Organic light-emitting element, composition and film

Abstract

An organic light-emitting device comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2) has high light-emitting efficiency. The a to c rings are condensable benzene rings, R 1 , R 2 is a substituted or unsubstituted aryl group, etc., R 31 ~R 35 Four of them are substituted or unsubstituted carbazole-9-yl groups, but not all of them are the same, and the remaining one is a hydrogen atom, a cyano group, etc. #imgabs0#

Description

Technical Field

[0001] The invention relates to an organic light emitting element, a composition and a film. Background Art

[0002] Research is actively being conducted on improving the luminous efficiency of light-emitting elements such as organic electroluminescent elements (organic EL elements). In particular, a lot of effort has been put into improving the luminous efficiency by newly developing electron transport materials, hole transport materials, luminescent materials, etc. that constitute organic electroluminescent elements. For example, Patent Document 1 states that polycyclic aromatic compounds formed by connecting multiple aromatic rings through boron atoms or nitrogen atoms can be used as luminescent materials for organic electroluminescent elements.

[0003] On the other hand, research on improving luminous efficiency by combining materials for the luminescent layer of organic electroluminescent elements is also carried out. For example, in patent document 2, it is recorded that a delayed fluorescent material with the lowest excited singlet energy level between the luminescent material and the host material is added to the luminescent layer comprising the luminescent material and the host material. In the excited state, the delayed fluorescent material easily produces the reverse intersystem crossing from the excited triplet state to the excited singlet state, so it is not only the excited singlet state, but the excited triplet state can also be used for luminescence by the path via the reverse intersystem crossing. Therefore, it is recorded that the luminous efficiency of the organic electroluminescent element can be improved by adding a delayed fluorescent material.

[0004] Previous technical literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent No. 5935199

[0007] Patent Document 2: Japanese Patent No. 5669163 Summary of the invention

[0008] Technical issues to be solved by the invention

[0009] By adding a delayed fluorescent material whose lowest excited singlet energy level is between that of the light-emitting material and the main material to a light-emitting layer comprising a light-emitting material and a main material, the luminous efficiency of an organic electroluminescent element is indeed improved. However, even the luminous efficiency improved by adding a delayed fluorescent material is generally not satisfactory, and few blue light-emitting elements can achieve a sufficiently high external quantum yield. Therefore, it is necessary to provide a new technology that can open up a way for achieving high luminous efficiency and realizing efficient blue light-emitting elements.

[0010] Means for solving technical problems

[0011] Under such circumstances, the present inventors have conducted research with the goal of finding a combination of materials that can provide an organic light-emitting element with high light-emitting efficiency. In particular, the present inventors have conducted research with the goal of finding a combination of materials that can pave the way for realizing an efficient blue light-emitting element.

[0012] As a result of intensive studies, the present inventors have found that an organic light-emitting element with high light emission efficiency can be provided by using a polycyclic aromatic compound having a specific structure and a delayed fluorescent material having a specific structure in combination, thereby providing the present invention described below.

[0013] [1] An organic light-emitting device comprising a compound having a structure represented by one or more of the following general formula (1) and a compound represented by the following general formula (2).

[0014] [Chemical formula 1]

[0015] General formula (1)

[0016]

[0017] In the general formula (1), the a ring, the b ring and the c ring each independently represent a benzene ring which may be condensed with other rings to form an aromatic ring or a heteroaromatic ring, and at least one hydrogen atom in these rings may be substituted. 1 , R 2 R each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded via a benzene ring. 1 Can be through -O-, -S-, -C(-R c1 )2- or a single bond to a carbon atom adjacent to the bonding position (atom) to N in the a ring and / or c ring. R 2 Can be through -O-, -S-, -C(-R c2 )2- or a single bond to a carbon atom adjacent to the bonding position (atom) to N in the a ring and / or b ring. c1 and R c2 Each independently represents a hydrogen atom or an alkyl group.

[0018] [Chemical formula 2]

[0019]

[0020] In the general formula (2), R 31 ~R 35 Four of the above independently represent substituted or unsubstituted carbazole-9-yl groups, but the four are not all the same. The remaining one represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted carbazole-9-yl group, or a cyano group.

[0021] [2] The organic light-emitting element according to [1], wherein the compound having one or more structures represented by the general formula (1) is a compound having two structures represented by the general formula (1).

[0022] [3] The organic light-emitting element according to [2], wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1a).

[0023] [Chemical formula 3]

[0024] General formula (Ia)

[0025]

[0026] In the general formula (1a), R 11 ~R 17 Each independently represents a substituent, R 18 ~R 23 Each independently represents a hydrogen atom or a substituent, n11, n13, n14, and n17 each independently represent an integer of 0 to 5, n12 represents an integer of 0 to 2, and n15 and n16 each independently represent an integer of 0 to 4.

[0027] [4] The organic light-emitting element according to [3], wherein R 19 and R 22 Each independently represents a substituent.

[0028] [5] The organic light-emitting element according to any one of [1] to [4], wherein R in the general formula (2) 31 ~R 35 At least one of the groups is at least one substituted carbazole-9-yl group at the 3-position or the 6-position.

[0029] [6] An organic light-emitting element according to any one of [1] to [5], wherein the carbazole-9-yl group in the general formula (2) is unsubstituted or substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group.

[0030] [7] The organic light-emitting element according to [6], wherein the compound represented by the general formula (2) is a compound represented by the following general formula (2a).

[0031] [Chemical formula 4]

[0032] General formula (2a)

[0033]

[0034] In the general formula (2a), R 41 ~R 44 , R 46 ~R 49 Each independently represents a substituent, but the four substituted or unsubstituted carbazole-9-yl groups bonded to the benzonitrile of the general formula (2a) are not all the same. n41 to n44 and n46 to n49 each independently represent an integer of 0 to 4. 45 represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted carbazole-9-yl group or a cyano group.

[0035] [8] The organic light-emitting element according to any one of [1] to [7], wherein the light-emitting layer contains the compound represented by the general formula (1).

[0036] [9] The organic light-emitting element according to any one of [1] to [8], comprising the compound represented by the general formula (1) and the compound represented by the general formula (2) in the same layer.

[0037]

[10] A composition comprising both the compound represented by the general formula (1) and the compound represented by the general formula (2).

[0038]

[11] A film comprising both the compound represented by the general formula (1) and the compound represented by the general formula (2).

[0039] Effects of the Invention

[0040] Since the organic light-emitting element of the present invention contains both the compound represented by the general formula (1) and the compound represented by the general formula (2), it has high light-emitting efficiency. In addition, according to the present invention, a blue light-emitting element with high light-emitting efficiency can also be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] Figure 1 It is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescent element.

[0042] Figure 2 It is the absorption spectrum of compound 1 and the emission spectra of compound 1, compounds 2-38 and example 1.

[0043] Figure 3 These are the transient decay curves of the element of Example 2, Comparative element 1, and Comparative element 2. DETAILED DESCRIPTION

[0044] The content of the present invention is described in detail below. The description of the constituent elements described below is based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, in this specification, the numerical range represented by "to" refers to a range that includes the numerical values ​​recorded before and after "to" as the lower limit and upper limit. In addition, the isotope types of hydrogen atoms present in the molecules of the compounds used in the present invention are not particularly limited. For example, all hydrogen atoms in the molecules can be 1 H, or part or all of it 2 H (deuterium D).

[0045] <Compound represented by general formula (1)>

[0046] In the present invention, a compound having one or more structures represented by the following general formula (1) is used.

[0047] [Chemical formula 5]

[0048] General formula (1)

[0049]

[0050] In the general formula (1), the a ring, the b ring and the c ring each independently represent a benzene ring which may be condensed with other rings to form an aromatic ring or a heteroaromatic ring, and at least one hydrogen atom in these rings may be substituted. 1 , R 2 R each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded via a benzene ring. 1 Can be through -O-, -S-, -C(-R c1 )2- or a single bond to a carbon atom adjacent to the bonding position (atom) to N in the a ring and / or c ring. R 2 Can be through -O-, -S-, -C(-R c2 )2- or a single bond to a carbon atom adjacent to the bonding position (atom) to N in the a ring and / or b ring. c1 and R c2 Each independently represents a hydrogen atom or an alkyl group.

[0051] The a ring, b ring and c ring may be a monocyclic ring or a polycyclic ring, but the ring directly bonded to B and N shown in the general formula (1) is a benzene ring. When the benzene ring directly bonded to B and N is condensed with other rings to form a polycyclic ring, the formed polycyclic ring is an aromatic ring or a heteroaromatic ring. The number of carbon atoms of the aromatic ring described herein is preferably 6 to 30, more preferably 6 to 16, further preferably 6 to 12, and particularly preferably 6 to 10. Furthermore, the number of carbon atoms of the heteroaromatic ring described herein is preferably 6 to 30, more preferably 6 to 25, further preferably 6 to 20, further preferably 6 to 15, and particularly preferably 6 to 10. The heterocyclic ring constituting the heteroaromatic ring is preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring. As the ring-constituting atoms of the heterocyclic ring, in addition to carbon atoms, 1 to 5 heteroatoms selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms can be mentioned. Examples of the aromatic ring or heteroaromatic ring formed by condensation include a naphthalene ring, an acenaphthene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a tetracene ring, a perylene ring, a pentacene ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a carbazole ring, an acridine ring, a phenoxatiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring.

[0052] As R 1 , R 2 The aryl group that can be used includes, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Examples of the aromatic ring constituting the aryl group include a benzene ring, a naphthalene ring, an acenaphthene ring, a fluorene ring, a phenanthren ring, a triphenylene ring, a pyrene ring, a tetracene ring, a perylene ring, and a pentacene ring.

[0053] R 1 , R 2 The heteroaryl group that can be used has at least a polycyclic structure formed by condensing benzene rings, and is a group bonded via the benzene rings constituting the polycyclic structure. 1 , R 2 For the description and preferred range of the heteroaromatic ring that can be used in the heteroaryl group, reference can be made to the description and preferred range of the heteroaromatic ring that can be used in the a ring, b ring and c ring.

