can be used. At this time, permanent resist materials can also be used.

[0562] Examples of materials used for the bank include polysaccharides and their derivatives, homopolymers and copolymers of ethylenic monomers having hydroxyl groups, biopolymer compounds, 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 copolymer polymers (ABS), silicone resins, polyvinyl chlorides, chlorinated polyethylenes, chlorinated polypropylenes, polyacetates, polynorbornenes, synthetic rubbers, fluoropolymers such as polyvinylidene fluoride, polytetrafluoroethylene, polyhexafluoropropylene, copolymer polymers of fluoroolefin-hydrocarbon olefin, and fluorocarbon polymers, but are not limited to only these.

[0563] <Composition for forming an organic layer used in the wet film forming method> The composition for forming an organic layer is obtained by dissolving a low-molecular compound capable of forming each organic layer of an organic EL element or a high-molecular compound obtained by polymerizing the low-molecular compound in an organic solvent. For example, the composition for forming a light-emitting layer contains, as a first component, at least one polycyclic aromatic compound (or its high-molecular compound) which is a dopant material, as a second component, at least one host material, and as a third component, at least one organic solvent. The first component functions as a dopant component of the light-emitting layer obtained from the composition, and the second component functions as a host component of the light-emitting layer. The third component functions as a solvent for dissolving the first and second components in the composition, and during coating, it imparts a smooth and uniform surface shape due to its controlled evaporation rate.

[0564] <Organic solvent> The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, the film-forming property, the presence or absence of defects in the coating film, the surface roughness, and the smoothness can be controlled and improved. Also, during film formation using the inkjet method, the meniscus stability at the pinholes of the inkjet head can be controlled, and the ejection property can be controlled and improved. Furthermore, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical characteristics, light-emitting characteristics, efficiency, and lifetime of the organic EL element having an organic layer obtained from the composition for forming an organic layer can be improved.

[0565] (1) Physical properties of the organic solvent The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of the ejection property of the inkjet. Also, when the boiling point is lower than 300°C, it is preferable from the viewpoints of defects in the coating film, surface roughness, residual solvent, and smoothness. The organic solvent preferably has a configuration containing two or more organic solvents from the viewpoints of good inkjet ejection property, film-forming property, smoothness, and low residual solvent. On the other hand, in some cases, considering transportability etc., the composition may be in a solid state by removing the solvent from the composition for forming an organic layer.

[0566] 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 GS ) of the good solvent (GS) is preferably lower than the boiling point (BP PS ) of the poor solvent (PS).

[0567] By adding a high-boiling poor solvent, the low-boiling good solvent volatilizes first during film formation, increasing the concentration of the inclusion and the concentration of the poor solvent in the composition, and promoting rapid film formation. As a result, a coating film with few defects, small surface roughness, and high smoothness can be obtained.

[0568] The solubility difference (S GS -S PS ) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. The boiling point difference (BP PS -BP GS ) is preferably 10°C or more, more preferably 30°C or more, and even more preferably 50°C or more.

[0569] The organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating after film formation. When heating is performed, from the viewpoint of improving coating film formability, it is preferably performed at a temperature of at least one glass transition temperature (Tg) of the solute + 30°C or lower. Also, from the viewpoint of reducing residual solvent, it is preferably heated to at least one glass transition point (Tg) of the solute - 30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Also, drying may be performed multiple times at different temperatures, or a plurality of drying methods may be used in combination.

[0570] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming the 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, hexan-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 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 - fluoroveratrole, 2,6 - dimethylanisole, n - butylbenzene, 3 - fluorobenzonitrile, decalin (decalin), 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, veratrole, 1,2,3,4 - 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, benzyl octyl ether, etc. can be mentioned, but are not limited to these. Also, the solvent may be used alone or in combination.,

[0571] <Optional component> The composition for forming an organic layer may contain any component as long as its properties are not impaired. Examples of the optional component include a binder and a surfactant, etc.,

[0572] (1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and at the same time bonds the obtained film to the substrate. Further, among the composition for forming an organic layer, it plays a role of dissolving, dispersing, and binding other components.

[0573] Examples of the binder used in the composition for forming an organic layer include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, ionomer, chlorinated polyether, diaryl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile-styrene copolymer (AS) resin, phenol resin, epoxy resin, melamine resin, urea resin, alkyd resin, polyurethane, and copolymers of the above resins and polymers. However, it is not limited to only these.

[0574] The binder used in the composition for forming an organic layer may be only one type, or a plurality of types may be mixed and used.

[0575] (2) Surfactant The composition for forming an organic layer may contain a surfactant, for example, for controlling the film surface uniformity, the solvent wettability of the film surface, and the liquid discharging property of the composition for forming an organic layer. Surfactants are classified into ionic and non-ionic types according to the structure of the hydrophilic group, and are also classified into alkyl-based, silicone-based, and fluorine-based types according to the structure of the hydrophobic group. Further, according to the molecular structure, they are classified into a single-molecule type having a relatively small molecular weight and a simple structure, and a polymer type having a large molecular weight and side chains or branches. Further, according to the composition, they are classified into a single type, a mixed type in which two or more surfactants and a substrate are mixed. Any type of surfactant can be used as the surfactant that can be used in the composition for forming an organic layer.

[0576] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade names, manufactured by Big Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), Supreon SC-101, Supreon KH-40 (trade names, manufactured by Seimi Chemical Co., Ltd.), Pluragent 222F, Pluragent 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), Megapack F-470, Megapack F-471, Megapack F-475, Megapack R-08, Megapack F-477, Megapack F-479, Megapack F-553, Megapack 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, alkylbenzenesulfonates and alkyldiphenyl ether disulfonates can be mentioned. Also, the surfactant may be used alone or in combination of two or more.

[0577] <Composition and Physical Properties of Composition for Forming Organic Layer> The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability, and film-forming property 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 ejection property when the inkjet method is used, and the good electrical characteristics, light-emitting characteristics, efficiency, and lifespan of the organic EL element having an organic layer produced using the composition. For example, in the case of the composition for forming a light-emitting layer, the first component is preferably 0.0001% by mass to 2.0% by mass based on the total mass of the composition for forming a light-emitting layer, the second component is preferably 0.0999% by mass to 8.0% by mass based on the total mass of the composition for forming a light-emitting layer, and the third component is preferably 90.0% by mass to 99.9% by mass based on the total mass of the composition for forming a light-emitting layer.

[0578] More preferably, the first component is 0.005% by mass to 1.0% by mass based on the total mass of the composition for forming a light-emitting layer, the second component is 0.095% by mass to 4.0% by mass based on the total mass of the composition for forming a light-emitting layer, and the third component is 95.0% by mass to 99.9% by mass based on the total mass of the composition for forming a light-emitting layer. Even more preferably, the first component is 0.05% by mass to 0.5% by mass based on the total mass of the composition for forming a light-emitting layer, the second component is 0.25% by mass to 2.5% by mass based on the total mass of the composition for forming a light-emitting layer, and the third component is 97.0% by mass to 99.7% by mass based on the total mass of the composition for forming a light-emitting layer.

[0579] The composition for forming an organic layer can be produced by appropriately selecting known methods such as stirring, mixing, heating, cooling, dissolving, and dispersing the aforementioned components. Further, after preparation, filtration, degassing (also referred to as double degassing), ion exchange treatment, and inert gas substitution and encapsulation treatment, etc. can be appropriately selected and carried out.

[0580] As for the viscosity of the composition for forming an organic layer, a higher viscosity results in better film-forming properties and better ejection properties when using the inkjet method. On the other hand, a lower viscosity makes it easier to form a thin film. In this regard, the viscosity of the composition for forming an organic layer preferably has a viscosity at 25 °C of 0.3 to 3 mPa·s, 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).