[0054] R 1 Can be through -O-, -S-, -C(-R c1 )2- or a single bond to a carbon atom adjacent to the bonding position (atom) to N in the a ring and / or c ring. R2 Can be through -O-, -S-, -C(-R c2 )2- or a single bond is bonded to a carbon atom adjacent to the bonding position (atom) of N in the a ring and / or b ring. The carbon atom adjacent to the bonding position (atom) of N mentioned here is a carbon atom not bonded to B. R c1 and R c2 Each independently represents a hydrogen atom or an alkyl group. The alkyl group mentioned here is preferably an alkyl group having 1 to 4 carbon atoms, for example, a methyl group and an ethyl group. 1 , R 2 Through -O-, -S-, -C(-R c1 )2-、-C(-R c2 )2- or a single bond is bonded to the a ring, b ring and / or c ring to form a cyclic structure, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, and a carbazole ring.

[0055] R 1 , R 2 The substituents when the group is a substituted aryl group or a substituted heteroaryl group and the substituents when the a, b and c rings are substituted are preferably halogen atoms, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, substituted or unsubstituted diheteroarylamino groups, substituted or unsubstituted arylheteroarylamino groups (amino groups having aryl groups and heteroaryl groups), substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups or substituted or unsubstituted aryloxy groups. When these groups have substituents, the substituents include aryl groups, heteroaryl groups or alkyl groups. 1 , R 2 The total number of substituents in the a ring, b ring and c ring is preferably 0 to 15, more preferably 0 to 10, for example, can be selected from 1 to 10, selected from 2 to 10, selected from 0 to 6, selected from 0 to 4 or selected from 0 to 2.

[0056] The halogen atom which can be used as a substituent is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom.

[0057] As the aryl group that can be used as a substituent, and as the aryl group included in the diarylamino, arylheteroarylamino, and aryloxy groups that can be used as a substituent, for example, an aryl group having 6 to 30 carbon atoms can be mentioned, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. As the aromatic ring constituting the aryl group, a monocyclic benzene ring, a condensed bicyclic naphthalene ring, a condensed tricyclic acenaphthene ring, a fluorene ring, a phenanthren ring, a condensed tetracyclic triphenylene ring, a pyrene ring, a tetracene ring, a condensed pentacyclic perylene ring, a pentacene ring, etc. can be mentioned. As described later, the aryl group can be further substituted with an aryl group, so for example, as a substituted aryl group, a tricyclic terphenyl ring (meta-terphenyl, o-terphenyl, p-terphenyl) can also be used.

[0058] Examples of the heteroaryl group that can be used as a substituent and the heteroaryl group included in the diheteroarylamino group and the arylheteroarylamino group that can be used as a substituent include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, further preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl ring constituting the heteroaryl group include a heterocyclic ring containing 1 to 5 hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms as ring constituent atoms in addition to carbon atoms. Examples of the heteroaromatic ring constituting the heteroaryl group include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxatiin ring, a phenoxazine ... ring), phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thianthracene ring and the like.

[0059] The alkyl group that can be used as a substituent may be any of linear, branched, and cyclic, and examples thereof include linear alkyl groups having 1 to 24 carbon atoms, branched alkyl groups having 3 to 24 carbon atoms, and cyclic alkyl groups having 3 to 8 carbon atoms. Preferably, the alkyl group is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, and a cyclic alkyl group having 4 to 8 carbon atoms; more preferably, the alkyl group is a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, and a cyclic alkyl group having 5 to 7 carbon atoms; further preferably, the alkyl group is a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, and a cyclic alkyl group having 5 to 6 carbon atoms; and most preferably, the alkyl group is a linear alkyl group having 1 to 4 carbon atoms, and a branched alkyl group having 3 or 4 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6 -dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2,2,1]heptyl, bicyclo[2.2.2]octyl, decahydronaphthyl, adamantyl, etc. In the present specification, "n" is an abbreviation for normal, "s" is an abbreviation for secondary, and "t" is an abbreviation for tertiary.

[0060] As the alkoxy group which can be used as the substituent, for example, there can be mentioned a linear alkoxy group having 1 to 24 carbon atoms, a branched alkoxy group having 3 to 24 carbon atoms, or a cyclic alkoxy group having 3 to 8 carbon atoms. Preferably, it is a linear alkoxy group having 1 to 18 carbon atoms, a branched alkoxy group having 3 to 18 carbon atoms, or a cyclic alkoxy group having 4 to 8 carbon atoms; more preferably, it is a linear alkoxy group having 1 to 12 carbon atoms, a branched alkoxy group having 3 to 12 carbon atoms, or a cyclic alkoxy group having 5 to 7 carbon atoms; further preferably, it is a linear alkoxy group having 1 to 6 carbon atoms, a branched alkoxy group having 3 to 6 carbon atoms, or a cyclic alkoxy group having 5 to 6 carbon atoms; and particularly preferably, it is a linear alkoxy group having 1 to 4 carbon atoms, or a branched alkoxy group having 3 to 4 carbon atoms. Specific examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, cyclohexyloxy, bicyclo[2,2,1]heptyloxy, bicyclo[2.2.2]octyloxy, decahydronaphthyloxy and adamantyloxy.

[0061] The two aryl groups constituting the diarylamino group, the two heteroaryl groups constituting the diheteroarylamino group, and the aryl and heteroaryl groups constituting the arylheteroarylamino group that can be used as substituents may be bonded to each other via a single bond or a linking group, or may not be bonded to each other. The number of atoms constituting the linking chain of the linking group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Examples of the linking group include -O-, -S-, -C(=O)-, -C(=S)-, -N(R 51 )-、-B(R 52 )-、-C(R 53 )(R 54 )-、-Si(R 55 )(R 56 )-or two or more connecting groups thereof. Here, R 51 ~R 56 Each independently represents a hydrogen atom or a substituent, and preferred examples of the substituent include a substituted or unsubstituted alkyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 10 carbon atoms, and further preferably having 1 to 6 carbon atoms), a substituted or unsubstituted aryl group (preferably having 6 to 20 carbon atoms, more preferably having 6 to 14 carbon atoms, and further preferably having 6 to 10 carbon atoms), and a substituted or unsubstituted heteroaryl group (preferably having 5 to 20 ring skeleton atoms, more preferably having 5 to 14 ring skeleton atoms, and further preferably having 5 to 10 ring skeleton atoms).

[0062] A compound having a plurality of structures represented by the general formula (1) is a multimer of the structure represented by the general formula (1). The multimer is preferably a 2-6-mer, more preferably a 2-3-mer, and particularly preferably a 2-mer. The multimer may be in the form of a compound having a plurality of structures represented by the general formula (1). For example, in addition to a form in which the above-mentioned structures are bonded to each other by a single bond, a connecting group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, etc., it may also be in the form in which any ring (a ring, b ring or c ring) contained in the above-mentioned structure is shared among the structures represented by the general formula (1), and it may also be in the form in which any ring (a ring, b ring or c ring) contained in the structure represented by the general formula (1) is bonded to each other by condensation.

[0063] Examples of preferred compound groups represented by the general formula (1) include compound groups represented by the following general formula (1a).

[0064] [Chemical formula 6]

[0065] General formula (Ia)

[0066]

[0067] In the general formula (1a), R11 ~R 17 Each independently represents a substituent, R 18 ~R 23 Each independently represents a hydrogen atom or a substituent, n11, n13, n14, and n17 each independently represent an integer of 0 to 5, n12 represents an integer of 0 to 2, and n15 and n16 each independently represent an integer of 0 to 4.

[0068] R in the general formula (1a) 11 ~R 23 The substituents that can be used are preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino group having aryl and heteroaryl groups), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy. When these groups have substituents, aryl, heteroaryl or alkyl can be mentioned as the substituents. For the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy and aryloxy groups described herein, reference can be made to the description of these groups in general formula (1).

[0069] R bonded to the 2-position of the benzene ring 14 and R bonded to the 2-position of the benzene ring 15 They may be bonded to each other to form a single bond or a linking group (here, the 1-position of the benzene ring is the position bonded to the nitrogen atom N shown in the general formula (1a)). 16 and R bonded to the 2-position of the benzene ring 17 They may be bonded to each other to form a single bond or a linking group (here, the 1-position of the benzene ring is the position bonded to the nitrogen atom N shown in the general formula (1a)). For the linking group mentioned here, the description of the linking group in the general formula (1) can be referred to.

[0070] In the general formula (1a), n11 and n13 to n17 are preferably any integer from 0 to 3, and more preferably any integer from 0 to 2.

[0071] In the compound represented by the general formula (1a), R 11 ~R 23 The number of substituents present is preferably 0 to 26, more preferably 0 to 16, for example, 1 to 8, 2 to 8, 0 to 4, or 0 to 2.

[0072] Preferred compounds represented by the general formula (1a) include: 18 , R 20 , R21 , R 23 A more preferred compound group includes a compound group in which R 18 , R 20 , R 21 , R 23 A group of compounds in which n11 to n17 are each independently an integer of 0 to 2.

[0073] Another preferred group of compounds represented by the general formula (1a) include: 18 ~R 23 The compound group is a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group.

[0074] Another preferred group of compounds represented by the general formula (1a) include: 19 and R 22 As a more preferred compound group, R 19 and R 22 The compound group is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group. When these groups have a substituent, the substituent may be an aryl group, a heteroaryl group or an alkyl group.

[0075] Examples of a preferred compound group represented by the general formula (1) include a compound group represented by the following general formula (1b).

[0076] [Chemical formula 7]

[0077] General formula (1b)

[0078]

[0079] In the general formula (1b), R 31 ~R 37 Each independently represents a substituent; n31 to n33 and n35 each independently represent an integer of 0 to 5; n34 and n37 each independently represent an integer of 0 to 3; and n36 represents an integer of 0 to 4.

[0080] R in the general formula (1b) 31 ~R 37The substituents that can be used are preferably substituted or unsubstituted aryl groups, substituted or unsubstituted alkyl groups. When these aryl groups or alkyl groups have substituents, aryl groups or alkyl groups can be mentioned as substituents. For the aryl groups and alkyl groups described herein, reference can be made to the description of these groups in the general formula (1). In particular, R in the general formula (1b) 31 ~R 37 The number of carbon atoms of the alkyl group that can be used is preferably 1 to 12, more preferably 1 to 4. In particular, R 31 ~R 37 The aryl group that can be used is preferably an aryl group having 6 to 10 carbon atoms, and more preferably a phenyl group.