[0581] As for the surface tension of the composition for forming an organic layer, a lower surface tension results in better film-forming properties and a defect-free coating film. On the other hand, a higher surface tension results in better inkjet ejection properties. In this regard, 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 sessile drop method.

[0582] <Crosslinkable polymer compound: a compound represented by formula (XLP-1)> Next, the case where the aforementioned 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).

Chemical formula

[0583] In formula (XLP-1), MUx, ECx, and k are defined in the same way as MU, EC, and k in formula (H3), provided 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% by mass in the molecule.

[0584] The content of the monovalent or divalent aromatic compound group having a crosslinkable substituent is preferably 0.5 to 50% by mass in the molecule, more preferably 1 to 20% by mass.

[0585] The crosslinkable substituent (XLS) is not particularly limited as long as it can further crosslink the aforementioned polymer compound, but substituents having the following structures are preferred. In each structural formula, * indicates the bonding position. [Chemical formula]

[0586] L is independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and polyoxyalkylene having 1 to 12 carbon atoms, respectively. 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.

[0587] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures. [Chemical formula]

[0588] [Chemical formula]

[0589] [Chemical formula]

[0590] [Chemical formula]

[0591] [Method for Producing Polymer Compound and Crosslinkable Polymer Compound] Regarding the production methods of the polymer compound and the crosslinkable polymer compound, the compound represented by the aforementioned formula (H3) and the compound represented by (XLP-1) will be described as examples. These compounds can be synthesized by appropriately combining known production methods.

[0592] Examples of the solvent used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc., such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, etc.

[0593] Also, the reaction may be carried out in a two-phase system. When reacting in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[0594] When producing the compound of formula (H3) and the compound of (XLP-1), it may be produced in one step or through multiple steps. Also, after all the raw materials are put into the reaction vessel, it may be carried out by a batch polymerization method in which the reaction is started, by a dropwise polymerization method in which the raw materials are added dropwise to the reaction vessel, or by a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these can be appropriately combined for synthesis. For example, when synthesizing the compound represented by formula (H3) in one step, the target product is obtained by carrying out the reaction with the monomer having a polymerizable group bonded to the monomer unit (MU) and the monomer having a polymerizable group bonded to the end cap unit (EC) added to the reaction vessel. Also, when synthesizing the compound represented by formula (H3) in multiple steps, after polymerizing the monomer having a polymerizable group bonded to the monomer unit (MU) to the desired molecular weight, the monomer having a polymerizable group bonded to the end cap unit (EC) is added and reacted to obtain the target product. When adding and reacting monomers having polymerizable groups bonded to different types of monomer units (MU) in multiple steps, a polymer having a concentration gradient with respect to the structure of the monomer unit can be produced. Also, after preparing the precursor polymer, the target polymer can be obtained by a post-reaction.

[0595] In addition, by selecting the polymerizable group of the monomer, the primary structure of the polymer can be controlled. For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (Synthesis Scheme 1), a polymer having a regular primary structure (Synthesis Schemes 2 and 3), etc., and they can be appropriately combined and used according to the target product. Further, when using a monomer having three or more polymerizable groups, hyperbranched polymers or dendrimers can be synthesized.

[0596]

Chemical Formula

[0597] As the monomer that can be used in the present invention, it can be synthesized according to the methods described in JP-A-2010-189630, WO 2012 / 086671, WO 2013 / 191088, WO 2002 / 045184, WO 2011 / 049241, WO 2013 / 146806, WO 2005 / 049546, WO 2015 / 145871, JP-A-2010-215886, JP-A-2008-106241, WO 2016 / 031639, and JP-A-2011-174062.

[0598] Regarding the specific polymer synthesis sequence, it can be synthesized according to the methods described in JP-A-2012-036388, WO 2015 / 008851, JP-A-2012-36381, JP-A-2012-144722, WO 2015 / 194448, WO 2013 / 146806, WO 2015 / 145871, WO 2016 / 031639, WO 2016 / 125560, and WO 2011 / 049241.