[0081] In the general formula (1b), n31 to n37 are preferably any integer from 0 to 2, and more preferably any integer from 0 to 1.

[0082] The total of n31 to n37 in the general formula (1b) is preferably 0 to 14, more preferably 0 to 8, and can be selected from 1 to 8, 2 to 8, 0 to 4, or 0 to 2, for example.

[0083] Preferred compounds represented by the general formula (1b) include: 31 ~R 37 The compound group is a substituted or unsubstituted phenyl group. As a more preferred compound group, R 31 ~R 37 The compound group is an unsubstituted phenyl group.

[0084] Another preferred group of compounds represented by the general formula (1b) include a group of compounds wherein n35 is an integer of 1 to 5, a group of compounds wherein n35 is an integer of 1 to 3, a group of compounds wherein n35 is 1 and R 35 In addition, there can be mentioned a compound group in which n36 is an integer of 1 to 4, a compound group in which n36 is an integer of 1 to 3, a compound group in which n36 is 1 and R 36 In addition, there can be mentioned a compound group in which n35 and n36 are each independently an integer of 1 to 3, a compound group in which n35 and n36 are 1, a compound group in which n35 and n36 are 1 and R 35 and R 36 A group of compounds each independently being a substituted or unsubstituted phenyl group.

[0085] The compound represented by the general formula (1) or the general formula (1a) can be synthesized with reference to paragraphs

[0281] to

[0316] and the description of the synthesis examples in Japanese Patent Gazette No. 5935199. It can also be synthesized by combining known synthesis methods. For the specific synthesis steps, reference can be made to Synthesis Example 1 described later.

[0086] Specific examples of the compound represented by the general formula (1) are given below, but the compounds that can be used in the present invention are not to be construed as being limitative of the following specific examples.

[0087] [Chemical formula 8-1]

[0088]

[0089] [Chemical formula 8-2]

[0090]

[0091] <Compound represented by general formula (2)>

[0092] In the present invention, a compound represented by the following general formula (2) is used.

[0093] [Chemical formula 9]

[0094] General formula (2)

[0095]

[0096] In the general formula (2), R 31 ~R 35 Four of the above independently represent substituted or unsubstituted carbazole-9-yl groups, but the four are not all the same. The remaining one represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted carbazole-9-yl group, or a cyano group.

[0097] As R 31 ~R 35 Substituents for the carbazole-9-yl group that can be used include preferably substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, substituted or unsubstituted diheteroarylamino groups, substituted or unsubstituted arylheteroarylamino groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, or substituted or unsubstituted aryloxy groups. These groups may be further substituted by these substituents.

[0098] Regarding the aryl group, heteroaryl group, diarylamino group, diheteroarylamino group, arylheteroarylamino group, alkyl group, alkoxy group and aryloxy group mentioned herein, reference can be made to the description of these groups in the general formula (1).

[0099] In R31 ~R 35 When the carbazole-9-yl group that can be used is substituted, the bonding position of the substituent is preferably the 3-position or both the 3-position and the 6-position of the carbazole ring.

[0100] As R 31 ~R 35 Specific examples of carbazole-9-yl that can be used include 3-methylcarbazole-9-yl, 3,6-dimethylcarbazole-9-yl, 3-ethylcarbazole-9-yl, 3,6-diethylcarbazole-9-yl, 3-tert-butylcarbazole-9-yl, 3,6-di-tert-butylcarbazole-9-yl, 3-phenylcarbazole-9-yl, 3,6-diphenylcarbazole-9-yl, 3-(carbazole-9-yl)carbazole-9-yl, and 3,6-bis(carbazole-9-yl)carbazole-9-yl.

[0101] R 31 ~R 35 The four of them independently represent a substituted or unsubstituted carbazole-9-yl group, but not all of them are the same. The four may be different, but preferably three are the same and one is different, or two are the same and the other two are also the same. For example, R 31 and R 35 Same and R 32 and R 34 In the same situation, R 31 and R 32 Same and R 34 and R 35 In the same situation, R 31 and R 34 Same and R 32 and R 35 In the same situation, R 32 and R 34 and R 35 Same but only R 31 Different situations, R 31 and R 34 and R 35 Same but only R 32 Different situations.

[0102] The difference between the substituted or unsubstituted carbazole-9-yl groups in the general formula (2) may be whether the carbazole-9-yl group has a substituent, the type of the substituent bonded to the carbazole-9-yl group, or the bonding position of the substituent bonded to the carbazole-9-yl group. Preferably, the difference between whether the carbazole-9-yl group has a substituent and the type of the substituent bonded to the carbazole-9-yl group are different. As examples of different types of substituents bonded to the carbazole-9-yl group, alkyl-substituted carbazole-9-yl and aryl-substituted carbazole-9-yl can be cited. As examples of different bonding positions of the substituent bonded to the carbazole-9-yl group, 3-position and 6-position carbazole-9-yl groups respectively and 3-position carbazole-9-yl groups only substituted by alkyl groups can be cited.

[0103] R 31 ~R 35 The remaining one of the four represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted carbazole-9-yl group or a cyano group. When the remaining one represents a substituted or unsubstituted carbazole-9-yl group, the substituted or unsubstituted carbazole-9-yl group may be the same as at least one of the other four, or may be different from the other four. 31 ~R 35 The other aryl group that can be used may refer to the description of the aryl group in the description of the general formula (1). 31 ~R 35 The remaining aryl group may be substituted, preferably an alkyl or aryl group as a substituent. 31 ~R 35 The remaining one of the aryl groups may be substituted with an alkyl or aryl group at position 4, or substituted with an alkyl or aryl group at positions 3 and 5. When the remaining one of the aryl groups is a hydrogen atom, a substituted or unsubstituted aryl group, or a cyano group, it may be R 31 ~R 35 Any one of, but preferably R 33 .

[0104] Examples of preferred compound groups represented by the general formula (2) include compound groups represented by the following general formula (2a).

[0105] [Chemical formula 10]

[0106] General formula (2a)

[0107]

[0108] In the general formula (2a), R 41 ~R 44 , R 46 ~R 49Each independently represents a substituent, but the four substituted or unsubstituted carbazole-9-yl groups bonded to the benzonitrile of the general formula (2a) are not all the same. n41 to n44 and n46 to n49 each independently represent an integer of 0 to 4. 45 represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted carbazole-9-yl group or a cyano group.

[0109] About R 41 ~R 44 , R 46 ~R 49 The substituents that can be used can refer to R in the description of the general formula (2). 31 ~R 35 Description of substituents that can be used for carbazole-9-yl. 45 The groups that can be used can refer to R in the description of general formula (2). 31 ~R 35 The remaining one can be used for the record of the group.

[0110] When n41 is 2 or more, multiple R 41 They can be the same or different, and two adjacent R 41 They may be bonded to form a ring structure or may not form a ring structure. 42 They can be the same or different, and two adjacent R 42 They may be bonded to form a ring structure or may not form a ring structure. 43 They can be the same or different, and two adjacent R 43 They may be bonded to form a ring structure or may not form a ring structure. 44 They can be the same or different, and two adjacent R 44 They may be bonded to form a ring structure or may not form a ring structure. 46 They can be the same or different, and two adjacent R 46 They may be bonded to form a ring structure or may not form a ring structure. 47 They can be the same or different, and two adjacent R 47 They may be bonded to form a ring structure or may not form a ring structure. 48 They can be the same or different, and two adjacent R 48 They may be bonded to form a ring structure or may not form a ring structure. 49They can be the same or different, and two adjacent R 49 They may be bonded to form a ring structure or may not form a ring structure. Regarding the ring structure described here, the description of the ring structure in the general formula (1) can be referred to.

[0111] n41 to n49 are preferably any integer of 0 to 3, and more preferably any integer of 0 to 2. The sum of n41 to n49 is preferably 1 to 24, more preferably 1 to 16, and even more preferably 1 to 8.

[0112] As examples of combinations of n41 to n44, n46 to n49, there can be cited the case where only n41 is 1 and the others are 0, the case where only n43 is 1 and the others are 0, the case where n41 and n42 are 1 and the others are 0, the case where n43 and n44 are 1 and the others are 0, the case where n41 and n43 are 1 and the others are 0, the case where n41 and n46 are 1 and the others are 0, the case where n41 and n48 are 1 and the others are 0, the case where n41 to n44 are 1 and the others are 0, the case where n41, n42, n46, and n47 are 1 and the others are 0, the case where n43, n44, n46, and n47 are 1 and the others are 0, the case where n41 and n42 are 0 and the others are 1, and the case where n43 and n44 are 0 and the others are 1.

[0113] The compound represented by the general formula (2) or the general formula (2a) can be synthesized with reference to Synthesis Example 2 described later. That is, it can be synthesized by introducing a substituted or unsubstituted carbazole-9-yl group to the 2-position and the 6-position by reacting a substituted or unsubstituted carbazole with 4-phenyl-2,3,5,6-tetrafluorobenzonitrile, and further introducing a substituted or unsubstituted diarylcarbazole-9-yl group to the 3-position and the 5-position by reacting with a substituted or unsubstituted diarylcarbazole. It can also be synthesized by combining known synthesis methods.

[0114] Specific examples of compounds represented by general formula (2) are given in Tables 1 and 2 below, but the compounds that can be used in the present invention are not to be construed as being restrictive by the following specific examples. General formulas (3a) and (3b) representing substituents in general formula (2) are also described below.

[0115] [Chemical formula 11]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] [Chemical formula 12]

[0122]

[0123] [Combination of a compound represented by the general formula (1) and a compound represented by the general formula (2)]

[0124] The compound represented by the general formula (1) and the compound represented by the general formula (2) can be used as a material for an organic light-emitting element. In an organic light-emitting element, energy is efficiently transferred from the compound represented by the general formula (2) to the compound represented by the general formula (1), and the energy is used for light emission. Taking an organic electroluminescent element including a compound represented by the general formula (1) and a compound represented by the general formula (2) as an example, the mechanism is described below.