[0599] 3-1-10. Application examples of organic electroluminescent device In addition, the present invention can also be applied to a display device including an organic EL element or a lighting device including an organic EL element, etc.

[0600] A display device or a lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element according to the present embodiment and a known driving device, and can be driven by appropriately using a known driving method such as direct current driving, pulse driving, or alternating current driving.

[0601] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Further, examples of the display method of the display include a matrix and / or a segment method. Further, the matrix display and the segment display may coexist in the same panel.

[0602] In a matrix, pixels for display are two-dimensionally arranged in a lattice shape, a mosaic shape, etc., and characters and images are displayed by a set of pixels. The shape and size of the pixels are determined according to the application. For example, for image and character display of a computer, a monitor, or a television, pixels in the shape of a square with a side length of 300 μm or less are usually used. In the case of a large display such as a display panel, pixels with a side length on the order of mm are used. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, pixels of red, green, and blue are arranged and displayed. In this case, there are typically a delta type and a stripe type. And as the driving method of this matrix, either a line sequential driving method or an active matrix may be used. The line sequential driving has the advantage of simple structure, but considering the operating characteristics, the active matrix method may be superior in some cases, so it is also necessary to use them separately according to the application.

[0603] In the segment method (type), a pattern is formed to display predetermined information, and a determined area is caused to emit light. For example, time and temperature displays on digital clocks and thermometers, operation state displays on audio devices and electronic cookers, and panel displays on automobiles, etc. can be cited.

[0604] Examples of the lighting device include lighting devices such as indoor lighting, backlights of liquid crystal display devices, etc. (see, for example, Japanese Patent Application Laid-Open No. 2003-257621, Japanese Patent Application Laid-Open No. 2003-277741, Japanese Patent Application Laid-Open No. 2004-119211, etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used for liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, as a backlight for a liquid crystal display device, especially for computer applications where thinning is an issue, considering that the conventional method consists of a fluorescent lamp and a light guide plate and it is difficult to thin, the backlight using the light-emitting element according to this embodiment is characterized by being thin and lightweight.

[0605] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used for the production of organic field effect transistors or organic thin film solar cells, etc., in addition to the aforementioned organic electroluminescent elements.

[0606] An organic field effect transistor is a transistor that controls current by an electric field generated by a voltage input, and in addition to a source electrode and a drain electrode, a gate electrode is provided. When a voltage is applied to the gate electrode, an electric field is generated, and it is a transistor that can arbitrarily block the flow of electrons (or holes) flowing between the source electrode and the drain electrode to control the current. The field effect transistor is easier to miniaturize compared to a simple transistor (bipolar transistor), and is often used as an element constituting an integrated circuit, etc.

[0607] The structure of an organic field effect transistor usually has a source electrode and a drain electrode provided so as to be in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode may be further provided with an insulating layer (dielectric layer) interposed therebetween in contact with the organic semiconductor active layer. Examples of the element structure include the following structures.

[0608] (1) Substrate / gate electrode / insulator layer / source electrode and drain electrode / organic semiconductor active layer (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode and drain electrode (3) Substrate / organic semiconductor active layer / source electrode and drain electrode / insulator layer / gate electrode (4) Substrate / source electrode and drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor configured as described above can be applied as a pixel driving switching element of a liquid crystal monitor or an organic light emitting element display using an active matrix driving method.

[0609] An organic thin film solar cell has a structure in which a positive electrode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a negative electrode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the positive electrode side and an n-type semiconductor layer on the negative electrode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, the p-type semiconductor layer, the n-type semiconductor layer, and the electron transport layer according to its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell. In addition to the above, the organic thin film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. Known materials used for the organic thin film solar cell can be appropriately selected and combined for use in the organic thin film solar cell.

[0610] 4. Wavelength conversion material The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.