[0125] In an organic electroluminescent element, if excitation energy is generated by the recombination of holes and electrons injected from the electrodes, the organic compound contained in the organic layer between the electrodes transitions from the ground state to an excited singlet state and an excited triplet state. According to statistics, the formation probability of an organic compound in an excited singlet state (singlet exciton) and an organic compound in an excited triplet state (triplet exciton) is 25% for a singlet exciton and 75% for a triplet exciton. Moreover, the energy of the compound of the general formula (2) in the excited singlet state among the excitons is transferred to the compound of the general formula (1), and the compound of the general formula (1) in the ground state transitions to an excited singlet state. The compound of the general formula (1) in the excited singlet state emits fluorescence when it returns to the ground state thereafter. Alternatively, the energy of the compound of the general formula (1) in the excited singlet state is transferred to another luminescent material, and the luminescent material in the ground state transitions to an excited singlet state and emits fluorescence when it returns to the ground state thereafter.

[0126] At this time, in the organic electroluminescent element of the present invention, the compound of the general formula (2) is a compound that easily undergoes reverse intersystem crossing from the excited triplet state to the excited singlet state, and thus the singlet excitation energy based on the reverse intersystem crossing is also transferred to the compound of the general formula (1). Therefore, the energy of the excited triplet state with a large existence ratio also indirectly contributes to luminescence, and compared with the structure not containing the compound of the general formula (2), the luminous efficiency of the organic electroluminescent element can be greatly improved.

[0127] The compound of general formula (2) is preferably a compound that can perform reverse intersystem crossing as easily as possible. Therefore, it is preferably a thermally activated delayed fluorescent body that reversely crosses from the excited triplet state to the excited singlet state by absorbing thermal energy. The thermally activated delayed fluorescent material absorbs the heat emitted by the device and relatively easily reverses the intersystem crossing from the excited triplet state to the excited singlet state, thereby enabling the excited triplet state to contribute to luminescence with good energy efficiency. The compound of general formula (2) preferably has an energy level E in the lowest excited singlet state. S1 The energy level E of the lowest excited triplet state at 77K T1 The difference ΔE ST It is 0.3 eV or less, more preferably 0.2 eV or less, further preferably 0.15 eV or less, and further preferably 0.10 eV or less. Energy difference ΔE ST Small compounds are relatively easy to cause reverse intersystem crossing from the excited triplet state to the excited singlet state, so that the excited triplet state energy efficiency can be good to contribute to luminescence. In addition, the accumulation of triplet excitons during the excitation process is effectively suppressed. Therefore, by using the compound represented by the general formula (2), the exciton annihilation or device degradation caused by the accumulation of triplet excitons can be suppressed, thereby obtaining excellent high durability in addition to higher luminous efficiency. In addition, by suppressing exciton annihilation, it can also greatly contribute to the realization of organic lasers.

[0128] By using the compound represented by the general formula (1) and the compound represented by the general formula (2) in an organic light-emitting element, an organic light-emitting element that emits good blue light can be realized. For example, an organic light-emitting element that can emit light having a color coordinate x of less than 0.23 and y of less than 0.40 (preferably x is less than 0.20 and y is less than 0.30, more preferably x is less than 0.16 and y is less than 0.26) in the CIE-XYZ color system can be provided. There are almost no organic light-emitting elements that provide satisfactory high luminous efficiency and emit good blue light, so the usefulness of the present invention is extremely high. In addition, the luminous color of the organic light-emitting element of the present invention is not necessarily limited to blue. Even if it is an organic light-emitting element that realizes light emission other than blue, as long as it is an organic light-emitting element using the compound represented by the general formula (1) and the compound represented by the general formula (2), it is included in the scope of the present invention.

[0129] [Organic light emitting device]

[0130] The compound represented by the general formula (1) and the compound represented by the general formula (2) may be contained together in any layer constituting the organic light-emitting element, and each compound may be contained in a different layer. In the case of being contained in different layers, it is preferred that each compound is contained in mutually adjacent layers. For example, it is possible to configure that the compound represented by the general formula (1) and the compound represented by the general formula (2) are simultaneously contained in the light-emitting layer, the compound represented by the general formula (1) and the compound represented by the general formula (2) are simultaneously contained in the layer adjacent to the light-emitting layer, or the compound represented by the general formula (1) is contained in the light-emitting layer and the compound represented by the general formula (2) is contained in the layer adjacent to the light-emitting layer.

[0131] In an organic light-emitting element, it is preferred to use a larger amount of the compound represented by the general formula (2) than the compound represented by the general formula (1). When the total amount of these compounds is 100 parts by weight, the compound represented by the general formula (1) is preferably used in an amount of 0.01 to 49.9 parts by weight, more preferably 1 to 35 parts by weight.

[0132] When the compound represented by the general formula (1) and the compound represented by the general formula (2) are simultaneously contained in the light-emitting layer, a host material may be contained in addition to these compounds. The host material is an organic compound whose lowest excited singlet energy is greater than that of the compound represented by the general formula (1) or the compound represented by the general formula (2), and the host material has the function of being a host material responsible for transporting carriers or the function of sealing the energy of the compound represented by the general formula (1) into the compound. Thus, the organic compound represented by the general formula (1) can efficiently convert the energy generated by the recombination of holes and electrons within the molecule and the energy received from the host material and the compound represented by the general formula (2) into luminescence, thereby realizing an organic electroluminescent element with high luminescence efficiency.

[0133] As the host material, it is preferred to use an organic compound that has hole transport capability, electron transport capability, prevents the emission of light at a long wavelength, and has a high glass transition temperature. It is preferred that more host material is included in the light-emitting layer than the compound represented by the general formula (1) or the compound represented by the general formula (2). Specifically, it is preferably set to 40% by weight or more of the total weight of the light-emitting layer, more preferably to 50% by weight or more, and preferably to 99.9% by weight or less, more preferably to 95% by weight or less. In the case where the light-emitting layer only contains the compound represented by the general formula (1) and the compound represented by the general formula (2), and in the case where the light-emitting layer contains the compound represented by the general formula (1), the compound represented by the general formula (2), and the host material, after energy transfer from the compound represented by the general formula (2) to the compound represented by the general formula (1), the light is mainly emitted by the compound represented by the general formula (1).

[0134] When the compound represented by the general formula (1) and the compound represented by the general formula (2) are simultaneously contained in the light-emitting layer, a light-emitting material may be contained in addition to these compounds. The light-emitting material is a compound whose lowest excited singlet energy is less than that of the compound represented by the general formula (1). In this case, the light-emitting layer may also contain a host material. The light-emitting material receives energy transfer from the compound represented by the general formula (1), the compound represented by the general formula (2), or both of them and emits light. In this case, light emission from the compound represented by the general formula (1) is sometimes observed. The content of the light-emitting material in the light-emitting layer is preferably set to 0.01% by weight to 30% by weight of the total weight of the light-emitting layer, and more preferably set to 0.1% by weight to 15% by weight.

[0135] In the case where the compound represented by the general formula (1) and the compound represented by the general formula (2) are simultaneously contained in a layer adjacent to the light-emitting layer, the light-emitting layer contains a light-emitting material. The light-emitting layer may contain a compound represented by the general formula (1). The light-emitting material of the light-emitting layer receives energy transfer from the compound represented by the general formula (1), the compound represented by the general formula (2), or both of the adjacent layers and emits light.

[0136] The compound represented by the general formula (1) may be contained in the light-emitting layer and the compound represented by the general formula (2) may be contained in a layer adjacent to the light-emitting layer. The compound represented by the general formula (1) may receive energy transfer from the compound represented by the general formula (2) and emit light, or the light-emitting layer may further contain a light-emitting material and emit light from the light-emitting material.

[0137] The use of the compound represented by the general formula (1) and the compound represented by the general formula (2) in the organic light-emitting device can be appropriately adjusted according to the purpose of production or the function of the organic light-emitting device.

[0138] Next, the structure of the organic light-emitting element will be described.

[0139] An organic photoluminescent (PL) element has a structure in which at least a light-emitting layer is formed on a substrate. Furthermore, an organic electroluminescent (EL) element has a structure in which at least an anode, a cathode, and an organic layer is formed between the anode and the cathode. The organic layer at least includes a light-emitting layer, and may be composed of only the light-emitting layer, or may have one or more organic layers in addition to the light-emitting layer. Examples of such other organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, an exciton blocking layer, and the like. The hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function. When the compound represented by the general formula (1) and the compound represented by the general formula (2) are included in a layer adjacent to the light-emitting layer, these compounds may be included in any of the above-mentioned layers adjacent to the light-emitting layer. The structure of a specific organic electroluminescent element is shown in Figure 1 .exist Figure 1 , 1 represents a substrate, 2 represents an anode, 3 represents a hole injection layer, 4 represents a hole transport layer, 5 represents a light emitting layer, 6 represents an electron transport layer, and 7 represents a cathode.

[0140] The following describes the components and layers of the organic electroluminescent element. In addition, the description of the substrate and the light-emitting layer also corresponds to the substrate and the light-emitting layer of the organic photoluminescent element.

[0141] (Substrate)

[0142] The organic electroluminescent element of the present invention is preferably supported by a substrate. The substrate is not particularly limited as long as it is a substrate conventionally used in organic electroluminescent elements, and for example, a substrate made of glass, transparent plastic, quartz, silicon, etc. can be used.

[0143] (anode)

[0144] As the anode of the organic electroluminescent element, it is preferred to use an anode that uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (above 4 eV) as an electrode material. As specific examples of such electrode materials, conductive transparent materials such as Au, CuI, indium tin oxide (ITO), SnO2, and ZnO can be cited. In addition, amorphous materials such as IDIXO (In2O3-ZnO) that can be used to make transparent conductive films can also be used. Regarding the anode, these electrode materials can be formed into a thin film by methods such as evaporation or sputtering, and a pattern of the desired shape can be formed by photolithography, or in the case where the pattern accuracy is not required (about 100 μm or more), a pattern can be formed through a mask of the desired shape during the evaporation or sputtering of the above-mentioned electrode material. Alternatively, in the case of using a material that can be coated such as an organic conductive compound, a wet film forming method such as a printing method or a coating method can also be used. In the case of extracting luminescence from the anode, it is preferred that the transmittance is set to be greater than 10%, and the film resistance of the anode is preferably less than hundreds of Ω / □. The film thickness also depends on the material, but is usually selected within the range of 10 to 1000 nm, preferably 10 to 200 nm.

[0145] (cathode)

[0146] On the other hand, as a cathode, a cathode using a metal (called an electron injecting metal) with a small work function (less than 4 eV), an alloy, a conductive compound, and a mixture thereof as an electrode material can be used. Specific examples of such electrode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al2O3) mixtures, indium, lithium / aluminum mixtures, and rare earth metals. Among them, from the perspective of electron injectability and durability to oxidation, it is preferred that the electron injecting metal and a metal having a larger work function value than the metal and being stable, i.e., a second metal, be a mixture, for example, a magnesium / silver mixture, a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al2O3) mixture, a lithium / aluminum mixture, and aluminum. As for the cathode, it can be made by forming these electrode materials into a thin film using methods such as evaporation or sputtering. In addition, the film resistance of the cathode is preferably less than several hundred Ω / □, and the film thickness is usually selected in the range of 10nm to 5μm, preferably in the range of 50 to 200nm. In addition, if either the anode or cathode of the organic electroluminescent element is transparent or semi-transparent in order to transmit the emitted light, the emission brightness is improved, which is preferred.

[0147] Furthermore, by using the conductive transparent material mentioned in the description of the anode for the cathode, a transparent or semi-transparent cathode can be produced, and by using this cathode, two translucent elements, the anode and the cathode, can be produced.

[0148] (Luminous layer)

[0149] The light-emitting layer is a layer that emits light after the holes and electrons injected from the anode and the cathode are re-bonded to generate excitons. The light-emitting layer can be a layer containing a compound represented by the general formula (1) and a compound represented by the general formula (2), a layer containing a compound represented by the general formula (1), a compound represented by the general formula (2) and a host material, a layer containing a compound represented by the general formula (1), a compound represented by the general formula (2) and a light-emitting material, a layer containing a compound represented by the general formula (1), a compound represented by the general formula (2), a light-emitting material and a host material, a layer containing a light-emitting material, a layer containing a light-emitting material and a host material, a layer containing a light-emitting material and a compound represented by the general formula (1), etc. In the case where the light-emitting layer does not contain a compound represented by the general formula (1), the layer adjacent to the light-emitting layer contains a compound represented by the general formula (1). In the case where the light-emitting layer does not contain a compound represented by the general formula (2), the layer adjacent to the light-emitting layer contains a compound represented by the general formula (2).

[0150] (Injection layer)

[0151] The injection layer refers to a layer provided between the electrode and the organic layer in order to reduce the driving voltage or increase the luminance of the light. There are hole injection layers and electron injection layers, and they can be provided between the anode and the light-emitting layer or the hole transport layer and between the cathode and the light-emitting layer or the electron transport layer. The injection layer can be provided as required.

[0152] (Barrier layer)

[0153] The blocking layer is a layer that can prevent the charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. The electron blocking layer can be arranged between the light-emitting layer and the hole transport layer to prevent electrons from passing through the light-emitting layer toward the hole transport layer. Similarly, the hole blocking layer can be arranged between the light-emitting layer and the electron transport layer to prevent holes from passing through the light-emitting layer toward the electron transport layer. The blocking layer can also be used to prevent excitons from diffusing to the outside of the light-emitting layer. That is, the electron blocking layer and the hole blocking layer can also have the function of an exciton blocking layer respectively. The electron blocking layer or exciton blocking layer described in this specification is used in the sense of including a layer having the functions of an electron blocking layer and an exciton blocking layer as a layer.

[0154] (Hole Blocking Layer)

[0155] The hole blocking layer has the function of an electron transport layer in a broad sense. The hole blocking layer has the function of transporting electrons and preventing holes from reaching the electron transport layer, thereby increasing the probability of re-bonding of electrons and holes in the light-emitting layer. As the material of the hole blocking layer, the material of the electron transport layer described later can be used as needed.

[0156] (Electron blocking layer)

[0157] The electron blocking layer has a function of transporting holes in a broad sense. The electron blocking layer has the function of transporting holes and preventing electrons from reaching the hole transporting layer, thereby increasing the probability of re-bonding of electrons and holes in the light-emitting layer.

[0158] (Exciton blocking layer)

[0159] The exciton blocking layer refers to a layer used to block the excitons generated by the rebonding of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. The insertion of this layer can effectively seal the excitons in the light-emitting layer, which can improve the luminous efficiency of the element. The exciton blocking layer is adjacent to the light-emitting layer and can be inserted on either side of the anode side and the cathode side, and can also be inserted on both sides at the same time. That is, in the case of having an exciton blocking layer on the anode side, the layer can be inserted between the hole transport layer and the light-emitting layer, adjacent to the light-emitting layer, and in the case of inserting it on the cathode side, the layer can be inserted between the light-emitting layer and the cathode, adjacent to the light-emitting layer. In addition, there can be a hole injection layer or an electron blocking layer between the anode and the exciton blocking layer on the anode side adjacent to the light-emitting layer, and there can be an electron injection layer, an electron transport layer, a hole blocking layer, etc. between the cathode and the exciton blocking layer on the cathode side adjacent to the light-emitting layer. When a blocking layer is provided, it is preferred that at least one of the singlet energy and triplet energy of a material used as the blocking layer is higher than the singlet energy and triplet energy of the light-emitting material.

[0160] (Hole Transport Layer)

[0161] The hole transport layer is composed of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.

[0162] As a hole transport material, it has any one of the properties of hole injection or transport and electron blocking, and can be any one of organic and inorganic substances. As known hole transport materials that can be used, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indole and carbazole derivatives, polyaryl alkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers can be cited, conductive polymer oligomers can also be cited, especially thiophene oligomers can be cited, preferably porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds are used, and more preferably aromatic tertiary amine compounds are used.

[0163] (Electron Transport Layer)

[0164] The electron transport layer is composed of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.

[0165] As an electron transport material (which also serves as a hole blocking material), it is sufficient as long as it has the function of transferring electrons injected from the cathode to the light-emitting layer. As the electron transport layer that can be used, for example, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenyl methane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, etc. can be cited. Moreover, among the above-mentioned oxadiazole derivatives, thiadiazole derivatives obtained by replacing the oxygen atom of the oxadiazole ring with a sulfur atom, and quinoxaline derivatives having a quinoxaline ring known as an electron-withdrawing group can also be used as electron transport materials. Moreover, polymer materials that introduce these materials into polymer chains or use these materials as the main chain of polymers can also be used.

[0166] The following specifically illustrates preferred materials that can be used in organic electroluminescent elements. Among them, the materials that can be used in the present invention are not interpreted restrictively by the following exemplified compounds. Moreover, even if the compounds are illustrated as materials with specific functions, they can also be used as materials with other functions.

[0167] First, preferred compounds that can be used as a host material for the light-emitting layer are listed.

[0168] [Chemical formula 13]

[0169]

[0170] [Chemical formula 14]

[0171]

[0172] [Chemical formula 15]

[0173]

[0174] [Chemical formula 16]

[0175]

[0176] [Chemical formula 17]

[0177]

[0178] Next, preferred examples of compounds that can be used as hole injection materials are given.

[0179] [Chemical formula 18]

[0180]

[0181] Next, preferred examples of compounds that can be used as hole transport materials are given.

[0182] [Chemical formula 19]

[0183]

[0184] [Chemical formula 20-1]

[0185]

[0186] [Chemical formula 20-2]

[0187]

[0188] [Chemical formula 21]

[0189]

[0190] [Chemical formula 22]

[0191]

[0192] [Chemical formula 23]

[0193]

[0194] [Chemical formula 24]

[0195]

[0196] Next, preferred examples of compounds that can be used as the electron blocking material are given.

[0197] [Chemical formula 25]

[0198]

[0199] Next, preferred examples of compounds that can be used as hole blocking materials are given.

[0200] [Chemical formula 26]

[0201]

[0202] Next, preferred examples of compounds that can be used as electron transport materials are given.

[0203] [Chemical formula 27]

[0204]

[0205] [Chemical formula 28]

[0206]

[0207] [Chemical formula 29]

[0208]

[0209] Next, preferred examples of compounds that can be used as electron injection materials are given.

[0210] [Chemical formula 30]

[0211]

[0212] Furthermore, examples of compounds which are more preferable as materials that can be added are given. For example, it is considered that compounds can be added as stabilizing materials.

[0213] [Chemical formula 31]

[0214]

[0215] Organic electroluminescent elements emit light by applying an electric field between the anode and cathode of the obtained element. At this time, as long as it is based on the luminescence of the excited singlet energy, the light of the wavelength corresponding to its energy level is confirmed as fluorescent luminescence and delayed fluorescent luminescence. And, as long as it is based on the luminescence of the excited triplet energy, the wavelength corresponding to its energy level is confirmed as phosphorescence. The fluorescence lifetime of common fluorescence is shorter than delayed fluorescent luminescence, so the luminescence lifetime can be distinguished according to fluorescence and delayed fluorescence.

[0216] On the other hand, regarding phosphorescence, in common organic compounds such as the compound of the present invention, triplet excited state energy is unstable and is converted into heat, etc., resulting in a short life span and immediate deactivation, and therefore, it is almost impossible to observe at room temperature. In order to measure the triplet excited state energy of common organic compounds, it can be measured by observing the luminescence under extremely low temperature conditions.

[0217] The organic electroluminescent element of the present invention can be applied to any of a single element, an element composed of a structure arranged in an array, and a structure in which the anode and the cathode are arranged in an XY matrix. According to the present invention, by containing a compound represented by the general formula (1) and a compound represented by the general formula (2), an organic light-emitting element with high luminous efficiency can be provided. Organic light-emitting elements such as the organic electroluminescent element of the present invention can be further applied to various purposes. For example, an organic electroluminescent display device can be manufactured using the organic electroluminescent element of the present invention. For details, reference can be made to "Organic EL Display" (Ohmsha, Ltd.) co-authored by Shizuo Tokito, Chiba Ando, ​​and Hideyuki Murata. In addition, the organic electroluminescent element of the present invention can also be applied to organic electroluminescent lighting or backlighting, which has a large demand.

[0218] [Composition and film]

[0219] The present invention also provides a composition comprising a compound represented by the general formula (1) and a compound represented by the general formula (2). The composition may be in a solution state or in a solid state. When the composition is in a solution state, it is dissolved in a solvent in which both the compound represented by the general formula (1) and the compound represented by the general formula (2) are dissolved. For example, toluene can be used.