[0611] Currently, the technology of multi-color conversion by color conversion methods is being actively studied for application to liquid crystal monitors, organic EL displays, lighting, etc. Color conversion means converting the light emitted from a light emitter into light with a longer wavelength, for example, converting ultraviolet light or blue light into green light or red light emission. By forming a wavelength conversion material having this color conversion function into a film and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By using such a white light source formed by combining a blue light source and a wavelength conversion film having a color conversion function as a light source unit and combining it with a liquid crystal driving part and a color filter, it becomes possible to fabricate a full-color display. Also, if there is no liquid crystal driving part, it can be used as a white light source as it is, and for example, it can be applied as a white light source for LED lighting etc. Further, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green light and red light, it becomes possible to fabricate a full-color organic EL display without using a metal mask. Furthermore, by using a blue micro LED as a light source and combining it with a wavelength conversion film that converts blue light into green light and red light, it becomes possible to fabricate a low-cost full-color micro LED display.

[0612] The polycyclic aromatic compound of the present invention can be used as this wavelength conversion material. By using a wavelength conversion material containing the polycyclic aromatic compound of the present invention, the light from a light source or light emitting element that generates ultraviolet light or blue light with a shorter wavelength can be converted into blue light or green light with high color purity suitable for use in a display device (a display device using an organic EL element or a liquid crystal display device). The adjustment of the color to be converted can be performed by appropriately selecting the substituents of the polycyclic aromatic compound of the present invention, the binder resin used as the wavelength conversion composition described later, etc. The wavelength conversion material can be prepared as a wavelength conversion composition containing the polycyclic aromatic compound of the present invention. Also, a wavelength conversion film may be formed using this wavelength conversion composition.

[0613] In addition to the polycyclic aromatic compound of the present invention, the wavelength conversion composition may contain a binder resin, other additives, and a solvent. As the binder resin, for example, those described in paragraphs 0173 to 0176 of WO 2016 / 190283 can be used. As other additives, the compounds described in paragraphs 0177 to 0181 of WO 2016 / 190283 can be used. As the solvent, reference can be made to the description of the solvent contained in the composition for forming the light-emitting layer described above.

[0614] The wavelength conversion film includes a wavelength conversion layer formed by curing the wavelength conversion composition. As a method for producing the wavelength conversion layer from the wavelength conversion composition, a known film formation method can be referred to. The wavelength conversion film may consist only of a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, or may include other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light into green light or red light, a wavelength conversion layer that converts blue light or green light into red light). The wavelength conversion film may further include a substrate layer and a barrier layer for preventing deterioration of the color conversion layer due to oxygen, moisture, or heat.

Examples

[0615] Hereinafter, the present invention will be described more specifically by way of examples, but the present invention is not limited thereto.

[0616] <Synthesis Example> Synthesis Example (1): Synthesis of Compound (1-1)

Chemical Formula

[0617] To a flask containing Compound (S-1-1) (1.2 g) and tert-butylbenzene (7.0 ml), 1.6 M tert-butyllithium pentane solution (1.6 ml) was added at -30 °C under a nitrogen atmosphere.

[0618] After the dropping was completed, the temperature was raised to 60 °C and stirred for 2 hours, and then the components with a lower boiling point than tert-butylbenzene were distilled off under reduced pressure. It was cooled to -30 °C, boron tribromide (0.63 g) was added, the temperature was raised to room temperature and stirred for 0.5 hour. Then, it was cooled to 0 °C again, N,N-diisopropylethylamine (0.43 ml) was added, stirred at room temperature until the exotherm stopped, then the temperature was raised to 120 °C and heated with stirring for 3 hours. After the reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled in an ice bath and heptane were added and separated by liquid separation. Subsequently, it was purified by a silica gel short path column (eluent: toluene), the solvent was distilled off under reduced pressure, the obtained solid was dissolved in toluene, and then heptane was added for reprecipitation to obtain Compound (1-1) (0.24 g).

[0619] Compounds (1-2) to (1-10) and Compounds (Ref-1-1) to (Ref-1-4) were synthesized by the method according to Synthesis Example (1). Compounds (Ref-1-1) to (Ref-1-4) are the compounds described in Science Advances. 8, eabq1641 (2022), International Publication No. 2020 / 200884, U.S. Patent Application Publication No. 2022 / 336783, and JP-A-2023-133223.

[0620]

Chemical formula

[0621]

Chemical formula

[0622] The formation of the target product was confirmed by MALDI-TOF-MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry).

[0623]

Table 1

[0624] <Manufacture and Evaluation of Vapor Deposition-Type Organic Light-Emitting Diode Devices> Using each of the synthesized compounds of the present invention and comparative compounds, each of the organic EL elements of TTF, TADF, TAF, and PSF was manufactured.

[0625] <TTF configuration: Examples 1-1-1 to 1-1-10 and Comparative Examples 1-1-1 to 1-1-4> ITO (120 nm) / HI (40 nm) / HAT-CN (5 nm) / HT-1 (45 nm) / HT-2 (10 nm) / BH: Each compound described in Table 2 (97:3) / ET-1 (5 nm) / ET-2:Liq (1:1) (25 nm) / LiF (1 nm) / Al (100 nm) The chemical structures of the compounds used in the manufacture of the above elements are shown below.

[0626]

Chemical formula

[0627] An ITO film formed to a thickness of 180 nm by sputtering was polished to 120 nm, and a 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) 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), and molybdenum vapor deposition boats containing HI, HAT-CN, HT-1, HT-2, BH, each compound described in Table 2, ET-1 and ET-2, and aluminum nitride vapor deposition boats containing Liq, LiF and aluminum were attached.

[0628] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is 5×10 -4The pressure was reduced to Pa, and first HI was heated and vapor-deposited to a film thickness of 40 nm. Next, HAT-CN was heated and vapor-deposited to a film thickness of 5 nm. Then, HT-1 was heated and vapor-deposited to a film thickness of 45 nm. Next, HT-2 was heated and vapor-deposited to a film thickness of 10 nm to form a four-layer hole layer. Next, BH and each compound described in Table 2 were simultaneously heated and vapor-deposited to a film thickness of 25 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of BH to each compound described in Table 2 was about 97 to 3. Further, ET-1 was heated and vapor-deposited to a film thickness of 5 nm. Next, ET-2 and Liq were simultaneously heated and vapor-deposited to a film thickness of 25 nm to form a two-layer electron layer. The deposition rate was adjusted so that the mass ratio of ET-2 to Liq was about 50 to 50. 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 film thickness of 1 nm, and subsequently aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a negative electrode, obtaining an organic EL element.

[0629] <TADF Structure: Examples 2-1-1 to 2-1-10 and Comparative Examples 2-1-1 to 2-1-4> 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) An ITO film formed to a thickness of 200 nm by sputtering was polished to 50 nm, and a 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) was used as a transparent support substrate. This transparent support substrate was fixed to a 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 mounted.

[0630] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was evacuated to 5×10 -4 Pa, and first, HAT-CN was heated and vapor-deposited to a film thickness of 10 nm to form a hole injection layer. Next, HT-1 was heated and vapor-deposited to a film thickness of 60 nm to form a hole transport layer 1, and further, SiCzCz was heated and vapor-deposited to a film thickness of 5 nm to form a hole transport layer 2. Next, SiCzCz, SiTrzCz2, and each compound described in Table 2 were simultaneously heated and vapor-deposited to a film 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 film thickness of 5 nm to form an electron transport layer 1, and again, mSiTrz and Liq were heated and vapor-deposited to a film 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 film thickness of 1 nm, and subsequently, aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a negative electrode, obtaining an organic EL element. At this time, the deposition rate of aluminum was adjusted to be 1 - 10 nm / second. Note that SiCzCz in the light-emitting layer corresponds to a hole-transporting host material, and SiTrzCz2 corresponds to an electron-transporting host material.