[0220] The present invention also provides a film comprising a compound represented by the general formula (1) and a compound represented by the general formula (2). The compound represented by the general formula (1) and the compound represented by the general formula (2) may be mixed in the film, or may include a structure in which a layer comprising the compound represented by the general formula (1) and a layer comprising the compound represented by the general formula (2) are stacked. The film comprising the compound represented by the general formula (1) and the compound represented by the general formula (2) can be used as a film for an organic light-emitting element, but can also be used for other purposes.

[0221] Example

[0222] The following examples are given to further specifically describe the features of the present invention. The materials, processing contents, processing steps, etc. shown below can be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention should not be interpreted restrictively by the specific examples shown below.

[0223] The evaluation of the luminescence characteristics described below was performed using an ultraviolet-visible-near-infrared spectrophotometer (manufactured by PerkinElmeRCo., Ltd.: Lambda950-PKA), a fluorescence spectrophotometer (manufactured by HORIBA: Fluoro Max-4), a multi-channel spectrometer (manufactured by Hamamatsu Photonics KK: PMA-12C10027-01), a photoexcitation absolute luminescence quantum yield measuring device (manufactured by Hamamatsu Photonics KK: C9920PMA-11), a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics KK: C11367-25) and a streak camera (manufactured by Hamamatsu Photonics KK: U8167-1). In addition, in this example, fluorescence with a luminescence lifetime of 100 ns or less was determined as transient fluorescence, and fluorescence with a luminescence lifetime of 0.1 μs or more was determined as delayed fluorescence.

[0224] (Synthesis Example 1) Synthesis of Compound 1

[0225] [Phase 1]

[0226] [Chemical formula 32]

[0227]

[0228] Under a nitrogen atmosphere, a flask containing 1,3-dibromobenzene (25.0 g, 106 mmol), aniline (20.3 ml, 223 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (971 mg, 1.06 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP: 1.98 g, 3.18 mmol), NaOtBu (25.5 g, 265 mmol) and toluene (400 ml) was heated to 110°C and stirred for 18 hours. The reaction solution was cooled to room temperature, filtered using silica gel (eluent: toluene), and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was dissolved in toluene, and an appropriate amount was distilled off under reduced pressure, and hexane was added to reprecipitate it, thereby obtaining N 1 ,N 3 -diphenylbenzene-1,3-diamine (16.5 g, yield 60%) as a white solid.

[0229] 1 H-NMR (400MHz, CDCl3): δ=5.63(s,2H), 6.60(dd,2H), 6.74(t,1H), 6.90(t,2H), 7.06(d,4H), 7.12(t,1H), 7.24(dt,4H).

[0230] [Phase 2]

[0231] [Chemical formula 33]

[0232]

[0233] Under a nitrogen atmosphere, a flask containing 1,3-dibromo-5-chlorobenzene (8.11 g, 30 mmol), diphenylamine (10.1 g, 60 mmol), Pd2(dba)3 (550 mg, 0.6 mmol), 2-dicyclohexylphenylphosphine-2',6'-dimethoxydiphenyl (SPhos: 0.493 g, 1.2 mmol), NaOtBu (8.60 g, 90 mmol) and toluene (300 ml) was heated to 80°C and stirred for 15 hours. The reaction solution was cooled to room temperature, filtered using silica gel (eluent: toluene), and the solvent was distilled under reduced pressure to obtain a crude product. The obtained crude product was dissolved in toluene and then distilled under reduced pressure to prepare a saturated solution, and hexane was added to reprecipitate it, thereby obtaining 5-chloro-N 1 ,N 1 ,N 3 ,N 3-tetraphenylbenzene-1,3-diamine (5.66 g, yield 43%) as a white solid.

[0234] 1 H-NMR (400MHz, CDCl3): δ=6.56(d,2H), 6.64(t,1H), 7.00(t,4H), 7.05(d,8H), 7.21(dd,8H).

[0235] [Phase 3]

[0236] [Chemical formula 34]

[0237]

[0238] In a nitrogen atmosphere, the N synthesized in the first stage was introduced 1 ,N 3 -diphenylbenzene-1,3-diamine (1.34 g, 5.1 mmol), 5-chloro-N- 1 ,N 1 ,N 3 ,N 3 -tetraphenylbenzene-1,3-diamine (4.80 g, 11 mmol), Pd2(dba)3 (0.140 g, 0.15 mmol), tri-tert-butylphosphine (60.7 mg, 0.30 mmol), NaOtBu (1.47 g, 15 mmol) and toluene (200 ml) were heated to 110°C in a flask and stirred for 8 hours. The reaction solution was cooled to room temperature, filtered using silica gel (eluent: toluene), and the solvent was distilled under reduced pressure to obtain a crude product. The obtained crude product was washed with hexane and methanol in turn to obtain N 1 ,N 1 '-(1,3-phenylene)bis(N 1 ,N 3 ,N 3 ,N 5 ,N 5 -pentaphenylbenzene-1,3,5-triamine (4.80 g, yield 87%) as a white solid.

[0239] 1 H-NMR (400MHz, CDCl3): δ=6.38(d,4H), 6.41(t,2H), 6.58(dd,2H), 6.70(t,1H), 6.88-6.90(m,14H), 6.85(t,1H), 6.99(d,16H), 7.08-7.15(m,20H).

[0240] [Phase 4]

[0241] [Chemical formula 35]

[0242]

[0243] In a nitrogen atmosphere, at room temperature, 1 ,N 1 '-(1,3-phenylene)bis(N 1 ,N 3 ,N 3 ,N 5 ,N 5 -pentaphenylbenzene-1,3,5-triamine (3.24 g, 3.0 mmol) and o-dichlorobenzene (400 ml) were added with boron tribromide (1.13 ml, 12 mmol). After the addition was completed, the temperature was raised to 180°C and stirred for 20 hours. After that, it was cooled to room temperature again, N-diisopropylethylamine (7.70 ml, 45 mmol) was added, and stirred until the heat stopped. After that, the reaction solution was distilled off under reduced pressure at 60°C to obtain a crude product. The obtained crude product was washed with acetonitrile, methanol, and toluene in turn, purified by silica gel column chromatography (eluent: toluene), and the crude product was recrystallized twice with o-dichlorobenzene, and then at 1×10 - 4 Sublimation purification was performed at 440° C. under a reduced pressure of 0.17 mmH g to obtain 1.17 g of Compound 1.

[0244] 1 H-NMR (400MHz, CDCl3): δ=5.72(s,2H), 5.74(s,2H), 5.86(s,1H), 6.83(d ,2H), 6.88-6.93(m,12H), 7.05(t,8H), 7.12-7.19(m,6H), 7.24-7.26(m, 4H), 7.05(d,4H), 7.12(dd,8H), 7.12-7.19(m,6H), 7.32(d,4H), 7.38(dd ,2H), 7.42(t,2H), 7.46(dd,2H), 7.47(dd,4H), 9.30(d,2H), 10.5(s,1H).

[0245] 13C-NMR (101MHz, CDCl3): 99.5(2C+2C), 103.4(1C), 116.8(2C), 120.0(2C), 123.1(4C), 125.3(8C), 127.1(2C), 127.6(2C), 128.5(8C), 129.6(4C), 12 9.8(4C), 130.2(4C+2C), 130.3(4C), 135.0(2C), 142.1(2C), 142.5(2C), 1 43.3(1C), 146.8(4C), 147.9(2C+2C), 148.0(2C), 150.1(2C), 151.1(2C).

[0246] (Synthesis Example 2) Synthesis of Compound 2-38

[0247] [Phase 1 and Phase 2]

[0248] [Chemical formula 36]

[0249]

[0250] Under nitrogen flow, tributyltin chloride (5.06g, 4.45mL, 13.78mmol) and 4-bromo-2,3,5,6-tetrafluorobenzonitrile (2.92g, 11.50mmol) were added to a toluene solution (50mL) of tri(o-toluene)phosphine (0.525g, 1.72mmol) and tri(dibenzylideneacetone)palladium (0) (1.57g, 1.72mmol), and the temperature was raised to 100°C and stirred for 21 hours. The mixture was returned to room temperature and quenched with water, extracted with ethyl acetate, and filtered with diatomaceous earth. Then, the organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate. It was concentrated under reduced pressure, and the obtained mixture was purified by silica gel column chromatography (dichloromethane: hexane = 1: 2) to obtain compound a (2.42g, 9.63mmol, yield 83.7%) as a white solid.

[0251] 1 H-NMR (500MHz, CDCl3): δ=7.56-7.51(m,3H),7.48-7.45(m,2H)

[0252] ASAP mass spectrometry analysis: theoretical value 251.0, observed value 251.1

[0253] Under nitrogen flow, 9H-carbazole (0.397g, 2.38mmol) was added to a tetrahydrofuran solution (10mL) of sodium hydride (60% mineral oil dispersion, 0.125g, 3.14mmol), and stirred at room temperature for 1 hour. The mixture was cooled to -50 ° C and compound a (0.3g, 1.19mmol) was added, the cooling bath was removed, and the mixture was gradually returned to room temperature and stirred for 22 hours. The reaction mixture was added to ice water for quenching, extracted with ethyl acetate, the organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate. It was concentrated under reduced pressure, and the obtained mixture was purified by silica gel column chromatography (chloroform: hexane = 1: 2) to obtain compound b (0.486g, 0.89mmol, yield 74.8%) as a yellow solid.

[0254] 1 H-NMR (500MHz, CDCl3): δ=8.16(d,J=7.5Hz,4H), 7.62-7.59(m,2H), 7.54-7.49(m,7H), 7.38(dt,J=7.5Hz,1.0Hz,4H), 7.30(d,J=7.5Hz,4H),

[0255] ASAP mass spectrometry analysis: theoretical value 545.2, observed value 545.2

[0256] [Phase 3]

[0257] [Chemical formula 37]

[0258]

[0259] Under nitrogen flow, compound b (0.45 g, 0.825 mmol) was added to a 1-methyl-2-pyrrolidone solution (10 mL) of 3,6-diphenylcarbazole (0.66 g, 2.06 mmol) and potassium carbonate (0.43 g, 3.11 mmol), and stirred at 100 ° C for 48 hours. The mixture was returned to room temperature and quenched with water, extracted with ethyl acetate, washed with saturated brine, and dried with anhydrous magnesium sulfate. It was concentrated under reduced pressure, and the obtained mixture was purified by silica gel column chromatography (chloroform: hexane = 1: 1) to obtain compound 2-38 (0.575 g, 0.502 mmol, yield 60.9%) as a yellow solid.