[0631] <TAF configuration: Examples 3-1-1 to 3-1-10, Comparative Examples 3-1-1 to 3-1-4> ITO(50 nm) / HAT-CN(10 nm) / HT-1(60 nm) / SiCzCz(5 nm) / SiCzCz:SiTrzCz2:TADF-1: each compound described in Table 2(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 manufactured in the same manner as the TADF structure. In the light-emitting layer, SiCzCz, SiTrzCz2, (TADF-1), and each compound described in Table 2 were simultaneously heated and vapor-deposited to a film 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 2 was approximately 60:26:13:1.

[0632] <PSF structure: Examples 4-1-1 to 4-1-10, Comparative Examples 4-1-1 to 4-1-4> ITO(50 nm) / HAT-CN(10 nm) / HT-1(60 nm) / SiCzCz(5 nm) / SiCzCz:SiTrzCz2:PtON-TBBI: each compound described in Table 2(60:26:13:1)(35 nm) / mSiTrz(5 nm) / mSiTrz:Liq(1:1)(30 nm) / LiF(1 nm) / Al(100 nm) The device was manufactured in the same manner by replacing (TADF-1) of the TAF structure with PtON-TBBI.

[0633] The chemical structures of the compounds used in the manufacture of each device are shown below.

Chemical formula

[0634] 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 light emission, for example, at 1000 cd / m 2 The value at the time of light emission can be used.

[0635] The quantum efficiency of a light-emitting device includes internal quantum efficiency and external quantum efficiency. The internal quantum efficiency indicates the ratio at which the external energy injected into the light-emitting layer of the light-emitting device as electrons (or holes) is converted into pure photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons emitted outside the light-emitting device. Since some of the photons generated in the light-emitting layer are absorbed inside the light-emitting device or continue to be reflected and not emitted outside the light-emitting device, the external quantum efficiency is lower than the internal quantum efficiency.

[0636] The measurement methods for spectral radiance (emission spectrum) and external quantum efficiency are as follows. Using a voltage / current generator R6144 manufactured by Advantest Corporation, a voltage is applied to make the device emit light such that the luminance of the device becomes 1000 cd / m 2 The spectral radiance in the visible light region is measured from the perpendicular direction to the emission surface using a spectral radiance meter SR-3AR manufactured by TOPCON Corporation. Assuming that the emission surface is a perfect diffuser surface, the value obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π is the number of photons at each wavelength. Subsequently, in the entire observed wavelength range, the number of photons is integrated to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the elementary charge is taken as the number of carriers injected into the device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency. Also, the full width at half maximum of the emission spectrum is obtained as the width between the upper and lower wavelengths centered on the maximum emission wavelength at which the intensity becomes 50%.

[0637] A DC voltage is applied with the ITO electrode as the positive electrode and the LiF / aluminum electrode as the negative electrode, and the characteristics during emission are measured at 1000 cd / m 2 For the TTF-structured device, the time (lifetime) to maintain a luminance of 95% or more of the initial luminance was measured, and for the TADF-structured, TAF-structured, and PSF-structured devices, the time (lifetime) to maintain a luminance of 50% or more of the initial luminance was measured. Note that the emission peaks of all the devices were in the range of 450 to 470 nm. The results are shown in Table 2.

[0638]

Table 2

[0639] From the results obtained, it can be seen that the device of the example is highly efficient as compared with the device of the comparative example using the compound having the same skeleton as the compound of the example.