[0260] 1H-NMR (500MHz, CDCl3): δ=7.81 (d, J=1.5Hz, 4H), 7.72-7.70 (m, 4H), 7.54-7.52 (m, 8H), 7.43 (t, J=7.5Hz ,8H), 7.32(t,J=7.5Hz,4H), 7.29-7.06(m,20H), 6.86-6.83(m,2H), 6.61-6.58(m,1H), 6.56-6.52(m,2H)

[0261] ASAP mass spectrometry analysis: theoretical value 1143.4, observed value 1143.4

[0262] (Synthesis Example 3) Synthesis of Compound 2-117

[0263] [Phase 1]

[0264] [Chemical formula 38]

[0265]

[0266] Under a nitrogen atmosphere, 9H-carbazole (167 mg, 1 mmol) was dried and dissolved in N,N-dimethylformamide (30 mL), and NaH (40 mg, 1 mmol) was added at 0°C, and stirred at room temperature for 30 minutes. Then, tetrafluorobenzonitrile (175 mg, 1 mmol) was added and stirred at room temperature for 16 hours. The precipitate was quenched with water and filtered out, and the crude product was purified by column chromatography to obtain intermediate a (yield 193 mg, yield 60%).

[0267] 1 H NMR (500 MHz, CDCl3, 298 K, relative to Me4Si): δ = 8.16 (d, 2H, 7.5 Hz), 7.53-7.58 (m, 1H), 7.48 (t, 2H, 7.0 Hz), 7.38 (t, 2H, 7.5 Hz), 7.11 (d, 2H, 8.0 Hz); 13 C NMR (126MHz, CDCl3): δ=155.8,155.7,153.8,153.7,150.9,150.8,150.7,150.1,150.0,149.9,148.8,148.7,148.6,148.0,147.9,147.8 ,140.0,126.6,124.4,124.3,124.3,124.2,124.2,121.6,120.8,112.2,112.0,111.9,111.8,109.4,109.3,109.2,109.2,105.5,105.4;

[0268] 19 F NMR (471MHz, CDCl3): δ=-114.32(m,1H),-128.05(m,1H),-130.54(m,1H);

[0269] Calculate C 19 MS of H9F3N2 (APCI):

[0270] m / z=322.08; Found: 322.17[M] + .

[0271] [Phase 2]

[0272] [Chemical formula 39]

[0273]

[0274] Under nitrogen atmosphere, 3,6-diphenyl-9H-carbazole (957 mg, 3 mmol) was dried and dissolved in N,N-dimethylformamide (30 mL), and NaH (120 mg, 3 mmol) was added at 0°C, and stirred at room temperature for 30 minutes. Then, 2-(9H-carbazole-9-yl)-3,5,6-trifluorobenzonitrile (322 mg, 1 mmol) was added, and heated at 150°C for 16 hours. The precipitate was quenched with water and filtered, and the crude product was purified by column chromatography to obtain compound 2-117 (yield 976 mg, yield 80%).

[0275] 1 H NMR (500 MHz, deuterated acetone, 298 K, relative to Me4Si): δ = 9.07 (s, 1H), 8.36 (s, 2H), 8.29 (d, 4H, 10.0 Hz), 7.95-8.00 (m, 10H), 7.55-7.70 (m, 18H), 7.30-7.45 (m, 20H), 7.18 (t, 2H, 7.0 Hz). 13 C NMR (126 MHz, deuterated acetone): δ = 143.1, 143.1, 142.1, 142.0, 141.6, 141.5, 141.0, 140.7, 140.2, 140.0, 136.2, 135.9, 135.8, 130.6, 130.5, 128.8, 128.8, 128.7, 128.5, 128.4, 127.6, 126.8, 126.7, 126.7, 126.5, 126.42, 125.8, 122.9, 122.0, 120.5, 120.4, 120.4, 113.4, 112.9, 112.7, 112.7.

[0276] Calculate C 91 H 57 MS of N5 (APCI):

[0277] m / z=1220.5; Found:1221.0[M] + .C 91 H 57 Elemental analysis calculated values ​​of N5 (%): C89.55, H4.71, N5.74; measured values: C89.51, H4.65, N5.72.

[0278] (Preliminary determination) Determination of compound 1 and compounds 2-38

[0279] Toluene solutions of compound 1 and compounds 2-38 (each with a concentration of 10 -5 mol / L).

[0280] The results of spectroscopic measurements of the toluene solutions of Compound 1 and Compound 2-38 at 300 K are shown in FIG. Figure 2 In. Figure 2 The upper part shows the absorption spectrum of the toluene solution of compound 1 and the emission spectrum when the toluene solution of compound 2-38 is irradiated with excitation light of wavelength 360nm. In the region around 450nm, it is confirmed that the two overlap. Figure 2 The lower part of represents the emission spectrum when the toluene solution of Compound 1 is irradiated with excitation light having a wavelength of 360 nm by the dotted line.

[0281] The lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ).

[0282] (1) The lowest excited singlet energy level (E S1 )

[0283] A tangent line was drawn relative to the rise of the short-wavelength side of the emission spectrum of the toluene solution of compound 2-38, and the wavelength value λedge [nm] of the intersection of the tangent line and the horizontal axis was obtained. The wavelength value was converted into an energy value using the conversion formula shown below, and the obtained value was taken as E S1 . E S1 It is 2.79eV.

[0284] Conversion formula: E S1 [eV] = 1239.85 / λedge

[0285] (2) The lowest excited triplet energy level (E T1 )

[0286] The toluene solution of compound 2-38 was cooled to 77 [K] and irradiated with excitation light (337nm), and the phosphorescence intensity was measured using a streak camera. The luminescence from 1 millisecond after the excitation light was incident to 10 milliseconds after the incident was accumulated to obtain a phosphorescence spectrum with the ordinate as the luminescence intensity and the abscissa as the wavelength. A tangent was drawn relative to the rise of the short-wavelength side of the phosphorescence spectrum, and the wavelength value λedge [nm] of the intersection of the tangent and the abscissa was obtained. The wavelength value was converted into an energy value using the conversion formula shown below, and the obtained value was taken as E T1 .

[0287] Conversion formula: E T1 [eV] = 1239.85 / λedge

[0288] The rising tangent line for the short wavelength side of the phosphorescence spectrum is drawn as follows. Consider the tangent line at each point on the curve toward the long wavelength side when moving from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values ​​of the spectrum on the spectrum curve. As the curve rises (that is, as the vertical axis increases), the slope of the tangent line increases. The tangent line drawn at the point where the value of the slope takes the maximum value is set as the rising tangent line for the short wavelength side of the phosphorescence spectrum.

[0289] The maximum point with a peak intensity of less than 10% of the maximum peak intensity of the spectrum does not include the maximum value on the above-mentioned shortest wavelength side, and the tangent drawn at the point closest to the maximum value on the shortest wavelength side and where the slope value takes the maximum value is set as the rising tangent to the short wavelength side of the phosphorescence spectrum.

[0290] (3) Measurement results

[0291] The lowest excited singlet energy level (E S1 ) is 2.79 eV, and the lowest excited triplet energy level (E T1 ) is 2.66eV. By calculating E S1 -E T1 , ΔE ST Calculated to be 0.13 eV.

[0292] (Example 1) Preparation and determination of thin films containing compound 1 and compounds 2-38

[0293] On a quartz substrate, the vacuum degree was 5×10 -4 Pa below, compound 1, compound 2-38 and mCBP [3,3'-di(9H-carbazole-9-yl)-1,1'-biphenyl] were co-evaporated from different evaporation sources to form a 50 nm thick thin film (compound 1 is 1 wt%, compound 2-38 is 25 wt%, and mCBP is 74 wt%). This thin film was used as the thin film of Example 1.

[0294] exist Figure 2 The lower part of the solid line represents the emission spectrum (FWHM is 20 nm) when the film of Example 1 is irradiated with an excitation light of a wavelength of 360 nm. It is confirmed that it is consistent with the emission spectrum of Compound 1. The photoluminescence quantum efficiency of the film of Example 1 is 75%, and the delayed component is 30%. Here, the fluorescence with a luminescence lifetime of less than 0.1 μs is determined as instantaneous fluorescence, and the fluorescence with a luminescence lifetime of more than 0.1 μs is determined as delayed fluorescence, and the ratio of the delayed component is calculated.

[0295] (Example 2) Preparation and determination of organic electroluminescent elements containing compound 1 and compounds 2-38

[0296] By vacuum evaporation method, the vacuum degree is 2×10 -5 Pa Each thin film was stacked on a glass substrate on which an anode composed of indium / tin oxide (ITO) with a film thickness of 50 nm was formed.

[0297] First, HATCN was evaporated on ITO with a thickness of 10nm to form a hole injection layer, and TrisPCz was evaporated thereon with a thickness of 30nm to form a hole transport layer. Then, mCBP was evaporated with a thickness of 5nm to form an electron blocking layer. Then, compound 1, compound 2-38 and mCBP were co-evaporated from different evaporation sources to form a 50nm thick light-emitting layer (compound 1 was 1% by weight, compound 2-38 was 25% by weight, and mCBP was 74% by weight). SF3-TRZ was evaporated thereon with a thickness of 10nm to form a hole blocking layer, and SF3-TRZ:LiQ (weight ratio 7:3) was evaporated thereon with a thickness of 20nm to form an electron transport layer. Moreover, the organic electroluminescent element of Example 2 was prepared by forming LiQ with a thickness of 2nm and then forming aluminum (Al) with a thickness of 100nm to form a cathode.

[0298] (Example 3) Preparation and determination of organic electroluminescent elements containing compound 8 and compound 2-117

[0299] By vacuum evaporation method, the vacuum degree is 2×10 -5 Pa Each thin film was stacked on a glass substrate on which an anode composed of indium / tin oxide (ITO) with a film thickness of 50 nm was formed.