Explanation of Reference Numerals

[0640] 100: Organic electroluminescent device 101: Substrate 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 composed of one or more structural units represented by formula (1): 【Chemical 1】 In formula (1), Ring A, Ring B, and Ring C are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, However, at least one selected from the group consisting of Ring A, Ring B, and Ring C is an aryl ring having a group represented by the formula (E ＡＢＣ ) as a substituent, or a heteroaryl ring having a group represented by the formula (E ＡＢＣ ) as a substituent, Ar is each independently a group represented by formula (Ar), Formula (E) ＡＢＣ ), in # indicates the bonding position to the aryl ring or heteroaryl ring, Ring P and Ring Q are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, In formula (Ar), * indicates the bonding position to nitrogen, Ring D 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, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted trialkylsilyl, a substituted or unsubstituted dialkylarylsilyl, a substituted or unsubstituted alkyldiarylsilyl, a substituted or unsubstituted triarylsilyl, a substituted or unsubstituted diarylamine, a substituted or unsubstituted arylheteroarylamine, or a substituted or unsubstituted diheteroarylamine. At least one G is a substituted alkyl having 1 to 24 carbon atoms, an unsubstituted alkyl having 4 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl. Here, when G is a substituted alkyl having 1 to 24 carbon atoms or an unsubstituted alkyl having 4 to 24 carbon atoms, the carbon atom bonded to Ring D is a quaternary carbon atom. When G is a substituted or unsubstituted cycloalkyl, the carbon atom bonded to Ring D is a tertiary carbon atom or a quaternary carbon atom. In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring can be fused to at least one cycloalkane, the cycloalkane can be substituted with at least one substituent, and among the cycloalkanes, at least one -CH ２ - can be substituted with -O-, At least one hydrogen within the said structure can be replaced by deuterium, cyano or halogen, and at least one nitrogen can be replaced by nitrogen-15 ( １５ N), at least one sulfur can be replaced by sulfur-33 ( ３３ S), sulfur-34 ( ３４ S) or sulfur-36 ( ３６ S), at least one oxygen can be replaced by oxygen-17 ( １７ O) or oxygen-18 ( １８ O), at least one carbon can be replaced by carbon-13 ( １３ C), and at least one boron can be replaced by boron-11 ( １１ B).

2. The polycyclic aromatic compound according to claim 1, wherein formula (Ar) is independently a group represented by the following formula (2Ar): [Chemical Formula 2] In formula (2Ar), G is the same as defined in claim 1, and at least one G is a substituted alkyl having 1 to 24 carbon atoms, an unsubstituted alkyl having 4 to 24 carbon atoms, or a substituted or unsubstituted cycloalkyl. When G is a substituted alkyl having 1 to 24 carbon atoms or an unsubstituted alkyl having 4 to 24 carbon atoms, the carbon atom bonded to the D ring is a quaternary carbon. When G is a substituted or unsubstituted cycloalkyl, the carbon atom bonded to the D ring is a quaternary carbon. R ｄ is independently hydrogen, unsubstituted alkyl, unsubstituted cycloalkyl or unsubstituted aryl, R ｄｄ is hydrogen, or a substituted or unsubstituted aryl.

3. Formula (1) is the polycyclic aromatic compound according to claim 1, represented by the following formula (1X1): 【Chemical 3】 In formula (1X1), Ar is the same as the definition of Ar in formula (1), R ａ is hydrogen or unsubstituted alkyl, R ｂ is a substituted or unsubstituted 9-carbazolyl or a substituted or unsubstituted diarylamino, Z Ｅ is each independently —C(—R ＺＥ )═ or —N═, and Said R ＺＥ is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, provided that substituents substituted on adjacent atoms can be bonded to each other to form a ring.

4. Formula (1) is the polycyclic aromatic compound according to claim 1, represented by any one of the following chemical formulas: 【Chemical Formula 4】 In the above chemical formula, Ad is 1 - adamantyl.

5. An organic electroluminescent device having a pair of electrodes consisting of a positive electrode and a negative electrode 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 4.

6. The organic electroluminescent device according to claim 5, wherein the organic layer is a light-emitting layer.

7. The organic electroluminescent device according to claim 6, wherein the light-emitting layer contains at least one selected from the group consisting of an assisting dopant and a phosphorescent material.

8. A display device or a lighting device including the organic electroluminescent device according to claim 6.

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