[0300] First, HATCN was evaporated on ITO with a thickness of 10nm to form a hole injection layer, and TrisPCz was evaporated thereon with a thickness of 30nm to form a hole transport layer. Then, mCBP was evaporated with a thickness of 5nm to form an electron blocking layer. Then, compound 8, compound 2-117 and mCBP were co-evaporated from different evaporation sources to form a 30nm thick light-emitting layer (compound 8 was 0.5 wt%, compound 2-117 was 15 wt%, and mCBP was 84.5 wt%). SF3-TRZ was evaporated thereon with a thickness of 10nm to form a hole blocking layer, and SF3-TRZ:LiQ (weight ratio 7:3) was evaporated thereon with a thickness of 20nm to form an electron transport layer. Moreover, the organic electroluminescent element of Example 3 was prepared by forming LiQ with a thickness of 2nm and then forming aluminum (Al) with a thickness of 100nm to form a cathode.

[0301] [Chemical formula 40]

[0302]

[0303] The light emission from the organic electroluminescent element of Example 2 has color coordinates x of 0.151 and y of 0.256 in the CIE-XYZ color system, and is good blue light emission. The fluorescence spectrum of the organic electroluminescent element of Example 2 was measured, and it had the same maximum wavelength of light emission as Compound 1, so it was confirmed that the light emission was from Compound 1. The element of Example 2, the comparative organic electroluminescent element (comparative element 1) that differed only in that the light-emitting layer was changed to be composed of Compound 1 (1 wt %) and mCBP (99 wt %), and the comparative organic electroluminescent element (comparative element 2) that differed only in that the light-emitting layer was changed to be composed of Compound 2-38 (25 wt %) and mCBP (75 wt %) were measured for each transient decay curve, and the results are shown in Figure 3 Since the ratio of the delayed component increased when the comparative element 1 was changed to the element of Example 2, energy transfer from the compound 2-38 to the compound 1 was confirmed.

[0304] The external quantum efficiency of the organic electroluminescent element of Example 2 is a high value of more than 20% at 1000nit (1.8lm / W). The external quantum efficiency of the comparative organic electroluminescent element (comparative element 1) which is different only in that the light-emitting layer is composed of compound 1 (1 wt%) and mCBP (99 wt%) is 8%, so the organic electroluminescent element of Example 2 achieves a significant improvement in quantum efficiency. In addition, it is confirmed that the time (LT95) until the luminous intensity of the organic electroluminescent element of Example 2 reaches 95% at the start of the measurement is about 100 hours at 750nit (1.35lm / W), which has a long life.

[0305] Furthermore, the maximum emission wavelength of the organic electroluminescent element of Example 3 was 469 nm, and the maximum external quantum efficiency was 22.5%. In Example 3, it was also confirmed that the organic electroluminescent element of the present invention had a high emission efficiency.

[0306] Industrial Applicability

[0307] The organic light-emitting element of the present invention has high light-emitting efficiency. In addition, according to the present invention, a highly efficient organic light-emitting element that emits good blue light can be provided. Therefore, the present invention has high industrial applicability.

[0308] Explanation of symbols

[0309] 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-light-emitting layer, 6-electron transport layer, 7-cathode.

Claims

1. An organic light-emitting element comprising a compound having a structure represented by one or more of the following general formula (1) and a compound represented by the following general formula (2), [Chemical formula 1] General formula (1) In the general formula (1), the ring a, the ring b and the ring c each independently represent a benzene ring which may be condensed with other rings to form an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 6 to 30 carbon atoms, at least one hydrogen atom in these rings may be substituted, and R 1 , R 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms bonded via a benzene ring, wherein the heteroaryl ring and the heteroaryl group have 1 to 5 heteroatoms selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms, and the substituents when the a ring, b ring and c ring are substituted, and R 1 , R 2 In the case of a substituted aryl or substituted heteroaryl group, the substituent is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms, wherein the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino group, alkyl group, alkoxy group, and aryloxy group described herein may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an alkyl group having 1 to 24 carbon atoms, or may be unsubstituted, [Chemical formula 2] General formula (2) In the general formula (2), R 31 ~R 35 Four of them independently represent substituted or unsubstituted carbazole-9-yl groups, but the four are not all the same, and the remaining one represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbazole-9-yl group or a cyano group, R 31 ~R 35 The substituent for substituted carbazole-9-yl is an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms wherein the amino group is an alkylamino group, an arylheteroarylamino group, an alkyl group, an alkoxy group, or an aryloxy group is further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms, or is unsubstituted; and R 31 ~R 35 When the other one of the groups is a substituted aryl group having 6 to 30 carbon atoms, the substituent is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl group, alkoxy group, and aryloxy group described herein may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an alkyl group having 1 to 24 carbon atoms, or may be unsubstituted.

2. The organic light emitting element according to claim 1, wherein The compound having one or more structures represented by the general formula (1) is a compound having two structures represented by the general formula (1).

3. The organic light emitting element according to claim 2, wherein: The compound represented by the general formula (1) is a compound represented by the following general formula (1a), [Chemical formula 3] General formula (1a) In the general formula (1a), R 11 ~R 17 Each independently represents a substituent, R 18 ~R 23 Each independently represents a hydrogen atom or a substituent, R 11 ~R 23 The substituent is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl group described herein is , heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy, aryloxy may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, or an alkyl having 1 to 24 carbon atoms, n11, n13, n14, n17 each independently represent an integer from 0 to 5, n12 represents an integer from 0 to 2, and n15 and n16 each independently represent an integer from 0 to 4.

4. The organic light emitting element according to claim 3, wherein: R 19 and R 22 Each independently represents the substituent.

5. The organic light emitting element according to any one of claims 1 to 4, wherein In the general formula (2), R 31 ~R 35 At least one of the above is a carbazole-9-yl group substituted with the substituent at the 3-position or the 6-position.

6. The organic light emitting element according to claim 1, wherein: The compound represented by the general formula (2) is a compound represented by the following general formula (2a), [Chemical formula 4] General formula (2a) In the general formula (2a), R 41 ~R 44 , R 46 ~R 49 Each independently represents a substituent, but the four substituted or unsubstituted carbazole-9-yl groups bonded to the benzonitrile of the general formula (2a) are not all the same, n41 to n44 and n46 to n49 each independently represent an integer of 0 to 4, and R 45 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbazole-9-yl group or a cyano group, and R 41 ~R 44 , R 46 ~R 49 The substituents and R 45 The substituent for substituted carbazole-9-yl is an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms arylamino, arylheteroarylamino, alkyl, alkoxy, aryloxy further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino in which each aryl has 6 to 30 carbon atoms, a diheteroarylamino in which each heteroaryl has 2 to 30 carbon atoms, an arylheteroarylamino in which the aryl has 6 to 30 carbon atoms and the heteroaryl has 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, or an aryloxy having 6 to 30 carbon atoms, or unsubstituted, R 45 The substituent of the substituted aryl group is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino group, alkyl group, alkoxy group, and aryloxy group described herein may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an alkyl group having 1 to 24 carbon atoms, or may be unsubstituted. 7 . The organic light-emitting element according to claim 1 , comprising a compound represented by the general formula (1) in a light-emitting layer. 8 . The organic light-emitting element according to claim 1 , comprising the compound represented by the general formula (1) and the compound represented by the general formula (2) in the same layer.

9. A composition comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2). [Chemical formula 5] General formula (1) In the general formula (1), the ring a, the ring b and the ring c each independently represent a benzene ring which may be condensed with other rings to form an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 6 to 30 carbon atoms, at least one hydrogen atom in these rings may be substituted, and R 1 , R 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms bonded via a benzene ring, wherein the heteroaryl ring and the heteroaryl group have 1 to 5 heteroatoms selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms, and the substituents when the a ring, b ring and c ring are substituted, and R 1 , R 2 In the case of a substituted aryl or substituted heteroaryl group, the substituent is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms, wherein the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino group, alkyl group, alkoxy group, and aryloxy group described herein may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an alkyl group having 1 to 24 carbon atoms, or may be unsubstituted, [Chemical formula 6] General formula (2) In the general formula (2), R 31 ~R 35 Four of them independently represent substituted or unsubstituted carbazole-9-yl groups, but the four are not all the same, and the remaining one represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbazole-9-yl group or a cyano group, R 31 ~R 35 The substituent for substituted carbazole-9-yl is an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms wherein the amino group is an alkylamino group, an arylheteroarylamino group, an alkyl group, an alkoxy group, or an aryloxy group is further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms, or is unsubstituted; and R 31 ~R 35 When the other one of the groups is a substituted aryl group having 6 to 30 carbon atoms, the substituent is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl group, alkoxy group, and aryloxy group described herein may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an alkyl group having 1 to 24 carbon atoms, or may be unsubstituted.

10. A film comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2) at the same time, [Chemical formula 7] General formula (1) In the general formula (1), the ring a, the ring b and the ring c each independently represent a benzene ring which may be condensed with other rings to form an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 6 to 30 carbon atoms, at least one hydrogen atom in these rings may be substituted, and R 1 , R 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms bonded via a benzene ring, wherein the heteroaryl ring and the heteroaryl group have 1 to 5 heteroatoms selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms, and the substituents when the a ring, b ring and c ring are substituted, and R 1 , R 2 In the case of a substituted aryl or substituted heteroaryl group, the substituent is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms, wherein the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino group, alkyl group, alkoxy group, and aryloxy group described herein may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an alkyl group having 1 to 24 carbon atoms, or may be unsubstituted, [Chemical formula 8] General formula (2) In the general formula (2), R 31 ~R 35 Four of them independently represent substituted or unsubstituted carbazole-9-yl groups, but the four are not all the same, and the remaining one represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbazole-9-yl group or a cyano group, R 31 ~R 35 The substituent for substituted carbazole-9-yl is an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms wherein the amino group is an alkylamino group, an arylheteroarylamino group, an alkyl group, an alkoxy group, or an aryloxy group is further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms, or is unsubstituted; and R 31 ~R 35 When the other one of the groups is a substituted aryl group having 6 to 30 carbon atoms, the substituent is a halogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group in which each aryl group has 6 to 30 carbon atoms, a diheteroarylamino group in which each heteroaryl group has 2 to 30 carbon atoms, an arylheteroarylamino group in which the aryl group has 6 to 30 carbon atoms and the heteroaryl group has 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms. The aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl group, alkoxy group, and aryloxy group described herein may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an alkyl group having 1 to 24 carbon atoms, or may be unsubstituted.

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